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Gallocatechol

From Wikipedia, the free encyclopedia
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.[1]

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.[2]

Biosynthesis

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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.[3][4][5]

See also

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References

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  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.
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