Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms
Abstract
:1. Introduction
2. Malabaricanes: Structures, Distribution, Biological Activities, and Biogenesis
2.1. Isolation and Structures
2.2. Biogenesis of Malabaricane Triterpenoids and Their Biological Activities
3. Isomalabaricane Triterpenoids. Structures, Properties, Distribution, and Synthesis
3.1. Isolation and Structures
3.1.1. Stellettins
N | Name | Structure | Collection | Source | Ref. |
---|---|---|---|---|---|
57 | Stellettin A | | Hainan Island | S. tenuis, | [32] |
Cape Wilberforce (Australia) | Stelletta sp. | [33] | |||
Mindanao (Philippines) | Rhabdastrella globostellata | [34] | |||
Hainan Island | R. aff. distincta | [39] | |||
Xisha Island (South China Sea) | Geodia japonica | [43] | |||
43 | Stellettin B | | Fiji | Jaspis stellifera | [28] |
Great Barrier Reef | J. stellifera | [29] | |||
Somalian waters | Stelletta sp. | [30] | |||
Hainan Island | S. tenuis | [32] | |||
Cape Wilberforce (Australia) | Stelletta sp. | [33] | |||
Mindanao (Philippines) | R. globostellata | [34] | |||
Hainan Island | R. aff. distincta | [39] | |||
Xisha Island (South China Sea) | Geodia japonica | [43] | |||
58 | Stellettin C | | Cape Wilberforce (Australia) | Stelletta sp. | [33] |
Mindanao (Philippines) | R. globostellata | [34] | |||
Hainan Island | R. aff. distincta | [39] | |||
Hainan Island | S. tenuis | [40] | |||
Hainan Island | R. globostellata | [44] | |||
59 | Stellettin D | | Cape Wilberforce (Australia) | Stelletta sp. | [33] |
Mindanao (Philippines) | R. globostellata | [34] | |||
Hainan Island | Stelletta sp. | [37] | |||
Hainan Island | S. tenuis | [40] | |||
Hainan Island | R. globostellata | [44] | |||
60 | Stellettin E | | Cape Wilberforce (Australia) | Stelletta sp. | [33] |
Mindanao (Philippines) | R. globostellata | [34] | |||
Hainan Island | R. aff. distincta | [39] | |||
Hainan Island | R. globostellata | [44] | |||
61 | Stellettin F | | Cape Wilberforce (Australia) | Stelletta sp. | [33] |
41 | Stellettin G | | Fiji | J. stellifera | [28] |
Cape Wilberforce (Australia) | Stelletta sp. | [33] | |||
Hainan Island | Stelletta sp. | [37] | |||
62 | Stellettin H | | Mindanao (Philippines) | R. globostellata | [34] |
Hainan Island | Stelletta sp. | [37] | |||
63 | Stellettin I | | Mindanao (Philippines) | R. globostellata | [34] |
64 | Stellettin J | | Fiji | R. globostellata | [35] |
65 | Stellettin K | | Fiji | R. globostellata | [35] |
66 | Stellettin L | | Hainan Island | S. tenuis | [36] |
Hainan Island | R. aff. distincta | [45] | |||
67 | Stellettin M | | Hainan Island | S. tenuis | [36] |
Hainan Island | R. aff. distincta | [45] | |||
68 | Stellettin N | | Hainan Island | Stelletta sp. | [37] |
69 | 22,23-Dihydrostellettin D | | Hainan Island | Stelletta sp. | [37] |
South China Sea, | Jaspis sp. | [38] | |||
South China Sea | J. stellifera | [46] | |||
70 | 22,23-Dihydrostellettin B | | Hainan Island | Rhabdastrella aff. distincta | [39] |
71 | Stellettin N | | Hainan Island | S. tenuis | [40] |
72 | Stellettin O | | Hainan Island | S. tenuis | [40] |
73 | Stellettin P | | Hainan Island | S. tenuis | [40] |
74 | Stellettin Q | | Cham Island (Vietnam) | Stelletta sp. | [42] |
75 | Stellettin R | | Cham Island (Vietnam) | Stelletta sp. | [42] |
76 | Stellettin S | | Cham Island (Vietnam) | Stelletta sp. | [42] |
77 | Stellettin T | | Cham Island (Vietnam) | Stelletta sp. | [42] |
78 | Stellettin U | | Cham Island (Vietnam) | Stelletta sp. | [42] |
79 | Stellettin V | | Cham Island (Vietnam) | Stelletta sp. | [42] |
3.1.2. Stelliferins
N | Name | Structure | Collection | Source | Ref. |
---|---|---|---|---|---|
80 | Stelliferin A | | Isigaki Island (Japan) | Jaspis stellifera | [47] |
Mage-jima Island (Japan) | Stelletta globostellata | [49] | |||
81 | Stelliferin B | | Isigaki Island (Japan) | J. stellifera | [47] |
82 | Stelliferin C | | Isigaki Island (Japan) | J. stellifera | [47] |
83 | Stelliferin D | | Isigaki Island (Japan) | J. stellifera | [47] |
Mage-jima Island (Japan) | S. globostellata | [49] | |||
84 | Stelliferin E | | Isigaki Island (Japan) | J. stellifera | [47] |
85 | Stelliferin F | | Isigaki Island (Japan) | J. stellifera | [47] |
86 | Stelliferin G | | Tonga (South Pacific) | Jaspis sp. | [48] |
87 | 29-Hydroxy- stelliferin A | | Tonga (South Pacific) | Jaspis sp. | [48] |
88 | 29-Hydroxy- stelliferin E | | Tonga (South Pacific) | Jaspis sp. | [48] |
89 | 3-Epi-29- Hydroxy- stelliferin A | | Mage-jima Island (Japan) | S. globostellata | [49] |
90 | 3-Epi-29- Hydroxy- stelliferin E | | Mage-jima Island (Japan) | S. globostellata | [49] |
Tonga (South Pacific) | Jaspis sp. | [48] | |||
91 | 29-Hydroxy- stelliferin D | | Mage-jima Island (Japan) | S. globostellata | [49] |
92 | Stelliferin J | | Ishigaki (Japan) | Rhabdastrella cf. globostellata | [50] |
93 | Stelliferin K | | Ishigaki (Japan) | R. cf. globostellata | [50] |
94 | Stelliferin L | | Ishigaki (Japan) | R. cf. globostellata | [50] |
95 | Stelliferin M | | Ishigaki (Japan) | R. cf. globostellata | [50] |
96 | Stelliferin N | | Ishigaki (Japan) | R. cf. globostellata | [50] |
97 | 29-Hydroxy- stelliferin B | | Tonga (South Pacific) | Jaspis sp. | [48,51] |
98 | 13(E)-29- Hydroxy- stelliferin E | | Tonga (South Pacific) | Jaspis sp. | [48] |
99 | 3-epi-29- Hydroxy- stelliferin E | | Tonga (South Pacific) | Jaspis sp. | [48] |
100 | 13(E)- stelliferin G | | Tonga (South Pacific) | Jaspis sp. | [48] |
101 | Stelliferin riboside | | Vanua Levu Island (Fiji) | Geodia Globostellifera | [52] |
Kapoposang Island (Indonesia) | R. globostellata | [53] | |||
102 | 3-O-Deacetyl-13(Z)- stelliferin riboside | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
103 | 13(E)- Stelliferin riboside | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
3.1.3. Globostellatic Acids
N | Name | Structure | Collection | Source | Ref. |
---|---|---|---|---|---|
104 | Globostellatic acid A | | Mage Island (Japan) | Stelletta globostellata | [54] |
Kapoposang Island (Indonesia) | Rhabdastrella globostellata | [53] | |||
105 | Globostellatic acid B | | Mage Island (Japan) | S. globostellata | [54] |
Vanuatu Islands | Jaspis sp. | [55] | |||
106 | Globostellatic acid C | | Mage Island (Japan) | S. globostellata | [54] |
Vanuatu Islands | Jaspis sp. | [55] | |||
107 | Globostellatic acid D | | Mage Island (Japan) | S. globostellata | [54] |
Kapoposang Island (Indonesia) | R. globostellata | [53] | |||
108 | Globostellatic acid E methyl ester | | Vanuatu Islands | Jaspis sp. | [55] |
109 | Globostellatic acid F | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
110 | Globostellatic acid G | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
111 | Globostellatic acid H | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
112 | Globostellatic acid I | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
113 | Globostellatic acid J | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
114 | Globostellatic acid K | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
115 | Globostellatic acid L | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
116 | Globostellatic acid M | | Kapoposang Island (Indonesia) | R. globostellata | [53] |
117 | 13Z,17Z- Globostellatic acid X methyl ester | | Sulawesi Island (Indonesia) | R. globostellata | [57] |
118 | 13Z,17E- Globostellatic acid X methyl ester | | Sulawesi Island (Indonesia) | R. globostellata | [57] |
119 | 13E,17Z- Globostellatic acid X methyl ester | | Sulawesi Island (Indonesia) | R. globostellata | [57] |
120 | 13E,17E- Globostellatic acid X methyl ester | | Sulawesi Island (Indonesia) | R. globostellata | [57] |
121 | Globostellatic acid F methyl ester | | Sulawesi Island (Indonesia) | R. globostellata | [57] |
122 | 13E-Globostellatic acid B methyl ester | | Sulawesi Island (Indonesia) | R. globostellata | [57] |
3.1.4. Other Isomalabaricane Triterpenoids and Nor-Triterpenoids
3.2. Biogenesis, Taxonomic Distribution, and Biological Activities of Isomalabaricanes
4. Syntheses of Isomalabaricane-Type Compounds
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compounds | Biological Source | ||||
---|---|---|---|---|---|
Kingdom | Class/Clade | Order | Family | Species | |
1–5, 8–11 | Plantae | Angiosperms | Sapindales | Simaroubaceae | Ailanthus tryphysa (=malabarica) |
6,7 | Plantae | Angiosperms | Malpighiales | Flacourtiaceae | Caloncoba echinata |
16,17 | Plantae | Angiosperms | Sapindales | Burseraceae | Bursera microphylla |
18,19 | Plantae | Spermatophyta | Asterales | Asteraceae | Pyrethrum santolinoides |
18,22 | Plantae | Pistacia | Sapindales | Anacaridiaceae | Pistacia lentiscus |
24–26 | Plantae | Magnoliopsida | Fabales | Fabaceae | Adesmia aconcaguensis |
27–32 | Mycota | Basidiomycota | Agaricales | Cortinariaceae | Cortinarius arcuatorum, C. sadagnitus, C. fulvoincarnatus |
34,35 | Plantae | Tracheophyta | Polypodiales | Adiantaceae | Lemmaphyllum microphyllum var. obovatum |
38 | Plantae | Tracheophyta | Polypodiales | Polypodiaceae | Colysis elliptica |
35 | Unknown | Bottom sediment, Lake Cadagno (Switzerland) |
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Stonik, V.A.; Kolesnikova, S.A. Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms. Mar. Drugs 2021, 19, 327. https://doi.org/10.3390/md19060327
Stonik VA, Kolesnikova SA. Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms. Marine Drugs. 2021; 19(6):327. https://doi.org/10.3390/md19060327
Chicago/Turabian StyleStonik, Valentin A., and Sophia A. Kolesnikova. 2021. "Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms" Marine Drugs 19, no. 6: 327. https://doi.org/10.3390/md19060327