Isolation, Stereochemical Study, and Antioxidant Activity of Benzofuranone Derivatives from a Mangrove-derived Fungus Eurotium rubrum MA-150

Ling Hong Meng, Attila Mándi, Xiao Ming Li, Yang Liu, Tibor Kurtán, Bin Gui Wang

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8 Citations (Scopus)

Abstract

Enantiomers of a 2-benzofuran-1(3H)-one derivative [(–)-1 and (+)-1] and four known analogs (2, 3, 4, 5) were isolated and identified from the culture extract of Eurotium rubrum MA–150, a fungus obtained from the mangrove-derived rizospheric soil. Their structures were established by detailed interpretation of nuclear magnetic resonance (NMR) data and the structure of (±)-1 was confirmed by single-crystal X-ray diffraction analysis. The absolute configuration of the enantiomers (–)-1 and (+)-1 was determined by means of online high-performance liquid chromatography – electronic circular dichroism (HPLC-ECD) measurements and time-dependent Density Functional Theory – electronic circular dichroism (TDDFT-ECD) calculations. Compounds (±)-1 as well as 2 and 3 exhibited potent DPPH radical scavenging activities with IC50values of 1.23, 2.26, and 3.99 μg/mL, respectively. Chirality 28:581–584, 2016.

Original languageEnglish
Pages (from-to)581-584
Number of pages4
JournalChirality
DOIs
Publication statusPublished - Jan 1 2016

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Keywords

  • DPPH
  • HPLC-ECD
  • TDDFT calculations
  • benzofuran-1(3H)-one
  • marine-derived fungus
  • radical scavenging activity

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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