Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro

Phytochemistry
Iris DjordjevićSlobodan Milosavljević

Abstract

Quantitative (1)H NMR measurements revealed delta(11(13)) sesquiterpene gamma-lactones as the main constituents ( >or= 1% per weight of dried plant material) in the crude extracts of the aerial parts of Amphoricarpos neumayeri ssp. neumayeri and ssp. murbeckii from mountains Orjen and Visitor (Montenegro), respectively. Preparative silica gel chromatography afforded thirteen guai-11(13)-en-12,6alpha-olides, named amphoricarpolides (1-13), with the same relative (1alphaH,4betaH,5alphaH,7betaH) configuration of the basic skeleton. The common structural feature of lactones 2-13 was 3beta,15-dioxygenation pattern. The only exception was 1 (3-deoxyamphoricarpolide), containing a single oxygen substituent (15-OH). Eight of them exhibited an additional oxygen substituent, 9beta-OH (5 and 6), 2alpha-OH (8-12), or 2alpha-OAc (13). Compound 7 was epoxydated at 10alpha(14)-position, whereas the remaining lactones contained a 10(14) double bond.

References

Mar 27, 2004·Plant Biology·T GarnatjeS Siljak-Yakovlev

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Citations

Sep 23, 2014·Chemistry & Biodiversity·Mirjana CvetkovićVele Tešević
Jul 28, 2005·Natural Product Reports·Braulio M Fraga
Nov 12, 2019·Natural Product Research·Mirjana CvetkovićLjubodrag Vujisić

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