Catechin-7-O-glucoside

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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
ChemSpider 8965102
Jmol 3D model Interactive image
PubChem 10789789
  • 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 452.41 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

Natural occurrences

Catechin-7-O-glucoside can be found in Bergenia ciliata[1] or can be isolated from the hemolymph of the European pine sawfly (Neodiprion sertifer).[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 roots of the Chinese peony (Paeonia lactiflora),[4] in the red knotweed (Bistorta macrophylla, also known as Polygonum macrophyllum),[5] in the stem barks of the Nepali hog plum (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 buckwheat groats,[10] in the red bean (the seed of Vigna umbellata, formerly known as Phaseolus calcaratus),[11] in barley (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

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Biotransformation of (+)-catechin by plant cultured cells of Eucalyptus perriniana. Otani S, Kondo Y, Asada Y, Furuya, Hamada, Nakajima, Ishihara and Hamada H, Plant Biotechnol., 2004, Vol. 21, No. 5, pages 407-409 (abstract)
  4. ↑ New Monoterpene Glycoside Esters and Phenolic Constituents of Paeoniae Radix, and Increase of Water Solubility of Proanthocyanidins in the Presence of Paeoniflorin. Takashi Tanaka, Maki Kataoka, Nagisa Tsuboi and Isao Kouno, Chem. Pharm. Bull., 2000, 48(2), pages 201—207
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Flavanoidal constituents of Choerospondias axillaries and their in vitro antitumor and anti-hypoxia activities. Li Chang-wei, Cui Cheng-bin, Cai Bing, Han Bing, Li Ming-ming and Fan Ming, Chinese Journal of Medicinal Chemistry, 2009, 19 (1), pages 48-51,64 (abstract)
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ 9.0 9.1 Flavanol glucosides from rhubarb and Rhaphiolepis umbellata. Gen-Ichiro Nonaka, Emiko Ezakia, Katsuya Hayashia and Itsuo Nishioka, Phytochemistry, Volume 22, Issue 7, 1983, Pages 1659–1661, doi:10.1016/0031-9422(83)80105-8
  10. ↑ Report on cereals at Phenol-Explorer.eu. Retrieved 18 December 2012.
  11. ↑ 11.0 11.1 Lua error in package.lua at line 80: module 'strict' not found., INIST:23809899
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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