Amphidinin G, a putative biosynthetic precursor of amphidinin A from marine dinoflagellate Amphidinium sp.

Takaaki Kubota; Takahiro Iwai; Haruaki Ishiyama; Kanae Sakai; Tohru Gonoi; Jun'Ichi Kobayashi

doi:10.1016/j.tetlet.2015.01.058

Amphidinin G, a putative biosynthetic precursor of amphidinin A from marine dinoflagellate Amphidinium sp.

Takaaki Kubota, Takahiro Iwai, Haruaki Ishiyama, Kanae Sakai, Tohru Gonoi, Jun'Ichi Kobayashi

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

A new linear polyketide, amphidinin G (1), has been isolated from a symbiotic marine dinoflagellate Amphidinium sp. The planar structure of 1 was established mainly based on the 2D NMR data and the stereochemistry was elucidated by the combination of J-value analysis, modified Mosher's method, and NMR chemical shift comparison with synthetic analogues. Amphidinin G (1) was expected to be a biosynthetic precursor of amphidinin A (2), a known linear dinoflagellate polyketide. Amphidinin G (1) showed antifungal activity against Trichophyton mentagrophytes.

Original language	English
Pages (from-to)	990-993
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.058
Publication status	Published - Feb 18 2015
Externally published	Yes

Keywords

Amphidinium sp.
Antifungal
Biosynthetic precursor
Dinoflagellate
Linear polyketide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2015.01.058

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title = "Amphidinin G, a putative biosynthetic precursor of amphidinin A from marine dinoflagellate Amphidinium sp.",

abstract = "A new linear polyketide, amphidinin G (1), has been isolated from a symbiotic marine dinoflagellate Amphidinium sp. The planar structure of 1 was established mainly based on the 2D NMR data and the stereochemistry was elucidated by the combination of J-value analysis, modified Mosher's method, and NMR chemical shift comparison with synthetic analogues. Amphidinin G (1) was expected to be a biosynthetic precursor of amphidinin A (2), a known linear dinoflagellate polyketide. Amphidinin G (1) showed antifungal activity against Trichophyton mentagrophytes.",

keywords = "Amphidinium sp., Antifungal, Biosynthetic precursor, Dinoflagellate, Linear polyketide",

author = "Takaaki Kubota and Takahiro Iwai and Haruaki Ishiyama and Kanae Sakai and Tohru Gonoi and Jun'Ichi Kobayashi",

note = "Funding Information: We thank Ms. S. Oka and Ms. A. Tokumitsu, Center for Instrumental Analysis, Hokkaido University, for measurements of ESIMS. This work was partly supported by The Naito Foundation, The Takeda Science Foundation, Cooperative Research Program of Medical Mycology Research Center, Chiba University, and Grant-in-Aid for Sports, Science and Technology of Japan. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

year = "2015",

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day = "18",

doi = "10.1016/j.tetlet.2015.01.058",

language = "English",

volume = "56",

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journal = "Tetrahedron Letters",

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T1 - Amphidinin G, a putative biosynthetic precursor of amphidinin A from marine dinoflagellate Amphidinium sp.

AU - Kubota, Takaaki

AU - Iwai, Takahiro

AU - Ishiyama, Haruaki

AU - Sakai, Kanae

AU - Gonoi, Tohru

AU - Kobayashi, Jun'Ichi

N1 - Funding Information: We thank Ms. S. Oka and Ms. A. Tokumitsu, Center for Instrumental Analysis, Hokkaido University, for measurements of ESIMS. This work was partly supported by The Naito Foundation, The Takeda Science Foundation, Cooperative Research Program of Medical Mycology Research Center, Chiba University, and Grant-in-Aid for Sports, Science and Technology of Japan. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/2/18

Y1 - 2015/2/18

N2 - A new linear polyketide, amphidinin G (1), has been isolated from a symbiotic marine dinoflagellate Amphidinium sp. The planar structure of 1 was established mainly based on the 2D NMR data and the stereochemistry was elucidated by the combination of J-value analysis, modified Mosher's method, and NMR chemical shift comparison with synthetic analogues. Amphidinin G (1) was expected to be a biosynthetic precursor of amphidinin A (2), a known linear dinoflagellate polyketide. Amphidinin G (1) showed antifungal activity against Trichophyton mentagrophytes.

AB - A new linear polyketide, amphidinin G (1), has been isolated from a symbiotic marine dinoflagellate Amphidinium sp. The planar structure of 1 was established mainly based on the 2D NMR data and the stereochemistry was elucidated by the combination of J-value analysis, modified Mosher's method, and NMR chemical shift comparison with synthetic analogues. Amphidinin G (1) was expected to be a biosynthetic precursor of amphidinin A (2), a known linear dinoflagellate polyketide. Amphidinin G (1) showed antifungal activity against Trichophyton mentagrophytes.

KW - Amphidinium sp.

KW - Antifungal

KW - Biosynthetic precursor

KW - Dinoflagellate

KW - Linear polyketide

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DO - 10.1016/j.tetlet.2015.01.058

M3 - Article

AN - SCOPUS:84921943417

VL - 56

SP - 990

EP - 993

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -

Amphidinin G, a putative biosynthetic precursor of amphidinin A from marine dinoflagellate Amphidinium sp.

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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