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Bioactive secondary metabolites from symbiotic marine dinoflagellates: symbiodinolide and durinskiols
Author(s) -
Kita Masaki,
Ohno Osamu,
Han Chunguang,
Uemura Daisuke
Publication year - 2010
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.200900007
Subject(s) - dinoflagellate , polyol , allylic rearrangement , abiogenesis , marine ecosystem , biology , symbiodinium , chemistry , ecosystem , botany , ecology , symbiosis , biochemistry , catalysis , astrobiology , organic chemistry , bacteria , genetics , polyurethane
Symbiotic relationships play critical roles in marine ecosystems. Among symbionts, marine dinoflagellates have attracted the attention of natural products chemists, biologists, and ecologists, since they are rich sources of unique bioactive secondary metabolites. The polyol compound symbiodinolide, which was isolated from the symbiotic dinoflagellate Symbiodinium sp., exhibits significant voltage‐dependent N ‐type Ca 2+ channel‐opening activity and may serve as a defense substance to prevent digestion of the host animals. Durinskiols are also unique long carbon‐chain polyol compounds that were isolated from the dinoflagellate Durinskia sp. We found a selective cleavage reaction of allylic 1,2‐diol using an olefin metathesis catalyst, and developed a fluorescent‐labeling method for MS/MS analysis to achieve the structural elucidation of huge polyol compounds. This review highlights recent advances in structural and biological studies on symbiodinolide, durinskiols, and related polyol compounds. © 2010 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 10: 57–69; 2010: Published online in Wiley InterScience ( www.interscience.wiley.com ) DOI 10.1002/tcr.200900007