Robinin
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| Names | |
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| IUPAC name
4′,5-Dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranosyloxy]-7-(α-L-rhamnopyranosyloxy)flavone
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| Systematic IUPAC name
(12S,13R,14R,15R,16S,52S,53R,54S,55R,56R,82R,83R,84R,85R,86S)-13,14,15,35,53,54,55,83,84,85-Decahydroxy-32-(4-hydroxyphenyl)-16,86-dimethyl-34H-2,4,7-trioxa-3(7,3)-[1]benzopyrana-1,8(2),5(2,6)-tris(oxana)octaphan-34-one | |
| Other names | |
| Identifiers | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C33H40O19 | |
| Molar mass | 740.66 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
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 Page Module:Chem2/styles.css has no content.C33H40O19 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
References
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- ^ Page Module:Citation/CS1/styles.css has no content.Akhmedzhanova, V. (1986). "Robinin and kaempfereol fromVinca erecta". Chemistry of Natural Compounds. 22 (5): 601–602. Bibcode:1986CNatC..22..601A. doi:10.1007/BF00599275. S2CID 4827681.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content."Robinin - ChemicalBook". ChemicalBook. Retrieved 30 October 2025.
- ^ Page Module:Citation/CS1/styles.css has no content."Robinin - Product Data". ChemicalBook. Retrieved 30 October 2025.
- ^ Page Module:Citation/CS1/styles.css has no content."Robinin - Chemical Properties". ChemicalBook. Retrieved 30 October 2025.
- ^ Page Module:Citation/CS1/styles.css has no content."Robinin - PubChem". PubChem. Retrieved 30 October 2025.
- ^ Page Module:Citation/CS1/styles.css has no content."Robinin - GLPBio Product Information". GLPBio. Retrieved 30 October 2025.
- ^ Page Module:Citation/CS1/styles.css has no content."Natural Flavonoids and Polyphenols Review". MDPI International Journal of Molecular Sciences. Retrieved 30 October 2025.
