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Chemical Compound Review:

Calycosin 7-hydroxy-3-(3-hydroxy-4- methoxy...

Synonyms: SureCN73013, CHEMBL241608, CPD-9539, CHEBI:17793, MEGxp0_001325, ...

Fan, Y. et al., Shen, P. et al., Ma, X. et al., Du, X. et al., Ohkawara, S. et al., et al.

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Disease relevance of C01562

Effects of calycosin on the impairment of barrier function induced by hypoxia in human umbilical vein endothelial cells [1].
Calycosin (5) exhibited selective toxicity against Trypanosoma brucei brucei (IC50 12.7 microM) compared to L. donovani amastigotes and Vero cells (IC50 100 and 159 microM, respectively) [2].

High impact information on C01562

At low doses, only biochanin A and formononetin, but not genistein, calycosin, or daidzein, activated PPARgamma-driven reporter-gene activity and induced differentiation of 3T3-L1 preadipocytes [3].
Bioassay-guided fractionation resulted in the isolation of the isoflavones, formononetin, and calycosin from Astragalus membranaceus, and daidzein from Pueraria thomsonii as the PPAR-activating compounds [3].
The inhibitory effects of astrapterocarpan, formononetin, and calycosin isolated from Astragalus membraneceus on platelet-derived growth factor (PDGF)-BB-induced proliferative response in rat vascular smooth muscle cells (A10 cells) were investigated [4].
These findings indicate that calycosin protected endothelial cells from hypoxia-induced barrier impairment by increasing intracellular energetic sources and promoting regeneration of the cAMP level, as well as improving cytoskeleton remodeling [1].
Application of calycosin inhibited the hypoxia-induced increase in endothelial permeability in a dose-dependent fashion, which is compatible with inhibition of lactate dehydrogenase release, decrease of the fall in ATP and cAMP contents, and improvement of F-actin rearrangements [1].

Anatomical context of C01562

The relaxant effect of calycosin on denuded endothelium aortic rings was the same as on intact endothelium aortic rings, and its vasorelaxant effect was not influenced by L-NAME or indomethacin [5].
Calycosin exhibits the most potent antioxidant activity both in the cell-free system and in the cell system [6].

Associations of C01562 with other chemical compounds

Four 3'-hydroxy-4'-methoxy-isoflavonoids: calycosin-7-O-beta-D-glucopyranoside (1), calycosin (2), pratensein-7-O-beta-D-glucopyranoside (3), and pratensein (4) were isolated from Astragalus membranaceus var. mongholicus, among which compound 4 was obtained from this plant for the first time [7].
Formononetin and calycosin were found to inhibit XA/XO-induced cell injury significantly, with an estimated EC50 of 50 ng/mL [6].

Analytical, diagnostic and therapeutic context of C01562

From 200 mg of the crude extract, 14.8 mg of calycosin was obtained at over 99% purity as determined by HPLC analysis, and its chemical structure was confirmed by MS, 1H and 13C nuclear magnetic resonance [8].

References

Effects of calycosin on the impairment of barrier function induced by hypoxia in human umbilical vein endothelial cells. Fan, Y., Wu, D.Z., Gong, Y.Q., Zhou, J.Y., Hu, Z.B. Eur. J. Pharmacol. (2003) [Pubmed]
Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities. Salem, M.M., Werbovetz, K.A. J. Nat. Prod. (2006) [Pubmed]
Differential effects of isoflavones, from Astragalus membranaceus and Pueraria thomsonii, on the activation of PPARalpha, PPARgamma, and adipocyte differentiation in vitro. Shen, P., Liu, M.H., Ng, T.Y., Chan, Y.H., Yong, E.L. J. Nutr. (2006) [Pubmed]
Astrapterocarpan isolated from Astragalus membranaceus inhibits proliferation of vascular smooth muscle cells. Ohkawara, S., Okuma, Y., Uehara, T., Yamagishi, T., Nomura, Y. Eur. J. Pharmacol. (2005) [Pubmed]
Calcium channel blocking activity of calycosin, a major active component of Astragali Radix, on rat aorta. Wu, X.L., Wang, Y.Y., Cheng, J., Zhao, Y.Y. Acta Pharmacol. Sin. (2006) [Pubmed]
Studies of chemical constituents and their antioxidant activities from Astragalus mongholicus Bunge. Yu, D.H., Bao, Y.M., Wei, C.L., An, L.J. Biomed. Environ. Sci. (2005) [Pubmed]
Solvent effect in 1H NMR spectra of 3'-hydroxy-4'-methoxy isoflavonoids from Astragalus membranaceus var. mongholicus. Du, X., Bai, Y., Liang, H., Wang, Z., Zhao, Y., Zhang, Q., Huang, L. Magnetic resonance in chemistry : MRC. (2006) [Pubmed]
Preparative isolation and purification of calycosin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography. Ma, X., Zhang, T., Wei, Y., Tu, P., Chen, Y., Ito, Y. Journal of chromatography. A. (2002) [Pubmed]

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