Catechin-7-O-glucoside

Source: Wikipedia, the free encyclopedia.
Catechin-7-O-glucoside
Chemical structure of catechin-7-O-glucoside
Names
IUPAC name
(2S,4S,5S)-2-[[(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
(2R,3S)-Catechin-7-O-β-D-glucopyranoside
Catechin 7-O-β-glucopyranoside
(+)-Catechin 7-O-β-glucoside
(+)-Catechin 7-O-beta-D-glucopyranoside
Catechin 7-glucoside
C7G
CA-G
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)30-9-4-12(24)10-6-14(26)20(31-15(10)5-9)8-1-2-11(23)13(25)3-8/h1-5,14,16-29H,6-7H2/t14-,16+,17+,18-,19+,20+,21+/m0/s1
    Key: VLFIBROLAXKPQK-DPRDWZRASA-N
  • InChI=1/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)30-9-4-12(24)10-6-14(26)20(31-15(10)5-9)8-1-2-11(23)13(25)3-8/h1-5,14,16-29H,6-7H2/t14-,16+,17+,18-,19+,20+,21+/m0/s1
    Key: VLFIBROLAXKPQK-DPRDWZRABG
  • O(c2cc3O[C@H](c1ccc(O)c(O)c1)[C@@H](O)Cc3c(O)c2)[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO
Properties
C21H24O11
Molar mass 452.412 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Catechin-7-O-glucoside is a flavan-3-ol glycoside formed from catechin.

Natural occurrences

Catechin-7-O-glucoside can be isolated from the hemolymph of the European pine sawfly (

Neodiprion sertifer).[1] It also occurs in relatively large quantities in cowpea (Vigna unguiculata) as the dominant flavan-3-ol monomer, and actually accounts for up to 70% of cowpea proanthocyanidins (tannins).[2]

It can also be produced by biotransformation of (+)-catechin by cultured cells of Eucalyptus perriniana.[3]

Presence in natural traditional drugs

Catechin-7-O-glucoside can be found in paeoniae radix, the crude drug made from the roots of Chinese peony (

Choerospondias axillaris),[6] in the Korean plum yew (Cephalotaxus koreana)[7] and in Huanarpo Macho (Jatropha macrantha).[8] (−)-Catechin 7-O-β-D-glucopyranoside is found in the bark of Rhaphiolepis umbellata.[9]

Presence in food

It is found in

Hordeum vulgare L.) and malt.[12] (−)-Catechin 7-O'-β-D-glucopyranoside is found in rhubarb.[9]

Health effects

This compound has an antioxidant activity leading to a cytoprotective effect.[11][13]

References

  1. S2CID 17064750
    .
  2. PMID 23561075
    .
  3. doi:10.5511/plantbiotechnology.21.407
    .
  4. PMID 10705504
    .
  5. PMID 15524292
    .
  6. ^ Li, Chang-wei; Cui, Cheng-bin; Cai, Bing; Han, Bing; Li, Ming-ming; Fan, Ming (2009). "Flavanoidal constituents of Choerospondias axillaris and their in vitro antitumor and anti-hypoxia activities". Chinese Journal of Medicinal Chemistry. 19 (1): 48–51, 64. Archived from the original on 2014-03-09.)
  7. PMID 17994703
    .
  8. PMID 16300918
    .
  9. ^
    doi:10.1016/0031-9422(83)80105-8
    .
  10. ^ Report on cereals at Phenol-Explorer.eu. Retrieved 18 December 2012.
  11. ^
    S2CID 85203995., INIST 23809899
  12. S2CID 84221785
    .
  13. S2CID 205550585
    .
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