New Humulane-Type Sesquiterpenes from the Liverworts Tylimanthus tenellus and Marchantia emarginata subsp. tosana

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  • Toyota Masao
    Faculty of Pharmaceutical Sciences, Tokushima Bunri University
  • Omatsu Ikuko
    Faculty of Pharmaceutical Sciences, Tokushima Bunri University
  • Braggins John
    Plant Systematics, School of Biological Sciences, University of Auckland
  • Asakawa Yoshinori
    Faculty of Pharmaceutical Sciences, Tokushima Bunri University

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Abstract

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-γ-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 1H-NMR resolution of its diastereomeric methoxy-α-trifluoromethylphenylacetyl (MTPA) esters. It was shown to be (3S,10R)-1,6-humuladien-10-ol.

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