Calycosin-7-O-beta-D-glucoside

Modify Date: 2024-01-02 12:49:58

Calycosin-7-O-beta-D-glucoside structure	Common Name	Calycosin-7-O-beta-D-glucoside
	CAS Number	20633-67-4	Molecular Weight	446.404
	Density	1.5±0.1 g/cm3	Boiling Point	745.2±60.0 °C at 760 mmHg
	Molecular Formula	C₂₂H₂₂O₁₀	Melting Point	N/A
	MSDS	N/A	Flash Point	262.0±26.4 °C

Use of Calycosin-7-O-beta-D-glucoside

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].

Name	3-(3-hydroxy-4-methoxyphenyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonym	More Synonyms

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,

Description

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,

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