41 FERN CONSTITUENTS : FILICENOLS A AND B, TETRAHYMANOL, AND ISOADIANTOL B, ISOLATED FROM ADIANTUM MONOCHLAMYS

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  • 41 シダ植物成分:ハコネシダのトリテルペンアルコール,Filicenol AおよびB,Tetrahymanol,ならびにIsoadiantol Bの分離と構造

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From the leaves of Adiantum monochlamys EATON (Pteridaceae), four triterpenoid mono alcohols, filicenol A (I), filicenol B(VIII), tetrahymanol (XIV) and Isoadiantol B (XVII), were isolated together with hydroxyhopane (XV). Filicenol A was assigned to be filic-3-en-6β-ol (I) by the studies on the IR, NMR and Mass spectra, and the structure was confirmed by the reactions giving the compounds (III), (IV), (V), (VI) and (VII). The structure of filicenol B was also assumed to be filic-3-en-25-ol (VIII) by the physical methods, and the reactions, affording the compounds (X), (IV), (XI), (XII) and (XIII), were carried out. Tetrahymanol (XIV) was the first example of gammaceranes isolated from the plant kingdom, and co-existence with hydroxyhopane (XV) in the same plant was very interesting. Isoadiantol B (XVII) was synthesized from isoadiantone and the configuration at C 22 was assigned as to be XVII by the comparison of optical rotatories with those of 20-hydroxypregnenes. The chemical shifts of the methyl groups of the triterpenoids having the filicane skeleton were shown in Table I.

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