Journal
CRYSTAL GROWTH & DESIGN
Volume 18, Issue 8, Pages 4724-4730Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.cgd.8b00696
Keywords
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Funding
- National Natural Science Foundation of China [21503105]
- Natural Science Foundation of Fujian Province [2015J01599, 2017J05025, 2018J01434]
- Project for Outstanding Young Talents of Fujian Provincial Universities (2016)
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A novel salt cocrystal of chrysin (ChrH) with berberine (BerbOH), [Berb(+)-Chr(-)]-2ChrH (1), was prepared. Crystal structure analysis shows one chrysin lost its proton in 7-hydroxyl group and turned into a chrysin anion. Two neutral chrysin molecules interact simultaneously with chrysin anion through charge-assisted strong hydrogen-bonding interactions between phenolic anion and hydroxyl groups of chrysin to give rise to a 1:3 salt cocrystal based on berberine and chrysin. Density functional theoretical calculations indicate that the 1:3 stoichiometry of berberine and chrysin is more stable due to its largest interaction energies. The bioavailability of chrysin in the form of cocrystal 1 in rats is about 1.7 times than that of pure chrysin.
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