Calycosin

Names

[ CAS No. ]:
20575-57-9

[ Name ]:
Calycosin

[Synonym ]:
7,5'-dihydroxy-4'-methoxyisoflavone
4H-1-Benzopyran-4-one, 7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-
7,3'-dihydroxy-4'-methoxyisoflavone
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one
3'-hydroxyformononetin
3',7-Dihydroxy-4'-methoxy-isoflavone
Calycosin
3',7-dihydroxy-4'-methoxyisoflavone
7,3'-dihydroxy-4'-methoxyisoflavanon-2-ene

Biological Activity

[Description]:

Calycosin (Cyclosin) is a natural active compound with anti-oxidative and anti-inflammation activity.IC50 value:Target: in vitro: calycosin had obvious anti-proliferation effects on SKOV3 cells in a dose- and time-dependent manner. calycosin up-regulated the Bax/Bcl-2 ratio and cleaved caspase-3, cleaved caspase-9 expression in a dose-dependent manner. In summary, calycosin might exert anti-growth and induce-apoptosis activity against ovarian cancer SKOV3 cells through activating caspases and Bcl-2 family proteins, therefore presenting as a promising therapeutic agent for the treatment of ovarian cancer [1]. Both calycosin and genistein inhibited proliferation and induced apoptosis in MCF-7 breast cancer cells, especially after treatment with calycosin. Treatment of MCF-7 cells with calycosin or genistein resulted in decreased phosphorylation of Akt, and decreased expression of its downstream target, HOTAIR [2]. incubation of calycosin resulted in enhanced expression ERβ in MCF-7 and T-47D cells, rather than MDA-231 and MDA-435 cells. Moreover, with the upregulation of ERβ, successive changes in downstream signaling pathways were found, including inactivation of insulin-like growth factor 1 receptor (IGF-1R), then stimulation of p38 MAPK and suppression of the serine/threonine kinase (Akt), and finally poly(ADP-ribose) polymerase 1 (PARP-1) cleavage [3].in vivo: calycosin stimulated a dramatic increase in uterine weight and downregulated the level of ERα protein in OVX mice [4].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Flavonoids

[References]

[1]. Zhou Y, et al. Calycosin induces apoptosis in human ovarian cancer SKOV3 cells by activating caspases and Bcl-2 family proteins. Tumour Biol. 2015 Feb 12.

[2]. Chen J, et al. Calycosin and genistein induce apoptosis by inactivation of HOTAIR/p-Akt signaling pathway in human breast cancer MCF-7 cells. Cell Physiol Biochem. 2015;35(2):722-8.

[3]. Chen J, et al. Calycosin suppresses breast cancer cell growth via ERβ-dependent regulation of IGF-1R, p38 MAPK and PI3K/Akt pathways. PLoS One. 2014 Mar 11;9(3):e91245.

[4]. Chen J, et al. Calycosin promotes proliferation of estrogen receptor-positive cells via estrogen receptors and ERK1/2 activation in vitro and in vivo. Cancer Lett. 2011 Sep 28;308(2):144-51.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
536.8±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₆H₁₂O₅

[ Molecular Weight ]:
284.263

[ Flash Point ]:
205.7±23.6 °C

[ Exact Mass ]:
284.068481

[ PSA ]:
79.90000

[ LogP ]:
2.41

[ Appearance of Characters ]:
white to light yellow

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.669

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
methanol: soluble1mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Hazard Codes ]:
T

[ Risk Phrases ]:
25

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 3462 6.1 / PGIII

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

Thermal stability of kudzu root (Pueraria Radix) isoflavones as additives to beef patties.

J. Food Sci. Technol. 52(3) , 1578-85, (2015)

Kudzu root, Pueraria radix, extracts are a rich source of isoflavones. This study investigates the thermal stability of Pueraria radix extracts as a natural nutraceutical supplement in beef patties. T...

Calycosin orchestrates the functions of Danggui Buxue Tang, a Chinese herbal decoction composing of Astragali Radix and Angelica Sinensis Radix: An evaluation by using calycosin-knock out herbal extract.

J. Ethnopharmacol. 168 , 150-7, (2015)

Danggui Buxue Tang (DBT) is a classical Chinese herbal decoction containing two herbs, Astragali Radix (AR) and Angelicae Sinensis Radix (ASR), which serves as dietary supplement for treating women me...

Protective effects of calycosin against CCl4-induced liver injury with activation of FXR and STAT3 in mice.

Pharm. Res. 32(2) , 538-48, (2015)

Investigating the hepatoprotective effect of calycosin against acute liver injury in association with FXR activation and STAT3 phosphorylation.The acute liver injury model was established by intraperi...