46(P-3) 海綿Strongylophora strongylataの新規イトマキヒトデ卵成熟阻害活性Meroditerpenoidsの構造と活性(ポスター発表の部)

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By using starfish (Asterina pectinifera) oocytes as a model and occurrence of GVBD as an indicator, inhibitor of starfish oocytes reinitiation and maturation were sought to obtain biologically active substances which act on either hormonal signal transduction or cell cycle regulation. As a part of our continuous efforts on the search for bioactive agents from the sea, marine sponges collected at Iriomote Island were screened by an oocytes assay. The extract of Strongvlophora stongylata displayed potent inhibitory activity on GVBD and was subjected to bioassay-guided isolation. The frozen sponge sample was thawed and extracted with ethanol. The ethanol extract was partitioned between chloroform and water, and the organic layer was separated by ODS column and then reversed-phase HPLC to afford nine new meroditerpenoids, strongylophorines 13, 14, 15, 16, 17, 18, 19, 20, and 21 together with two known strongylophorines 2 and 8. The new compounds were named in accordance with the early nomenclature system. Their planar structures were definitely determined by detailed analysis of spectral data (^1H and ^<13>C NMR, ^1H-^1H COSY, HMQC, HMBC, and FAB-MS). The stereochemistries were assigned by NOESY experiments and optical rotations. Strongylophorines 13/14 and 15/16 were two pairs of isomers with the formation of 6-membered hemiacetal ring between the 24 and 26 positions. Although each isomer was well separated by HPLC (ODS), the isomer was easily converted to a mixture of two isomers in both solution and solid states. The ratio of the mixtures of 13/14 and 15/16 were both 3:1. Strongylophorines 13/14, 15/16, 17, 18, 20, 21, 8, and 2 showed inhibitory activities on the GVBD with IC_<50>'s of 35.0, 36.4, 1.2, 37.6, 36.4, 35.2, 1.1, and 36.6μM, respectively. Strongylophorine 19 was not active even at 100μg/mL.
天然有機化合物討論会の論文
2002-09-01

46(P-3) 海綿Strongylophora strongylataの新規イトマキヒトデ卵成熟阻害活性Meroditerpenoidsの構造と活性(ポスター発表の部)

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