Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Nov 26;18(12):590.
doi: 10.3390/md18120590.

A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate Amphidinium gibbosum: Absolute Configuration and Multi-Segment Modification

Wan-Shan Li  1 , Zeng Luo  1 , Yan-Lan Zhu  1 , Yi Yu  2 , Jun Wu  1   3 , Li Shen  2
Affiliations

A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate Amphidinium gibbosum: Absolute Configuration and Multi-Segment Modification

Wan-Shan Li et al. Mar Drugs. .

Abstract

A super-carbon-chain compound, named gibbosol C, featuring a polyoxygenated C70-linear-carbon-chain backbone encompassing two acyclic polyol chains, was obtained from the South China Sea dinoflagellate Amphidinium gibbosum. Its planar structure was elucidated by extensive NMR investigations, whereas its absolute configurations, featuring the presence of 36 carbon stereocenters and 30 hydroxy groups, were successfully established by comparison of NMR data of the ozonolyzed products with those of gibbosol A, combined with J-based configuration analysis, Kishi's universal NMR database, and the modified Mosher's MTPA ester method. Multi-segment modification was revealed as the smart biosynthetic strategy for the dinoflagellate to create remarkable super-carbon-chain compounds with structural diversity.

Keywords: Amphidinium gibbosum; absolute configuration; marine dinoflagellate; multi-segment modification; super-carbon-chain compound.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
(a) The structures and absolute configurations of gibbosols A and B. (b) The structure and absolute configurations of gibbosol C (1). (c) Key 1H–1H COSY, H2BC, and HMBC correlations and diagnostic NOE interactions of gibbosol C (1).
Figure 2
Figure 2
(a) Structures of the ozonolyzed fragments gAa–c of gibbosol A. (b) Structures of the ozonolyzed fragments 1a–1c of gibbosol C (1).
Figure 3
Figure 3
(a) Rotamers and coupling constants for the C-5–C-9 segment of 1a. (b) ΔδSR values obtained for 1a.
Figure 4
Figure 4
(a) Rotamers and coupling constants for the C-16–C-17 segment of 1b. (b) Rotamers and coupling constants for the C36–C39 segment of 1c.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Kobayashi J., Ishibashi M. Bioactive metabolites of symbiotic marine microorganisms. Chem. Rev. 1993;93:1753–1769. doi: 10.1021/cr00021a005. - DOI
    1. Kobayashi J., Kubota T. Bioactive macrolides and polyketides from marine dinoflagellates of the genus Amphidinium. J. Nat. Prod. 2007;70:451–460. doi: 10.1021/np0605844. - DOI - PubMed
    1. Uemura D. Bioorganic studies on marine natural products-diverse chemical structures and bioactivities. Chem. Rec. 2006;6:235–248. doi: 10.1002/tcr.20087. - DOI - PubMed
    1. Kita M., Uemura D. Marine huge molecules: The longest carbon chains in natural products. Chem. Rec. 2010;10:48–52. doi: 10.1002/tcr.200900030. - DOI - PubMed
    1. Satake M., Murata M., Yasumoto T., Fujita T., Naoki H. Amphidinol, a polyhydroxypolyene antifungal agent with an unprecedented structure, from a marine dinoflagellate, Ampbidnium klebsii. J. Am. Chem. Soc. 1991;113:9859–9861. doi: 10.1021/ja00026a027. - DOI

MeSH terms

LinkOut - more resources