Catechin-7-O-glucoside explained

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 (Paeonia lactiflora),[4] in 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]

Notes and References

  1. 10.1007/s10886-012-0113-y . Flavonoid Metabolites in the Hemolymph of European Pine Sawfly (Neodiprion sertifer) Larvae . 2012 . Vihakas . Matti . Tähtinen . Petri . Ossipov . Vladimir . Salminen . Juha-Pekka . Journal of Chemical Ecology . 38 . 5 . 538–46 . 22527054. 17064750 .
  2. Ojwang. Leonnard O.. Yang. Liyi. Dykes. Linda. Awika. Joseph. 2013-08-15. Proanthocyanidin profile of cowpea (Vigna unguiculata) reveals catechin-O-glucoside as the dominant compound. Food Chemistry. 139. 1–4. 35–43. 10.1016/j.foodchem.2013.01.117. 23561075.
  3. Biotransformation of (+)-catechin by plant cultured cells of Eucalyptus perriniana . Shuichi . Otani . Yoko . Kondo . Yoshihisa . Asada . Tsutomu . Furuya . Hatsuyuki . Hamada . Nobuyoshi . Nakajima . Kohji . Ishihara . Hiroki . Hamada . Plant Biotechnology . 2004 . 21 . 5 . 407–409 . 10.5511/plantbiotechnology.21.407. free .
  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 . Isao . Kouno . Chemical and Pharmaceutical Bulletin . 2000 . 48 . 2 . 201—207 . 10.1248/cpb.48.201 . 10705504. free .
  5. 15524292 . 2004 . Wang . S. . Wang . D. . Feng . S. . Studies on chemical constituents from Polygonum macrophyllum . 27 . 6 . 411–413 . Journal of Chinese Medicinal Materials.
  6. Flavanoidal constituents of Choerospondias axillaris and their in vitro antitumor and anti-hypoxia activities . Li . Chang-wei . Cui . Cheng-bin . Cai . Bing . Han . Bing . Li . Ming-ming . Fan . Ming . Chinese Journal of Medicinal Chemistry . 2009 . 19 . 1 . 48–51, 64 . https://web.archive.org/web/20140309191625/http://www.zgyhzz.cn/qikan/epaper/zhaiyao.asp?bsid=14526 . 2014-03-09 .)
  7. 10.1021/np070327e . Inhibitors of Osteoclast Differentiation from Cephalotaxus koreana . 2007 . Yoon . Kee-dong . Jeong . Doc-gyun . Hwang . Yun-ha . Ryu . Jei-man . Kim . Jin-woong . Journal of Natural Products . 70 . 12 . 2029–2032 . 17994703.
  8. 10.1016/j.jpba.2005.10.004 . Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis . 2006 . Benavides . Angelyne . Montoro . Paola . Bassarello . Carla . Piacente . Sonia . Pizza . Cosimo . Journal of Pharmaceutical and Biomedical Analysis . 40 . 3 . 639–647 . 16300918.
  9. Flavanol glucosides from rhubarb and Rhaphiolepis umbellata . Gen'ichiro . Nonaka . Emiko . Ezakia . Katsuya . Hayashia . Itsuo . Nishioka . Phytochemistry . 22 . 7 . 1983 . 1659–1661 . 10.1016/0031-9422(83)80105-8.
  10. http://www.phenol-explorer.eu/reports/41 Report on cereals
  11. 10.1007/s10068-011-0021-x . Catechin-7-O-β-D-glucopyranoside scavenges free radicals and protects human B lymphoma BJAB cells on H2O2-mediated oxidative stress . 2011 . Baek . Jin-a . Son . Young-ok . Fang . Minghao . Lee . Young-jae . Cho . Hyoung-kwon . Whang . Wan-kyunn . Lee . Jeong-Chae . Food Science and Biotechnology . 20 . 151–158. 85203995 .,
  12. 10.1007/s00217-002-0498-x . Identification of a new flavanol glucoside from barley (Hordeum vulgare L.) and malt . 2002 . Friedrich . Wolfgang . Galensa . Rudolf . European Food Research and Technology . 214 . 5 . 388. 84221785 .
  13. 10.1002/cbf.1703 . Cytoprotective effects of catechin 7-O-β-D-glucopyranoside against mitochondrial dysfunction damaged by streptozotocin in RINm5F cells . 2010 . Kim . Ki-cheon . Kim . Jin-sook . Kang . Kyoung-ah . Kim . Jong-min . Hyun . Jin-won . Cell Biochemistry and Function . 28 . 8 . 651–660 . 21104932. 205550585 .

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