Biosynthetic study of amphidinin A and Amphidinolide P

Takaaki Kubota; Hayato Sato; Takahiro Iwai; Jun'ichi Kobayashi

doi:10.1248/cpb.c16-00202

Biosynthetic study of amphidinin A and Amphidinolide P

Takaaki Kubota, Hayato Sato, Takahiro Iwai, Jun'ichi Kobayashi

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

3 Citations (Scopus)

Abstract

The biogenetic origins of amphidinin A (1) and amphidinolide P (2) were investigated by feeding experiments with ¹³C-labeled acetates. ¹³C-NMR data of ¹³C-enriched samples revealed that the all carbons of 1 and 2 were derived from acetates. The polyketide chain of 1 was formed from one triketide chain, two diketide chains, and three unusual isolated C₁ units derived from C-2 of cleaved acetates, while the polyketide chain of 2 was formed from one pentaketide chain, two acetate units, and three unusual isolated C₁ units derived from C-2 of cleaved acetates. The all branched C₁ units of 1 and 2 were derived from C-2 of cleaved acetates.

Original language	English
Pages (from-to)	979-981
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	64
Issue number	7
DOIs	https://doi.org/10.1248/cpb.c16-00202
Publication status	Published - 2016
Externally published	Yes

Keywords

Amphidinin A
Amphidinium sp.
Amphidinolide P
Biosynthesis
Marine dinoflagellate
Polyketide

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.c16-00202

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title = "Biosynthetic study of amphidinin A and Amphidinolide P",

abstract = "The biogenetic origins of amphidinin A (1) and amphidinolide P (2) were investigated by feeding experiments with 13C-labeled acetates. 13C-NMR data of 13C-enriched samples revealed that the all carbons of 1 and 2 were derived from acetates. The polyketide chain of 1 was formed from one triketide chain, two diketide chains, and three unusual isolated C1 units derived from C-2 of cleaved acetates, while the polyketide chain of 2 was formed from one pentaketide chain, two acetate units, and three unusual isolated C1 units derived from C-2 of cleaved acetates. The all branched C1 units of 1 and 2 were derived from C-2 of cleaved acetates.",

keywords = "Amphidinin A, Amphidinium sp., Amphidinolide P, Biosynthesis, Marine dinoflagellate, Polyketide",

author = "Takaaki Kubota and Hayato Sato and Takahiro Iwai and Jun'ichi Kobayashi",

note = "Funding Information: We thank Dr. E. Fukushi, Graduate School of Agriculture, Hokkaido University, for measurements of INADEQUATE spectrum. This work was partially supported by the Naito Foundation, the Takeda Science Foundation, MEXT-Supported Program for the Strategic Research Foundation at Private Universities (2013-2017), and JSPS KAKENHI Grant Number 23108502. Publisher Copyright: {\textcopyright} 2016 The Pharmaceutical Society of Japan.",

year = "2016",

doi = "10.1248/cpb.c16-00202",

language = "English",

volume = "64",

pages = "979--981",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "7",

}

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T1 - Biosynthetic study of amphidinin A and Amphidinolide P

AU - Kubota, Takaaki

AU - Sato, Hayato

AU - Iwai, Takahiro

AU - Kobayashi, Jun'ichi

N1 - Funding Information: We thank Dr. E. Fukushi, Graduate School of Agriculture, Hokkaido University, for measurements of INADEQUATE spectrum. This work was partially supported by the Naito Foundation, the Takeda Science Foundation, MEXT-Supported Program for the Strategic Research Foundation at Private Universities (2013-2017), and JSPS KAKENHI Grant Number 23108502. Publisher Copyright: © 2016 The Pharmaceutical Society of Japan.

PY - 2016

Y1 - 2016

N2 - The biogenetic origins of amphidinin A (1) and amphidinolide P (2) were investigated by feeding experiments with 13C-labeled acetates. 13C-NMR data of 13C-enriched samples revealed that the all carbons of 1 and 2 were derived from acetates. The polyketide chain of 1 was formed from one triketide chain, two diketide chains, and three unusual isolated C1 units derived from C-2 of cleaved acetates, while the polyketide chain of 2 was formed from one pentaketide chain, two acetate units, and three unusual isolated C1 units derived from C-2 of cleaved acetates. The all branched C1 units of 1 and 2 were derived from C-2 of cleaved acetates.

AB - The biogenetic origins of amphidinin A (1) and amphidinolide P (2) were investigated by feeding experiments with 13C-labeled acetates. 13C-NMR data of 13C-enriched samples revealed that the all carbons of 1 and 2 were derived from acetates. The polyketide chain of 1 was formed from one triketide chain, two diketide chains, and three unusual isolated C1 units derived from C-2 of cleaved acetates, while the polyketide chain of 2 was formed from one pentaketide chain, two acetate units, and three unusual isolated C1 units derived from C-2 of cleaved acetates. The all branched C1 units of 1 and 2 were derived from C-2 of cleaved acetates.

KW - Amphidinin A

KW - Amphidinium sp.

KW - Amphidinolide P

KW - Biosynthesis

KW - Marine dinoflagellate

KW - Polyketide

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DO - 10.1248/cpb.c16-00202

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AN - SCOPUS:84978042644

SN - 0009-2363

VL - 64

SP - 979

EP - 981

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 7

ER -

Biosynthetic study of amphidinin A and Amphidinolide P

Abstract

Keywords

ASJC Scopus subject areas

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