13 パプアニューギニア産海綿Cinachyrella enigmaticaから得られた新規細胞毒性マクロライドenigmazole Aの構造研究(口頭発表の部)

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概要

• 論文の詳細を見る

• Marine sponges are known to be a prolific source of secondary metabolites with antitumor property. As part of our program to discover novel antitumor leads from natural sources, we discovered a group of novel cytotoxic macrolides from an aqueous extract of the Papua New Guinea marine sponge Cinachyrella enigmatica. In this session, we will present complete structure determination of enigmazole A, one of the most abundant and structurally the simplest members of this class of sponge metabolites. Spectroscopic analyses based on NMR and MS experiments revealed that 1 is a novel 16-membered macrolide of mixed polyketide/peptide origin and is characterized by a phosphate ester and a uniquely substituted oxazole as a side chain moiety. The complete stereochemical assignment of all of its 8 chiral centers was achieved through extensive chemical derivatization/degradation studies including N,N'-dimethyl diamidation of the phosphate group, anisotropic shift analysis after derivatization with PGME or MTPA, and non-enzymatic dephosphorylation accompanied by subsequent hydrolysis of the macrolide ring and δ-lactonization, and by development of a novel chiral analysis procedure for volatile ketones. Compound 1 was cytotoxic against IC-2 mouse mast cell progenitor cells with IC_<50> values of 0.3μg/mL. Studies on the structure of other congeners as well as on the mode of action of these unique macrolides are currently under way.

• 天然有機化合物討論会の論文
• 2006-09-15

著者

• 奥 直也

  海洋バイオ研

• Gustafson Kirk

  National Cancer Institute At Frederick National Institute Of Health

• 奥 直也

  National Cancer Institute at Frederick, National Institute of Health

• Fuller Richard

  National Cancer Institute at Frederick, National Institute of Health

• Wilson Jennifer

  National Cancer Institute at Frederick, National Institute of Health

• Pannell Lewis

  National Institute of Diabetes and Digestive and Kidney Diseases, National Institute of Health

• McMahon James

  National Cancer Institute at Frederick, National Institute of Health

• Fuller Richard

  National Cancer Institute At Frederick National Institute Of Health

• Pannell Lewis

  National Institute Of Diabetes And Digestive And Kidney Diseases National Institute Of Health

• Mcmahon James

  National Cancer Institute At Frederick National Institute Of Health

• Wilson Jennifer

  National Cancer Institute At Frederick National Institute Of Health

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• 13 パプアニューギニア産海綿Cinachyrella enigmaticaから得られた新規細胞毒性マクロライドenigmazole Aの構造研究(口頭発表の部)
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