Mohangic Acids A-E, p-Aminoacetophenonic Acids from a Marine-Mudflat-Derived Streptomyces sp

J Nat Prod. 2016 Feb 26;79(2):332-9. doi: 10.1021/acs.jnatprod.5b00956. Epub 2016 Jan 22.

Abstract

Mohangic acids A-E (1-5) were isolated from a marine Streptomyces sp. collected from a mudflat in Buan, Republic of Korea. Comprehensive spectroscopic analysis revealed that the mohangic acids are new members of the p-aminoacetophenonic acid class. The relative and absolute configurations of the mohangic acids were determined by J-based configuration analysis and by the application of bidentate chiral NMR solvents followed by (13)C NMR analysis, chemical derivatization, and circular dichroism spectroscopy. Mohangic acid E (5), which is the first glycosylated compound in the p-aminoacetophenonic acid family, displayed significant quinone reductase induction activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry
  • Acetophenones / isolation & purification*
  • Acetophenones / pharmacology
  • Algorithms
  • Drug Screening Assays, Antitumor
  • Kenya
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Quinone Reductases / metabolism
  • Streptomyces / chemistry*

Substances

  • Acetophenones
  • mohangic acid A
  • Quinone Reductases