91 海綿Hyrtios altum由来の新規抗腫瘍マクロリドAltohyrtin類の化学構造(ポスター発表の部)

概要

論文の詳細を見る
During the course of our investigations in search of new biologically active substances from marine organisms, we have investigated the chemical constituents of the Okinawan marine sponge Hyrtios altum by taking advantage of bioassay-guided fractionations and separations. Examinations of cytotoxicity against L1210 and KB cell lines have led us to the isolation of four very potent cytotoxic macrolides named altohyrtin A (1), altohyrtin B (2), altohyrtin C (3), and 5-desacetyl-altohyrtin A (4). The plane structure and parts of relative configurations of altohyrtin A (1) and 5-desacetylaltohyrtin A (4) have been elucidated on the basis of the detailed analyses of ^1H-^1H COSY, HMQC, HOHAHA, HMBC, and NOESY spectra. Furthermore, altohyrtin B and altohyrtin C have been elucidated to be a 50-bromo analog 2 and a deschloro analog 3 of altohyrtin A (1), respectively. In order to determine the absolute stereostructures of these macrolides, we have prepared hexa-MTPA esters 6 and 7 from 4 and tri-p-bromo-benzoate 8 from 1 which were suitable for applying a modified Mosher's method and a CD allyl benzoate rule. Detailed NMR analyses of 6 and 7 have led us to propose the absolute stereostructures of these macrolides being expressed as 1-4. Altohyrtins A (1), B (2) and C (3) and 5-desacetylaltohyrtin A (4) exhibit extremely potent cytotoxicities against KB cells with IC_<50> values of 0.01, 0.02, 0.4, and 0.3ng/ml, respectively.
天然有機化合物討論会の論文
1993-09-10

91 海綿Hyrtios altum由来の新規抗腫瘍マクロリドAltohyrtin類の化学構造(ポスター発表の部)

スポンサーリンク

概要

著者

関連論文

スポンサーリンク