Trifolin

Trifolin

Names
IUPAC name 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Other names Kaempferol 3-O-beta-D-galactoside Kaempferol-3-O-galactoside
Identifiers
CAS Number	23627-87-4
ChEBI	CHEBI:31742
ChemSpider	10306173
Jmol interactive 3D	Image
PubChem	5282149
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

1. 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.
2. Roshchin, Y. V. (1977). "Trifolin from Euphorbia condylocarpa". Chemistry of Natural Compounds 13 (4): 481–482. doi:10.1007/BF00565849.
3. 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.
4. 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.
5. 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. Nariyuki Ishikura and Masami Mato, Plant Cell Physiol, 1993, 34 (2), pages 329-335, (abstract)