Gallocatechol

Gallocatechol
Names
Other names
(+)-Gallocatechin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH Gallocatechol
UNII
  • InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1 checkY
    Key: XMOCLSLCDHWDHP-SWLSCSKDSA-N checkY
  • C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
Properties
C15H14O7
Molar mass 306.270 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gallocatechol or gallocatechin (GC) is a flavan-3-ol, a type of chemical compound including catechin, with the gallate residue being in an isomeric trans position.

This compound possesses two epimers. The most common, (+)-gallocatechin (GC), is found notably in green tea. The other enantiomer is called (−)-gallocatechin or ent-gallocatechin. It was first isolated from green tea by Michiyo Tsujimura in 1934.

Epigallocatechin is another type of catechin, with the gallate residue being in an isomeric cis position. It can be found in St John's wort.

Biosynthesis

In the flavonoid biosynthesis pathway in plants, (+)-gallocatechol is produced in two steps from ampelopsin via leucodelphinidin:

2D representation of the chemical structure of ampelopsin .
ampelopsin
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of leucodelphinidin .
leucodelphinidin
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q72479982.
(+)-gallocatechol

The two enzymes, dihydroflavonol 4-reductase and leucoanthocyanidin reductase, both use nicotinamide adenine dinucleotide phosphate as cofactors.

See also

References

  1. ↑ Tsujimura, Michiyo (1934). "Isolation of a New Catechin, Tea Catechin II or Gallo-Catechin from Green Tea". Bulletin of the Agricultural Chemical Society of Japan. 10 (7–9): 140–147. doi:10.1080/03758397.1934.10857092.
  2. ↑ Wei, Yun; Xie, Qianqian; Dong, Wanting; Ito, Yoichiro (2009). "Separation of epigallocatechin and flavonoids from Hypericum perforatum L. By high-speed counter-current chromatography and preparative high-performance liquid chromatography". Journal of Chromatography A. 1216 (19): 4313–4318. doi:10.1016/j.chroma.2008.12.056. PMC 2777726. PMID 19150073.
  3. ↑ Stafford, Helen A.; Lester, Hope H. (1985). "Flavan-3-ol Biosynthesis". Plant Physiology. 78 (4): 791–794. doi:10.1104/pp.78.4.791. PMC 1064823. PMID 16664326.
  4. ↑ Tanner, Gregory J.; Francki, Kathy T.; Abrahams, Sharon; Watson, John M.; Larkin, Philip J.; Ashton, Anthony R. (2003). "Proanthocyanidin Biosynthesis in Plants". Journal of Biological Chemistry. 278 (34): 31647–31656. doi:10.1074/jbc.M302783200. PMID 12788945.
  5. ↑ Liu, Weixin; Feng, Yi; Yu, Suhang; Fan, Zhengqi; Li, Xinlei; Li, Jiyuan; Yin, Hengfu (2021). "The Flavonoid Biosynthesis Network in Plants". International Journal of Molecular Sciences. 22 (23) 12824. doi:10.3390/ijms222312824. PMC 8657439. PMID 34884627.