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

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11 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 languageEnglish
Pages (from-to)1406-1409
Number of pages4
JournalOrganic Letters
Volume19
Issue number6
DOIs
Publication statusPublished - 2017 Mar 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Igarashi, Y., Matsuoka, N., In, Y., Kataura, T., Tashiro, E., Saiki, I., Sudoh, Y., Duangmal, K., & Thamchaipenet, A. (2017). Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp. Organic Letters, 19(6), 1406-1409. https://doi.org/10.1021/acs.orglett.7b00318