Symbiodinolactone A, a new 12-membered macrolide from symbiotic marine dinoflagellate Symbiodinium sp

[Display omitted] •A novel macrolide was isolated from the marine dinoflagellate.•The macrolide is the first non-nitrogen-containing macrolide from Symbiodinium sp.•The macrolide might be generated by the unexplained biosynthetic machinery. A new 12-membered macrolide, symbiodinolactone A, was isola...

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Bibliographic Details
Published in:Tetrahedron letters 2018-12, Vol.59 (51), p.4496-4499
Main Authors: Kurimoto, Shin-ichiro, Iinuma, Yurika, Kobayashi, Jun'ichi, Kubota, Takaaki
Format: Article
Language:English
Subjects:
Dinoflagellate
Macrolide
Symbiodinium sp
Symbiodinolactone A
Symbiotic
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Summary:[Display omitted] •A novel macrolide was isolated from the marine dinoflagellate.•The macrolide is the first non-nitrogen-containing macrolide from Symbiodinium sp.•The macrolide might be generated by the unexplained biosynthetic machinery. A new 12-membered macrolide, symbiodinolactone A, was isolated from the culture broth of symbiotic marine dinoflagellate Symbiodinium sp. The gross structure of symbiodinolactone A was elucidated by spectroscopic analyses, and the relative configuration was elucidated by the J-based configuration analysis and density-functional theory calculations. Symbiodinolactone A is the new 12-membered macrolide possessing an E double bond between C-4 and C-5, a branched methyl group at C-7, and a 1,2,3-trihydroxybutyl group at C-11. Symbiodinolactone A is the first usual size macrolide and the first non-nitrogen-containing macrolide from dinoflagellate Symbiodinium sp. Symbiodinolactone A might be generated by the unexplained dinoflagellate polyketide biosynthetic machinery.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.11.018