Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp.

Yasuhiro Igarashi; Noriaki Matsuoka; Yasuko In; Tetsushi Kataura; Etsu Tashiro; Ikuo Saiki; Yuri Sudoh; Kannika Duangmal; Arinthip Thamchaipenet

doi:10.1021/acs.orglett.7b00318

Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp.

Yasuhiro Igarashi, Noriaki Matsuoka, Yasuko In, Tetsushi Kataura, Etsu Tashiro, Ikuo Saiki, Yuri Sudoh, Kannika Duangmal, Arinthip Thamchaipenet

Department of Biosciences and Informatics

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

14 Citations (Scopus)

Abstract

Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.

Original language	English
Pages (from-to)	1406-1409
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.7b00318
Publication status	Published - 2017 Mar 17

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp. / Igarashi, Yasuhiro; Matsuoka, Noriaki; In, Yasuko; Kataura, Tetsushi; Tashiro, Etsu; Saiki, Ikuo; Sudoh, Yuri; Duangmal, Kannika; Thamchaipenet, Arinthip.

In: Organic Letters, Vol. 19, No. 6, 17.03.2017, p. 1406-1409.

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

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abstract = "Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.",

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AU - Igarashi, Yasuhiro

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AU - In, Yasuko

AU - Kataura, Tetsushi

AU - Tashiro, Etsu

AU - Saiki, Ikuo

AU - Sudoh, Yuri

AU - Duangmal, Kannika

AU - Thamchaipenet, Arinthip

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AB - Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.

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Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp.

Abstract

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