B9938
Calycosin
≥98% (HPLC)
Synonym(s):
3′,7-Dihydroxy-4′-methoxy-isoflavone, 3′-Hydroxyformononetin, Cyclosin
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About This Item
Empirical Formula (Hill Notation):
C16H12O5
CAS Number:
Molecular Weight:
284.26
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.25
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Assay
≥98% (HPLC)
form
powder
color
white to light yellow
solubility
methanol: 1 mg/mL, clear, colorless
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
2-8°C
SMILES string
O=C1C(C(C=C2)=CC(O)=C2OC)=COC3=CC(O)=CC=C13
InChI
1S/C16H12O5/c1-20-14-5-2-9(6-13(14)19)15-8-12(18)11-4-3-10(17)7-16(11)21-15/h2-8,17,19H,1H3
InChI key
QAGGICSUEVNSGH-UHFFFAOYSA-N
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General description
Calycosin is a plant estrogen exhibiting both agonistic and antagonistic attitude towards estrogen. It is an isoflavone, occurring as the primary component of the Radix astragali extract.
Application
Calycosin has been used:
- to study its effect on the repression of glioblastomas by having an inhibitory effect on the expression of tyrosine-protein kinase Met (c-Met)
- to analyze its effect on the growth of nasopharyngeal carcinoma cells by modulating the long non-coding RNA, Ewing sarcoma-associated transcript 1(EWSAT1)
- to evaluate its effect on the left ventricular ejection fraction in rat model with myocardial ischemia
Biochem/physiol Actions
Calycosin exhibits various therapeutic properties such as anti-inflammatory, antioxidant, antiviral, and neuroprotective effects. It is shown to exercise its anticarcinogenic effects against the cluster of breast cancer, osteosarcoma, hepatocellular carcinoma, and colorectal cancer. It is also being promoted as a probable treatment for myocardial infarction due to its ability to hasten the process of angiogenesis and increase the expression of vascular endothelial growth factor (VEGF). It has been found to show hyperpermeability induced by the conditions of low osmolarity. Finally, calycosin is being suggested to be used as a prodrug for the treatment of hypoxia-related vascular diseases.
Isoflavone and phytoestrogen isolated froma traditional Chinese medicinal herb. Calycosin induces angiogenesis in HUVEC and promotes proliferation of estrogen-receptor positive cells in vivo and in vitro. Also functions as a vasorelaxant on rat thoracic aorta.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Sens. 1
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Guang Hu et al.
Xenobiotica; the fate of foreign compounds in biological systems, 42(3), 294-303 (2011-10-04)
Although zebrafish has become a popular animal model for drug discovery and screening, drug metabolism in zebrafish remains largely unknown. In this study, we probed the metabolic capability of zebrafish larvae with calycosin, one of the major isoflavone constituents of
Yan Zhou et al.
Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine, 36(7), 5333-5339 (2015-02-13)
Calycosin is widely used as a natural active compound for its anti-oxidative and anti-inflammation activity. Recently, several studies have shown that calycosin can inhibit growth and induce apoptosis in human cancer cell lines; however, the mechanisms are not completely clarified
Dongqing Zhang et al.
Oxidative medicine and cellular longevity, 2012, 209843-209843 (2012-08-01)
Flavonoids are found in most parts of plants and have been shown to have multiple biological activities such as anticancer, anti-inflammation, antibacteria, antivirus, and immune-stimulation. Existing data showed that the total flavonoids of Astragalus (TFA) can provide biological system with
Jian Chen et al.
JPEN. Journal of parenteral and enteral nutrition, 35(6), 763-769 (2011-07-30)
Calycosin is one of main components in the herb radix astragali and is considered a typical phytoestrogen. It has either estrogenic or antiestrogenic effects that mainly depend on estrogen levels in vivo. This study investigated the effects and mechanisms of
Chao Guo et al.
Journal of ethnopharmacology, 144(3), 768-774 (2012-11-06)
Radix Astragali has been commonly used as traditional herbal medicine in China for reinforcing vital energy, strengthening superficial resistance and promoting the discharge of pus and the growth of new tissue. The present study was to investigate the neuroprotective effect
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