Microbial transformation of the triterpene nigranoic acid in Trichoderma sp

Two new metabolites, 15α, 16α-dihydroxy-3,4-secocyloarta-4 (28), 17 (20), 17 (E), 24 (E)-triene-3,26-dioic acid (2) with an unusual 17(20), 17 (E)-ene structure and 16α, 20α-dihydroxy-18 (13→17β) abeo-3,4-secocyloarta-4 (28), 12 (13), 24 (Z)-triene-3,26-dioic acid (3) with an unprecedented 18(13→17β...

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Veröffentlicht in:Phytochemistry letters 2012-03, Vol.5 (1), p.123-127
Hauptverfasser: Yang, Yu-Hong, Sun, Rong, Song, Hong-Chuang, Xu, Yao-Bo, Yang, Pan, Yang, Dong-Yan, Shen, Ze-Kai, Wang, An-Ran, Chen, Ye-Gao, Dong, Jin-Yan
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Sprache:eng
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Zusammenfassung:Two new metabolites, 15α, 16α-dihydroxy-3,4-secocyloarta-4 (28), 17 (20), 17 (E), 24 (E)-triene-3,26-dioic acid (2) with an unusual 17(20), 17 (E)-ene structure and 16α, 20α-dihydroxy-18 (13→17β) abeo-3,4-secocyloarta-4 (28), 12 (13), 24 (Z)-triene-3,26-dioic acid (3) with an unprecedented 18(13→17β)-abeo-secocyloarta skeleton were isolated and identified from the co-cultures of nigranoic acid (1) and Trichoderma sp. JY-1, which is a fungus obtained from the branches of Kadsura angustifolia. Both biotransformation products showed anti-HIV activity with EC50 values of less than 10.5μg/mL. [Display omitted] ► Two new metabolites, 15α, 16α-dihydroxy-3,4-secocycloarta-4 (28), 17 (20), 17 (E), 24 (E)-triene-3,26-dioic acid (2) and 16α, 20α-dihydroxy-18 (13→17β) abeo-3,4-secocycloarta-4 (28), 12 (13), 24 (Z)-triene-3,26-dioic acid (3) were isolated and identified from the co-cultures of nigranoic acid (1) and Trichoderma sp. JY-1. ► Compound 2 was found to possess an unusual 17(20), 17 (E)-ene structure and compound 3 featured an unprecedented 18(13→17β)-abeo-secocyloarta skeleton. ► Both biotransformation products, compound 2 and compound 3 showed anti-HIV-1 activity with EC50 values of less than 10.5μg/mL, superior to that of nigranoic acid (1). Two new metabolites were obtained by microbial transformation of the triterpene nigranoic acid (3,4-secocyloarta-4 (28), 24 (Z)-diene-3,26-dioic acid), (1) in the culture of Trichoderma sp. JY-1, a fungus obtained from the branches of Kadsura angustifolia. Their structures were established as 15α, 16α-dihydroxy-3,4-secocyloarta-4 (28), 17 (20), 17 (E), 24 (E)-triene-3,26-dioic acid (2) and 16α, 20α-dihydroxy-18 (13→17β) abeo-3,4-secocyloarta-4 (28), 12 (13), 24 (Z)-triene-3,26-dioic acid (3) by analysis of NMR and MS data and by analogy with the data for the substrate nigranoic acid (1). Compound 2 was found to possess an unusual 17(20), 17 (E)-ene structure while compound 3 featured an unprecedented 18(13→17β)-abeo-secocyloarta skeleton. Additionally, compounds 1–3 showed weak anti-HIV activity with EC50 values of 10.5, 8.8 and 7.6μg/mL, therapeutic index values (CC50/EC50) of 8.48, 9.12 and 10.1, respectively.
ISSN:1874-3900
1876-7486
DOI:10.1016/j.phytol.2011.11.007