α-Pyrones with Diverse Hydroxy Substitutions from Three Marine-Derived Nocardiopsis Strains

Haibo Zhang, Kumar Saurav, Ziquan Yu, Attila Mándi, Tibor Kurtán, Jie Li, Xinpeng Tian, Qingbo Zhang, Wenjun Zhang, Changsheng Zhang

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20 Citations (Scopus)

Abstract

Eight new α-pyrones 1-8 and three known α-pyrones 9-11 were isolated from three marine-derived Nocardiopsis strains SCSIO 10419, SCSIO 04583, and SCSIO KS107. The structures of compounds 1-8 were elucidated by comprehensive spectral analyses. The absolute configurations of 4-deoxyphomapyrone C (1), 4-deoxy-11-hydroxyphomapyrone C (3), 4-deoxy-7R-hydroxyphomapyrone C (5), and phomapyrone C (11) were determined by TDDFT-ECD calculations for the solution conformers, which revealed that the conformation of the side chain was decisive for the sign of the characteristic high-wavelength ECD transition. (-)-4-Deoxy-8-hydroxyphomapyrone C (4) was isolated from SCSIO 10419 and was deduced as a diastereomeric mixture containing (8S)- and (8R)-4-deoxy-8-hydroxyphomapyrone C in a ratio of 2.6:1 (8R:8S), by chiral-phase HPLC analysis and Mosher's ester analysis. Interestingly, 7-hydroxymucidone (9) was isolated from both SCSIO 04583 and SCSIO KS107, as an enantiomeric mixture containing (7S)-hydroxymucidone (major in 9 from SCSIO 04583) and (7R)-hydroxymucidone (major in 9 from SCSIO KS107). α-Pyrones 3-5 were identified as three isomers of phomapyrone C (11) with diverse hydroxy substitutions. α-Pyrones 10-hydroxymucidone (6), 4-hydroxymucidone (8), and 9, differed in the position of the hydroxy group. Several α-pyrones exhibited moderate growth inhibitory activity against Micrococcus luteus and Bacillus subtilis.

Original languageEnglish
Pages (from-to)1610-1618
Number of pages9
JournalJournal of Natural Products
Volume79
Issue number6
DOIs
Publication statusPublished - Jun 24 2016

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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  • Cite this

    Zhang, H., Saurav, K., Yu, Z., Mándi, A., Kurtán, T., Li, J., Tian, X., Zhang, Q., Zhang, W., & Zhang, C. (2016). α-Pyrones with Diverse Hydroxy Substitutions from Three Marine-Derived Nocardiopsis Strains. Journal of Natural Products, 79(6), 1610-1618. https://doi.org/10.1021/acs.jnatprod.6b00175