13 マナマコStichopus japonicus SELENKAの抗真菌性配糖体holotoxinの構造

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概要

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• It has been known that various species of sea cucumber and starfish(Phylum Echinodermata) contain saponin as the toxic principle. In 1968, Elyakov,et al. reported the isolation of two triterpenoid glycosides (stichoposide A and C) from the MeOH extract of Far Eastern sea cucumber (Stichopus japonicus) and proposed the structure of two aglycones, stichopogenin A_2(1) and A_4(2), which were obtained by acid hydrolysis of stichoposide A. On the other hand, in 1969 Shimada isolated an antifungal glycoside named holotoxin from the same species of sea cucumber. However, the structures of these glycosides have not been elucidated. In the present study, we have isolated holotoxin (identical with the Shimada's specimen), which has been separated into three glycosides now designated as holotoxin A (major), B, and C by droplet countercurrent chromatography. Upon ordinary acid hydrolysis, holotoxin A furnished xylose, quinovose, 3-O-methyl-glucose, glucose, and a mixture of aglycones, Ge-1 (a mixture of 1 and other double bond isomer) and 2, while under the mild acid conditions, 2 and 6 were isolated. Based on the chemical and enzymatic degradation of holotoxin A and its derivatives in conjunction with the physicochemical analyses thereof, the structure of holotoxin A has been established as 8, which is characteristic by the possession of two α-linkages of xylose and quinovose. Finally, the antifungal activity of holotoxin A, B, and C has been summarized as shown in Table 2.

• 1974-10-01

著者

• 北川 勲

  阪大薬

• 吉岡 一郎

  阪大薬学部

• 菅原 民雄

  Faculty Of Pharmaceutical Sciences Osaka University:(present Address)shionogi Research Laboratory Sh

• 菅原 民雄

  阪大薬

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