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Calycosin 7-O-β-D-glucopyranoside

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-C1005

  • Specification : 98%

  • CAS number : 20633-67-4

  • Formula : C22H22O10

  • Molecular Weight : 446.4

  • PUBCHEM ID : 5318267

  • Volume : 20mg

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Catalogue Number

BF-C1005

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

446.4

Appearance

White crystalline powder

Botanical Source

Astragalus membranaceus var. mongholicus

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O

Synonyms

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

IUPAC Name

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

Applications

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].

Density

1.5±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

262.0±26.4 °C

Boiling Point

745.2±60.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C22H22O10/c1-29-15-5-2-10(6-14(15)24)13-9-30-16-7-11(3-4-12(16)18(13)25)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1

InChl Key

WACBUPFEGWUGPB-MIUGBVLSSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:20633-67-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

26579475

Abstract

The isoflavone calycosin-7-O-β-d-glucopyranoside (CG) is a principal constituent of Astragalus membranaceus (AR) and has been reported to inhibit osteoclast development in vitro and bone loss in vivo. The aim of this study was to investigate the osteogenic effects of CG and its underlying mechanism in ST2 cells. The results show that exposure of cells to CG in osteogenic differentiation medium increases ALP activity, osteocalcin (Ocal) mRNA expression and the osteoblastic mineralization process. Mechanistically, CG treatment increased the expression of bone morphogenetic protein 2 (BMP-2), p-Smad 1/5/8, β-catenin and Runx2, all of which are regulators of the BMP- or wingless-type MMTV integration site family (WNT)/β-catenin-signaling pathways. Moreover, the osteogenic effects of CG were inhibited by Noggin and DKK-1 which are classical inhibitors of the BMP and WNT/β-catenin-signaling pathways, respectively. Taken together, the results indicate that CG promotes the osteoblastic differentiation of ST2 cells through regulating the BMP/WNT signaling pathways. On this basis, CG may be a useful lead compound for improving the treatment of bone-decreasing diseases and enhancing bone regeneration.
Keywords: ALP, alkaline phosphatase; AR, Astragalus membranaceus; BMP signaling pathway; BMP, bone morphogenetic protein; CG, calycosin-7-O-β-d-glucopyranoside; Calycosin-7-O-β-d-glucopyranoside; DKK-1, dickkopf-1; ECL, enhanced chemiluminescence; FGF, fibroblast growth factor; HAase, hyaluronidase; IGF1, insulin-like growth factor 1; MAPK, mitogen-activated protein kinase; MTT, 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide; OBM, osteogenic differentiation medium; OPN, osteopontin; OVX, ovariectomized; Ocal, osteocalcin; Osteoblastic differentiation; PVDF, polyvinylidine fluoride; ST2 cells; TGF-β, transforming growth factor β; WNT, wingless-type MMTV integration site family; WNT/β-catenin signaling pathway.

Title

Calycosin-7-O-β-d-glucopyranoside Stimulates Osteoblast Differentiation Through Regulating the BMP/WNT Signaling Pathways

Author

Jing Jian 1 , Lijuan Sun 1 , Xun Cheng 1 , Xiaofang Hu 1 , Jichao Liang 1 , Yong Chen 1

Publish date

2015 Sep

PMID

26246727

Abstract

Background: Calycosin-7-O-β-D-glucopyranoside (CG) is a natural isoflavone found in traditional Chinese medicines Astragali Radix (AR).
Objective: Calycosin-7-O-β-D-glucopyranoside, an isoflavone isolated from AR, has been found to have potent antioxidantive effects. This study was designed to investigate whether CG prevents oxidative stress induced by thioacetamide (TAA).
Materials and methods: BRL-3A cells were pretreated with different concentrations of CG (10, 20, 40 mg/mL) for 12 h and then exposed to 0.18 mol/L TAA for 2 h. The cell viability were examined by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium assay, total antioxidant capacity, malondialdehyde (MDA) and the activity of antioxidant enzymes, including catalase, glutathione peroxidase and superoxide dismutase were determined by microplate method. Reactive oxygen species (ROS) generation was quantified by the 2′,7′-dichlorofluorescin-diacetate method. Protein and mRNA expression of CYP2E1 were determined by western blotting and real-time PCR.
Results: The cell oxidative stress was significantly increased after 2 h of TAA exposure. Pretreatment of BRL-3A cells with CG significantly increased the activities of antioxidant enzymes, scavenged ROS and reduced MDA production. CG decreased the expression of CYP2E1, and ultimately decreased TAA-induced BRL-3A cells oxidative stress.
Conclusions: Calycosin-7-O-β-D-glucopyranoside has a protective effect against TAA-induced oxidative stress in BRL-3A cells, and that the underlying mechanism involves in scavenging of ROS and the modulating expression of CYP2E1.

Title

Protective Effect of calycosin-7-O-β-D-glucopyranoside Against Oxidative Stress of BRL-3A Cells Induced by Thioacetamide

Author

Li Jian 1 , Lin Xin 1 , Ma Yufang 1 , Huang Yifan 1

Publish date

Jul-Sep 2015

PMID

17408983

Abstract

Objective: This work was undertaken to assess the protective effect of an isoflavonoid, calycosin-7-O-beta-D-glucopyranoside (CG), isolated from Astragali radix (AR) on the pathogenesis of osteoarthritis (OA)-like lesion in a rabbit model.
Methods: Nine rabbits underwent an anterior cruciate ligament and menisectomy transection (ACLMT) of the rear knee joints to induce OA-like lesion. They were randomly divided into three groups (n=6/group): a negative control group treated with 200 microl of 0.5% (v/v) dimethyl sulfoxide (DMSO), a positive control group treated with 200 microl of 100 microM piroxicam, and a test group treated with 100 microg/500 microl of CG, where the test agents were administered by injection once a week for 4 weeks starting from the third week. Rabbits were then sacrificed to observe the progression of OA-like lesion. The synovial fluid was analyzed for the amounts of total proteins, glycosaminoglycans (GAG) and prostaglandin E(2) (PGE(2)). In addition, histopathologic analyses were performed on the OA-like articular cartilage with or without therapeutic treatments.
Results: The total synovial fluid volume (P<0.05) was most strikingly reduced by the treatment with CG. Moreover, the CG treatment also significantly alleviated the OA-induced accumulation of prostaglandin (PG) (P<0.001) and total proteins (P<0.001) in the synovial fluid. The histopathologic analyses revealed that the CG treatment reduced the severity of the OA-like structural damages in the cartilage. However, the level of PGE(2), a pathologic inflammatory molecule, was not diminished by CG or piroxicam.
Conclusion: These results indicate that the isoflavonoid CG isolated from AR significantly alleviated the pathologic changes in the OA-like rabbit knee joints. This suggests that CG from AR could be a promising treatment for the therapy of OA.

Title

Alleviation of Osteoarthritis by calycosin-7-O-beta-D-glucopyranoside (CG) Isolated From Astragali Radix (AR) in Rabbit Osteoarthritis (OA) Model

Author

S I Choi 1 , T R Heo, B-H Min, J H Cui, B H Choi, S R Park

Publish date

2007 Sep