Catequina-7-O-glucósido

Catequina-7-O-glucósido
Nombre IUPAC
	(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
General
Otros nombres	(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
Fórmula molecular	C; 21H; 24O; 11
Identificadores
ChemSpider	10290170 8965102, 10290170
PubChem	44257085
	SMILES C1C(C(OC2=CC(=CC(=C21)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)O)O
	InChI InChI=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-RJNJCGSWSA-N
Propiedades físicas
Masa molar	452,131862 g/mol
	Valores en el SI y en condiciones estándar; (25 ℃ y 1 atm), salvo que se indique lo contrario.
	[editar datos en Wikidata]

Catequina-7-O-glucósido es un glucósido flavan-3-ol formado a partir de la catequina.

Presencia natural

Catequina-7-O-glucósido se encuentra en Bergenia ciliata^[1] o puede ser aislado de la hemolinfa de la mosca de sierra de pino europea (Neodiprion sertifer).^[2]

También puede ser producido por biotransformación de (+)-catequina por células cultivadas de Eucalyptus perriniana.^[3]

Presencia en los medicamentos tradicionales naturales

Catequina-7-O-glucósido se puede encontrar en Paeoniae Radix, la droga cruda a partir de raíces de la peonía china (Paeonia lactiflora),^[4] en la (Bistorta macrophylla, también conocida como Polygonum macrophyllum),^[5] en la corteza del tallo de (Choerospondias axillaris),^[6] y en (Cephalotaxus koreana)^[7] y en Huanarpo Macho (Jatropha macrantha).^[8] (−)-Catequina 7-O-β-d-glucopiranosida se encuentra en la corteza de Rhaphiolepis umbellata.^[9]

Presencia en alimentos

Se encuentra en el alforfón,^[10] en el frijol rojo (la semilla de Vigna umbellata, antes conocida como Phaseolus calcaratus),^[11] en la cebada (Hordeum vulgare L.) y malta.^[12] (−)-Catequina 7-O-β-d-glucopiranosido se encuentra en el ruibarbo.^[9]

Efectos sobre la salud

Este compuesto tiene una actividad antioxidante que conduce a un efecto citoprotector.^[11]^[13]

Referencias

↑ Dharmender, Rathee; Madhavi, Thanki; Reena, Agrawal; Sheetal, Anandjiwala (2010). «Simultaneous Quantification of Bergenin, (+)-Catechin, Gallicin and Gallic acid; and Quantification of β-Sitosterol using HPTLC from Bergenia ciliata (Haw.) Sternb. Forma ligulata Yeo (Pasanbheda)». Pharmaceutica Analytica Acta 01. doi:10.4172/2153-2435.1000104.
↑ Vihakas, Matti; Tähtinen, Petri; Ossipov, Vladimir; Salminen, Juha-Pekka (2012). «Flavonoid Metabolites in the Hemolymph of European Pine Sawfly (Neodiprion sertifer) Larvae». Journal of Chemical Ecology 38 (5): 538-46. PMID 22527054. doi:10.1007/s10886-012-0113-y.
↑ 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)
↑ 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
↑ Wang, S; Wang, D; Feng, S (2004). «Studies on chemical constituents from Polygonum macrophyllum». Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 27 (6): 411-3. PMID 15524292.
↑ 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)
↑ Yoon, Kee Dong; Jeong, Doc Gyun; Hwang, Yun Ha; Ryu, Jei Man; Kim, Jinwoong (2007). «Inhibitors of Osteoclast Differentiation fromCephalotaxus koreana». Journal of Natural Products 70 (12): 2029-32. PMID 17994703. doi:10.1021/np070327e.
↑ Benavides, Angelyne; Montoro, Paola; Bassarello, Carla; Piacente, Sonia; Pizza, Cosimo (2006). «Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis». Journal of Pharmaceutical and Biomedical Analysis 40 (3): 639-47. PMID 16300918. doi:10.1016/j.jpba.2005.10.004.
↑ ^a ^b 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
↑ Report on cereals at Phenol-Explorer.eu. Retrieved 18 December 2012.
↑ ^a ^b Baek, Jin-A; Son, Young-Ok; Fang, Minghao; Lee, Young Jae; Cho, Hyoung-Kwon; Whang, Wan Kyunn; Lee, Jeong-Chae (2011). «Catechin-7-O-β-d-glucopyranoside scavenges free radicals and protects human B lymphoma BJAB cells on H2O2-mediated oxidative stress». Food Science and Biotechnology 20: 151. doi:10.1007/s10068-011-0021-x. ,
↑ Friedrich, Wolfgang; Galensa, Rudolf (2002). «Identification of a new flavanol glucoside from barley ( Hordeum vulgare L.) and malt». European Food Research and Technology 214 (5): 388. doi:10.1007/s00217-002-0498-x.
↑ Kim, Ki Cheon; Kim, Jin Sook; Ah Kang, Kyoung; Kim, Jong Min; Won Hyun, Jin (2010). «Cytoprotective effects of catechin 7-O-β-D glucopyranoside against mitochondrial dysfunction damaged by streptozotocin in RINm5F cells». Cell Biochemistry and Function 28 (8): 651-60. PMID 21104932. doi:10.1002/cbf.1703.

Enlaces externos

Esta obra contiene una traducción derivada de «Catechin-7-O-glucoside» de Wikipedia en inglés, publicada por sus editores bajo la Licencia de documentación libre de GNU y la Licencia Creative Commons Atribución-CompartirIgual 4.0 Internacional.

Datos: Q5051792

[1] Dharmender, Rathee; Madhavi, Thanki; Reena, Agrawal; Sheetal, Anandjiwala (2010). «Simultaneous Quantification of Bergenin, (+)-Catechin, Gallicin and Gallic acid; and Quantification of β-Sitosterol using HPTLC from Bergenia ciliata (Haw.) Sternb. Forma ligulata Yeo (Pasanbheda)». Pharmaceutica Analytica Acta 01. doi:10.4172/2153-2435.1000104.

[2] Vihakas, Matti; Tähtinen, Petri; Ossipov, Vladimir; Salminen, Juha-Pekka (2012). «Flavonoid Metabolites in the Hemolymph of European Pine Sawfly (Neodiprion sertifer) Larvae». Journal of Chemical Ecology 38 (5): 538-46. PMID 22527054. doi:10.1007/s10886-012-0113-y.

[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] Wang, S; Wang, D; Feng, S (2004). «Studies on chemical constituents from Polygonum macrophyllum». Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 27 (6): 411-3. PMID 15524292.

[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] Yoon, Kee Dong; Jeong, Doc Gyun; Hwang, Yun Ha; Ryu, Jei Man; Kim, Jinwoong (2007). «Inhibitors of Osteoclast Differentiation fromCephalotaxus koreana». Journal of Natural Products 70 (12): 2029-32. PMID 17994703. doi:10.1021/np070327e.

[8] Benavides, Angelyne; Montoro, Paola; Bassarello, Carla; Piacente, Sonia; Pizza, Cosimo (2006). «Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis». Journal of Pharmaceutical and Biomedical Analysis 40 (3): 639-47. PMID 16300918. doi:10.1016/j.jpba.2005.10.004.

[Nonaka-9] 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.

[Baek-11] Baek, Jin-A; Son, Young-Ok; Fang, Minghao; Lee, Young Jae; Cho, Hyoung-Kwon; Whang, Wan Kyunn; Lee, Jeong-Chae (2011). «Catechin-7-O-β-d-glucopyranoside scavenges free radicals and protects human B lymphoma BJAB cells on H2O2-mediated oxidative stress». Food Science and Biotechnology 20: 151. doi:10.1007/s10068-011-0021-x. ,

[12] Friedrich, Wolfgang; Galensa, Rudolf (2002). «Identification of a new flavanol glucoside from barley ( Hordeum vulgare L.) and malt». European Food Research and Technology 214 (5): 388. doi:10.1007/s00217-002-0498-x.

[13] Kim, Ki Cheon; Kim, Jin Sook; Ah Kang, Kyoung; Kim, Jong Min; Won Hyun, Jin (2010). «Cytoprotective effects of catechin 7-O-β-D glucopyranoside against mitochondrial dysfunction damaged by streptozotocin in RINm5F cells». Cell Biochemistry and Function 28 (8): 651-60. PMID 21104932. doi:10.1002/cbf.1703.

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