Antifungal activity against Botrytis cinerea of labdane-type diterpenoids isolated from the resinous exudate of Haplopappus velutinus Remy (Asteraceae)

Natural Product Research
Javier EcheverríaAlejandro Urzúa

Abstract

Two labdane diterpenoids were isolated, from the resinous exudate of Haplopappus velutinus Remy (Asteraceae); the main compound was identified as 7,13-(E)-labdadien-15,18-dioic-acid-18-methyl ester (1) and the minor compound identified as 7-labden-15,18-dioic-acid-18-methyl ester (2). Their structures were obtained using FTIR, MS, HRMS and NMR data: 1D NMR (1H, 13C and DEPT-135), 2D homonuclear NMR (COSY and NOESY) and heteronuclear NMR (HSQC and HMBC). The trans stereochemistry of the decalin moiety of compounds 1 and 2 was established through NOESY experiments of the reduction product of 1; 7-labden-15,18-diol (1a). Diterpenoids 1 and 1a are described for the first time and showed antifungal activity, inhibiting approximately 40% mycelial growth of Botrytis cinerea.

References

Aug 10, 2002·Natural Product Letters·Francesca FainiFranco Delle Monache
Jun 11, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Leonora MendozaMilena Cotoras
Apr 11, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Javier EcheverríaMarcela Wilkens

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Citations

Apr 24, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yilin QiaoRobert P Borris

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Methods Mentioned

BETA
NMR

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