Structures and Biological Activities of Secondary Metabolites from Trichoderma harzianum
Abstract
:1. Introduction
2. Structural and Biological Activity Studies
2.1. Terpenoids
2.2. Polyketides
2.3. Peptides
2.4. Alkaloids
2.5. Lactones
3. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Compounds | Sequences of Peptides | |
---|---|---|
96 | Trichokindin Ia | Ac Aib Ser Ala Aib Aib Gln Iva Leu Aib Ala Aib Aib Pro Leu Aib Aib Gln Ile OH |
97 | Trichokindin Ib | Ac Aib Ser Ala Aib Iva Gln Aib Leu Aib Ala Aib Aib Pro Leu Aib Aib Gln Ile OH |
98 | Trichokindin IIa | Ac Aib Ser Ala Aib Aib Gln Aib Leu Aib Ala Iva Aib Pro Leu Aib Aib Gln Ile OH |
99 | Trichokindin IIb | Ac Aib Ser Ala Aib Iva Gln Iva Leu Aib Ala Aib Aib Pro Leu Aib Aib Gln Leu OH |
100 | Trichokindin IIIa | Ac Aib Ser Ala Aib Aib Gln Iva Leu Aib Ala Iva Aib Pro Leu Aib Aib Gln Leu OH |
101 | Trichokindin IIIb | Ac Aib Ser Ala Aib Iva Gln Aib Leu Aib Ala Iva Aib Pro Leu Aib Aib Gln Leu OH |
102 | Trichokindin IV | Ac Aib Ser Ala Aib Iva Gln Iva Leu Aib Ala Aib Aib Pro Leu Aib Aib Gln Ile OH |
103 | Trichokindin Va | Ac Aib Ser Ala Aib Aib Gln Iva Leu Aib Ala Iva Aib Pro Leu Aib Aib Gln Ile OH |
104 | Trichokindin Vb | Ac Aib Ser Ala Aib Iva Gln Aib Leu Aib Ala Iva Aib Pro Leu Aib Aib Gln Ile OH |
105 | Trichokindin VI | Ac Aib Ser Ala Aib Iva Gln Iva Leu Aib Ala Iva Aib Pro Leu Aib Aib Gln Leu OH |
106 | Trichokindin VII | Ac Aib Ser Ala Aib Iva Gln Iva Leu Aib Ala Iva Aib Pro Leu Aib Aib Gln Ile OH |
107 | Harzianin HB I | Ac Aib Asn Leu Ile Aib Pro Iva Leu Aib Pro Leu OH |
108 | Trichorzin HA I | Ac Aib Gly Ala Aib Aib Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Leu OH |
109 | Trichorzin HA II | Ac Aib Gly Ala Aib Aib Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Iva Gln Leu OH |
110 | Trichorzin HA III | Ac Aib Gly Ala Aib Iva Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Leu OH |
111 | Trichorzin HA V | Ac Aib Gly Ala Aib Iva Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Iva Gln Leu OH |
112 | Trichorzin HA VI | Ac Aib Gly Ala Aib Iva Gln Iva Val Aib Gly Leu Aib Pro Leu Aib Iva Gln Leu OH |
113 | Trichorzin HA VII | Ac Aib Gly Ala Aib Iva Gln Val Val Aib Gly Leu Aib Pro Leu Aib Iva Gln Leu OH |
114 | Trichorzin MA I | Ac Aib Ser Ala Aib Aib Gln Aib Leu Aib Gly Leu Aib Pro Leu Aib Aib Gln Val OH |
115 | Trichorzin MA II | Ac Aib Ser Ala Aib Iva Gln Aib Leu Aib Gly Leu Aib Pro Leu Aib Aib Gln Val OH |
116 | Trichorzin MA III | Ac Aib Ser Ala Aib Iva Gln Iva Leu Aib Gly Leu Aib Pro Leu Aib Aib Gln Val OH |
117 | Trichorozin I | Ac Aib Asn Ile Leu Aib Pro Ile Leu Aib Pro Val OH |
118 | Trichorozin II | Ac Aib Gln Ile Leu Aib Pro Ile Leu Aib Pro Val OH |
119 | Trichorozin III | Ac Aib Asn Ile Leu Aib Pro Ile Leu Aib Pro Leu OH |
120 | Trichorozin IV | Ac Aib Gln Ile Leu Aib Pro Ile Leu Aib Pro Leu OH |
121 | Harzianin HC I | Ac Aib Asn Leu Aib Pro Ser Val Aib Pro Aib Leu Aib Pro Leu OH |
122 | Harzianin HC III | Ac Aib Asn Leu Aib Pro Ser Val Aib Pro Iva Leu Aib Pro Leu OH |
123 | Harzianin HC VI | Ac Aib Asn Leu Aib Pro Ala Val Aib Pro Aib Leu Aib Pro Leu OH |
124 | Harzianin HC VIII | Ac Aib Asn Leu Aib Pro Ala Val Aib Pro Iva Leu Aib Pro Leu OH |
125 | Harzianin HC IX | Ac Aib Asn Leu Aib Pro Ala Ile Aib Pro Iva Leu Aib Pro Leu OH |
126 | Harzianin HC X | Ac Aib Gln Leu Aib Pro Ala Val Aib Pro Iva Leu Aib Pro Leu OH |
127 | Harzianin HC XI | Ac Aib Asn Leu Aib Pro Ser Ile Aib Pro Aib Leu Aib Pro Leu OH |
128 | Harzianin HC XII | Ac Aib Asn Leu Aib Pro Ser Ile Aib Pro Iva Leu Aib Pro Leu OH |
129 | Harzianin HC XIII | Ac Aib Gln Leu Aib Pro Ser Ile Aib Pro Iva Leu Aib Pro Leu OH |
130 | Harzianin HC XIV | Ac Aib Asn Leu Aib Pro Ala Ile Aib Pro Aib Leu Aib Pro Leu OH |
131 | Harzianin HC XV | Ac Aib Gln Leu Aib Pro Ala Ile Aib Pro Iva Leu Aib Pro Leu OH |
132 | Harzianin PCU4 | Ac Aib Asn Leu Aib Pro Ser Ile Aib Pro Aib Leu Aib Pro Val OH |
133 | Trichorzin PAU4 | Ac Aib Ser Ala Aib Aib Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Trp OH |
134 | Trichorzin PA II | Ac Aib Ser Ala Aib Iva Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Trp OH |
135 | Trichorzin PA IV | Ac Aib Ser Ala Aib Iva Gln Iva Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Trp OH |
136 | Trichorzin PA V | Ac Aib Ser Ala Iva Iva Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Trp OH |
137 | Trichorzin PA VI | Ac Aib Ser Ala Aib Iva Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Phe OH |
138 | Trichorzin PA VII | Ac Aib Ser Ala Iva Iva Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Trp OH |
139 | Trichorzin PA VIII | Ac Aib Ser Ala Aib Iva Gln Iva Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Phe OH |
140 | Trichorzin PA IX | Ac Aib Ser Ala Iva Iva Gln Aib Val Aib Gly Leu Aib Pro Leu Aib Aib Gln Phe OH |
141 | Trichorzianine TA IIIc | Ac Aib Ala Ala Aib Aib Gln Aib Aib Aib Ser Leu Aib Pro Val Aib Ile Gln Gln Trp OH |
142 | Trichorzianine TB IIa | Ac Aib Ala Ala Aib Aib Gln Aib Aib Aib Ser Leu Aib Pro Leu Aib Ile Gln Glu Trp OH |
143 | Trichorzianine TB IIIc | Ac Aib Ala Ala Aib Aib Gln Aib Aib Aib Ser Leu Aib Pro Val Aib Ile Gln Glu Trp OH |
144 | Trichorzianine TB IVb | Ac Aib Ala Ala Aib Iva Gln Aib Aib Aib Ser Leu Aib Pro Val Aib Ile Gln Glu Trp OH |
145 | Trichorzianine TB Vb | Ac Aib Ala Ala Aib Aib Gln Aib Aib Aib Ser Leu Aib Pro Leu Aib Ile Gln Glu Phe OH |
146 | Trichorzianine TB VIa | Ac Aib Ala Ala Aib Iva Gln Aib Aib Aib Ser Leu Aib Pro Leu Aib Ile Gln Glu Phe OH |
147 | Trichorzianine TB VIb | Ac Aib Ala Ala Aib Aib Gln Aib Aib Aib Ser Leu Aib Pro Val Aib Ile Gln Glu Phe OH |
148 | Trichorzianine TB VII | Ac Aib Ala Ala Aib Iva Gln Aib Aib Aib Ser Leu Aib Pro Val Aib Ile Gln Glu Phe OH |
Compounds | Bioactivities | Habitats | Refs |
---|---|---|---|
Harzianelactone A (1) * | Phytotoxicity | Soft coral | [13] |
Harzianelactone B (2) * | phytotoxicity | Soft coral | [13] |
Harzianone A (3) * | phytotoxicity | Soft coral | [13] |
Harzianone B (4) * | phytotoxicity | Soft coral | [13] |
Harzianone C (5) * | phytotoxicity | Soft coral | [13] |
Harzianone D (6) * | phytotoxicity | Soft coral | [13] |
Harzianone E (7) * | Antibacterial | Soft coral | [14] |
3R-Hydroxy-9R,10R-dihydroharzianone (8) * | phytotoxicity | Brown alga | [17] |
Harziane (9) * | phytotoxicity | Soft coral | [13] |
Trichodermanin C (10) * | Cytotoxicity | Sponge | [15,16] |
Trichodermanin D (11) * | — | Sponge | [15,16] |
Trichodermanin E (12) * | Cytotoxicity | Sponge | [15,16] |
Trichodermanin F (13) * | Cytotoxicity | Sponge | [15,16] |
Trichodermanin G (14) * | — | Sponge | [15,16] |
Trichodermanin H (15) * | — | Sponge | [15,16] |
3,7,11-Trihydroxy-cycloneran (16) * | — | Soft coral | [14] |
Methyl 3,7-dihydroxy-15-cycloneranate (17) * | Antibacterial | Soft coral | [14] |
phytotoxicity | Brown alga | [17] | |
Catenioblinc (18) * | — | Soft coral | [14] |
Ascotrichic acid (19) * | — | Soft coral | [14] |
Cyclonerotriol (20) * | — | Soft coral | [14] |
(10E)-12-Acetoxy-10-cycloneren-3,7-diol (21) * | — | Sediment | [9] |
— | Soft coral | [14] | |
Cyclonerodiol (22) * | — | Soft coral | [14] |
phytotoxicity | Brown alga | [17] | |
11-Methoxy-9-cycloneren-3,7-diol (23) * | phytotoxicity | Brown alga | [17] |
9-Cycloneren-3,7,11-triol (24) * | phytotoxicity | Brown alga | [17] |
10-Cycloneren-3,5,7-triol (25) * | phytotoxicity | Brown alga | [17] |
12-Acetoxycycloneran-3,7-diol (26) * | — | Sediment | [9] |
Cyclonerodiol oxide (27) * | — | Soft coral | [14] |
Epicyclonerodiol oxide (28) * | — | Soft coral | [14] |
ent-Trichoacorenol (29) * | — | Soft coral | [14] |
Trichoacorenol (30) * | — | Soft coral | [14] |
phytotoxicity | Brown alga | [17] | |
15-Hydroxyacorenone (31) | — | Mushroom | [19] |
Acorenone (32) | — | Mushroom | [19] |
Acorenone-B (33) | — | Mushroom | [19] |
4-Epiacorenone (34) | — | Mushroom | [19] |
4-Epiacorenone-B (35) | — | Mushroom | [19] |
8-Acoren-3,11-diol (36) * | phytotoxicity | Brown alga | [17] |
Trichoacorenol B (37) * | phytotoxicity | Brown alga | [17] |
Harzianoic acid A (38) * | Antivirus | Sponge | [18] |
Harzianoic acid B (39) * | Antivirus | Sponge | [18] |
Ophioceric acid (40) * | — | Soft coral | [14] |
Harzianolic acid A (41) * | — | Soft coral | [14] |
11R-Methoxy-5,9,13- proharzitrien-3-ol (42) * | phytotoxicity | Brown alga | [17] |
Stigmasta-7,22-dien-3β,5α,6α-triol (43) * | Antifouling and DNA top I inhibitory activity | Soft coral | [20] |
Stigmasterol (44) | — | Soil | [21] |
β-Sitosterol (45) | — | Soil | [21] |
Ergosterol (46) | — | Soil | [21] |
Trichosordarin A (47) * | Toxic to zooplankton | Sediment | [22] |
Harzianumol A (48) * | — | Sponge | [23] |
Harzianumol B (49) * | — | Sponge | [23] |
Harzianumol C (50) * | — | Sponge | [23] |
Harzianumol D (51) * | — | Sponge | [23] |
Harzianumol E (52) * | — | Sponge | [23] |
Harzianumol F (53) * | — | Sponge | [23] |
Harzianumol G (54) * | — | Sponge | [23] |
Harzianumol H (55) * | — | Sponge | [23] |
Trichoharzin B (56) * | — | Soft coral | [20] |
Methyl-trichoharzin (57) * | Antifouling | Soft coral | [20] |
Trichoharzin (58) * | Antifouling | Soft coral | [20] |
— | Sponge | [29] | |
Eujavanicol A (59) * | — | Soft coral | [20] |
Tandyukisin A (60) * | Cytotoxicity | Sponge | [11] |
Tandyukisin B (61) * | Cytotoxicity | Sponge | [25] |
Tandyukisin C (62) * | Cytotoxicity | Sponge | [25] |
Tandyukisin D (63) * | Cytotoxicity | Sponge | [25] |
Tandyukisin E (64) * | Cytotoxicity | Sponge | [24] |
Tandyukisin F (65) * | Cytotoxicity | Sponge | [24] |
Palmitic acid (66) | — | Soil | [21] |
Harzianum A (67) | Antifungal | Soil | [26] |
Harziphilone (68) | Cytotoxicity | Soil | [27] |
Keto triol 3 (69) | Antifungal | Wheat roots | [28] |
Keto diol 7 (70) | Antifungal | Wheat roots | [28] |
Keto diol 6 (71) | Antifungal | Wheat roots | [28] |
Keto diol 8 (72) | Antifungal | Wheat roots | [28] |
Triacetate 9 (73) | Antifungal | Wheat roots | [28] |
Triol 10 (74) | Antifungal | Wheat roots | [28] |
Acetal diol 2 (75) | Antifungal | Wheat roots | [28] |
Tribenzoate (76) * | — | Sponge | [29] |
Triacetate (77) * | — | Sponge | [29] |
T22azaphilone (78) | — | Commercial products | [30] |
Trichoharzianol (79) | Antifungal | Soil | [31] |
Trichodenone A (80) * | Cytotoxicity | Sponge | [32] |
Trichodenone B (81) * | Cytotoxicity | Sponge | [32] |
Trichodenone C (82) * | Cytotoxicity | Sponge | [32] |
Homodimericin A (83) | — | Florida termite nest | [33,34] |
Cryptenol (84) | — | Florida termite nest | [34] |
Pachybasin (85) | — | Laboratory environment | [37] |
Chrysophanol (86) | — | Laboratory environment | [37] |
1,7-Dihydroxy-3-hydroxymethyl-9,10-anthraquinone (87) | Antifungal | Plant roots | [38] |
1,5-Dihydroxy-3-hydroxymethyl-9,10- anthraquinone (88) | Antifungal | Plant roots | [38] |
Emodin (89) | Antifungal | Plant roots | [38] |
ω-Hydroxypachybasin (90) | Antifungal | Plant roots | [38] |
Phomarin (91) * | — | Soft coral | [12] |
(+)-2′S-Isorhodoptilometrin (92) * | Cytotoxicity | Soft coral | [12] |
1,6-Dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione (93) * | — | Soft coral | [12] |
Harzianumnone A (94) * | — | Soft coral | [12] |
Harzianumnone B (95) * | — | Soft coral | [12] |
Trichokindin_Ia (96) | — | Soil | [40] |
Trichokindin_Ib (97) | — | Soil | [40] |
Trichokindin_IIa (98) | — | Soil | [40] |
Trichokindin_IIb (99) | — | Soil | [40] |
Trichokindin_IIIa (100) | — | Soil | [40] |
Trichokindin_IIIb (101) | — | Soil | [40] |
Trichokindin_IV (102) | — | Soil | [40] |
Trichokindin_Va (103) | — | Soil | [40] |
Trichokindin_Vb (104) | — | Soil | [40] |
Trichokindin_VI (105) | — | Soil | [40] |
Trichokindin_VII (106) | Induced catecholamine secretion | Soil | [40] |
Harzianin_HB_I (107) | Membrane-modifying activity | Soil | [42] |
Trichorzin_HA_I (108) | Antifungal | Soil | [43,44] |
Trichorzin_HA_II (109) | Antifungal | Soil | [43,44] |
Trichorzin_HA_III (110) | Antifungal | Soil | [43,44] |
Trichorzin_HA_V (111) | Antifungal | Soil | [43,44] |
Trichorzin_HA_VI (112) | Antifungal | Soil | [43,44] |
Trichorzin_HA_VII (113) | Antifungal | Soil | [43,44] |
Trichorzin_MA_I (114) | Antifungal | Soil | [43,44] |
Trichorzin_MA_II (115) | Antifungal | Soil | [43,44] |
Trichorzin_MA_III (116) | Antifungal | Soil | [43,44] |
Trichorozin_I (117) | ion channel activity | Soil | [45] |
Trichorozin_II (118) | ion channel activity | Soil | [45] |
Trichorozin_III (119) | ion channel activity | Soil | [45] |
Trichorozin_IV (120) | ion channel activity | Soil | [45] |
Harzianin_HC_I (121) | Antibacterial | — | [46] |
Harzianin_HC_III (122) | Antibacterial | — | [46] |
Harzianin_HC_VI (123) | Antibacterial | — | [46] |
Harzianin_HC_VIII (124) | Antibacterial | — | [46] |
Harzianin_HC_IX (125) | Antibacterial | — | [46] |
Harzianin_HC_X (126) | Antibacterial | — | [46] |
Harzianin_HC_XI (127) | Antibacterial | — | [46] |
Harzianin_HC_XII (128) | Antibacterial | — | [46] |
Harzianin_HC_XIII (129) | Antibacterial | — | [46] |
Harzianin_HC_XIV (130) | Antibacterial | — | [46] |
Harzianin_HC_XV (131) | Antibacterial | — | [46] |
Harzianin_PCU4 (132) | — | — | [47] |
Trichorzin_PAU4 (133) | — | — | [47] |
Trichorzin_PA_II (134) | — | — | [47] |
Trichorzin_PA_IV (135) | — | — | [47] |
Trichorzin_PA_V (136) | — | — | [47] |
Trichorzin_PA_VI (137) | — | — | [47] |
Trichorzin_PA_VII (138) | — | — | [47] |
Trichorzin_PA_VIII (139) | — | — | [47] |
Trichorzin_PA_IX (140) | — | — | [47] |
Trichorzianine_TA_IIIc (141) | Anti-parasite | — | [48] |
Trichorzianine_TB_IIa (142) | — | — | [49] |
Trichorzianine_TB_IIIc (143) | — | — | [49] |
Trichorzianine_TB_IVb (144) | — | — | [49] |
Trichorzianine_TB_Vb (145) | — | — | [49] |
Trichorzianine_TB_VIa (146) | — | — | [49] |
Trichorzianine_TB_VIb (147) | — | — | [49] |
Trichorzianine_TB_VII (148) | — | — | [49] |
Trichodermamide G (149) * | — | Mangrove | [50] |
Trichodermamide A (150) * | — | Mangrove | [50] |
Aspergillazin A (151) * | — | Mangrove | [50] |
Fleephilone (152) | Antivirus | Soil | [27] |
Harzianic acid (153) * | Antibacterial | Water sample | [51] |
Isoharzianic acid (154) | Plant growth promotion | Hardwood bark | [52] |
Ethyl 2-bromo-4-chloroquinoline-3-carboxylate (155) | — | Soft coral | [20] |
Harzianopyridone (156) | Antifungal | Soil | [21] |
MR566A(157) | Melanin synthesis inhibition | Soil | [54,55] |
MR566B (158) | Melanin synthesis inhibition | Soil | [54] |
MR93A (159) | — | leaf | [53] |
MR93B (160) | — | Soil | [54] |
MR304A (161) | — | Soil | [54] |
1-(1,4,5-Trihydroxy-3-isocyanocyclopenten-2-enyl)-ethanol (162) | — | Soil | [54] |
2-Hydroxy-4-isocyano-α-methyl-6-oxabicyclo[3.1.0]-hex-3-ene-2-Methanol (163) | — | Soil | [54] |
4-Hydroxy-8-isocyano-1-oxaspiro[4.4]cyclonon-8-en-2-one (164) | — | Soil | [54] |
Methyl-3-(1,5-dihydroxy-3-isocyanocyclopent-3-enyl)prop-2-enoate (165) | — | Soil | [54] |
3 -(3′-Isocyanocyclopent -2′-eny1idene)propionic acid (166) | Melanin synthesis inhibition | Soil | [54,55] |
Xylogibloactone A (167) * | — | Soft coral | [20] |
Xylogibloactone B (168) * | — | Soft coral | [20] |
Nafuredin C (169) * | Antifungal | Mangrove | [50] |
Nafuredin A (170) * | — | Mangrove | [50] |
Antifouling | Soft coral | [20] | |
Dichlorodiaportin (171) * | — | Soft coral | [20] |
6-Pentyl-2H-pyran-2-one (172) | Antifungal | Soil | [21,58] |
2(5H)-Furanone (173) | — | Soil | [21] |
δ-Decanolactone (174) | — | Soil | [21] |
Peniisocoumarin H (175) * | — | Mangrove | [50] |
Harzialactone A (176) * | — | Sponge | [32] |
Harzialactone B (177) * | — | Sponge | [32] |
R-Mevalonolactone (178) * | — | Sponge | [32] |
Harzianolide (179) | — | Commercial products | [30] |
T39butenolide (180) | Antifungal | Commercial products | [30] |
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Guo, R.; Li, G.; Zhang, Z.; Peng, X. Structures and Biological Activities of Secondary Metabolites from Trichoderma harzianum. Mar. Drugs 2022, 20, 701. https://doi.org/10.3390/md20110701
Guo R, Li G, Zhang Z, Peng X. Structures and Biological Activities of Secondary Metabolites from Trichoderma harzianum. Marine Drugs. 2022; 20(11):701. https://doi.org/10.3390/md20110701
Chicago/Turabian StyleGuo, Rui, Gang Li, Zhao Zhang, and Xiaoping Peng. 2022. "Structures and Biological Activities of Secondary Metabolites from Trichoderma harzianum" Marine Drugs 20, no. 11: 701. https://doi.org/10.3390/md20110701