New humulane-type sesquiterpenes from the liverworts Tylimanthus tenellus and Marchantia emarginata subsp. tosana.
The ether extract of the New Zealand liverwort Tylimanthus tenellus produced three new sesquiterpenes, together with (+)-3,11-eudesmadiene and (-)-4(15),11-eudesmadiene which were enantiomeric to those isolated from higher plants. The structures of the new sesquiterpenes were established by 2D NMR spectral data and/or X-ray crystallographic analysis. Those structures were shown to be humulane type sesquiterpene alcohol, and its esters of 2,4-hexadienedioic acid 3,4-dihydroxy-2,5-diphenyl-gamma-lactone. 1,6-Humuladien-10-ol was also isolated from Japanese liverwort Marchantia emarginata subsp. tosana. The absolute configuration of 1,6-humuladien-10-ol was determined by (1)H-NMR resolution of its diastereomeric methoxy-alpha-trifluoromethylphenylacetyl (MTPA) esters. It was shown to be (3S,10R)-1,6-humuladien-10-ol.
Toyota
Masao
M
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Omatsu
Ikuko
I
Braggins
John
J
Asakawa
Yoshinori
Y
D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D035926:Hepatophyta / Q000737:chemistry*; D006868:Hydrolysis; D008958:Models, Molecular; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet
D010936:Plant Extracts; D012717:Sesquiterpenes