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Calycosin-7-O-beta-D-glucoside

Names

[ CAS No. ]:
20633-67-4

[ Name ]:
Calycosin-7-O-beta-D-glucoside

[Synonym ]:
N1413
4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-3-(3-hydroxy-4-methoxyphenyl)-
3-(3-Hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl β-D-glucopyranoside
calycosin-7-O-beta-D-glucoside
Calycosin-7-glucoside
Calycosin-7-O-β-D-glucoside
Calycosin 7-O-β-D-glucopyranoside

Biological Activity

[Description]:

Calycosin-7-O-β-D-glucoside, a melanin biosynthesis inhibitor, is isolated from the methanol extract of astragalus. IC50 value: 68 μM in inhibition of Tyrosinase Target:In vitro: Calycosin-7-O-β-d-glucoside showed a melanin biosynthesis inhibition zone in a culture plate of Streptomyces bikiniensis. Furthermore, 75.78 μM of calycosin-7-O-β-d-glucoside dramatically decreased 50% of the melanin content on Melan-a cells without any apparent cytotoxicity [1]. Calycosin-7-O-β-D-glucoside was revealed to scavenge NO, inhibit the activities of MMP-2 and MMP-9, and attenuate cell death in the in vitro cultured brain microvascular endothelial cells under OGD condition.In vivo: Calycosin-7-O-β-D-glucoside treatment significantly reduced infarct volume, histological damage and blood–brain barrier permeability in the in vivo MCAO ischemia–reperfusion rat model [2]. To reveal its physiological functions under stress, seedlings with different isoflavonoid levels were established using a phenylalanine ammonia lyase (PAL) enzyme inhibitor, l-α-aminooxy-β-phenylpropionic acid (AOPP). The results showed that the significant promotion of antioxidant capacity in this species might be associated with the remarkable accumulation of Calycosin-7-O-β-D-glucoside after cold pretreatment. The results provided the first evidence that a type of isoflavonoid, Calycosin-7-O-β-D-glucoside, might play a very important role against freezing stress in vivo [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Natural Products >> Flavonoids
Research Areas >> Others

[References]

[1]. Jin Hee Kim, et al. Melanin biosynthesis inhibitory effects of calycosin-7-O -β-d -glucoside isolated from astragalus (Astragalus membranaceus ). Food Science and Biotechnology December 2011, Volume 20, Issue 6, pp 1481-1485

[2]. Shuping Fu, et al. Calycosin-7-O-β-d-glucoside regulates nitric oxide /caveolin-1/matrix metalloproteinases pathway and protects blood–brain barrier integrity in experimental cerebral ischemia–reperfusion injury. Journal of Ethnopharmacology Volume 155,

[3]. Haiyun Pan, et al. Evidence of calycosin-7-O-β-d-glucoside's role as a major antioxidant molecule of Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao plants under freezing stress. Environmental and Experimental Botany Volume 109, January 2015,


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
745.2±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C22H22O10

[ Molecular Weight ]:
446.404

[ Flash Point ]:
262.0±26.4 °C

[ Exact Mass ]:
446.121307

[ PSA ]:
159.05000

[ LogP ]:
0.09

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.675

Safety Information

[ RIDADR ]:
NONH for all modes of transport


Related Compounds