CALYCOSIN

Definition

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L. Calycosin is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position. It has a role as a metabolite and an antioxidant. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It derives from an isoflavone. It is a conjugate acid of a calycosin(1-).

Pharmaceutical Properties

The potential pharmaceutical properties of calycosin in the treatment of tumors, inflammation, stroke, and cardiovascular diseases have gained increasing attention in the recent years. The literature survey showed that calycosin exhibits promising effects for the treatment of several diseases and that these effects may be due to its isoflavonoid and phytoestrogenic properties. The effects of calycosin most likely result from its interaction with the ER receptors on the cell membrane and the modulation of the MAPK signaling pathway.
Through its effect on this pathway, calycosin can regulate several cell activities, such as apoptosis and angiogenesis, which enables its therapeutic functions. 

Chemical Properties

White crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Astragalus membranaceus.

Uses

Calycosin is a known antioxidant that prevent redox imbalance in organisms. Also, it possesses anti-tumor, anti-inflammation and osteogenic properties; Useful as a therapeutic reagent for bone loss-associated diseases.

Definition

ChEBI: Calycosin is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position. It has a role as a metabolite and an antioxidant. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It is functionally related to an isoflavone. It is a conjugate acid of a calycosin(1-).

Biological Activity

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 r at thoracic aorta.

Synthesis

1131-94-8

68-12-2

108-46-3

20575-57-9

1. Resorcinol (3 mmol) and 3-hydroxy-4-methoxyphenylacetic acid (3 mmol) were dissolved in freshly distilled boron trifluoride ethyl ether solution (2 mL), heated to 85-90 °C and stirred magnetically for 6-10 hours (monitored by TLC until the raw material essentially disappears). Upon completion of the reaction, cooled to 10 °C, N,N-dimethylformamide (5 mL) was added slowly and dropwise to give mixture I. The reaction was carried out in the presence of N,N-dimethylformamide (5 mL). 2. Preparation of Vilsmeier-Haack reagent: N,N-dimethylformamide (8.1 mL) was cooled to 10 °C, phosphorus pentachloride (5 mmol) was added in batches, followed by heating to 55 °C and magnetic stirring for 1 h to give a light red or yellow mixture II. 3. Within 30 minutes, mixture II was added to mixture I in batches and stirred at room temperature for 3 hours. Subsequently, the reaction solution was poured into methanolized hydrochloric acid (0.1 mol/L, 30 mL), heated to 70 °C, kept at a constant temperature for 50 min, and then left to stand. 4. The reaction solution was concentrated by distillation under reduced pressure, washed with 150 mL of water and subsequently extracted with ethyl acetate (150 mL × 3 times). The organic phase was washed with water (150 mL x 2 times) and dried by rotary evaporation (filtered over a large amount of ethyl acetate extract to remove some impurities). 5. Some of the pigments were precipitated by suspension in a small amount of ethanol, centrifuged and filtered, and crystallized with hot ethanol, the operation being carried out under nitrogen protection. 6. Finally, the target product gross isoflavones (1.6 mmol) was obtained in 50-60% yield by silica gel column chromatography using methanol: dichloromethane = 1:35 as the unfolding agent.

in vivo

References

[1] Patent: CN106749453, 2017, A. Location in patent: Paragraph 0091-0096