Journal
PHYTOCHEMISTRY
Volume 119, Issue -, Pages 62-69Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2015.09.005
Keywords
Androsace umbellata; Clausena excavata; Oxalis corniculata; Snakebite; Hyaluronidase inhibition; High-resolution profiling; HPLC-HRMS-SPE-NMR
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Funding
- Carlsberg Foundation
- Apotekerfonden af 1991
- Danish Agency for Science, Technology and Innovation via the National Research Infrastructure funds
- Chinese Scholarship Council
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Inhibition of the necrotizing hyaluronidase, phospholipase A(2) and protease enzymes in four snake venoms by crude water and ethanol extracts of 88 plant species used against snakebites in traditional Chinese medicine was measured. High-resolution hyaluronidase inhibition profiles were constructed for the 22 plants showing highest hyaluronidase inhibition, and the results were used to guide subsequent structural analysis towards specific hyaluronidase inhibitors. Structural analysis was performed by high-performance liquid chromatography, high-resolution mass spectrometry, solid-phase extraction and nuclear magnetic resonance spectroscopy, i.e., HPLC-HRMS-SPE-NMR. This allowed identification of four non-tannin inhibitors, i.e., lansiumamide B (6) from Clausena excavata Burm.f., myricetin 3-O-beta-D-glucopyranoside (7) from Androsace umbellata (Lour.) Men., and vitexin (8) and 4',7-dihydroxy-5-methoxyfiavone-8-C-beta-D-glucopyranoside (9) from Oxalis corniculata L. Absolute configuration of 2,3-dihydroxy-N-methyl-3-phenyl-N-[(Z)-styryl]propanamide (1) was determined using the Mosher method, which revealed two enantiomers, i.e., (2S,3R)-2,3-dihydroxy-N-methyl-3-phenyl-N-[(Z)-styryl]propanamide and (2R,3S)-2,3-dihydroxy-N-methyl-3-phenyl-N-[(Z)-styryl]propanamide with a ratio of 7:3. (C) 2015 Elsevier Ltd. All rights reserved.
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