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Characterization and Structural Analysis of Genkwanin, a Natural Product from Callicarpa americana

by Gina Porras 1,†, John Bacsa 2,†, Huaqiao Tang 1 and Cassandra L. Quave 1,3,4,*
1
Center for the Study of Human Health, Emory College of Arts and Sciences, Atlanta, GA 30322, USA
2
X-ray Crystallography Center, Emory University, 1515 Dickey Dr, Atlanta, GA 30322, USA
3
Department of Dermatology, Emory University School of Medicine, Atlanta, GA 30322, USA
4
Emory University Herbarium, Atlanta, GA 30322, USA
*
Author to whom correspondence should be addressed.
These authors contribute equally to this work.
Crystals 2019, 9(10), 491; https://doi.org/10.3390/cryst9100491
Received: 26 July 2019 / Revised: 30 August 2019 / Accepted: 18 September 2019 / Published: 24 September 2019
The natural compound Genkwanin (systematic name: 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one) C16H12O5 (1) is a non-glycosylated flavonoid isolated from Callicarpa americana. Microcrystals of Genkwanin were prepared by slow evaporation of a methanol solution under low temperature conditions. The structure of 1 was determined based on spectroscopic analyses, one-dimensional NMR, HRESIMS and was confirmed by single-crystal X-ray diffraction. The crystals grow as very thin needles with an extremely high aspect ratio and with the long axis (along the y-axis) corresponding to the very short unit cell b-axis. There are two independent molecules in the asymmetric unit with two different conformations and modes of packing in the crystal. One molecule has a higher degree on non-planarity than the other. The short stacking distance and separation between the molecules implies a high degree of co-planarity consistent with a conjugated system. The crystal structure is non-centrosymmetric but achiral. View Full-Text
Keywords: Crystal structure; Genkwanin; flavonoid; natural products; Callicarpa americana; bioactive substances; anti-bacterial and anti-tumor substances Crystal structure; Genkwanin; flavonoid; natural products; Callicarpa americana; bioactive substances; anti-bacterial and anti-tumor substances
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Porras, G.; Bacsa, J.; Tang, H.; Quave, C.L. Characterization and Structural Analysis of Genkwanin, a Natural Product from Callicarpa americana. Crystals 2019, 9, 491.

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