Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro
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2004
Authors
Đorđević, IrisVajs, Vlatka
Bulatović, V.
Menković, Nebojša
Tešević, Vele
Macura, S
Janaćković, Peđa
Milosavljević, S
Article (Published version)
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Quantitative H-1 NMR measurements revealed Delta(11(13)) sesquiterpene gamma-lactones as the main constituents (greater than or equal to 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,4PH,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.
Keywords:
Amphoricarpos neumayeri / Asteraceae / sesquiterpene lactones / guaianolides / amphoricarpolidesSource:
Phytochemistry, 2004, 65, 16, 2337-2345Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.1016/j.phytochem.2004.07.014
ISSN: 0031-9422
PubMed: 15381005
WoS: 000224440400005
Scopus: 2-s2.0-4544342932
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Fakultet veterinarske medicineTY - JOUR AU - Đorđević, Iris AU - Vajs, Vlatka AU - Bulatović, V. AU - Menković, Nebojša AU - Tešević, Vele AU - Macura, S AU - Janaćković, Peđa AU - Milosavljević, S PY - 2004 UR - https://vet-erinar.vet.bg.ac.rs/handle/123456789/304 AB - Quantitative H-1 NMR measurements revealed Delta(11(13)) sesquiterpene gamma-lactones as the main constituents (greater than or equal to 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,4PH,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. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Phytochemistry T1 - Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro VL - 65 IS - 16 SP - 2337 EP - 2345 DO - 10.1016/j.phytochem.2004.07.014 ER -
@article{ author = "Đorđević, Iris and Vajs, Vlatka and Bulatović, V. and Menković, Nebojša and Tešević, Vele and Macura, S and Janaćković, Peđa and Milosavljević, S", year = "2004", abstract = "Quantitative H-1 NMR measurements revealed Delta(11(13)) sesquiterpene gamma-lactones as the main constituents (greater than or equal to 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,4PH,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.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Phytochemistry", title = "Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro", volume = "65", number = "16", pages = "2337-2345", doi = "10.1016/j.phytochem.2004.07.014" }
Đorđević, I., Vajs, V., Bulatović, V., Menković, N., Tešević, V., Macura, S., Janaćković, P.,& Milosavljević, S.. (2004). Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro. in Phytochemistry Pergamon-Elsevier Science Ltd, Oxford., 65(16), 2337-2345. https://doi.org/10.1016/j.phytochem.2004.07.014
Đorđević I, Vajs V, Bulatović V, Menković N, Tešević V, Macura S, Janaćković P, Milosavljević S. Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro. in Phytochemistry. 2004;65(16):2337-2345. doi:10.1016/j.phytochem.2004.07.014 .
Đorđević, Iris, Vajs, Vlatka, Bulatović, V., Menković, Nebojša, Tešević, Vele, Macura, S, Janaćković, Peđa, Milosavljević, S, "Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro" in Phytochemistry, 65, no. 16 (2004):2337-2345, https://doi.org/10.1016/j.phytochem.2004.07.014 . .