天然有機化合物討論会講演要旨集
Online ISSN : 2433-1856
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2 新しい骨格のリコポジウムアルカロイド : Serratinineの構造
犬伏 康夫石井 永安井 凡平原山 尚橋本 真志
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会議録・要旨集 フリー

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Recently, the constituents of Lycopodium serratum Thunb. var. Thunbergii Makino (Lycopodiaceae) have been examined. The structures of serratenediol (I), a new skeletal triterpenoid contained a seven-membered ring, and several related triterpenoids have been established. Serratinine, a new alkaloid, was found in the basic component of this plant. Serratinine (II), m.p. 244-245°, C_<16>H_<25>O_3N, [α]^8_D-27.8 (C=1.44 in EtOH), IR 3472, 3436, 3185 (OH), 1724 (C=O) and 1424 cm^<-1> (-COCH_2-). Serratinine (II) on acetylation with Ac_2 O-pyridine at 100°gave diacetylserratinine (III) and on a treatment with bonsaldehyde gave benaylidene serratinine (IV). In addition to the above facts, the absence of signals due to vinyl proton and N-methyl group in the NMR spectra of diacetylserratinine (III) suggested that serratinine should be a tetracyclic alkaloid possessing the expanded molecular formula, C_<10>H_<15> (>CH-CH_3)(>CH_2-CO_)(>CH-OH)_2 (-N<). Mass spectroscopy of diacetylserratinine (III) gave the accurate molecular weight, and confirmed that serratinine should be a new skeletal alkaloid, since the fragmentation pattern of (III) was entirely different from those of lycopodium alkaloids reported hitherto. The degradative and spectroscopic evidence led to the conclusion that serratinine could be represented by the structure (II). The stereochemistry including the absolute configuration of serratinine will be discussed and the hypothetical biogenesis from a lycodoline type precursor to serratinine will be also presented.

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© 1966 天然有機化合物討論会電子化委員会
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