Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 68, Issue 51, Pages 15115-15122Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.0c04106
Keywords
dibenzo-alpha-pyrones; chiral separation; antibacterial; antifungal
Funding
- National Key Research and Development Program of China [2017YFD0201100, 2017YFD0200500]
- National Natural Science Foundation of China [32072443, 21602109, 31572043]
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Three pairs of enantiomeric dibenzo-a-pyrone derivatives (1-3) including two pairs of new racemates (+/-)-alternaone A (1) and (+/-)-alternaone B (2) and one new enantiomer (-)-alternatiol (3), together with five known compounds (4-8) were isolated from the fungus Alternaria alternata ZHJGS. Their structures were confirmed by spectroscopic data and single-crystal X-ray diffraction analysis. All enantiomers were separated via chiral high-performance liquid chromatography, with their configurations determined by electronic circular dichroism calculation. Biogenetically, a key epoxy-rearrangement step was proposed for the formation of skeletons in 1-3; (+) 1, ( - ) 1, and 5 presented moderate antibacterial inhibition on phytopathogenic bacteria Xanthomonas oryzae pv. oryzae and Xanthomonas oryzae pv. oryzicola. In the antifungal test, compounds 7 and 8 showed a moderate protective effect against Botrytis cinerea in vivo.
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