Laricitrin

Laricitrin
Chemical structure of laricitrin
Chemical structure of laricitrin
Names
IUPAC name
3,3′,4′,5,7-Pentahydroxy-5′-methoxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
Other names
3'-O-Methylmyricetin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3 X markN
    Key: CFYMYCCYMJIYAB-UHFFFAOYSA-N X markN
  • InChI=1/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3
    Key: CFYMYCCYMJIYAB-UHFFFAOYAK
  • O=C1c3c(O/C(=C1/O)c2cc(O)c(O)c(OC)c2)cc(O)cc3O
Properties
C16H12O8
Molar mass 332.264 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Laricitrin is an O-methylated flavonol, a type of flavonoid. It is found in red grape (absent in white grape) and in Vaccinium uliginosum (bog bilberries). It is one of the phenolic compounds present in wine.

Metabolism

Laricitrin is formed from myricetin by the action of the enzyme myricetin O-methyltransferase. It is further methylated by laricitrin 5'-O-methyltransferase into syringetin.

Glycosides

References

  1. 1 2 Mattivi, F; Guzzon, R; Vrhovsek, U; Stefanini, M; Velasco, R (October 2006). "Metabolite profiling of grape: Flavonols and anthocyanins". J. Agric. Food Chem. 54 (20): 7692–702. Bibcode:2006JAFC...54.7692M. doi:10.1021/jf061538c. PMID 17002441.
  2. ↑ Anja; Jaakola, Laura; Riihinen, Kaisu R.; Kainulainen, Pirjo S. (2010). "Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosumL.) in Finland". Journal of Agricultural and Food Chemistry. 58 (1): 427–433. Bibcode:2010JAFC...58..427L. doi:10.1021/jf903033m. PMID 20000402.
  3. ↑ Castillo-Munoz, Noelia; Gomez-Alonso, Sergio; Garcia-Romero, Esteban; Hermosin-Gutierrez, Isidro (2007). "Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines". Journal of Agricultural and Food Chemistry. 55 (3): 992–1002. Bibcode:2007JAFC...55..992C. doi:10.1021/jf062800k. PMID 17263504.
  4. ↑ Syringetin biosynthesis pathway on metacyc.org
  5. ↑ Tyukavkina, N. A.; Medvedeva, S. A.; Ivanova, S. Z. (1974). "New flavonol glycosides from the needles of Larix sibirica". Chemistry of Natural Compounds. 10 (2): 170–172. Bibcode:1974CNatC..10..170T. doi:10.1007/BF00563605.
  6. ↑ Flavonoids isolated from Medicago littoralis Rhode (Fabaceae): their ecological and chemosystematic significance Archived 2011-07-22 at the Wayback Machine