Trifolin

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Trifolin
Trifolin structure Trifolin.svg
Trifolin structure
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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • 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
  • 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
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).

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. S2CID   4813721.
  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. S2CID   1783362.
  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" . Plant and Cell Physiology. 34 (2): 329–335. March 1993. doi:10.1093/oxfordjournals.pcp.a078424. ISSN   1471-9053.


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