Colopsinol A, a Novel Polyhydroxyl Metabolite from Marine Dinoflagellate Amphidinium sp

Jun'ichi Kobayashi; Takaaki Kubota; Miho Takahashi; Masami Ishibashi; Masashi Tsuda; Hideo Naoki

doi:10.1021/jo981882b

Colopsinol A, a Novel Polyhydroxyl Metabolite from Marine Dinoflagellate Amphidinium sp

J Org Chem. 1999 Mar 5;64(5):1478-1482. doi: 10.1021/jo981882b.

Authors

Jun'ichi Kobayashi¹, Takaaki Kubota, Miho Takahashi, Masami Ishibashi, Masashi Tsuda, Hideo Naoki

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, and Suntory Institute for Bioorganic Research, Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan.

PMID: 11674207
DOI: 10.1021/jo981882b

Abstract

Colopsinol A (1), a novel polyhydroxyl compound, has been isolated from the cultured marine dinoflagellate Amphidinium sp., from which a number of cytotoxic macrolides, amphidinolides, have been obtained to date, and the gross structure of 1 was elucidated on the basis of extensive spectroscopic analyses including recent 2D NMR techniques of CH(2)-selected editing HSQC as well as FABMS/MS experiments and chemical means. Colopsinol A (1), C(71)H(119)O(25)SNa, is the first member of a new class of polyketide natural products possessing a gentiobioside moiety and a sulfate ester. The polyketide aglycon consisted of a C(56)-linear aliphatic chain with one exo-methylene and two methyl branches as well as two ketones, five hydroxyl groups, and a tetrahydropyran and two epoxide rings.