(22S)-6-O-ACETYL-21βH-HOPANE-3β,6β,22,29-TETROL FROM OAKMOSS (EVERNIA PRUNASTRI)

Abstract

A novel hopanoid triterpene, (22S)-6-O-acetyl-21βH-hopane-3β,6β,22,29-tetraol, was isolated from oakmoss (Evernia prunastri (L.) Ach.), as identified from ¹H, ¹³C, DEPT, COSY, NOESY, HSQC and HMBC NMR, MS and IR spectroscopy. During recrystallisation a new compound, 30-nor-6-O-acetyl-3β,6β-dihydroxy-21αH-hopan-22-one, was formed by a formal loss of methanol from the dihydroxypropyl moiety. No biological activity was found for the naturally occurring compound upon testing against a series of fish and human pathogenic bacteria.

Keywords:

• Evernia prunastri
• Lichen
• Oakmoss
• Triterpenes
• Hopanoids
• Isolation

Acknowledgements

We thank prof. Kazuo Masuda, Showa Pharmaceutical University, Tokyo, Japan, for providing complete NMR data for both epimers of 22,29-dihydroxyhopane and Ingrid Salvesen, SINTEF Fisheries and Aquaculture, Trondheim, Norway for evaluation of biological activity.

Notes

*Corresponding author.

Additional information

Notes on contributors

Helge Kjøsen *

*Corresponding author.