8 紅藻ハネソゾのフィトエクジソンおよびジテルペン類の構造

概要

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A number of halogenated metabolites with C_<15> vinyl acetylenic or allenic cyclic ether structures and halogenated sesquiterpenes have been isolated from the genus Laurencia. We previously reported structure of two cyclic ethers, laurepinnacin and isolaurepinnacin (1 and 2), isolated from L. pinnata. In continuing studies on components of the alga collected at Motsuta point in early July, we newly isolated three halogenated diterpenes and two sterols, designated as pinna-terpenes A, B, and C, and acetylpinnasterol and pinnasterol, respectively. The present paper describes that the diterpenes and sterols are represented by formulas 3, 4, 5, 6, and 7, respectively, on the basis of the X-ray crystallographic analysis and chemical evidence. The present study indicates that the alga L. pinnata is characterized by the following: (i) the alga does not contain halogenated sesquiterpenes but halogenated diterpenes (3〜5), (ii) the alga includes the marine phytosterols (6 and 7 with moulting hormone activity related structurally to ecdysones, and (iii) the alga contains the C_<15> cyclic ethers (1 and 2), considered to be formed in vivo from a new precursor, (3E,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraen-1-yne, rather than the potential precursor, laurediol, with (12E)- configuration.
天然有機化合物討論会の論文
1981-09-10