78 軟サンゴ、Sinularia mayiおよびLobohytum strictumから得られたステロイドとセンブラノイドの構造(ポスター発表の部)
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Five new marine C_<29> sterols (2-6) were isolated from the soft coral Sinular ia mayi of the Ishigaki Island, Okinawa. The Spectrosocpic data showed that they are the polyhydroxy derivative of sarcosterol (1), a marine sterol having a unique 23-methyl and a 17(20)E-double bond. Sterol 2 was the 25-monohydroxy derivative of 1. The NOE experiment of its 25, 26-didehydro derivative indicated that the stereochemistry at C-23 and 24 was identical with that of peridinosterol, whose absolute configuration has previously been established. Sterol 3 was the 25,26-dihydroxy derivative of 1. It was converted to 2 by reductive cleavage of the C-26 tosyloxy bond by LAH. Sterols 5 and 6 were shown, by spectroscopic analyses, to be 22, 25-dihydroxy and 22,23,25-trihydroxy derivatives of 1. The stereochemistry in the side chain was derived from interpretation of the coupling pattern and the results obtained by NOE experiments. On storage sterol 5 was found to be converted, by dehydration, to sterol 4 having a tetrahydrofuran ring on the side chain Two new cembranoids sinulariol E (7) and mayolide E (8), simultaenously isolated from S. mayi, were correlated to the known compounds sinulariol A (9) and mayolide B (10) by dehydration. The pyridine-induced deshielding effects, observed in the ^1H NMR spectra of 8 and 10-12, indicated that the absolute configuration at C-8 of 8 to be (R) and that of 10-12 to be (S). A new polyhydroxygorgostane (15) was obtained from the Andaman Sea soft coral Lobophytum strictum. The structure was derived, by spectroscopic data. to be 1β-hydroxy-9-deoxy derivative of the known compound andamansterol.
- 天然有機化合物討論会の論文
- 1993-09-10
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