CHEMISTRY & BIODIVERSITY – Vol.

8 (2011) 13

REVIEW

Chemical and Pharmacological Research on Plants from the Genus Senecio

by Yan Yang a ) b ), Lei Zhao a ) b ), Yu-Fang Wang a ), Man-Li Chang a ), Chang-Hong Huo a ),
Yu-Cheng Gu a ) c ), Qing-Wen Shi* a ), and Hiromasa Kiyota* d )
a
) Department of Medicinal Natural Product Chemistry, School of Pharmaceutical Sciences,
Hebei Medical University, Shijiazhuang 050017, P. R. China
(phone: þ 86-311-86265634; e-mail: [email protected])
b
) The Tumor Hospital of Yunnan Province, the Third Affiliated Hospital of Kunming Medical
University, 519 Kunzhou Road, Kunming 650118, P. R. China
c
) Jealotts Hill International Research Centre, Syngenta, Berkshire, RG42 6EY, UK
d
) Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of
Agricultural Sciences, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai, 981-8555, Japan
(phone/fax: þ 81-22-7178785; e-mail: [email protected])

Contents

1. Introduction
2. Chemical Constituents
2.1. Pyrrolizidine Alkaloids
2.2. Sesquiterpenoids
2.2.1. Eremophilanes
2.2.2. Cacalols
2.2.3. Bisabolanes
2.2.4. Eudesmanes
2.2.5. Oplopanes
2.2.6. Germacranes
2.2.7. Phomalairdanes
2.2.8. Caryophyllanes
2.2.9. Humulanes
2.2.10. Presilphiperfolanes
2.2.11. Aromadendranes
2.2.12. Himachalanes
2.2.13. Africananes
2.2.14. Pentalenanes
2.2.15. Bakkanes
2.2.16. Valeranes
2.2.17. Benzofurane-Type Sesquiterpenes
2.2.18. Other Sesquiterpenoids
2.3. Monoterpenoids
2.4. Diterpenoids
2.5. Triterpenoids

 2011 Verlag Helvetica Chimica Acta AG, Zrich

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2.6. Steroids
2.7. Flavonoids
2.8. Coumarins
2.9. Phenolic acids
2.10. Alkanes
2.11. Others
3. Biological Activities
3.1. Antibacterial and Antifungal Activities
3.2. Antitubercular Activity
3.3. Anti-inflammatory Effects
3.4. Antiulcer Activity
3.5. Antifeedant Effects
3.6. Cytotoxicity towards the Human Hepatoma Cell Line Huh-7
3.7. Antimitotic Effects
3.8. Angiotensin-Converting Enzyme Inhibitory Activity
3.9. Insecticidal, Neurotoxic, and Glutathione-Depleting Activities
4. Conclusions

1. Introduction. – The genus Senecio, which belongs to the tribe Senecioneae, is the
largest and most complex genus in the family of the Asteraceae (Compositae) and
includes more than 1500 species with a worldwide distribution [1] that have been
extensively investigated for their secondary metabolites. Pyrrolizidine alkaloids (PAs),
eremophilanolides, and cacalolides are particularly characteristic for species of this
genus [2]. Some Senecio species have a negative impact in many agricultural countries,
because these plants are responsible for more deaths to livestock than any other
poisonous plant. The toxicity exhibited by these plants has been attributed to their
content of PAs and some furanoeremophilanes [3]. Senecio species were used in the
folk medicine for the treatment of wounds and as antiemetic, anti-inflammatory, and
vasodilatory preparations [1]. Chemically investigated parts of the Senecio species
include roots, leaves, stems, flowers, aerial parts, and whole plants. The PAs and
furanoeremophilanes are the most important constituents of this genus. Some
compounds isolated from the genus Senecio and even crude extracts are known to
possess antimicrobial activity, including antibacterial, antifungal, and antitubercular
activities.
In this article, the compounds isolated from the genus Senecio over the past few
decades are listed, and the phytochemical progress in this genus is summarized. The
biological activities of the isolated compounds and some structureactivity relation-
ships are also discussed.

2. Chemical Constituents. – The chemical constituents of the genus Senecio include

alkaloids, sesquiterpenoids, monoterpenoids, diterpenoids, triterpenoids, flavonoids,
coumarins, and some other compounds. Their structures are shown below, i.e.,
compounds 1 – 631, and their names and the corresponding plant sources are collected
in Tables 1 – 11. As can be seen, sesquiterpenoids are the predominant constituents
within the genus Senecio.
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1) As the numbering of the cited bisabolanes was not homogenous between the different literature
sources, they were systematically renumbered according to the IUPAC recommendations for the
numbering of bisabolane, as shown for compound 391.
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2.1. Pyrrolizidine Alkaloids (Table 1). Among the naturally occurring N-containing
compounds, the PAs of the macrocyclic senecionine type constitute an important group.
They are pharmacologically active constituents and characteristic secondary metabo-
lites for most species of the genus Senecio. These PAs are composed of a necine base
and a necic acid (Scheme 1) and are divided into two groups: i) PAs with a saturated
necine moiety, which are nontoxic, and ii) PAs with an unsaturated necine base, which
are hepatotoxic to mammals [8]. In Table 1, 98 PAs isolated from Senecio species
between 1940 and the end of 2008 are presented.
In 1993, a new alkaloid, neosarracine (6), was obtained from S. chrysocoma [6]. In
2002, Suau et al. [8] found the open-chain monoester 7-(angeloyloxy)heliotridine (9) in
S. elodes and the twelve-membered macrocyclic alkaloids 37, 39, 41, and 42 in S.
malacitanus, all of them contain retronecine as necine base. Moreover, Suau et al. [8]
also found that S. granatensis is rich in alkaloids (6.3 g/100 g dried plant), and that it
contains a single, nonhepatotoxic alkaloid with platynecine as necine base, i.e.,
platyphylline, isolated as the free base, 32, and its N-oxide 35 [8]. In 1991, a new
saturated PA, 14, a new H2O-soluble PA quaternary salt, 20, and a new saturated
otonecine pyrrolizidine, 74, were obtained from S. integrifolius var. fauriri. [11].
Moreover, a new saturated pyrrolizidine diester alkaloid, racemodine (16), was
isolated from S. racemosus in 1993 by Ahmed et al. [10]. In 1984, the new PA
sencalenine (21) and three known PAs, i.e., 15, 19, and 92, were isolated from S.
cacaliaster [12]. In 1993, the known compounds 33, 39, 44, 45, and 52 were isolated from
S. pterophorus, along with a new alkaloid, 34 [22]. S. argunensis is a traditional Chinese
medicinal plant, which is widespread in northwestern China and used to treat
dysentery, conjunctivitis, and tumefaction. Compounds 30, 37, 39, 44, 68, and the new
alkaloid (60) were isolated from this plant [17]. Apart from florosenine (72), a new
alkaloid was isolated from S. adonidifolius and identified as (12S,15R,20R)-15,20-
epoxy-15,20-dihydro-12,13,19-trihydroxysenecionane-11,16-dione (61) [31]. The new
macrocyclic PA 62 was isolated from the roots of S. uspallatensis, together with the
previously known compound 41 [35]. From S. pterophorus, pterophorin (65), a new
 36 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 1. Alkaloids 1 – 99 Isolated from Species of the Genus Senecio

No. Compound class and name Species Part Ref.

Pyrrolizidine alkaloids
1 Sarracine-N-oxide S. deformis roots [4]
2 7b-Hydroxy-1-methylidene-8a-pyrrolizidine S. schweinfurthii aerial parts [5]
3 7b-Hydroxy-1-methylidene-8b-pyrrolizidine S. schweinfurthii aerial parts [5]
4 7b-Hydroxy-1-methylidene-8a-pyrrolizidine S. schweinfurthii aerial parts [5]
N-oxide
5 Sarracine S. doratophyllus leaves and roots [4]
S. chrysocoma – [6]
6 Neosarracine S. doratophyllus leaves and roots [4]
S. chrysocoma – [6]
S. kaschkarovii – [7]
7 9-( Angeloyloxy)platynecine S. conzattii leaves and roots [4]
S. chrysocoma – [6]
8 7-( Tigloyloxy)platynecine S. conzattii leaves and roots [4]
9 7-( Angeloyloxy)heliotridine S. elodes aerial parts [8]
10 7b-( Angeloyloxy)-1-methylidene-8a-pyrrolizidine S. doratophyllus leaves and roots [4]
S. chrysocoma whole plants [9]
11 7a-( Angeloyloxy)-1-methylidene-8a-pyrrolizidine S. chrysocoma whole plants [9]
12 7-( Angeloyloxy)platynecine S. chrysocoma – [6]
S. racemosus – [10]
13 7a-( Angeloyloxy)-1-methylidene-8a-pyrrolizidine S. chrysocoma whole plants [9]
N-oxide
14 7-( Angeloyloxy)turneforcidine S. integrifolius var. – [11]
fauriri
15 7-( Senecioyloxy)retronecine S. cacaliaster – [12]
16 Racemodine S. racemosus – [10]
17 Triangularine S. kaschkarovii – [7]
18 Neotriangularine S. kaschkarovii – [7]
19 9-( Sarracinoyloxy)-7-(senecioyloxy)-retronecine S. kaschkarovii – [7]
S. cacaliaster – [12]
20 7,9-Bis(angeloyloxy)-1a-hydroxy-N- S. integrifolius var. – [11]
methylplatynecinium chloride fauriri
21 Sencalenine S. cacaliaster – [12]
22 9-( Angeloyloxy)hastanecine S. aquaticus aerial parts [13]
23 Senampelin E S. mikanoides aerial parts [14]
24 Senampelin F S. mikanoides aerial parts [14]
25 Senampelin G S. mikanoides aerial parts [14]
26 Hadiensine S. hadiensis – [15]
27 12-O-Acetylhadiensine S. hadiensis – [15]
28 12-O-Acetylhadiensine N-oxide S. hadiensis – [15]
29 Hadiensine N-oxide S. hadiensis – [15]
30 Erucifoline S. aquaticus aerial parts [13]
S. persoonii whole plants [16]
S. argunensis – [17]
31 Erucifoline N-oxide S. persoonii whole plants [16]
32 Platyphylline S. granatensis whole plants [8]
S. polypodioides whole plants [18]
S. tournefortii – [19]
S. jacalensis aerial parts [20]
33 Rosmarinine S. runcinatus whole plants [18]
S. rosmarinifolius – [21]
S. callosus aerial parts [20]
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 37

Table 1 (cont.)
No. Compound class and name Species Part Ref.
S. pterophorus – [22]
S. syringifolius aerial parts [15]
S. hadiensis – [15]
34 Isorosmarinine S. pterophorus – [22]
35 Platyphylline N-oxide S. granatensis whole plants [8]
S. polypodioides whole plants [18]
S. tournefortii – [19]
36 Rosmarinine N-oxide S. runcinatus whole plants [18]
S. syringifolius aerial parts [15]
37 Integerrimine S. miser aerial parts [23]
S. malacitanus whole plants [8]
S. brasiliensis leaves and inflores- [24]
cences
S. faberi – [25]
S. durieui – [26]
S. madagascariensis whole plants [27]
S. argunensis – [17]
S. glabellus – [28]
S. longilobus – [28]
S. jacobaea – [29]
S. samnitum aerial parts [30]
38 Integerrimine N-oxide S. miser aerial parts [23]
39 Senecionine S. malacitanus whole plants [8]
S. brasiliensis leaves and inflores- [24]
cences
S. madrensis roots [18]
S. aquaticus aerial parts [13]
S. jacalensis aerial parts [20]
S. madagascariensis whole plants [27]
S. pterophorus – [22]
S. argunensis – [17]
S. gallicus aerial parts [31]
S. glabellus – [28]
S. longilobus – [28]
S. jacobaea – [29]
S. gilliesiano roots [32]
S. samnitum aerial parts [30]
40 Senecionine N-oxide S. gallicus aerial parts [31]
41 Retrorsine S. malacitanus whole plants [8]
S. brasiliensis leaves and inflores- [24]
cences
S. prionopterus aerial parts and [18]
roots
S. swaziensis – [33]
S. madagascariensis whole plants [27]
S. oxiphyllus – [34]
S. uspallatensis roots [35]
S. oxyphyllus – [36]
S. longilobus – [28]
S. gilliesiano roots [32]
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Table 1 (cont.)
No. Compound class and name Species Part Ref.
42 Usaramine S. malacitanus whole plants [8]
S. brasiliensis leaves and [24]
inflorescences
S. madagascariensis whole plants [27]
S. oxiphyllus – [34]
43 Jacobine S. aquaticus aerial parts [13]
S. jacobaea – [29]
44 Seneciphylline S. aquaticus aerial parts [13]
S. lorenthii aerial parts [37]
S. oxiphyllus – [34]
S. pterophorus – [22]
S. persoonii whole plants [16]
S. argunensis – [17]
S. longilobus – [28]
S. jacobaea – [29]
S. samnitum aerial parts [30]
45 Spartioidine S. aquaticus aerial parts [13]
S. pterophorus – [22]
46 Jacozine S. aquaticus aerial parts [13]
S. jacobaea – [29]
47 Isoline S. ruwenzoriensis – [38]
48 Bisline S. ruwenzoriensis – [38]
49 Mucronatinine S. madagascariensis whole plants [27]
50 18-Hydroxyjaconine S. selloi – [34]
51 Riddelliine S. oxiphyllus – [34]
52 Acetylseneciphylline S. pterophorus – [22]
53 Angularine S. syringifolius aerial parts [15]
54 Angularine N-oxide S. syringifolius aerial parts [15]
55 Neorosmarinine S. hadiensis – [15]
56 12-O-Acetylrosmarinine N-oxide S. syringifolius aerial parts [15]
S. hadiensis – [15]
57 12-O-Acetylrosmarinine S. hadiensis – [15]
58 Seneciphylline N-oxide S. persoonii whole plants [16]
59 Dihydroretrorsine S. racemosus – [10]
60 21-Hydroxyintegerrimine S. argunensis – [17]
61 (12S,15R,20R)-15,20-Epoxy-15,20-dihydro-12,13,19- S. adonidifolius – [31]
trihydroxysenecionane-11,16-dione
62 Uspallatine S. uspallatensis roots [35]
63 Jacoline S. jacobaea – [29]
64 Jaconine S. jacobaea – [29]
65 Pterophorin S. pterophorus aerial parts [39]
66 Senecivernine S. madagascariensis whole plants [27]
67 Neoangularine S. syringifolius aerial parts [15]
68 Otosenine S. lorenthii aerial parts [37]
S. madagascariensis whole plants [27]
S. argunensis – [17]
69 Senkirkine S. madagascariensis whole plants [27]
S. gallicus aerial parts [31]
70 Acetylsenkirkine S. madagascariensis whole plants [27]
71 Desacetyldoronine S. madagascariensis whole plants [27]
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Table 1 (cont.)
No. Compound class and name Species Part Ref.
72 Florosenine S. madagascariensis whole plants [27]
S. gallicus aerial parts [31]
S. adonidifolius flowers [31] [40]
73 Doronine S. madagascariensis whole plants [27]
74 1,2-Dihydrosenkirkine S. integrifolius var. – [11]
fauriri
75 Ligularizine S. gallicus aerial parts [31]
S. oxyphyllus – [36]
76 Adonifoline S. adonidifolius flowers [40]
77 Merenskine N-oxide S. latifolius whole plants [41]
78 Sceleratine S. latifolius – [42]
79 Sceleratine N-oxide S. latifolius – [42]
80 7-epi-Desacetylsenaetnin S. portalesianus aerial parts [43]
81 (14E )-Senaetnin S. aucheri aerial parts [14]
82 Senaetnin S. aetnensis aerial parts and [44]
roots
83 Isopterophorin S. pulviniformis roots [45]
84 Inaequidenin S. inaequidens roots [44]
85 Oxyretroisosenine S. mulgediifolius leaves and roots [46]
86 Retroisosenine S. iodanthus aerial parts [47]
S. bracteatus roots [47]
S. roseus roots [48]
S. helodes roots [48]
S. mulgediifolius leaves and roots [46]
87 Mulgediifoliine S. iodanthus aerial parts [47]
S. bracteatus roots [47]
S. roseus roots [48]
S. helodes roots [48]
S. mulgediifolius leaves and roots [46]
88 (12S )-Hydroxyretroisosenine S. iodanthus aerial parts [47]
S. bracteatus roots [47]
S. roseus roots [48]
S. helodes roots [48]
89 (13R )-Hydroxyretroisosenine S. roseus roots [48]
90 Nemorensine S. nemorensis – [49]
91 Iodanthine S. iodanthus aerial parts [47]
S. bracteatus roots [47]
92 Bulgarsenine S. iodanthus aerial parts [47]
S. bracteatus roots [47]
S. callosus leaves [50]
S. mulgediifolius leaves and roots [46]
S. cacaliaster – [12]
93 Callosine S. callosus leaves [50]
94 11-O-Acetylbulgarsenine S. callosus leaves [50]
95 11-O-Acetylbulgarsenine N-oxide S. callosus leaves [50]
96 N-(Chloromethyl)bulgarsenine S. callosus leaves [50]
97 Neosenkirkine S. auricula – [26]
98 Swazine S. swaziensis – [33]
Other alkaloids
99 Cannabiloid B S. cannabifolius – [51]
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Table 2. Sesquiterpenoids 100 – 514 Isolated from Species of the Genus Senecio

No. Compound class and name Species Part Ref.

Eremophilanes
100 9,10-Dehydrofukinone S. aureus aerial parts [52]
S. humillimus aerial parts [53]
101 3a-[4’-( Angeloyloxy)angeloyloxy]-9a-hydroxy-10aH- S. lividus aerial parts [54]
eremophil-7(11)-en-8-one
102 3a-[5’-( Angeloyloxy)angeloyloxy]-9a-hydroxy-10aH- S. lividus aerial parts [54]
eremophil-7(11)-en-8-one
103 3a-[4’-( Angeloyloxy)angeloyloxy]-9-hydroxyeremophi- S. lividus aerial parts [54]
la-7(11),9-dien-8-one
104 3a-[5’-( Angeloyloxy)angeloyloxy]-9-hydroxyeremophi- S. lividus aerial parts [54]
la-7(11),9-dien-8-one
105 8b-Hydroxy-8a-methoxy-3-oxoeremophila-1,7(11)-di- S. pseudoorientalis aerial parts [55]
en-12-oic acid
106 3a-( Senecioyloxy)eremophila-9,11-dien-8-one S. greyi aerial parts [56]
107 8,12-Dioxoeremophila-7(11),9-diene S. mauricei roots [57]
108 4’-(Angeloyloxy)isosenspeciosone S. speciosus aerial parts and [58]
roots
109 5’-(Angeloyloxy)isosenspeciosone S. speciosus aerial parts and [58]
roots
110 5’-(Angeloyloxy)-8a,O-dihydrosenspeciosone S. speciosus roots [58]
111 5’-(Angeloyloxy)senspeciosone S. speciosus aerial parts and [58]
roots
S. glanduloso- aerial parts and [59]
pilosus roots
112 3a-( Senecioyloxy)-9b-(tigloyloxy)eremophil-11-en-8- S. rhyncholaenus aerial parts and [58]
one roots
113 9b,13-Diacetoxy-8-oxoisosenspeciosol triene ester S. speciosus roots [58]
114 8a-Hydroxy-9-oxosenspeciosol triene ester S. speciosus roots [58]
115 8a,13-Diacetoxy-9-oxosenspeciosol triene ester S. speciosus roots [58]
116 2’,3’-Epoxy-2’,3’-dihydropetasin S. polyodon roots [58]
117 8a-( Tigloyloxy)-1b,10b-epoxyeremophil-11(13)-ene S. portalesianus aerial parts [43]
118 8a-( Angeloyloxy)-1b,10b-epoxyeremophil-11(13)-ene S. portalesianus aerial parts [43]
119 la-Acetoxy-8a-(angeloyloxy)-10aH-eremophil-11(13)- S. portalesianus aerial parts [43]
en-9-one
120 la-Acetoxy-8a-(tigloyloxy)-10aH-eremophil-11(13)- S. portalesianus aerial parts [43]
en-9-one
121 3a-Hydroxy-7a,10aH-eremophil-11-en-9-one S. isatideus aerial parts and [60]
roots
122 3a-({(2Z)-4-[(2Z)-Hex-2-enoyl}oxy)hex-2-enoyl}oxy)- S. erubescens var. roots [60]
7a,10aH-eremophil-11-ene-8a,9a-diol crepidifolius
123 3a-{(2Z )-4-(Angeloyloxy)-hex-2-enoyl]oxy}-7a,10aH- S. erubescens var. roots [60]
eremophil-11-ene-8a,9a-diol crepidifolius
124 3a,9a-{[(2Z )-Dihex-2-enoyl]oxy}-7a,10aH-eremophil- S. erubescens var. roots [60]
11-en-8a-ol crepidifolius
125 9a,13-Dihydroxy-3a-{[(2E,4E,6E)-5-methyldodeca- S. macrocephalus aerial parts [60]
2,4,6-trienoyl]oxy}-10aH-eremophil-7(11)-en-8-one S. erubescens var. aerial parts [60]
crepidifolius
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Table 2 (cont.)
No. Compound class and name Species Part Ref.
126 9a-Hydroxy-3a-{[(2E,4E,6E )-5-methyldodeca-2,4,6- S. erubescens var. roots [60]
trienoyl]oxy}-10aH-eremophil-7(11)-ene-8-one crepidifolius
S. speciosus roots [60]
127 3a-((2Z)-4-{[(2Z)-Hex-2-enoyl]oxy}hex-2-enoyl- S. erubescens var. roots [60]
oxy)-9a-hydroxy-10aH-eremophil-7(11)-en-8-one crepidifolius
128 9a-[(2-Methylbutyryl)oxy]-3a-(senecioyloxy)- S. speciosus roots [60]
7a,10aH-eremophil-11-en-8-one
129 3a-((2Z)-4-{[(2Z)-Hex-2-enoyl]oxy}hex-2-enoyl- S. erubescens var. roots [60]
oxy)-9a-hydroxy-7a,10aH-eremophil-11-en-8-one crepidifolius
130 9b-Hydroxy-3a-(tigloyloxy)eremophil-7(11)-en-8-one S. ochoanus aerial parts and [61]
roots
131 10aH-Eremophil-11-en-4-ol S. amplexicaulis whole plants [62]
132 3a-( Angeloyloxy)-9b-hydroxyeremophil-7(11)-en-8- S. grisebachii var. aerial parts [44]
one balansae
133 3a-( Angeloyloxy)-9b-hydroxyeremophil-11-en-8-one S. sylvaticus aerial parts [44]
S. bicolor aerial parts and [44]
roots
S. viscosus aerial parts and [44]
roots
S. grisebachii var. aerial parts and [44]
balansae roots
134 9b-Hydroxy-3a-(tigloyloxy)eremophil-11-en-8-one S. sylvaticus aerial parts [44]
135 9b-Hydroxy-3a-(senecioyloxy)eremophil-11-en-8-one S. sylvaticus aerial parts [44]
136 4’-(Angeloyloxy)senspeciosone S. glanduloso-pilo- aerial parts and [59]
sus roots
137 Petasol tiglate S. capitatus aerial parts and [44]
roots
138 Mairetin S. mairetianus aerial parts [63]
139 10aH-Furanoeremophilan-9-one S. aureus aerial parts [52]
140 3a-{[(2E,4E,6E )-5-Methyldodeca-2,4,6-trienoyl]oxy}- S. speciosus roots [58]
10aH-furanoeremophilan-9-one
141 3a-{[(2E,4E,6E )-5-Methyldodeca-2,4,6-trienoyl]oxy}- S. speciosus roots [58]
10aH-furanoeremophilan-9a-ol
142 9a,13-Dihydroxy-3a-{[(2E,4E,6E)-5-methyldodeca- S. macrocephalus aerial parts [60]
2,4,6-trienoyl]oxy}-10aH-eremophil-11-en-8-one semi- S. speciosus roots [60]
acetal
143 9a,13-Dihydroxy-3a-{[(2E,4E,6E)-5-methyldodeca- S. speciosus roots [60]
2,4,6-trienoyl]oxy}-10aH-eremophil-11-en-8-one 8-O-
methyl acetal
144 1a,10a-Epoxyeuryopsin-6-ol S. toluccanus roots [2]
145 Euryopsin-6-ol S. toluccanus roots [2]
146 Furanoligularenone S. flavus aerial parts [64]
147 6b-( Isobutyryloxy)furanoeremophil-1(10)-ene S. boissieri aerial parts and [65]
rhizomes
148 6b-( Isobutyryloxy)-10aH-furanoeremophilan-1-one S. boissieri aerial parts and [65]
rhizomes
S. heliopsis roots [60]
149 6b-[(2-Methylbutyryl)oxy]-10aH-furanoeremophilan- S. auricula var. ma- roots [66]
1-one jor
 42 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 2 (cont.)
No. Compound class and name Species Part Ref.
150 6b-( Isobutyryloxy)senberginone S. auricula var. ma- roots [66]
jor
151 6b-[(2-Methylbutyryl)oxy]senberginone S. auricula var. ma- roots [66]
jor
152 6b-( Isobutyryloxy)-1a-(senecioyloxy)-10aH-furano- S. panduriformis aerial parts [39]
eremophilan-9-one
153 2b-Hydroxy-6b-(isobutyryloxy)-1a-(senecioyloxy)- S. panduriformis aerial parts [39]
10aH-furanoeremophilan-9-one
154 6b-( Senecioyloxy)furanoeremophil-1(10)-en-9-one S. lanceus aerial parts and [39]
roots
155 6b-( Propionyloxy)furanoeremophil-1(10)-en-9-one S. lanceus aerial parts [39]
156 6b-Hydroxyfuranoeremophil-1(10)-en-9-one S. lanceus aerial parts [39]
157 Furanoeremophilane-6,9-dione S. lanceus aerial parts [39]
158 3b-[(2-Methylbutyryl)oxy]euryopsin S. flavus aerial parts [64]
159 3b-( Senecioyloxy)euryopsin S. flavus aerial parts [64]
160 3b-( Angeloyloxy)euryopsin S. flavus aerial parts [64]
161 Euryopsin-3-one S. flavus aerial parts [64]
162 8,12-Dihydro-8a,12a-dimethoxy-10aH-furanoeremo- S. flavus aerial parts [64]
phil-1-en-3-one
163 6b-( Propionyloxy)-10aH-furanoeremophilan-9-one S. pachyphyllos aerial parts [67]
164 8,12-Epoxy-6b-(isobutyryloxy)-12a-methoxyeremo- S. pachyphyllos aerial parts [67]
phila-1(10),7(11),8-triene
165 8,12-Epoxy-6b-(isobutyryloxy)-12b-methoxyeremo- S. pachyphyllos aerial parts [67]
phila-1(10),7(11),8-triene
166 8,12-Epoxy-12a-methoxy-6b-(propionyloxy)eremo- S. pachyphyllos aerial parts [67]
phila-1(10),7(11),8-triene
167 8,12-Epoxy-12b-methoxy-6b-(propionyloxy)eremo- S. pachyphyllos aerial parts [67]
phila-1(10),7(11),8-triene
168 7,8 : 11,12-Diepoxy-3b-hydroxy-6b-(isobutyryloxy)- S. zoellneri aerial parts [68]
furanoeremophil-1(10)-ene
169 6b-( Angeloyloxy)-7,8 : 11,12-diepoxy-3b-hydroxy- S. zoellneri aerial parts [68]
furanoeremophil-1(10)-ene
170 6b-( Angeloyloxy)furanoeremophil-1(10)-en-9-one S. zoellneri aerial parts [68]
171 1b,10b-Epoxy-6b-hydroxyfuranoeremophilan-9-one S. smithii aerial parts [69]
172 1b,10b-Epoxyfuranoeremophilane-6,9-dione S. smithii aerial parts [69]
173 Euryopsonol senecioate S. smithii aerial parts [69]
174 1a-Hydroxyeuryopsonol senecioate S. smithii aerial parts and [69]
roots
175 1a-Hydroxyeuryopsonol angelate S. smithii aerial parts and [69]
roots
176 1a-Hydroxyeuryopsonol isobutyrate S. smithii aerial parts and [69]
roots
177 Furanoeremophil-1(10)-ene S. pseudoorientalis roots [55]
S. lyraticus roots [44]
S. othonnae roots [44]
178 Nemosenin A S. nemorensis rhizomes [70]
179 Nemosenin B S. nemorensis rhizomes [70]
180 Nemosenin C S. nemorensis rhizomes [70]
181 Nemosenin D S. nemorensis rhizomes [70]
182 Senemorin S. nemorensis rhizomes [70]
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 43

Table 2 (cont.)
No. Compound class and name Species Part Ref.
183 6b-( Isobutyryloxy)furanoeremophil-1(10)-en-9-one S. pseudoorientalis roots [55]
S. imparipinnatus aerial parts [71]
S. nemorensis aerial parts and [72]
roots
184 6a-( Angeloyloxy)furanoeremophil-9-en-1-one S. pseudoorientalis roots [55]
S. halimifolius roots [73]
185 6b-Hydroxyfuranoeremophil-9-en-1-one S. pseudoorientalis roots [55]
186 6b-( Isobutyryloxy)furanoeremophil-9-en-1-one S. pseudoorientalis roots [55]
187 6a-( Isobutyryloxy)furanoeremophil-9-en-1-one S. pseudoorientalis roots [55]
188 Furanoeremophil-1-en-3-one S. pseudoorientalis roots [55]
189 6b-Acetoxy-10b-hydroxy-la-(isobutyryloxy)furano- S. erosus aerial parts and [74]
eremophilan-9-one roots
190 6b-Acetoxy-la-(angeloyloxy)-10b-hydroxyfurano- S. erosus aerial parts and [74]
eremophilan-9-one roots
191 1a-Acetoxy-6b-(senecioyloxy)-10aH-furanoeremo- S. hypochoerideus roots [56]
philan-9-one
192 1a-Acetoxy-6b-(isovaleryloxy)-10aH-furanoeremo- S. hypochoerideus roots [56]
philan-9-one
193 1a-Hydroxy-6b-(senecioyloxy)-10aH-furanoeremo- S. hypochoerideus roots [56]
philan-9-one
194 1a-Hydroxy-6b-(isovaleryloxy)-10aH-furanoeremo- S. hypochoerideus roots [56]
philan-9-one S. chionophilus aerial parts and [75]
roots
195 1a,6b-Dihydroxy-10aH-furanoeremophilan-9-one S. hypochoerideus aerial parts [56]
196 1a,6b-Dihydroxyfuranoeremophilan-9-one S. hypochoerideus aerial parts and [56]
roots
197 3a-{[( E)-2-Hydroxymethylbut-2-enoyl]oxy}furano- S. greyi roots [56]
eremophilane
198 3a-( Tigloyloxy)furanoeremophilane S. greyi roots [56]
199 3b-Acetoxy-6b-[(2-methylbutyryl)oxy]furanoeremo- S. medley-woodii aerial parts and [73]
philane roots
200 3b-Acetoxy-6b-[(2-methylbutyryl)oxy]furanoeremo- S. medley-woodii roots [73]
philan-9-one
201 Senmauricinol isobutyrate S. mauricei aerial parts and [57]
roots
202 Senmauricinol methacrylate S. mauricei roots [57]
203 Hilliardinol isobutyrate S. mauricei aerial parts and [57]
roots
204 Hilliardinol methacrylate S. mauricei roots [57]
205 10b-Hydroxy-6b-(isobutyryloxy)furanoeremophil-2- S. mauricei aerial parts [57]
ene-1,9-dione
206 2,3-Desoxohilliardinol isobutyrate S. mauricei roots [57]
207 2,3-Desoxohilliardinol methacrylate S. mauricei roots [57]
208 1a,10a-Epoxyfuranoeremophilane S. silvaticus – [76]
209 3b-Acetoxy-6b-(propionyloxy)euryopsin S. subumbellatus aerial parts [43]
210 3b-Acetoxy-6b-(isovaleryloxy)euryopsin S. subumbellatus aerial parts [43]
211 3b-Acetoxy-6b-(isobutyryloxy)euryopsin S. subumbellatus aerial parts [43]
212 3b-Hydroxy-6b-(isovaleryloxy)euryopsin S. subumbellatus aerial parts [43]
213 (1S,4S,5R,10R )-1-Hydroxy-6-(isobutyryloxy)furano- S. chionophilus aerial parts and [75]
eremophilan-9-one roots
 44 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 2 (cont.)
No. Compound class and name Species Part Ref.
214 1a-Hydroxy-6b-[(2-methylbutyryl)oxy]-10aH-fura- S. chionophilus aerial parts and [75]
noeremophilan-9-one roots
215 6b-( Angeloyloxy)-1a-hydroxy-10aH-furanoeremo- S. chionophilus aerial parts and [75]
philan-9-one roots
216 1a-Hydroxy-6b-(isobutyryloxy)-10aH-furanoeremo- S. chionophilus aerial parts and [75]
philan-9-one roots
217 6b-( Propionyloxy)furanoeremophil-9-en-1-one S. pampse roots [45]
218 6b-Acetoxy-1a-hydroxy-10aH-furanoeremophilan-9- S. pampse aerial parts [45]
one
219 1a,6b-Diacetoxy-10aH-furanoeremophilan-9-one S. pampse aerial parts [45]
220 3b-Acetoxy-6b-(tigloyloxy)furanoeremophilan-9-one S. pyranidatus aerial parts and [14]
roots
221 3b-Acetoxy-6b-(angeloyloxy)furanoeremophilane S. pyranidatus aerial parts and [14]
roots
222 3b-Acetoxy-6b-(tigloyloxy)furanoeremophilane S. pyranidatus aerial parts and [14]
roots
223 3b-Acetoxy-6b-(senecioyloxy)furanoeremophilane S. pyranidatus roots [14]
224 6b-( Angeloyloxy)furanoeremophilan-3b-ol S. pyranidatus roots [14]
225 6b-( Tigloyloxy)furanoeremophilan-9b-ol S. pyranidatus roots [14]
226 2b-( Angeloyloxy)furanoeremophilane S. alatus aerial parts and [62]
roots
227 2b-{[( Z )-2-Hydroxymethylbut-2-enoyl]oxy}furano- S. alatus aerial parts and [62]
eremophilane roots
228 10b-( Isovaleryloxy)furanoeremophilan-9-one S. inaequidens roots [77]
229 6b-( Angeloyloxy)furanoeremophil-1(10)-en-9b-ol S. brachychaetus roots [44]
S. coriaceus roots [44]
S. macrophyllus roots [44]
S. vellereus roots [44]
230 6b-( Isovaleryloxy)furanoeremophil-1(10)-en-9b-ol S. brachychaetus roots [44]
S. aureus aerial parts [44]
231 6b-( Senecioyloxy)furanoeremophil-1(10)-en-9b-ol S. coriaceus roots [44]
S. macrophyllus roots [44]
S. vellereus roots [44]
232 6b-( Methacryloyloxy)furanoeremophil-1(10)-en-9b-ol S. umbrosus aerial parts and [44]
roots
233 6b-( Angeloyloxy)-10b-hydroxyfuranoeremophil-1-en- S. coriaceus aerial parts [44]
3-one S. doria aerial parts [44]
S. vellereus. [44]
234 10b-Hydroxy-6b-[(2-methylbutyryl)oxy]furanoeremo- S. coriaceus aerial parts [44]
phil-1-en-3-one S. doria aerial parts [44]
S. macrophyllus aerial parts [44]
235 10b-Hydroxy-6b-(isobutyloxy)furanoeremophil-1-en- S. vellereus aerial parts [44]
3-one
236 6b-( Angeloyloxy)-1,10b-epoxyfuranoeremophilan-9b- S. vellereus roots [44]
ol
237 1,10b-Epoxy-6b-(senecioyloxy)furanoeremophilan-9b- S. vellereus roots [44]
ol
238 1,10b-Epoxy-6b-(senecioyloxy)furanoeremophilan- S. vellereus roots [44]
3a-ol
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 45

Table 2 (cont.)
No. Compound class and name Species Part Ref.
239 3a-Acetoxy-1,10b-epoxy-6b-(senecioyloxy)furano- S. ruthenensis. roots [44]
eremophilane
240 6b-( Senecioyloxy)furanoeremophil-9-en-1-one S. vellereus roots [44]
S. fluviatilis roots [44]
241 6b-( Angeloyloxy)-1a,10b-dihydroxyfuranoeremo- S. nemorensis – [78]
philan-9-one
242 6b-[(2-Methylbutyryl)oxy]furanoeremophil-1(10)-en- S. canescens aerial parts and [79]
9-one roots
243 2b-Acetoxy-6b-(angeloyloxy)-1b,10b-epoxyfurano- S. pyrenaicus aerial parts [54]
eremophilane
244 8a-Methoxy-1-oxo-10aH-eremophil-7(11)-ene-12,8- S. aegyptius var. dis- aerial parts [80]
lactam coideus
245 8a-Methoxy-3-oxo-10aH-eremophila-1,7(11)-diene- S. flavus aerial parts [64]
12,8-lactam
246 1b-Hydroxy-8aH-eremophil-7(11),9-dien-12,8-olide S. aegyptius var. dis- aerial parts [80]
coideus
247 1b,8a-Dihydroxyeremophil-7(11),9-dien-12,8-olide S. aegyptius var. dis- aerial parts [80]
coideus
248 1b-Hydroxy-8a-methoxyeremophil-7(11),9-dien-12,8- S. aegyptius var. dis- aerial parts [80]
olide coideus
249 1b,10b-Epoxy-8a-hydroxyeremophil-7(11)-en-12,8- S. aegyptius var. dis- aerial parts [80]
olide coideus
250 1b,10b-Epoxy-8a-methoxyeremophil-7(11)-en-12,8- S. aegyptius var. dis- aerial parts [80]
olide coideus
251 1a,10a-Epoxy-8a-methoxyeremophil-7(11)-en-12,8- S. flavus rhizomes [64]
olide S. gallicus aerial parts [81]
S. mairetianus aerial parts and [63]
roots
252 1a-Acetoxy-8b-methoxyeremophil-7(11)-en-12,8-olide S. miser aerial parts [23]
253 1a-( Angeloyloxy)-6b-hydroxy-8b-methoxyeremophil- S. miser aerial parts [23]
7(11)-en-12,8-olide
254 1a-( Angeloyloxy)eremophil-7(11)-en-12,8-olide S. miser aerial parts [23]
255 Tsoongianolide F S. tsoongianus whole plant [82]
256 Tsoongianolide A S. tsoongianus whole plant [82]
257 Tsoongianolide B S. tsoongianus whole plant [82]
258 Tsoongianolide E S. tsoongianus whole plant [82]
259 Tsoongianolide C S. tsoongianus whole plant [82]
260 Tsoongianolide D S. tsoongianus whole plant [82]
261 Tetrahydroligularenolide S. aureus aerial parts [52]
262 8a-Ethoxy-10aH-eremophil-7(11)-en-12,8-olide S. aureus aerial parts [52]
263 Ligularenolide S. aureus aerial parts [52]
264 Toluccanolide A S. toluccanus var. roots [83]
modestus
S. toluccanus roots [2]
265 Toluccanolide B S. toluccanus var. roots [83]
modestus
266 Toluccanolide C S. toluccanus var. roots [83]
modestus
 46 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 2 (cont.)
No. Compound class and name Species Part Ref.
267 Toluccanolide D S. toluccanus var. roots [83]
modestus
268 8a-Methoxy-3-oxo-10aH-eremophila-1,7(11)-dien- S. pseudoorientalis aerial parts [55]
12,8-olide S. flavus aerial parts [64]
269 1,10-Epoxy-8a-ethoxyeremophil-7(11)-en-12,8-olide S. gallicus aerial parts [81]
270 1b,10b-Epoxy-8-hydroxy-6b-(methacryloyloxy)eremo- S. isatideus aerial parts and [60]
phil-7(11)-en-12,8-olide roots
271 1b,10b-Epoxy-8-hydroxy-6b-(senecioyloxy)eremophil- S. isatideus roots [60]
7(11)-en-12,8-olide
272 6b-( Angeloyloxy)-1b,10b-epoxy-8-hydroxyeremophil- S. isatideus roots [60]
7(11)-en-12,8-olide
273 1b,8-Dihydroxy-6b-(methacryloyloxy)eremophila- S. isatideus roots [60]
7(11),9-diene-12,8-olide
274 1b,8-Dihydroxy-6b-(senecioyloxy)eremophila-7(11),9- S. isatideus roots [60]
diene-12,8-olide
275 9a-Hydroxy-8-methoxy-3a-{[(2E,4E,6E )-5-methyl- S. erubescens var. aerial parts [60]
dodeca-2,4,6-trienoyl]oxy}-10aH-eremophil-7(11)-en- erubescens
12,8-olide
276 6b-( Angeloyloxy)-7,8-epoxy-3b-hydroxyeremophilan- S. pyranidatus aerial parts and [14]
12,8-olide roots
277 8a-Hydroxy-3-oxo-10aH-eremophila-1,7(11)-dien- S. flavus aerial parts [64]
12,8-olide
278 3-Oxoeremophila-1,7(11)-dien-12,8b-olide S. flavus aerial parts [64]
279 2b-{[( Z )-2-Hydroxymethylbut-2-enoyl]oxy}eremo- S. alatus aerial parts and [62]
phil-7(11)-en-12,8-olide roots
280 8b-Hydroxy-2b-{[( Z )-2-Hydroxymethylbut-2- S. alatus aerial parts and [62]
enoyl]oxy}eremophil-7(11)-en-12,8-olide roots
281 2b-( Angeloyloxy)-8b-hydroxyeremophil-7(11)-en- S. alatus aerial parts [62]
12,8-olide
282 1-Oxoeremophil-7(11)-en-12,8-olide S. rosmarinus aerial parts [84]
283 Istanbulin A S. rosmarinus aerial parts [84]
284 Istanbulin B S. rosmarinus aerial parts [84]
285 Mairetolide A S. mairetianus aerial parts and [63]
roots
286 Mairetolide B S. mairetianus aerial parts and [63]
roots
287 Mairetolide H S. mairetianus aerial parts [63]
288 Mairetolide C S. mairetianus aerial parts [63]
289 Mairetolide D S. mairetianus aerial parts [63]
290 Mairetolide E S. mairetianus aerial parts [63]
291 Mairetolide F S. mairetianus aerial parts [63]
292 Mairetolide G S. mairetianus aerial parts [63]
293 3b,8a-Dihydroxy-6b-(isobutyryloxy)eremophila- S. zoellneri aerial parts [68]
1(10),7(11)-dien-12,8-olide
294 3b-Hydroxy-6b-(isobutyryloxy)-8a-methoxyeremo- S. zoellneri aerial parts [68]
phila-1(10),7(11)-dien-12,8-olide
295 6b-( Angeloyloxy)-3b-hydroxy-8a-methoxyeremo- S. zoellneri aerial parts [68]
phila-1(10),7(11)-dien-12,8-olide
296 6b-Hydroxyligularenolid S. vellereus roots [44]
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 47

Table 2 (cont.)
No. Compound class and name Species Part Ref.
297 (4aR,4a’R,5S,5’S,9aR,9a’R )-4,4’,4a,4’a,5,5’,6,6’,7,7’,8,8’- S. tsoongianus whole plants [82]
Dodecahydro-3,3’,4a,4’a,5,5’-hexamethyl-2H,2’H-
9a,9’a-binaphtho[2,3-b]furan-2,2’-dione
298 (4aR,5S,9aS )-4a,5,6,7,8,9a-Hexahydro-3,4a,5-trimethyl- S. tsoongianus whole plants [82]
9a-[(4aR,5S,9aR )-4,4a,5,6,7,8-hexahydro-3,4a,5-tri-
methyl-2-oxonaphtho[2,3-b]furan-9a(2H )-yl]naph-
tho[2,3-b]furan-2(4H )-one
299 6b-( Angeloyloxy)secomacrotolide acetate S. macedonicus leaves [85]
S. macrotis roots [86]
300 6b-( Methacryloyloxy)secomacrotolide acetate S. macedonicus leaves [85]
301 8-epi-6b-( Angeloyloxy)secomacrotolide acetate S. macedonicus leaves [85]
S. macrotis roots [86]
302 8-epi-6b-( Methacryloyloxy)secomacrotolide acetate S. macedonicus leaves [85]
303 Secosenzoellneride S. zoellneri aerial parts [68]
304 3b-Acetoxy-6b-(isobutyryloxy)secomacrotolide S. zoellneri aerial parts [68]
305 3b-Acetoxy-6b-(angeloyloxy)secomacrotolide S. zoellneri aerial parts [68]
306 6b-( Tigloyloxy)secomacrotolide acetate S. macrotis roots [86]
307 8-epi-6b-( Tigloyloxy)secomacrotolide acetate S. macrotis roots [86]
308 6b-( Isovaleryloxy)secomacrotolide acetate S. macrotis roots [86]
Cacalols
309 1,2-Dehydro-14-(isovaleryloxy)-O-methylcacalol S. madagascariensis whole plants [87]
S. inaequidens aerial parts [73]
310 1,2,3,4-Dehydro-6-dehydroxy-1-hydroxy-2-methoxy- S. madagascariensis whole plants [87]
cacalone
311 1,2,3,4-Dehydro-1-hydroxy-2-methoxycacalone S. madagascariensis whole plants [87]
312 1,2,3,4-Dehydro-6-dehydroxy-1,2-dimethoxycacalone S. madagascariensis whole plants [87]
313 1,2,3,4-Dehydro-1,2-dimethoxycacalone S. madagascariensis whole plants [87]
314 2,3-Dehydro-4-hydroxy-2-methoxy-O-methyl-1-oxo- S. madagascariensis whole plants [87]
cacalol
315 13-Acetoxycacalohastin S. barba-johannis roots [3]
316 13-Hydroxy-14-oxocacalohastin S. barba-johannis roots [3]
317 13-Acetoxy-14-oxocacalohastin S. barba-johannis roots [3]
318 1,2-Dehydro-14-oxocacalol methyl ether S. fuertesii aerial parts [88]
S. othonnae roots [44]
319 13-Acetoxycacalol methyl ether S. picardae – [88]
320 14-Oxocacalol methyl ether S. picardae – [88]
S. fuertesii aerial parts [88]
321 13-Acetoxy-14-oxocacalol methyl ether S. picardae – [88]
322 13-Acetoxy-14-(angeloyloxy)cacalol methyl ether S. picardae – [88]
323 3b-Acetoxy-14-(angeloyloxy)cacalol propionate S. lydenburgensis roots [89]
324 2a,14-Diacetoxycacalol propionate S. lydenburgensis aerial parts [89]
325 2b,14-Diacetoxycacalol propionate S. lydenburgensis aerial parts [89]
326 14-Acetoxy-2a-(isovaleryloxy)cacalol propionate S. lydenburgensis aerial parts [89]
327 14-Acetoxy-2a-hydroxycacalol propionate S. lydenburgensis aerial parts [89]
328 2a-Hydroxy-14-(isobutyryloxy)cacalol propionate S. lydenburgensis aerial parts [89]
329 1-Oxocacalol methyl ether S. fuertesii aerial parts [88]
330 1,14-Dioxocacalol methyl ether S. fuertesii aerial parts [88]
331 2-Acetoxycacalol methyl ether S. fuertesii aerial parts [88]
332 14-(Propionyloxy)cacalohastin propionate S. lydenburgensis aerial parts [89]
 48 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 2 (cont.)
No. Compound class and name Species Part Ref.
333 14-(Angeloyloxy)-3b-hydroxycacalohastin propionate S. lydenburgensis roots [89]
334 2,3-Dehydro-4-hydroxy-3-methoxy-O-methyl-1-oxoca- S. inaequidens aerial parts [73]
calol
335 2,3-Dehydro-14-hydroxy-3-methoxy-O-methyl-1-oxo- S. inaequidens aerial parts [73]
cacalol
336 Calcalolpropionate S. inornatus aerial parts and [73]
roots
337 14-Acetoxycacalolpropionate S. inornatus aerial parts and [73]
roots
338 14-Hydroxycacalol propionate S. inornatus aerial parts [73]
339 13,14-Diacetoxycacalol propionate S. iydenburgensis aerial parts [60]
340 14-(Angeloyloxy)-2a-hydroxycacalol propionate S. iydenburgensis aerial parts [60]
341 2a-Hydroxy-14-(senecioyloxy)cacalol propionate S. iydenburgensis aerial parts [60]
342 2a-Hydroxy-14-(propionyloxy)cacalol propionate S. iydenburgensis aerial parts [60]
343 2a-Hydroxy-14-(isovaleryloxy)cacalol propionate S. iydenburgensis aerial parts [60]
344 2a-Hydroxy-14-[(2-methylbutyryl)oxy]cacalol propio- S. iydenburgensis aerial parts [60]
nate
345 14-Acetoxy-3b-(angeloyloxy)cacalohastin S. inequidens roots [60]
346 13-Hydroxydehydrocacalohastin-15-al S. heliopsis roots [60]
347 14-Methoxydehydrocacalohastin S. coronatus aerial parts and [60]
roots
348 14-(Hexadecyloxy)dehydrocacalohastin S. coronatus roots [60]
349 14-(Octadecyloxy)dehydrocacalohastin S. coronatus roots [60]
350 14-(Angeloyloxy)cacalol propionate S. affinis roots [14]
S. gathlambanus roots [14]
351 13,14-Diacetoxy-2b-hydroxycacalol propionate S. affinis aerial parts [14]
352 14-(Angeloyloxy)-2b-hydroxycacalol propionate S. affinis aerial parts and [14]
roots
353 2b,13,14-Triacetoxycacalol propionate S. affinis aerial parts [14]
354 2b,14-Diacetoxycacalol isobutyrate S. affinis aerial parts [14]
355 3b-Acetoxycacalol methyl ether S. affinis roots [14]
356 14-(Angeloyloxy)-3b-hydroxycacalol propionate S. affinis roots [14]
S. sandersonii roots [14]
357 14-(Angeloyloxy)cacalohastin propionate S. affinis roots [14]
358 14-Acetoxycacalohastin propionate S. affinis roots [14]
359 14-(Angeloyloxy)dehydrocacalohastin propionate S. affinis roots [14]
360 14-Acetoxydehydrocacalohastin propionate S. affinis roots [14]
361 2a-( Angeloyloxy)-1-oxocacalol S. inaequidens roots [77]
362 Isocacalone S. balsapampae roots [77]
363 1,2-Dehydro-3a-hydroxy-14-(senecioyloxy)cacalol S. trichopterygius aerial parts and [77]
methyl ether roots
364 1,2-Dehydro-14-acetoxycacalol methyl ether S. trichopterygius roots [77]
365 14-Hydroxycacalol methyl ether S. othonnae roots [44]
366 1,2-Dehydro-14-hydroxycacalol methyl ether S. othonnae aerial parts and [44]
roots
367 14-(Angeloyloxy)-1,2-dehydrocacalol methyl ether S. othonnae roots [44]
S. inaequidens roots [44]
368 14-(Angeloyloxy)-1,2-dehydro-3b-hydroxycacalol S. othonnae aerial parts and [44]
methyl ether roots
369 14-(Angeloyloxy)-1,2-dehydro-3b,13-dihydroxycacalol S. othonnae roots [44]
methyl ether
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 49

Table 2 (cont.)
No. Compound class and name Species Part Ref.
370 2,3-Dihydro-3-methoxy-1-oxocacalol S. inaequidens aerial parts and [44]
roots
371 2,3-Dehydro-3-methoxy-1-oxocacalol methyl ether S. inaequidens aerial parts [44]
372 2,3-Dehydro-2-methoxy-1-oxocacalol S. inaequidens aerial parts [44]
373 2,3-Dehydro-2-methoxy-1-oxocacalol methyl ether S. inaequidens aerial parts [44]
374 14-(Isobutyryloxy)cacalohastin S. coronatus aerial parts [90]
375 14-(Propioyloxy)cacalohastin S. coronatus aerial parts [90]
376 Cacalohastine S. canescens aerial parts and [79]
roots
377 14-(Angeloyloxy)cacalohastine S. canescens aerial parts and [79]
roots
378 3,4-Dehydrocacalohastine S. canescens aerial parts and [79]
roots
379 13-Acetoxy-3,4-dehydrocacalohastine S. canescens aerial parts and [79]
roots
380 3,4-Dehydro-13-hydroxycacalohastine S. canescens aerial parts and [79]
roots
381 Cacalonol S. canescens aerial parts and [79]
roots
382 Peroxycacalonol S. canescens aerial parts and [79]
roots
383 1-Oxo-9-desoxycacalol S. serratifolius roots [45]
384 3b-Acetoxycacalohastin S. panduriformis roots [39]
385 Isomaturinin S. panduriformis roots [39]
386 13-Dehydromaturin S. panduriformis roots [39]
387 Maturinacetate S. panduriformis roots [39]
388 1b-Hydroxy-4a-[(2-hydroxymethylprop-2-enoyl)oxy]- S. burtonii aerial parts [91]
14-(5 ! 6)abeo-eremophilan-12,8-olide
389 12-(Dehydrocacalohastin-14-yl)cacalol S. trichopterygius roots [77]
390 14-(Angeloyloxy)-12-(cacalohastin-14-yl)cacalohastine S. canescens aerial parts and [79]
roots
Bisabolanes1)
391 12-Acetoxybisabola-3,7(11)-dien-2-one S. smithii aerial parts [69]
392 2-Oxobisabola-3,7(11)-dien-12-al S. smithii aerial parts [69]
393 2,5-Dehydro-3-O-methylsenecioodontol S. oxyodontus aerial parts [92]
394 9-( Angeloyloxy)-3b,4b-epoxy-3,4-dihydro-b-bisabolen- S. oxyodontus roots [92]
5-one
395 3-O-Methylsenecioodontol S. oxyodontus roots [92]
396 3,5-Di-O-methylsenecioodontol S. oxyodontus aerial parts and [92]
roots
397 3-O-Angeloylsenecioodontol S. oxyodontus roots [92]
398 2b,9-Bis(angeloyloxy)-4b,5b : 7,11-diepoxybisabol- S. oxyriifolius roots [93]
10(15)-en-3b-ol
399 3b-Acetoxy-2b,9-bis(angeloyloxy)-4b,5b : 7,11-di- S. oxyriifolius roots [93]
epoxybisabol-10(15)-ene
400 2b,10-Dihydroxy-6b-(isobutyryloxy)bisabolola- S. pubigerus aerial parts [94]
3,7(11)-diene
401 2b,10-Dihydroxy-6b-[(2-methylbutyryl)oxy]bis- S. pubigerus aerial parts [94]
abolola-3,7(11)-diene
402 3-O-Methyl-5-O-acetylsenecioodontol S. longifolius aerial parts [94]
 50 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 2 (cont.)
No. Compound class and name Species Part Ref.
403 2,5-Di-O-acetyl-3-O-methylsenecioodontol S. longifolius aerial parts [94]
404 3-O-Angeloyl-2,5-dehydro-9-des(angeloyloxy)-9-[(2,3- S. longifolius aerial parts [94]
epoxy-2-methylbutyryl)oxy]senecioodontol
405 9-( Angeloyloxy)-4b,5b-epoxy-2a-(senecioyloxy)bisa- S. macrospermus aerial parts [95]
bola-7(11),10(15)-dien-3-one
406 2a-( Angeloyloxy)-4b,5b-epoxy-9-(senecioyloxy)bisa- S. macrospermus aerial parts [95]
bola-7(11),10(15)-dien-3-one
407 4b,5b-Epoxy-2a,9-bis(senecioyloxy)bisabola- S. macrospermus aerial parts [95]
7(11),10(15)-dien-3-one
408 14-Hydroxy-13-norbisabola-3,11-dien-2-one S. affinis aerial parts [60]
409 6a-Acetoxy-3b,4b-epoxy-9-{[(2Z)-hex-2-enoyl]oxy}bis- S. erubescens var. roots [60]
abola-7(11),10(15)-dien-5-one crepidifolius
410 Bisabola-3,7(11),10(15)-trien-5-one S. macroglossus roots [60]
411 9-( Angeloyloxy)-10,15-dehydro-6-desoxy-3-hydroxy- S. longifolius aerial parts [60]
perezone
412 2a,9-Bis(angeloyloxy)-4b,5b : 7,11-diepoxybisabol- S. fulgens roots [96]
10(15)-en-3-one
413 9-Acetoxy-2b,3b-bis(angeloyloxy)-4b,5b-epoxybisabola- S. fulgens roots [96]
7(11),10(15)-diene
414 9-Acetoxy-6a-(angeloyloxy)-3b,4b-epoxybisabola- S. lividus aerial parts [54]
7(11),10(15)-dien-5-one
415 9-Acetoxy-3b,4b-epoxy-6a-(senecioyloxy)bisabola- S. lividus aerial parts [54]
7(11),10(15)-dien-5-one
416 9-Acetoxy-5b,6b-bis(angeloyloxy)-3,4 : 7,11-diepoxy- S. coccineiflorus aerial parts and [97]
bisabol-10(15)-ene roots
417 9-Acetoxy-5a,6a-bis(angeloyloxy)-3,4 : 7,11-diepoxy- S. coccineiflorus aerial parts and [97]
bisabol-10(15)-ene roots
418 4,10-Oxidobisabol-7(11)-ene S. subrubriflorus aerial parts [98]
419 (6S )-Bisabola-3,7(11)-dien-2-one S. palmensis aerial parts [99]
420 1,2-Dihydrosenedigital-2-one S. digitalifolius aerial parts [100]
421 5,6-Dehydrosenedigitalene S. digitalifolius aerial parts [100]
422 Senedigitalene S. digitalifolius aerial parts [100]
Eudesmanes
423 Eudesm-4(15)-en-5b-ol S. rhyncholaenus aerial parts [58]
424 6a-( Tigloyloxy)eudesm-4(15)-ene S. rhyncholaenus aerial parts [58]
425 Eudesm-4(15)-ene-1b,6a-diol S. microglossus aerial parts [61]
426 1b-( Angeloyloxy)eudesm-6-en-4a-ol S. serpens aerial parts and [14]
roots
427 Oblodiol 3-(3-methylpent-2-enoate) S. phonolithicus aerial parts and [44]
roots
428 Oblodiol 3-angelicate S. crassulifolius aerial parts [44]
429 Oblodiol 3-tiglate S. crassulifolius aerial parts [44]
430 6,7-Dehydro-7,8-dihydrooblodiol-3-(3-methylpent-2- S. phonolithicus aerial parts and [44]
enoate) roots
431 1a-Acetoxy-4a-hydroxy-5a,6b,7a,11bH-eudesm-2-en- S. chrysanthemoides aerial parts [101]
12,6-olide
432 1a-Acetoxy-3a-hydroxy-5a,6b,7a,11bH-eudesm-4(15)- S. chrysanthemoides aerial parts [101]
en-12,6-olide
Oplopanes
433 14-Acetoxy-7a-(angeloyloxy)-6b-hydroxyoplop-8(10)- S. yegua aerial parts [102]
en-2-one
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 51

Table 2 (cont.)
No. Compound class and name Species Part Ref.
434 (3Z )-2b-Acetoxy-7a-(angeloyloxy)-6b-hydroxyoplopa- S. yegua aerial parts [102]
3(14),8(10)-diene
435 (3Z )-2b-Acetoxy-6b-(angeloyloxy)-7a-hydroxyoplopa- S. yegua aerial parts [102]
3(14),8(10)-diene
436 (3Z )-2b-Acetoxy-6b-hydroxy-7a-[(4-methylsenecioyl)- S. yegua aerial parts [102]
oxy]oplopa-3(14),8(10)-diene
437 (3Z )-2b-Acetoxy-6b,7a-dihydroxyoplopa-3(14),8(10)- S. yegua aerial parts [102]
diene
438 (3Z )-6b-Hydroxy-7a-[(4-methylsenecioyl)oxy]oplopa- S. yegua aerial parts [102]
3(14),8(10)-dien-2-one
439 (3Z )-6b-Hydroxy-7a-(senecioyloxy)oplopa-3(14),8(10)- S. yegua aerial parts [102]
dien-2-one
440 (3Z )-7a-( Angeloyloxy)-6b-hydroxyoplopa-3(14),8(10)- S. yegua aerial parts [102]
dien-2-one
441 (3Z )-6b-( Angeloyloxy)-7a-hydroxyoplopa-3(14),8(10)- S. yegua aerial parts [102]
dien-2-one
442 (3E )-7a-( Angeloyloxy)-6b-hydroxyoplopa-3(14),8(10)- S. yegua aerial parts [102]
dien-2-one
443 (3E )-6b-( Angeloyloxy)-7a-hydroxyoplopa-3(14),8(10)- S. yegua aerial parts [102]
dien-2-one
444 14-Acetoxy-7b-{[(Z )-3-methylpent-2-enoyl]oxy}notoni- S. kleinia roots [103]
petranone
445 14-Hydroxy-1a-[(2-methylbutyryl)oxy]-7b-{[( Z)-3-meth- S. kleinia roots [103]
ylpent-2-enoyl]oxy}notonipetranone
446 14-Acetoxy-1a-[(2-methylbutyryl)oxy]-7b-{[( Z)-3-meth- S. kleinia roots [103]
ylpent-2-enoyl]oxy}notonipetranone
447 (3E )-3,14-Dehydro-1a-[(2-methylbutyryl)oxy]-7b-{[( Z)- S. kleinia roots [103]
3-methylpent-2-enoyl]oxy}notonipetranone
448 (3Z )-3,14-Dehydro-1a-[(2-methylbutyryl)oxy]-7b-{[( Z)- S. kleinia roots [103]
3-methylpent-2-enoyl]oxy}notonipetranone
449 (3Z )-Implexin S. implexus roots [104]
450 (3E )-Implexin S. implexus aerial parts [104]
451 14-Acetoxy-3,14-dihydroimplexin S. implexus aerial parts and [104]
roots
452 4’-Acetoxyabrotanifolon S. ovirensis aerial parts [97]
453 4’-Acetoxy-7b-des(2-methylbutyryloxy)-7b-(angeloyl- S. ovirensis aerial parts [97]
oxy)abrotanifolon
Germacranes
454 9b-Acetoxy-3b-(angeloyloxy)-1b,10a:4a,5b-diepoxy-8b- S. galpinii aerial parts and [90]
(senecioyloxy)germacr-11-ene roots
455 3b-( Angeloyloxy)-1b,10a : 4a,5b-diepoxy-8b-(senecioyl- S. galpinii aerial parts [90]
oxy)germacr-11-en-9b-ol
456 5a,9b-Diacetoxy-3b,8b-bis(angeloyloxy)-1b,10a-epoxy- S. galpinii aerial parts and [90]
germacr-11-en-4a-ol roots
457 5a,9b-Diacetoxy-3b-(angeloyloxy)-1b,10a-epoxy-8b- S. galpinii aerial parts and [90]
(senecioyloxy)lgermacr-11-en-4a-ol roots
458 9b-Acetoxy-3b,8b-bis(angeloyloxy)-1b,10a-epoxy- S. galpinii aerial parts [90]
germacr-11-ene-4a,5a-diol
459 9b-Acetoxy-3b-(angeloyloxy)-1b,10a-epoxy-8b-(senecio- S. galpinii aerial parts [90]
yloxy)germacr-11-ene-4a,5a-diol
 52 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 2 (cont.)
No. Compound class and name Species Part Ref.
460 Germacrene D S. vitalis roots [55]
461 Germacrene C S. vitalis roots [55]
462 Bicyclogermacrene S. vitalis aerial parts [55]
463 8a-( Angeloyloxy)germacrene D S. cylindricus aerial parts [74]
464 6b-Acetoxy-3b-(angeloyloxy)-4,5-epoxygermacr-1(10)- S. vitalis aerial parts [55]
ene
465 6b-Acetoxy-4,5-epoxy-3b-(senecioyloxy)germacr-1(10)- S. vitalis roots [55]
ene
466 3b-( Angeloyloxy)-4,5-epoxygermacr-1(10)-en-6b-ol S. vitalis aerial parts [55]
467 4,5-Epoxy-3b-(senecioyloxy)germacr-1(10)-en-6b-ol S. vitalis aerial parts [55]
468 4,5-Epoxy-3b-(tigloyloxy)germacr-1(10)-en-6b-ol S. vitalis aerial parts [55]
469 6,7-Dihydro-6b-hydroxy-3b-(tigloyloxy)germacrene C S. cylindricus aerial parts [74]
470 3b-( Angeloyloxy)-6,7-dihydro-6b-hydroxygermacrene C S. cylindricus aerial parts [74]
471 6,7-Dihydro-6b-hydroxy-3b-(senecioyloxy)germacrene C S. cylindricus aerial parts [74]
472 8a-( Angeloyloxy)bicyclogermacrene S. cylindricus aerial parts [74]
473 8a-( Angeloyloxy)-4,14-dihydro-4a-hydroxygermacrene D S. cylindricus aerial parts [74]
474 3b-( Angeloyloxy)-4a,5b-epoxy-4,5,6,7-tetrahydro-6b- S. cylindricus aerial parts [74]
hydroxygermacrene C
475 4a,5b-Epoxy-4,5,6,7-tetrahydro-6b-hydroxy-3b-(senecio- S. cylindricus aerial parts [74]
yloxy)germacren C
476 (5E,9Z )-Germacra-4(15),5,9-trien-1b-ol S. philippicus aerial parts [43]
477 4,14-Dihydro-4a-hydroxygermacrene D S. phonolithicus aerial parts [44]
478 6,7-Dihydro-6b-{[( Z )-3-methylpent-2-enoyl]oxy}germa- S. phonolithicus aerial parts and [44]
crene C roots
479 6b-Acetoxy-3b-(angeloyloxy)-6,7-dihydrogermacrene C S. ficoides roots [44]
480 6,7-Dihydro-6b-(tigloyloxy)germacrene C S. crassulifolius aerial parts and [44]
roots
481 6b-( Angeloyloxy)-6,7-dihydrogermacrene C S. crassulifolius roots [44]
482 4,5-Epoxy-4,5,6,7-tetrahydro-6b-hydroxy-3b-(tigloyloxy)- S. ficoides aerial parts [44]
germacrene C
483 6b-Acetoxy-3b-(angeloyloxy)-4,5-epoxy-4,5,6,7-tetrahy- S. ficoides aerial parts [44]
drogermacrene C
484 6b-Acetoxy-4,5-epoxy-4,5,6,7-tetrahydro-3b-(tigloyloxy)- S. ficoides aerial parts [44]
germacrene C
485 8b,9b-Diacetoxy-3b-(angeloyloxy)-4,5-epoxy-4,5,6,7-tetra- S. platyphyl- aerial parts [44]
hydrogermacrene C loides
486 1b-Peroxygermacra-4(15),5,10(14)-triene S. glanduloso- aerial parts [59]
pilosus
Phomalairdanes
487 11b-Acetoxy-5a-(angeloyloxy)silphinen-3-one S. palmensis aerial parts [105]
488 5a-( Angeloyloxy)silphinen-3-one S. palmensis aerial parts [99]
489 5a-( Senecioyloxy)silphinen-3-one S. palmensis aerial parts [99]
490 5a-Acetoxysilphinen-3-one S. palmensis aerial parts [99]
491 5a-( Tigloyloxy)silphinen-3-one S. palmensis aerial parts [99]
492 5a-( Angeloyloxy)-3b-hydroxysilphinene S. palmensis aerial parts [99]
Caryophyllanes
493 6,7-Epoxycaryophyll-3(15)-ene S. palmensis aerial parts [99]
Humulanes
494 6,7-Epoxyhumula-2,9-diene S. palmensis aerial parts [99]
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 53

Table 2 (cont.)
No. Compound class and name Species Part Ref.
Presilphiperfolanes
495 5b-Acetoxy-2b-(angeloyloxy)-8b-hydroxypresilphiper- S. anteuphorbium aerial parts [106]
folane
Aromadendranes
496 Spathulenol S. canescens aerial parts [79]
and roots
S. subumbellatus aerial parts [43]
Himachalanes
497 9,10-Bis(angeloyloxy)cinaglabron S. deltoideus roots [107]
498 9-( Angeloyloxy)-10-[(2,3-epoxy-2-methylbutyryl)oxy]- S. deltoideus roots [107]
cinaglabron
Africananes
499 8b-( Angeloyloxy)senoxyri-4-en-3-one S. oxyriifolius roots [93]
Pentalenanes
500 Senoxyden S. oxyodontus roots [108]
Bakkanes
501 Senauricolide S. auricula var. roots [66]
major
Valeranes
502 (3aS,5aR,9aS,9bS )-3a,4,5,5a,6,7,9a,9b-Octahydro- S. densiflorus whole plants [109]
3,5a,9a-trimethylnaphtho[1,2-b]furan-2(3H )-one
Benzofurane-type sesquiterpenes
503 2,3-Dihydro-12-hydroxyeuparine S. halimifolius aerial parts [73]
504 2,3-Dihydro-3b-[(2-methylbutyryl)oxy]euparine S. rodriguezzii aerial parts [44]
S. squalidus aerial parts [44]
505 7-Methoxyeuparine methyl ether S. squalidus roots [44]
S. leucanthemifolius roots [44]
Other sesquiterpenoids
506 Senaequidolide S. inaequidens roots [77]
507 Maturinone S. canescens aerial parts [79]
and roots
508 Senoxepin S. platyphylloides roots [44]
509 6,7,9,10-Dehydrodesisopropylidenefukinone S. humillimus aerial parts [53]
510 2-Desoxyliguhodgonal S. nebrodensis roots [96]
511 1-Hydroxyplatyphyllide S. gilliesiano roots [32]
512 Platyphyllide S. gilliesiano roots [32]
S. platyphylloides roots [44]
513 Senecrassidiol S. crassissimus aerial parts [96]
514 b-Farnesene S. pseudoorientalis roots [55]

type of PA derivatives, was isolated [39]. It is well known that PAs are characteristic
metabolites of the genus Senecio.
In 1995, a systematic study was initiated to search for PAs in plants of the section
Mulgediifolii of the genus Senecio, which is made up of 15 species, most of them
indigenous to Mexico. Two years later, two new 13-membered macrocyclic PAs, (12S)-
hydroxyretroisosenine (88) and (13R)-hydroxyretroisosenine (89), were reported from
S. helodes and S. roseus, respectively [48]. In 1998, two new PAs, 93 and 94, were
isolated from S. callosus [50]. In 1999, Castorena et al. [4] isolated compounds 5, 6, and
54 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 3. Monoterpenoids 515 – 520 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

515 (4E )-4,5-Dihydrocleviolide S. clevelandii aerial parts [110]
516 (4Z )-4,5-Dihydrocleviolide S. clevelandii aerial parts [110]
517 Cleviolide S. clevelandii aerial parts [110]
518 Menth-2-ene-1,7-diol S. affinis aerial parts [60]
519 Cannabiside D S. cannabifolius whole plants [111]
520 Cannabiside E S. cannabifolius whole plants [111]

Table 4. Diterpenoids 521 – 532 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

521 9-Geranyl-a-terpinene S. pseudoorientalis aerial parts [55]
522 ent-15,16-Epoxy-labda-7,13(16),14-triene S. yegua aerial parts [102]
523 Rufusoside A S. rufus aerial parts [112]
524 Rufusoside B S. rufus aerial parts [112]
525 11a-(Senecioyloxy)sandaracopimar-15-ene- S. subrubriflorus aerial parts [98]
8b,12b-diol and roots
526 11a-(Tigloyloxy)sandaracopimar-15-ene-8b,12b-diol S. subrubriflorus aerial parts [98]
and roots
527 11a-(Senecioyloxy)sandaracopimar-15-en-8b-ol S. subrubriflorus aerial parts [98]
and roots
528 11a-(Tigloyloxy)sandaracopimar-15-en-8b-ol S. subrubriflorus aerial parts [98]
529 8b-Hydroxysandaracopimar-15-en-11-one S. subrubriflorus aerial parts [98]
530 20-Hydroxypimare-8(9),15-dien-7-one S. hypochoerideus aerial parts [56]
531 7,11,15-Trimethyl-3-methylidenehexadecane-1,2-diol S. gallicus aerial parts [81]
532 7,11,15-Trimethyl-3-methylidenehexadecane- S. gallicus aerial parts [81]
1,2-diol diacetate

10 from S. doratophyllus, 1 from S. deformis, and 7 and 8 from S. conzattii, respectively.

Furthermore, they had analyzed eight of these species and detected three different
kinds of PAs, 12- and 13-membered macrocyclic and open chain diester PAs. Each
species contains a single class of PAs, with the exception of S. callosus, which
synthesized different types of PAs, depending on its habitat. All the PAs discussed in
this section have the same configuration at C(7) and C(8), since they contain
rosmarinecine, platynecine, or retronecine as necine base [4]. The same year, a new 13-
membered macrocyclic PA, 91, was found in S. iodanthus and S. bracteatus [47]. In 2006,
the alkaloid cannabiloid B, 99, was isolated from S. cannabifolius and found to possess
significant antimicrobial activities against Staphylococcus aureus and Bacillus subtilis
[51].
2.2. Sesquiterpenoids (Table 2). Sesquiterpenoids are C15-terpenoids, which occur as
hydrocarbons or in oxygenated form, i.e., as alcohols, ketones, aldehydes, acids, or
lactones. They are important constituents of essential oils, which have many
applications as medicine and also in soap and perfume formulations [126]. The
sesquiterpenes of the genus Senecio can mainly be devided into 17 groups:
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 55

Table 5. Triterpenoids 533 – 556 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

533 (20S )-3a,10a-Epoxy-9-epicucurbitan-24,25-ozonide S. selloi aerial parts [113]
534 (20R )-3a,10a-Epoxy-9-epicucurbit-24-ene S. selloi aerial parts [114]
535 (20S )-3a,10a-Epoxy-9-epicucurbit-24-ene S. selloi aerial parts [114]
536 Dammaradienyl acetate S. canescens aerial parts [79]
and roots
537 Dammaradienone S. canescens aerial parts [79]
and roots
538 Lupenone S. vitalis roots [55]
539 Lupeol S. vitalis aerial parts [55]
540 3,28-Dioxolup-22(29)-ene S. phonolithicus aerial parts [44]
S. ficoides aerial parts [44]
and roots
S. crassulifolius aerial parts [44]
and roots
541 3-Oxolup-19-ene S. phonolithicus aerial parts [44]
S. crassulifolius aerial parts [44]
and roots
542 3,28-Dioxolup-19-ene S. phonolithicus aerial parts [44]
S. ficoides aerial parts [44]
and roots
S. crassulifolius aerial parts [44]
and roots
543 3,28-Dioxolup-12-ene S. phonolithicus aerial parts [44]
S. ficoides aerial parts [44]
and roots
S. crassulifolius aerial parts [44]
and roots
544 3,28-Dioxolup-9-ene S. phonolithicus aerial parts [44]
545 3b-Acetoxy-lup-12-ene S. ficoides aerial parts [44]
546 a-Amyrin S. cineraria leaves [115]
S. samnitum aerial parts [30]
547 19(29)-Dehydro-2a,23-dihydroxyursolic acid S. pseudotites leaves [116]
548 23-Acetoxy-19(29)-dehydro-2a-hydroxyursolic acid S. pseudotites leaves [116]
549 23-[( E )-4-Coumaryloxy]-19(29)-dehydro-2a- S. pseudotites leaves [116]
hydroxyursolic acid
550 Germanicone S. canescens aerial parts [79]
and roots
551 Oleanoic aldehyde S. vitalis roots [55]
552 Oleanoic acid S. vitalis roots [55]
553 Lutin-5(6)-en-3b-ol S. vitalis aerial parts [55]
554 b-Amyrin S. cineraria roots [115]
S. samnitum aerial parts [30]
555 Lanosterol S. burchelli aerial parts [117]
556 Cycloartenol S. burchelli aerial parts [117]

eremophilanes, cacalols, bisabolanes, eudesmanes, oplopanes, germacranes, phoma-

lairdanes, caryophyllanes, humulanes, presilphiperfolanes, aromadendranes, himacha-
lanes, africananes, pentalenanes, bakkanes, valeranes, and benzofuranes. The biosyn-
56 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 6. Steroids 557 – 563 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

557 Sitosterol S. burchelli aerial parts [117]
S. cineraria leaves [115]
558 Stigmasterol S. cineraria leaves [115]
S. densiflorus whole plants [109]
S. samnitum aerial parts [30]
559 Stigmasterol 3-O-b-d-glucopyranoside S. bonariensis roots [118]
560 Sitosterol 3-O-b-d-glucopyranoside S. bonariensis roots [118]
561 Sitosterol 3-O-b-d-glucuronopyranoside S. bonariensis roots [118]
562 Sitosterol 3-O-b-d-(6-O-methylglucuronopyranoside) S. bonariensis roots [118]
563 (22R,24S )-Dimethylcholesterol S. samnitum aerial parts [30]

Table 7. Flavonoids 564 – 583 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

564 Quercetin S. argunensis aerial parts [119]
565 Isorhamnetin 3-O-b-d-galactoside S. argunensis aerial parts [119]
566 Kaempferol 3-O-b-d-galactoside S. argunensis aerial parts [119]
567 Quercetin 3-O-b-d-galactoside S. argunensis aerial parts [119]
568 Quercetin 5-O-b-d-glucoside S. argunensis aerial parts [119]
569 Isorhamnetin 3-O-b-d-glucuronide S. argunensis aerial parts [119]
570 2,3-Dihydroquercetin S. cineraria leaves [115]
571 Apigenin 7-O-glucoside S. cineraria leaves [115]
572 Luteolin 7-O-glucoside S. cineraria leaves [115]
573 Quercetin 3-O-rhamnoside S. cineraria leaves [115]
574 Kumatakenin S. viscosissimus aerial parts [120]
575 Isokaempferide S. viscosissimus aerial parts [120]
576 Pachypodol S. viscosissimus aerial parts [120]
577 3-Methyl isorhamnetin S. viscosissimus aerial parts [120]
578 Okanin 4-methyl ether 3’-O-b-d-(6’’-acetyl)glucopyranoside S. pseudotites – [121]
579 Okanin 4-methyl ether 3’-O-b-d-glucopyranoside S. pseudotites – [121]
580 Okanin 4’-O-b-d-(3’’,4’’,6’’-triacetyl)glucopyranoside S. pseudotites – [121]
581 Mangiferin S. mikanioides leaves [122]
582 Tripteroside S. mikanioides leaves [122]
583 Muraxanthone S. mikanioides leaves [122]

Table 8. Coumarins 584 – 588 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

584 Isoscopoletin S. humillimus aerial parts [53]
585 Xanthotoxin S. cineraria leaves [115]
586 Isopimpinellin S. cineraria leaves [115]
587 Marmesin S. cineraria leaves [115]
588 Aesculetin S. cineraria leaves [115]
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 57

Table 9. Phenolic Acids 589 – 607 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

589 Hydroquinone S. scandens – [123]
590 p-Hydroxyphenylacetic acid S. scandens – [123]
591 Vanillic acid S. scandens – [123]
592 Salicylic acid S. scandens – [123]
593 5-Acetylsalicylaldehyde S. graveolens aerial parts [124]
594 4-Hydroxy-3-(3’-hydroxyisopentyl)acetophenone S. graveolens aerial parts [124]
595 Shikimic acid tris(phenylacetate) S. subrubriflorus aerial parts [98]
596 1-Methoxy-4-methyl-2-(propan-2-yl)benzene S. phonolithicus aerial parts [44]
597 (2E)-3-(3,4-Dimethoxyphenyl)prop-2-en-1-yl angelicate S. colaminus aerial parts [45]
598 3,5-Bis(3,3-dimethylallyl)-4-hydroxybenzaldehyde S. erubescens var. roots [60]
crepidifolius
599 3,4,5-Trimethoxy-8,9-bis(tigloyloxy)cumene S. macroglossus roots [60]
600 8,9-Bis(angeloyloxy)-3,4,5-trimethoxycumene S. macroglossus aerial parts [94]
and roots
601 (4-Methoxyphenyl)acetic acid S. scandens aerial parts [125]
602 4-Hydroxyacetophenone S. chionophilus aerial parts [75]
and roots
603 3,5-Bis(3-methylbut-2-enyl)-4-hydroxyacetophenone S. gallicus aerial parts [81]
604 3,5-Bis(3-methylbut-2-enyl)-4-acetoxyacetophenone S. gallicus aerial parts [81]
605 3-(2-Hydroxy-3-methylbut-3-enyl)-5-(3-methylbut- S. gallicus aerial parts [81]
2-enyl)-4-hydroxyacetophenone
606 9-Acetoxy-6-methoxyisoeugenol geranyl ether S. longifolius aerial parts [94]
607 Chlorogenic acid methyl ester S. samnitum aerial parts [30]

Table 10. Alkanes 608 – 613 Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

608 Tetradecane S. cerberoanus aerial parts [120]
609 Hexadecane S. cerberoanus aerial parts [120]
610 Docosane S. cerberoanus aerial parts [120]
611 Tricosane S. cerberoanus aerial parts [120]
612 7-Hexyleicosane S. cerberoanus aerial parts [120]
613 Tritetracontane S. cerberoanus aerial parts [120]

thetic routes to these sesquiterpenes and their biogenetic relationships are shown in
Schemes 2 to 5.
2.2.1. Eremophilanes. This group includes the eremophilanes 100 – 138, the
furanoeremophilanes 139 – 243, the eremophilanolides 244 – 298, and the secoeremo-
philanolides 299 – 308. In 1983, compounds 100, 139, and 261 – 263 were isolated from S.
aureus [52]. Compound 261 was a new natural product, and compounds 100 and 263
were reported for the first time as constituents of S. aureus [52]. In 1978, six new
furanoeremophilanes, 191 – 196, were obtained from S. hypochoerideus [56], while one
new eremophilene, 106, and the two new furanoeremophilanes 197 and 198 were
isolated from S. greyi [56]. In the same year, the seven new furanoeremophilanes 201 –
207 were isolated from S. mauricei, all of them being highly oxidized [57]. The acetates
58 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 11. Other Compounds, 614 – 631, Isolated from Species of the Genus Senecio

No. Compound name Species Part Ref.

614 Cannabiside B S. cannabifolius – [51]
615 Cannabiside C S. cannabifolius – [51]
616 Cannabilactone A S. cannabifolius – [51]
617 ( E )-Seneciolactone S. scandens aerial parts [125]
618 ( E )-Cannabifolactone A S. scandens aerial parts [125]
619 (1a,4b,5a)-3-( Hydroxymethyl)-4,5-dimethoxycyclohex- S. burtonii aerial parts [91]
2-en-1-yl (3E )-octadec-3-enoate
620 3,5-Bis-O-(2-methylbutyryl)-4-O-decanoylshikimic acid S. lividus aerial parts [54]
methyl ester
621 3,5-Di-O-isobutyryl-4-O-decanoylshikimic acid methyl ester S. lividus aerial parts [54]
622 5-O-Isobutyryl-3-O-(2-methylbutyryl)-4-O-decanoylshikimic S. lividus aerial parts [54]
acid methyl ester
623 3,5-Bis-O-(2-methylbutyryl)-4-O-octanoylshikimic acid S. lividus aerial parts [54]
methyl ester
624 Jacaranone S. minutus aerial parts [65]
S. scandens aerial parts [125]
625 Methyl 1’-hydroxy-2’,6’-dimethoxy-4’-oxocyclohexaneacetate S. minutus aerial parts [65]
626 (2E,4E,6E)-N-(2-phenylethyl)deca-2,4,6-trienamide S. colaminus aerial parts [45]
627 (2E,4E,6E)-N-(3-methylbutyl)deca-2,4,6-trienamide S. colaminus aerial parts [45]
628 (9Z,16E )-Octadeca-9,16-diene-12,14-diyn-1-ol S. brevilorus roots [94]
629 (2E,9Z,16E )-Octadeca-2,9,16-triene-12,14-diynal S. brevilorus roots [94]
630 (9E )-Undeca-1,9-diene-5,7-diyne S. deltoideus roots [107]
631 (3E,9E )-Undeca-1,3,9-triene-5,7-diyne S. deltoideus roots [107]

Scheme 1. Formation of Pyrrolizidine Alkaloids of the Senecionine Type

of four of them (203, 204, 206, and 207) showed very unusual chemical shifts of the
signals of the AcO groups [57]. Seven new eremophilenes, 108 – 111 and 113 – 115, and
the two new furanoeremophilanes 140 and 141 were isolated from S. speciosus [58]. Of
special interest are the eremophilenes with unusual ester groups, which have not been
found before among naturally occurring compounds, i.e., esters of (2Z)-4-angeloyloxy-
hex-2-enoic acid (e.g., compound 136 [59]), (2Z)-5-angeloyloxyhex-2-enoic acid (e.g.,
compound 111 [59]), and (2E,4E,6E)-5-methyldodeca-2,4,6-trienoic acid (e.g., com-
pounds 125 and 126 [60]). The two new eremophilenes 112 and 116 were isolated from
S. rhyncholaenus and S. polyodon, respectively [58]. From the aerial parts of S.
portalesianus, compounds 117 – 120 were obtained [43]. The four new furanoeremo-
philanes 209 – 212 were isolated from the aerial parts of S. subumbellatus [43]. The new
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 59

Scheme 2. Biogenetic Relationship of Germacranes, Eudesmanes, Elemanes, Eremophilanes, Bakkanes,

and Valeranes

Scheme 3. Biogenetic Relationship of Humulanes and Carophyllanes

eremophilane 130 was isolated from the aerial parts of S. ochoanus in 1983 by
Bohlmann et al. [61]. The new hydroxyeremophilane 131 was found in S. amplexicaulis,
and the two new furanoeremophilanes 226 and 227 and the three eremophilanolides
279 – 281 were isolated from S. alatus [62]. The new eremophilene derivative 136 was
obtained together with 111 from S. glanduloso-pilosus [59]. In 2006, the new
eremophilane 138 and the eight new eremophilanolides 285 – 292 were isolated from
the roots and aerial parts of S. mairetianus [63]. The roots of S. auricula var. major
60 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Scheme 4. Biogenetic Relationship of Bicyclogermacranes and Aromadendranes

Scheme 5. Biosynthetic Route to Bisabolanes

yielded the three new eremophilane derivatives 149 – 151 [66]. The aerial parts of S.
flavus contained the four new furanoeremophilanes 158, 159, 161, and 162, oxidized at
C(3), and a new eremophilenone lactam, 245. The rhizomes of the plant contained the
new epoxyeremophilanolide 251 [64]. In 1991, the new furanoeremophilane 163 and
two pairs of epimeric acetals, 164/165, and 166/167, with an eremophilane skeleton have
been isolated from the aerial parts of S. pachyphyllos [67].
The aerial parts of S. zoellneri afforded the five oxygenated furanoeremophilane
derivatives 168, 169, and 293 – 295 and the three secofuranoeremophilanolides 303 –
305, all of which are probably formed by oxidation of 3b-hydroxy-6b-acyloxyeuryopsin
[68]. In 1981, furanoeremophilanes 171 – 176 were isolated for the first time from S.
smithii, all bearing a keto group at C(9) [69]. The five new furanoeremophilanes 178 –
182 were found in the rhizomes of S. nemorensis [70]. The new furanoeremophilanes
189 and 190 were isolated from S. erosus [74], 199 and 200 from S. medley-woodii, and
184 from S. pseudoorientalis and S. halimifolius [55] [73]. In 1971, a new furanosesqui-
terpene, 1a,10a-epoxyfuranoeremophilane (208), was isolated from S. silvaticus [76].
Two new sesquiterpenoids, (1S,4S,5R,10R)-1-hydroxy-6-isobutyryloxyfuranoeremophi-
lan-9-one (213) and 1a-hydroxy-6b-(2-methylbutyryloxy)-10aH-furanoeremophilan-9-
one (214), along with three known furanoeremophilanes, 194, 215, and 216, were
isolated from the hexane and CH2Cl2 extracts of the aerial parts and roots of S.
chionophilus [75]. The three new furanoeremophilanes 217 – 219 were isolated from S.
pampse [45], and S. pyranidatus afforded the six new furanoeremophilanes 220 – 225
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 61

and compound 276 [14]. The furanoeremophilane 228 was found in the roots of S.
inaequidens [77]. In 2005, six new eremophilane-type sesquiterpenes, 244 and 246 – 250,
were isolated from the aerial parts of S. aegyptius var. discoideus [80]. From the whole
plant of S. tsoongianus, two pairs of epimers, 256 and 257 as well as 259 and 260, and two
new sesquiterpene lactones, 255 and 258, all of which possessing a eremophilane
skeleton, together with the two known eremophilane dimers 297 and 298, were isolated.
From a biogenetic point of view, the dimers 297 and 298 may be generated inside the
plant from 256 and 257 [82]. The roots of S. toluccanus var. modestus, collected in the
eastern part of Mexico, afforded the four new eremophilanolides 264 – 267 [83]. A new
sesquiterpene lactone of the eremophilanolide type, 282, was isolated together with the
known compounds 283 and 284 from S. rosmarinus [84]. Four sesquiterpene lactones
with a secoeremophilane skeleton, 299 – 302, were isolated from the leaves of S.
macedonicus [85]. Among them, compounds 300 and 302 were new C(8) epimeric
secomacrotolides [85]. The roots of S. macrotis afforded the five secoeremophilano-
lides 299, 301, and 306 – 308 [86].
2.2.2. Cacalols. Cacalolides are biogenetic Wagner – Meerwein rearrangement
products derived from furanoeremophilanes and derive their name from cacalol, a
sesquiterpenoid isolated from the antihyperglycemic species Cacalia decomposita, also
referred to as Psacalium decompositum and Odontorichum decompositum. Six new
cacalolides 309 – 314 were isolated from S. madagascariensis collected in Colombia
[87]. From the roots of S. barba-johannis, the two new cacalolides 315 and 316, together
with the known cacalolide 317, were isolated [3]. Two Senecio species (S. fuertesii and S.
picardae) from the Dominican Republic afforded seven new cacalol derivatives, 318 –
322 and 329 – 331 [88]. Eight new cacalol and cacalohastin derivatives 323 – 328, 332,
and 333 were isolated from S. lydenburgensis [89]. The 1H-NMR spectra of 324 – 328
showed the presence of cacalol derivatives with an O-atom function at C(2) and C(14),
while the phenolic OH group was esterified with propionic acid. The configuration of
the O-atom function at C(2) followed from the couplings of HC(2). Although the
relative position of the ester groups at C(2) and C(14) in 326 could not be established
with certainty, the observed chemical shifts favor the proposed structure [89]. The two
new compounds 374 and 375 were isolated from the aerial parts of S. coronatus [90].
From the aerial parts and roots of S. canescens, compounds 376 – 382 and 390 were
obtained, the latter being a dimer [79]. Compound 383 was isolated from S. serratifolius
[45], and the new cacalolide derivative 388 was isolated from S. burtonii [91].
2.2.3. Bisabolanes. In 1981, the two new bisabolone derivatives 391 and 392 were
isolated from the less polar fractions of an extract of the aerial parts of S. smithii. Their
structures were elucidated from their 1H-NMR data, which were close to those of
bisabolone (for 392) and the corresponding 12-oic acid methyl ester (for 391),
respectively. The configuration of the C(7)¼C(11) bond1) in 392 directly followed from
the chemical shifts of the signals of HC(7) and CH2(12). The configuration at C(1)
and C(10) was deduced from the observed coupling constants and by comparison with
the spectrum of bisabolone with known configuration. As the sign of the optical
rotation of both 391 and 392 was negative, their absolute configurations should be
identical [69].
The South African plant S. oxyodontus contained five new sesquiterpenes, 393 – 397,
which were all of the bisabolene type [92]. The new bisabolene derivatives 400 and 401
62 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

and 402 – 404 were isolated from S. pubigerus and S. longifolius, respectively [94]. The
aerial parts of S. macrospermus afforded the three new diesters 405 – 407 [95]. The new
compounds 416 and 417 were isolated from S. coccineiflorus [97] and the new 4,10-
oxide of bisabol-7(11)-ene, 418, from the aerial parts of S. subrubriflorus [98]. Three
new norsesquiterpenes, 420 – 422, all related to norbisabol-11-ene, were found in S.
digitalifolius [100].
2.2.4. Eudesmanes. The new eudesmane derivatives 423 and 424 were found in S.
rhyncholaenus [58]. From the aerial parts of S. microglossus, the new compound 425
was obtained [61]. The positions of the OH groups were assigned by spin decoupling.
The H-atom showing a broadened doublet at d(H) 1.77 was coupled with the vinyl H-
atoms and with the H-atom displaying a double doublet at d(H) 3.73, and this permitted
the assignment of the configuration of HC(5) and HC(6). As the second lowfield
signal was at d(H) 3.25, an allylic position at C(3) could be excluded. Accordingly, a 1b-
and a 6a-OH group were proposed for compound 425. The configuration followed from
the couplings of HC(1) and HC(6) [61]. Compound 426 was isolated from S. serpens
[14]. In 1991, compounds 431 and 432 were isolated the first time from the aerial parts
of S. chrysanthemoides [101].
2.2.5. Oplopanes. Oplopane derivatives, although rare, were found in three different
subtribes of the Senecioneae, viz., Tussilagininae, Senecioninae, and Tephroseridinae.
In 1988, eleven new oplopanes, 433 – 443, were isolated from the aerial parts of S. yegua
[102]. The five new notonipetrone-like sesquiterpenes 444 – 448 were found in the roots
of S. kleinia [103]. Compounds 449 and 450 were obtained from S. implexus [104], and
the aerial parts of S. ovirensis afforded compounds 452 and 453 [97].
2.2.6. Germacranes. Six new, highly oxygenated germacrene derivatives, 454 – 459,
were isolated from the aerial parts of S. galpinii [90], and eight new germacrene
derivatives, 463 and 469 – 475, were found in S. cylindricus. Among them, compound
472 represents a bicyclogermacrane derivative [74]. S. glanduloso-pilosus afforded
compound 486 [59]. In the mass spectrum of 486, a molecular ion consistent with the
molecular formula C15H24O2 was visible. The presence of an OOH group was indicated
by the loss of H2O2 and H2O (m/z 202 and 218). A singlet at d(H) 7.51 in the 1H-NMR
spectrum of 486 was obviously due to the H-atom of the OOH group. The proposed
structure was further confirmed by a chemical transformation of 486 into lb-germacra-
4(15),5,10(14)-triene and by comparing their 1H-NMR data [59].
2.2.7. Phomalairdanes. Three new sesquiterpenes, 489, 491, and 492, along with the
known compounds 488 and 490 were isolated from the aerial parts of S. palmensis [99].
Compounds 489 and 491 have the same molecular formula, i.e., C20H28O3 . Their
1
H-NMR spectra were very similar, having signals characteristic of the skeleton of the
tricyclopentanoid sesquiterpene silphinene with additional signals at d(H) 5.79 (br. s,
1 H), 1.92 (s, 3 H), and 2.20 (s, 3 H). These signals correlated with C-NMR reso-
nances at d(C) 116.0 (d, C(2’)), 27.4 (q, C(5’)), and 20.3 (q, C(4’)), corresponding to a
senecioyl group in compound 489. The signals at d(H) 6.99 (qq, J ¼ 7.0, 1.1, 1 H), 1.80
(dq, J ¼ 7.0, 1.2, 3 H), and 1.85 (quint., J ¼ 7.2, 3 H) correlated with the corresponding
C-atoms in the HSQC experiment at d(H) 137.9 (d, C(3’)), 11.9 (q, C(5’)), and 14.4 (q,
C(4’)), indicating a tigloyl group in compound 491. An HMBC experiment confirmed
the position of attachment of the acyl units at C(5) in compounds 489 and 491
[99].
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 63

2.2.8. Caryophyllanes. Only one compound with this skeleton, i.e., 6,7-epoxycar-
yophyll-3(15)-ene (493), was isolated from the aerial parts of S. palmensis [99].
2.2.9. Humulanes. The aerial parts of S. palmensis afforded also the humulane-type
sesquiterpene 494, which is an eleven-membered sesquiterpene [99].
2.2.10. Presilphiperfolanes. In 1982, the new sesquiterpene diester 495 was isolated
from the aerial parts of S. anteuphorbium [106].
2.2.11. Aromadendranes. Compound 496, with an aromadendrane skeleton, was
found in the aerial parts and roots of S. canescens [79].
2.2.12. Himachalanes. Only two himachalane-type compounds, i.e., 497 and 498,
were reported from S. deltoideus [107].
2.2.13. Africananes. The new tricyclic sesquiterpene 499 was isolated from the roots
of S. oxyriifolius [93]. Africanane-type sesquiterpenes are probably derived from a-
humulane, as shown in Scheme 6.

Scheme 6. Biosynthesis of Africanane-Type Sesquiterpenes

2.2.14. Pentalenanes. Although sesquiterpenes with a pentalenane skeleton are very

rare in natural sources, Bohlmann et al. isolated one, i.e., senoxyden (500), from the
roots of S. oxyodontus [108]. Pentalenane-type sesquiterpenes show close relationship
with phomalairdane- and presilphiperfolene-type sesquiterpenes from the viewpoint of
biosynthesis.
2.2.15. Bakkanes. A new bakkenolide, 1,10-dehydro-11b,12b-epoxy-6b-[(2-methyl-
butyryl)oxy]-7-epidihydrobakkenolide (501) was isolated from the roots of S. auricula
var. major. Because of the origin of the new bakkenolide, Torres et al. proposed the
name senauricolide for lactone 501 [66].
2.2.16. Valeranes. The whole plant of S. densiflorus afforded the valerane type
sesquiterpene 502 [109].
2.2.17. Benzofurane-Type Sesquiterpenes. Three sesquiterpenes with a benzofurane
skeleton, i.e., compounds 503 – 505, were found in some species of the genus Senecio,
[44] [73].
2.2.18. Other Sesquiterpenoids. Some other sesquiterpenes, 506 – 514, have also been
reported from the genus Senecio [32] [44] [53] [55] [77] [79] [96]. Of them, 507, 508, and
510 – 512 are closely related from the viewpoint of biosynthesis. Compounds 506 and
64 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

509 are norsesquiterpenes, compound 513 is a caryolane-type sesquiterpene, and

compound 514 is a linear farnesane-type sesquiterpene.
2.3. Monoterpenoids (Table 3). The aerial parts of S. clevelandii afforded the three
monoterpene lactones 515 – 517. Among them, compound 517 represents the first
acetylenic monoterpene isolated from natural sources [110]. The two new mono-
terpenoids 519 and 520 were isolated from S. cannabifolius [111].
2.4. Diterpenoids (Table 4). Many diterpenes and diterpene glycosides have been
isolated from species of the Compositae, but only a few diterpenes were obtained from
the genus Senecio. In 1992, Cheng et al. reported two new diterpene glycosides, 523 and
524, from S. rufus cultivated in the Zhang County, Gansu Province, P. R. China [112].
The five new sandaracopimarene derivatives 525 – 529 were isolated from the aerial
parts of S. subrubriflorus [98], and the pimarene derivative 530 was found in S.
hypochoerideus [56].
2.5. Triterpenoids (Table 5). In 1999, Rucker et al. [114] reported the isolation of the
two diastereomeric triterpenes 534 and 535, with a new 9-epi-cucurbitane skeleton,
from the aerial parts of S. selloi, a shrub growing in southern Brazil. More recently, they
isolated from the same plant the novel triterpene ozonide 533, which has the same 9-
epicucurbitane skeleton [113]. Three new polyhydroxylated ursane-type triterpenes,
547 – 549, with a novel 2a,3b,23-trihydroxyursa-12,19(29)-dien-28-oic acid skeleton
were isolated from the leaves of S. pseudotites [116], and the two tetracyclic triterpenes
555 and 556 were isolated from the aerial parts of S. burchelli [117].
2.6. Steroids (Table 6). Besides sitosterol (557) and stigmasterol (558), isolated
from S. burchelli [117], S. cineraria [115], and S. densiflorus [109], the new sterol
glycosides 559 – 561 were isolated from the roots of S. bonariensis [118]. Compound 561
was isolated as its methyl ester 562.
2.7. Flavonoids (Table 7). From the aerial parts of S. argunensis, the six flavonoids
564 – 569 were obtained. Compounds 568 and 569 were the first flavone glycosides with
a sugar moiety at the C(5) position and the first flavone glucuronide isolated from a
Senecio species, respectively [119]. The three chalcones 578 – 580 were found in S.
pseudotites. Among them, compounds 578 and 580 were new natural products [121].
The new 4-hydroxybenzoylated xanthone 583 and the two known xanthones 581 and
582 were obtained from the leaves of S. mikanioides [122].
2.8. Coumarins (Table 8). The aerial parts of S. humillimus afforded compound 584
[53] and the leaves of S. cineraria compounds 585 – 588, respectively [115].
2.9. Phenolic Acids (Table 9). The 18 phenolic acids 589 – 607 have been isolated
from various Senecio species [30] [44] [45] [60] [75] [81] [94] [98] [123 – 125].
2.10. Alkanes (Table 10). Six alkanes, 608 – 613, were obtained from the aerial parts
of S. cerberoanus [120].
2.11. Others (Table 11). Finally, compounds 614 – 631, including the two lactones 617
and 618 [125], the five shikimic acid derivatives 619 – 623 [54] [91], the two C10-amides
626 and 627 [45], and compounds 614 – 616 [51], 624, 625 [65], 628, 629 [94], 630, and
631 [107], have also been isolated from Senecio species.

3. Biological Activities. – 3.1. Antibacterial and Antifungal Activities. In the folk

medicine, Senecio species were used for the treatment of wounds and as antiemetic,
anti-inflammatory, and vasodilatory preparations. More recently, antibacterial and
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 65

antifungal activities of extracts and compounds isolated from Senecio species were
reported. The MeOH extract of S. vulgaris showed antimicrobial activity against the
Gram-positive bacteria Bacillus subtilis (minimal-inhibitory concentration (MIC)
0.5 mg/ml) and Staphylococcus aureus (MIC 0.125 mg/ml). The MeOH extracts from
both S. inaequidens and S. vulgaris showed low activity against dermatophytes. The
hexane extract of S. vulgaris showed significant activity against Trichophyton tonsurans
(MIC 0.031 mg/ml) [1]. Although their activities were less potent than those of
chloramphenicol, compounds 99 and 614 – 616, isolated from S. cannabifolius, showed
antibacterial activities against the Gram-positive bacteria S. aureus and B. subtilis, but
not against Gram-negative bacteria [51].
Assessed by the agar-well diffusion method, the isolated essential oil of S.
graveolens showed antimicrobial activity against Micrococcus luteus ATCC 9341,
oxacillin-sensitive and oxacillin-resistant S. aureus, as well as antifungal effects against
clinically isolated Candida albicans. The MIC values for M. luteus, oxacillin-sensitive S.
aureus, and C. albicans were 8.73, 10.91, and 2.13  10  2 mg/ml, respectively. The
antimicrobial activity related to known antibiotics was calculated. These results were
compatible with a potential concentration-dependent selectivity of the antifungal effect
of S. graveolens essential oil. Moreover, the minimal bactericidal concentration (MBC)
was above 87.3 mg/ml. Thus, the MBC/MIC ratio was clearly higher than 1 (above 8),
indicating a bacteriostatic effect of the essential oil [127].
The aerial parts of S. aegyptius var. discoideus afforded six new eremophilane
derivatives, 244 and 246 – 250. The antibacterial activities of these compounds were
tested against two microorganisms, a Gram-positive (Bacillus cereus) and a Gram-
negative bacterium (Serratia sp.), at concentrations of 200 and 400 mg/ml. The growth
of both microorganisms was inhibited by compounds 247 – 249. Compounds 246 and 250
inhibited the growth of B. cereus, but had no effect on the growth of Serratia sp. [80].
3.2. Antitubercular Activity. S. chionophilus is a small, woody shrub growing in the
Andes Mountains in South America, above 1500 m. Infusions of its aerial parts and
roots are traditionally used in Chile for treating heavy colds and runny noses. All
compounds isolated from this species were evaluated for their antitubercular potential
against Mycobacterium tuberculosis, in a microplate Alamar Blue assay. Compounds
214, 215, and 602 exhibited mild antitubercular activity, with MIC values of 119, 114,
and 121 mg/ml, respectively. This is the first evidence that sesquiterpenoids of the
furanoeremophilane type may be considered as potential antitubercular leads. In
addition, the comparison of the antitubercular activities of betulinic, oleanolic, and
ursolic acids, with MICs of 32, 64, and 32 mg/ml, respectively, with those of inactive
analogues indicated that the presence of a COO group in a polycyclic triterpene
skeleton appears to be necessary for the observed activity against M. tuberculosis [75].
3.3. Anti-Inflammatory Effects. To investigate the anti-inflammatory effect of the
total flavonoids of S. scandens, various inflammatory models, including the swelling of
ear induced by xylene in mice, the permeability increase of blood capillary by acetic
acid in mice, and the cotton-pellet granuloma in mice, were used. In addition, air-sac
models of synovitis in mice were set up and the amount of white blood cells (WBCs)
and the content of prostaglandin E2 (PGE2 ) were measured in the inflammatory
exudate. The total flavonoids had significant inhibitory action on auris swell induced by
xylene in mice and the penetration of capillary vessels in mice. The flavonoids also
66 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

significantly decreased the proliferation of granuloma caused by implantation of cotton

pellets in mice. The amount of WBCs and the content of PGE2 in the experimental
groups were obviously lower than those in the control groups. The total flavonoids
showed significant anti-inflammatory activity, which is relevant to the inhibition of the
production and release of the inflammatory factor PGE2 [128].
3.4. Antiulcer Activity. The leaves and inflorescences of S. brasiliensis are utilized in
the traditional medicine for the treatment of inflammatory processes as a blood
regulator. Moreover, this plant is also used in the folk medicine to relieve stomach pain.
The crude alkaloid extract of S. brasiliensis inflorescences, containing a mixture of the
PAs 37, 39, 41, 42, and 44, was evaluated for preventive antiulcer effects on standard
rodent models of induced gastric and duodenal ulcers. In the HCl/EtOH-, indometha-
cin/bethanechol-, and hypothermic restraint-induced gastric ulcers, the lesion was
significantly inhibited (p < 0.001) by the PAs (po). In the pylorus-ligature, PAs (id)
significantly increased the gastric juice content and the pH values and decreased the
acid output. In the cysteamine-induced duodenal ulcers, PAs (po) showed significant
inhibition (p < 0.001) of the duodenal lesions when compared to the respective control.
The levels of the somatostatin hormone in the blood samples of animals pretreated with
the PA mixture (12.5 mg/kg) and the free mucus and prostaglandin synthesis after the
administration of the PA extract (po) also increased (p < 0.001). The results suggested
that the PA extract from S. brasiliensis inflorescences presents a significant antiulcer
effect in the selected ulcer models. One of the mechanisms involved in the action of the
PA extract is cytoprotection. Additional studies are in progress to determine other
possible mechanisms involved in the antiulcer effect of PAs [129].
3.5. Antifeedant Effects. Species belonging to the family Asteraceae are an
important source of terpenes and alkaloids with biological activity. The tricyclopenta-
noid sesquiterpene 11b-acetoxy-5a-(angeloyloxy)silphinen-3-one (487), isolated from
S. palmensis [105], as well as related C(5)/C(11)-substituted derivatives were found to
be very efficient antifeedants against several divergent insect species [105]. To
demonstrate the importance of this class of molecules as model insect antifeedants and
their potential as new GABA modulators, Reina et al. [99] carried out additional
chemical work on S. palmensis, resulting in the isolation of the known sesquiterpenes
419, 488, 490, 493, and 494 and the new silphinenes 489, 491, and 492. A series of
semisynthetic analogues, such as silphinen-3,5-dione and 5-hydroxysilphinen-3-one,
was also generated, to carry out a preliminary structure – activity study on the
antifeedant action of these molecules against several divergent insect species, including
the lepidopteran Spodoptera littoralis, the chrysomelid Leptinotarsa decemlineata
(Colorado potato beetle, CPB), and five aphid species with diverse host adaptations. In
summary, C(5)-substituted silphinenes, such as 489, 491, and 492, are more efficient
CPB and aphid antifeedants than their biogenetic precursors 493 and 494. A
comparative study of their activities with that of C(5)/C(11)-substituted analogues
showed that esterification at C(5) and acetylation at C(11) are important structural
requirements for the antifeedant activity of these molecules [99].
Compounds 252 and 253, isolated from S. miser, were found to be effective
antifeedants against Myzus persicae and L. decemlineata, respectively [23]. Similarly,
several sesquiterpene lactones with a g-butenolactone group have been reported as
having moderate to high potency as L. decemlineata antifeedants. The PA 37 was found
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 67

to be an effective antifeedant against L. decemlineata (not adapted to PAs) [23].

Previous data have shown that the CPB is sensitive to the macrocyclic diester
senecionine (39), the open diester PA echimidine, and the saturated monoester PA 3’-
acetyltrachelanthamine, but with too few structural features in common to draw any
conclusions on structure – activity relationships. Also the PA N-oxide 38 was found to
be a strong CPB antifeedant [23]. Previous reports have shown that some PA N-oxides,
including senecionine N-oxide, are active antifeedants against some aphid species and
S. littoralis, but they were found to be less potent than their tertiary bases. The data
presented by Reina et al. [23] suggest that the CPB putative taste receptors can interact
with different PAs (and N-oxides) of different structural classes with high molecular
selectivity. Little is known, however, about the molecular mechanisms that modulate
PA insect taste reception. Several PAs, including N-oxides and 39, have demonstrated
significant binding activity to muscarinic and serotonin receptors, indicating that these
compounds can affect several molecular targets besides long-term toxicity through
DNA alkylation by PA metabolites generated in the liver. Therefore, the interference
of PAs with neuronal signal transduction could mediate insect taste regulation as
proposed for chrysomelid beetles. The PAs 37 and 39 were not toxic to S. littoralis.
Tertiary PAs are deleterious to organisms with a microsomal cytochrome P450 system,
but S. littoralis larvae can clearly tolerate PAs. These larvae prevent PA poisoning by
rapid and efficient excretion of the absorbed tertiary alkaloid. In contrast, compound
37 was moderately toxic to L. decemlineata, but 39 was not. A previous experiment has
shown that ten other PAs were not toxic to this insect. Oreina beetles (Chrysomelidae)
are able to take up plant alkaloid N-oxides and eliminate tertiary PAs. Similarly, L.
decemlineata beetles could eliminate tertiary PAs efficiently enough to avoid poisoning,
with some exceptions (such as compound 37) [23].
3.6. Cytotoxicity towards the Human Hepatoma Cell Line Huh-7. A number of
traditional remedies used in South Africa contain PAs, some of which are hepatotoxic.
Steenkamp et al. [130] investigated the effect on human Huh-7 cells of S. latifolius, a
plant that is a component of some traditional remedies and known to contain toxic PAs.
The cells were also treated with solutions of the standard pyrrolizidine retrorsine (41).
The changes in the gross morphology of the cells were studied using light microscopy
after haematoxylin and eosin staining. The cytoskeleton was investigated using
fluorescence-labelled anti-b-tubulin antibody and the nuclear organisation was studied
using fluorescence-labelled antinuclear antibodies. The plant extracts induced dose-
dependent gross morphological changes. At high doses, necrosis was observed and at
lower doses, destruction of the cytoskeleton, nuclear fragmentation, and apoptosis were
detected. Doses of less than the equivalent of 330 ng/ml retrorsine led to multi-
nucleated cells with failure in spindle formation and clumping of nuclear chromatin.
This latter finding suggests that chronic low-dose treatment with such traditional
remedies could induce teratogenic and/or carcinogenic effects [130].
3.7. Antimitotic Effects. Santos-Mello et al. [131] studied the antimitotic activity of
PAs extracted from S. brasiliensis, stored for more than 23 years under variable
conditions of temperature and humidity and exposed to light. Both the crude alkaloid
(containing 37, 41, and impurities) and pure integerrimine (37) conserved the ability to
induce acute toxicity in mice, leading to the death of the animals in less than 24 h. The
alkaloids also conserved the potential to induce significant increases in micronucleus
68 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

frequencies in polychromatic erythrocytes of mouse bone marrow, compared to the

negative control. The administration of alkaloids to lymphocyte cultures blocked with
cytochalasin-B showed no significant increase in the micronucleus frequency in
binucleated cells, probably due to the lack of a metabolic activation mechanism.
However, an antimitotic effect was observed [131].
3.8. Angiotensin-Converting Enzyme Inhibitory Activity. Extracts of S. samnitum
and the derived methyl ester of chlorogenic acid (607) have been shown to inhibit the
angiotensin-converting enzyme (ACE) by using an in vitro bioassay based on the
enzymatic cleavage of the chromophore-fluorophore labeled substrate dansyltriglycine
into dansylglycine, which was quantitatively measured by HPLC. The most effective
fraction of the S. samnitum extract, obtained in AcOEt, inhibited the activity of ACE to
52.56  0.23% (SD) at 300 mg/ml. The major constituent of this fraction, 607, showed a
significant ACE inhibition of 56.78  0.25% at a concentration of 82.5 mg/ml. The ACE
inhibitory property of different extracts of S. samnitum may imply that in vivo, these
extracts may have a hypotensive effect [30].
3.9. Insecticidal, Neurotoxic, and Glutathione-Depleting Activities. The active
insecticidal component of S. palmatus was identified as jacaranone (624), a neuro-
toxicant and glutathione-reactive quinol previously known to have insect antifeedant
activity. Further, it was observed that mono- and bisglutathione (GSH) adducts were
formed on incubation of 624 with GSH and rat liver GSH S-transferase. The toxic
action of 624 in mice (intraperitoneal LD50 ¼ 150 – 200 mg/kg) was associated with both
neurological signs and GSH depletion in the liver 90 min after the treatment. The
neurotoxic effect (tail raising, tremors, lachrymation, and ataxia) led to death in 30 –
90 min [132].

4. Conclusions. – The genus Senecio (Asteraceaca), widely distributed throughout

the world, is known to be a source of PAs, eremophilanolides, and furanoeremophilanes
[23]. Some species of the genus Senecio are used as ornamental plants and in the folk
medicine in South America [133]. PAs are widespread in this genus. They are
responsible for the heptatotoxic and carcinogenic effects of this genus [7]. The
sesquiterpenoids with eremophilane, cacalol, bisabolane, eudesmane, oplopane, and
germacrane skeletons are among the most studied sesquiterpenoids isolated from
Senecio species. Other types of sesquiterpenoids as phomalairdanes, caryophyllanes,
humulanes, presilphiperfolenes, aromadendranes, himachalanes, africananes, pentale-
nanes, bakkanes, and valeranes, along with diterpenoids, triterpenoids, steroids, and
flavonoids, are also important components. The present review compiles the majority of
the components isolated from Senecio species and summarizes the biological activities
of this genus. However, the activity screening and the structure – activity relationship
studies of sequiterpenoids, the major constituents of the genus Senecio, should be
continued to promote the search for new medicinal leads.
We are grateful for the financial support from the National Natural Science Foundation of China
(81072551), the Scientific Research Foundation for the Returned Overseas Chinese Scholars of Hebei
Province and the Scientific Research Foundation of Hebei Province (08B032 and C2010000489). We also
wish to extend our sincere thanks for financial support to Syngenta Ltd. (2008-Hebei Medical University-
Syngenta-02).
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 69

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Received January 27, 2010