Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro.
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.
Djordjević
Iris
I
Faculty for Veterinary Medicine, University of Belgrade, Bulevar JA 18, 11000 Belgrade, Serbia and Montenegro.
Vajs
Vlatka
V
Bulatović
Vanja
V
Menković
Nebojsa
N
Tesević
Vele
V
Macura
Slobodan
S
Janaćković
Pedja
P
Milosavljević
Slobodan
S
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry* / Q000145:classification; D002850:Chromatography, Gel; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010100:Oxygen; D010946:Plants, Medicinal / Q000737:chemistry*; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015022:Yugoslavia
D000935:Antifungal Agents; D007783:Lactones; D045789:Sesquiterpenes, Guaiane; D010100:Oxygen