TY - JOUR
T1 - Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro
AU - Djordjević, Iris
AU - Vajs, Vlatka
AU - Bulatović, Vanja
AU - Menković, Nebojša
AU - Tešević, Vele
AU - Macura, Slobodan
AU - Janaćković, Pedja
AU - Milosavljević, Slobodan
N1 - Funding Information:
The authors from Serbia and Montenegro acknowledge their gratitude to the Ministry for Science, Technologies and Development (Project 1755) for financial support. We also express our gratitude to Daniel Vincek, Botanic Garden, Dulovine, Kolašin and Milutin Praščević, Alpinetum of Prokletije, Plav (Montenegro) for the immense help in collecting the plant material.
PY - 2004/8
Y1 - 2004/8
N2 - Quantitative 1H NMR measurements revealed Δ 11(13) sesquiterpene γ-lactones as the main constituents (≥ 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-12,6α-olides, named amphoricarpolides (1-13), with the same relative (1αH,4βH,5αH, 7βH) configuration of the basic skeleton. The common structural feature of lactones 2-13 was 3β,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, 9β-OH (5 and 6), 2α-OH (8-12), or 2α-OAc (13). Compound 7 was epoxydated at 10α(14)-position, whereas the remaining lactones contained a 10(14) double bond.
AB - Quantitative 1H NMR measurements revealed Δ 11(13) sesquiterpene γ-lactones as the main constituents (≥ 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-12,6α-olides, named amphoricarpolides (1-13), with the same relative (1αH,4βH,5αH, 7βH) configuration of the basic skeleton. The common structural feature of lactones 2-13 was 3β,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, 9β-OH (5 and 6), 2α-OH (8-12), or 2α-OAc (13). Compound 7 was epoxydated at 10α(14)-position, whereas the remaining lactones contained a 10(14) double bond.
KW - Amphoricarpolides
KW - Amphoricarpos neumayeri
KW - Asteraceae
KW - Guaianolides
KW - Sesquiterpene lactones
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U2 - 10.1016/j.phytochem.2004.07.014
DO - 10.1016/j.phytochem.2004.07.014
M3 - Article
C2 - 15381005
AN - SCOPUS:4544342932
SN - 0031-9422
VL - 65
SP - 2337
EP - 2345
JO - Phytochemistry
JF - Phytochemistry
IS - 16
ER -