Trifolin

Trifolin
Names

IUPAC name 3-(β-D-Galactopyranosyloxy)-4′,5,7-trihydroxyflavone
Systematic IUPAC name 5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names Kaempferol 3-O-β-D-galactoside Kaempferol-3-O-galactoside
Identifiers
CAS Number	23627-87-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:31742^Y
ChemSpider	10306173
KEGG	C12626^Y
PubChem CID	5282149
UNII	7CKD5ET5SP^Y
CompTox Dashboard (EPA)	DTXSID30946447
InChI InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21+/m1/s1 Key: JPUKWEQWGBDDQB-DTGCRPNFSA-N
SMILES C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
Properties
Chemical formula	C₂₁H₂₀O₁₁
Molar mass	448.37 g/mol
Density	1.791 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trifolin is a chemical compound. It is the kaempferol 3-galactoside. It can be found in Camptotheca acuminata,^[1] in Euphorbia condylocarpa^[2] or in Consolida oliveriana.^[3]

Kaempferol 3-O-galactosyltransferase is an enzyme that catalyzes the chemical reaction:
UDP-galactose + kaempferol → UDP + kaempferol 3-O-beta-D-galactoside (trifolin).^[4] It can also be found in seedlings of Vigna mungo.^[5]

References

^ Li, S.; Zhang, Z.; Cain, A.; Wang, B.; Long, M.; Taylor, J. (2005). "Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated fromCamptotheca acuminata". Journal of Agricultural and Food Chemistry. 53 (1): 32–37. doi:10.1021/jf0484780. PMID 15631505.
^ Roshchin, Y. V. (1977). "Trifolin from Euphorbia condylocarpa". Chemistry of Natural Compounds. 13 (4): 481–482. doi:10.1007/BF00565849. S2CID 4813721.
^ Díaz, J. S.; Carmona, A.; Torres, F.; Quintana, J.; Estévez, F.; Herz, W. (2008). "Cytotoxic Activities of Flavonoid Glycoside Acetates from Consolida oliveriana". Planta Medica. 74 (2): 171–174. doi:10.1055/s-2008-1034278. PMID 18214815. S2CID 1783362.
^ Miller, K. D.; Guyon, V.; Evans, J. N.; Shuttleworth, W. A.; Taylor, L. P. (1999). "Purification, Cloning, and Heterologous Expression of a Catalytically Efficient Flavonol 3-O-Galactosyltransferase Expressed in the Male Gametophyte of Petunia hybrida". Journal of Biological Chemistry. 274 (48): 34011–34019. doi:10.1074/jbc.274.48.34011. PMID 10567367.
^ "Partial Purification and Some Properties of Flavonol 3-O-Glycosyltransferases from Seedlings of Vigna mungo, with Special Reference to the Formation of Kaempferol 3-O-Galactoside and 3-O-Glucoside". Plant and Cell Physiology. 34 (2): 329–335. March 1993. doi:10.1093/oxfordjournals.pcp.a078424. ISSN 1471-9053.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin
Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin
Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

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This page was last edited on 1 March 2024, at 09:24