title: Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro.
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.
authors.affiliation: Faculty for Veterinary Medicine, University of Belgrade, Bulevar JA 18, 11000 Belgrade, Serbia and Montenegro.
authors.forename: Iris
authors.initials: I
authors.lastname: Djordjević
authors.forename: Vlatka
authors.initials: V
authors.lastname: Vajs
authors.forename: Vanja
authors.initials: V
authors.lastname: Bulatović
authors.forename: Nebojsa
authors.initials: N
authors.lastname: Menković
authors.forename: Vele
authors.initials: V
authors.lastname: Tesević
authors.forename: Slobodan
authors.initials: S
authors.lastname: Macura
authors.forename: Pedja
authors.initials: P
authors.lastname: Janaćković
authors.forename: Slobodan
authors.initials: S
authors.lastname: Milosavljević
mesh_terms: 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
chemical_list: D000935:Antifungal Agents; D007783:Lactones; D045789:Sesquiterpenes, Guaiane; D010100:Oxygen