Chemistry:Robinin
Robinin (IUPAC: kaempferol-3-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranoside-7-O-(6-deoxy-α-L-mannopyranosyl)oxy) is a naturally occurring flavonoid glycoside, classified as a flavonol O-glycoside.[1] or from the common locust Robinia pseudoacacia.[2] It is chemically derived as a flavone glycoside from the aglycone Kaempferol, and occurs naturally in several plant species.[3]
Robinin is found in plants of the family Fabaceae, particularly in the genus Robinia, such as Robinia pseudoacacia (black locust or robinia). It has also been reported in other genera, including Vigna and Pueraria.[4]
Chemical properties
Robinin has the molecular formula C
33H
40O
19 and a molecular weight of 740.66 g/mol.[5]
It is a diglycoside of kaempferol, with sugar moieties attached at the -3 and -7 positions of the flavonol skeleton. These sugars include rhamnose and galactose residues linked through glycosidic bonds.[6]
Biological activities and applications
Preliminary research suggests that robinin exhibits anti-inflammatory, antibacterial, and cardioprotective properties.[7] It has been reported to inhibit the TLR4/NF-κB signaling pathway in human peripheral blood mononuclear cells and to reduce cardiotoxicity in animal models.
While robinin has demonstrated bioactivity in laboratory studies, it currently has no approved therapeutic or pharmacological use in humans.[8]
See also
- Flavonoid glycoside
- Kaempferol
- Robinose
References
- ↑ Akhmedzhanova, V. (1986). "Robinin and kaempfereol fromVinca erecta". Chemistry of Natural Compounds 22 (5): 601–602. doi:10.1007/BF00599275. Bibcode: 1986CNatC..22..601A.
- ↑ Sando, Charles E. (1932). "The Plant Coloring Matter, Robinin". Journal of Biological Chemistry 94 (3): 675–680. doi:10.1016/s0021-9258(18)76392-8.
- ↑ "Robinin - ChemicalBook". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0109097.htm.
- ↑ "Robinin - Product Data". https://www.chemicalbook.com/ProductChemicalPropertiesCB0109097_EN.htm.
- ↑ "Robinin - Chemical Properties". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0109097.htm.
- ↑ "Robinin - PubChem". https://pubchem.ncbi.nlm.nih.gov/compound/Robinin.
- ↑ "Robinin - GLPBio Product Information". https://www.glpbio.com/robinin.html.
- ↑ "Natural Flavonoids and Polyphenols Review". https://www.mdpi.com/1422-0067/26/19/9546.
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