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Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br.
Food Chem Toxicol. 2007 Mar; 45(3):472-85.FC

Abstract

The root bark of Anisophyllea dichostyla R. Br. is traditionally used in the Democratic Republic Congo for the treatment of several conditions such as anorexia, fatigue and intestinal infections. We have identified and quantitated several polyphenol antioxidants in the methanol extract of the root bark (120g). The polyphenol content (3.32g/kg) was predominantly ellagitannins (25%) and polyhydroxyflavan-3-ols (catechins and procyanidins, 75%) with 3'-O-methyl-3,4-methylenedioxo ellagic acid 4'-O-beta-d-glucopyranoside and (-)-epicatechin as the major species in each class. These two compounds and the following species were identified unequivocally by NMR spectroscopy: (+)-catechin, (-)-epicatechin 3-O-gallate, 3-O-methyl ellagic acid, 3,3'-di-O-methyl ellagic acid, 3'-O-methyl-3,4-methylenedioxo ellagic acid, 3'-O-methyl-3,4-methylenedioxo ellagic acid 4'-O-beta-d-glucopyranoside, and 3'-O-methyl ellagic acid 4-O-beta-d-xylopyranoside. The following additional compounds were purified by semi-preparative HPLC and tentatively identified on the basis of UV spectra, HPLC-ESI-MS and nano-ESI-MS-MS: (+)-catechin-3-O-beta-d-glucopyranoside, epicatechin-(4beta-->8)-catechin (procyanidin B(1)), epicatechin-(4beta-->8)-epicatechin (procyanidin B(2)), an (epi)catechin trimer, 3-O-methyl ellagic acid 4-O-beta-d-glucopyranoside, (-)-epicatechin 3-O-vanillate, 3,4-methylenedioxo ellagic acid 4'-O- beta-d-glucopyranoside, and 3,3'-di-O-methyl ellagic acid 4-O-beta-d-xylopyranoside. Fractionation of the raw extract by column chromatography on silicic acid yielded 10 fractions. In the hypoxanthine/xanthine oxidase antioxidant assay system, CC-9 which contained a range of polyphenols dominated by (-)-epicatechin-O-gallate proved to be the most potent antioxidant fraction (IC(50)=52 micro g/mL) in terms of ROS scavenging. In terms of XO inhibition CC-8, dominated by (epi)catechin trimer and which also contained appreciable amounts of 3'-O-methyl ellagic acid 4'-O-beta-d-xylopyranoside, as well as the catechins (+)-catechin-3-O-beta-d-glucopyranoside, epicatechin-(4beta-->8)-catechin (procyanidin B(1)), and (-)-epicatechin 3-O-gallate, proved to be the most potent (IC(50)=36 micro g/mL).

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Authors+Show Affiliations

Khallouki F
Division of Toxicology and Cancer Risk Factors, German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany.
Haubner R
No affiliation info available
Hull WE
No affiliation info available
Erben G
No affiliation info available
Spiegelhalder B
No affiliation info available
Bartsch H
No affiliation info available
Owen RW
No affiliation info available

MeSH

CatechinCucurbitaceaeDemocratic Republic of the CongoEllagic AcidHumansMedicine, African TraditionalPhytotherapyPlant ExtractsPlant RootsProanthocyanidins

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17084499

Citation

Khallouki, F, et al. "Isolation, Purification and Identification of Ellagic Acid Derivatives, Catechins, and Procyanidins From the Root Bark of Anisophyllea Dichostyla R. Br." Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association, vol. 45, no. 3, 2007, pp. 472-85.
Khallouki F, Haubner R, Hull WE, et al. Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br. Food Chem Toxicol. 2007;45(3):472-85.
Khallouki, F., Haubner, R., Hull, W. E., Erben, G., Spiegelhalder, B., Bartsch, H., & Owen, R. W. (2007). Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br. Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association, 45(3), 472-85.
Khallouki F, et al. Isolation, Purification and Identification of Ellagic Acid Derivatives, Catechins, and Procyanidins From the Root Bark of Anisophyllea Dichostyla R. Br. Food Chem Toxicol. 2007;45(3):472-85. PubMed PMID: 17084499.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br. AU - Khallouki,F, AU - Haubner,R, AU - Hull,W E, AU - Erben,G, AU - Spiegelhalder,B, AU - Bartsch,H, AU - Owen,R W, Y1 - 2006/10/01/ PY - 2006/01/19/received PY - 2006/09/15/revised PY - 2006/09/20/accepted PY - 2006/11/7/pubmed PY - 2007/3/21/medline PY - 2006/11/7/entrez SP - 472 EP - 85 JF - Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association JO - Food Chem Toxicol VL - 45 IS - 3 N2 - The root bark of Anisophyllea dichostyla R. Br. is traditionally used in the Democratic Republic Congo for the treatment of several conditions such as anorexia, fatigue and intestinal infections. We have identified and quantitated several polyphenol antioxidants in the methanol extract of the root bark (120g). The polyphenol content (3.32g/kg) was predominantly ellagitannins (25%) and polyhydroxyflavan-3-ols (catechins and procyanidins, 75%) with 3'-O-methyl-3,4-methylenedioxo ellagic acid 4'-O-beta-d-glucopyranoside and (-)-epicatechin as the major species in each class. These two compounds and the following species were identified unequivocally by NMR spectroscopy: (+)-catechin, (-)-epicatechin 3-O-gallate, 3-O-methyl ellagic acid, 3,3'-di-O-methyl ellagic acid, 3'-O-methyl-3,4-methylenedioxo ellagic acid, 3'-O-methyl-3,4-methylenedioxo ellagic acid 4'-O-beta-d-glucopyranoside, and 3'-O-methyl ellagic acid 4-O-beta-d-xylopyranoside. The following additional compounds were purified by semi-preparative HPLC and tentatively identified on the basis of UV spectra, HPLC-ESI-MS and nano-ESI-MS-MS: (+)-catechin-3-O-beta-d-glucopyranoside, epicatechin-(4beta-->8)-catechin (procyanidin B(1)), epicatechin-(4beta-->8)-epicatechin (procyanidin B(2)), an (epi)catechin trimer, 3-O-methyl ellagic acid 4-O-beta-d-glucopyranoside, (-)-epicatechin 3-O-vanillate, 3,4-methylenedioxo ellagic acid 4'-O- beta-d-glucopyranoside, and 3,3'-di-O-methyl ellagic acid 4-O-beta-d-xylopyranoside. Fractionation of the raw extract by column chromatography on silicic acid yielded 10 fractions. In the hypoxanthine/xanthine oxidase antioxidant assay system, CC-9 which contained a range of polyphenols dominated by (-)-epicatechin-O-gallate proved to be the most potent antioxidant fraction (IC(50)=52 micro g/mL) in terms of ROS scavenging. In terms of XO inhibition CC-8, dominated by (epi)catechin trimer and which also contained appreciable amounts of 3'-O-methyl ellagic acid 4'-O-beta-d-xylopyranoside, as well as the catechins (+)-catechin-3-O-beta-d-glucopyranoside, epicatechin-(4beta-->8)-catechin (procyanidin B(1)), and (-)-epicatechin 3-O-gallate, proved to be the most potent (IC(50)=36 micro g/mL). SN - 0278-6915 UR - https://www.unboundmedicine.com/medline/citation/17084499/Isolation_purification_and_identification_of_ellagic_acid_derivatives_catechins_and_procyanidins_from_the_root_bark_of_Anisophyllea_dichostyla_R__Br_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0278-6915(06)00274-2 DB - PRIME DP - Unbound Medicine ER -