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Structural characterization of native and oxidized procyanidins (condensed tannins) from coffee pulp (Coffea arabica) using phloroglucinolysis and thioglycolysis-HPLC-ESI-MS.
Food Chem. 2021 Mar 15; 340:127830.FC

Abstract

Procyanidins from coffee pulp are responsible from the limited valorization of this by-product. Information about procyanidin structure is still scarce and imprecise. The aim of this work was to study the native and oxidized procyanidins from coffee pulp with respect to composition and structure. An aqueous acetone extract from coffee pulp was purified using Sephadex LH-20. Butanolysis, phloroglucinolysis and thioglycolysis coupled to HLPC-ESI-MS were applied for the characterization of the native and oxidized procyanidins. The purification allowed to recovery three fractions (aqueous, ethanolic and acetonic) and only acetone fraction showed a high concentration of procyanidins (98%, w/w). HPLC-ESI-MS of procyanidins-rich fraction without any reaction resulted in a UV-Vis chromatogram unresolved typical of the presence of procyanidins. The extracted ion chromatogram and MS2 analysis revealed the presence from dimers to pentamers of native procyanidins. Interestingly, by first time an A-type trimeric procyanidin (m/z of 863) was observed in coffee pulp. In our study, (-)-epicatechin was the constitutive unit of procyanidins with an aDP of 6.8 (oligomeric native procyanidins) according to the phloroglucinolysis assay. Two oxidation markers useful to characterization of oxidized procyanidins were observed in the procyanidins-rich fraction after thioglycolysis, a dimer A2-ext and a molecule that corresponds to a linkage between an extension and a terminal unit. Coffee pulp procyanidins were presented with only a minor class of oxidized procyanidins. As far as we know, this is the first study about characterization of the oxidized procyanidins from coffee pulp.

Authors+Show Affiliations

Group of Bioprocesses and Bioproducts. Food Research Department, Universidad Autónoma de Coahuila, 25280 Saltillo, Coah, Mexico; Engineering Department, Instituto Tecnológico de Ciudad Valles, Tecnológico Nacional de México, Ciudad Valles, SLP, Mexico.INRA, UR1268 BIA, Team Polyphenol, Reactivity & Processing (PRP), BP 35327, 35653 Le Rheu, France.Group of Bioprocesses and Bioproducts. Food Research Department, Universidad Autónoma de Coahuila, 25280 Saltillo, Coah, Mexico; Engineering Department, Instituto Tecnológico de Ciudad Valles, Tecnológico Nacional de México, Ciudad Valles, SLP, Mexico.Group of Bioprocesses and Bioproducts. Food Research Department, Universidad Autónoma de Coahuila, 25280 Saltillo, Coah, Mexico; Engineering Department, Instituto Tecnológico de Ciudad Valles, Tecnológico Nacional de México, Ciudad Valles, SLP, Mexico.Group of Bioprocesses and Bioproducts. Food Research Department, Universidad Autónoma de Coahuila, 25280 Saltillo, Coah, Mexico.Group of Bioprocesses and Bioproducts. Food Research Department, Universidad Autónoma de Coahuila, 25280 Saltillo, Coah, Mexico. Electronic address: cristobal.aguilar@uadec.edu.mx.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32919355

Citation

Wong-Paz, Jorge E., et al. "Structural Characterization of Native and Oxidized Procyanidins (condensed Tannins) From Coffee Pulp (Coffea Arabica) Using Phloroglucinolysis and Thioglycolysis-HPLC-ESI-MS." Food Chemistry, vol. 340, 2021, p. 127830.
Wong-Paz JE, Guyot S, Aguilar-Zárate P, et al. Structural characterization of native and oxidized procyanidins (condensed tannins) from coffee pulp (Coffea arabica) using phloroglucinolysis and thioglycolysis-HPLC-ESI-MS. Food Chem. 2021;340:127830.
Wong-Paz, J. E., Guyot, S., Aguilar-Zárate, P., Muñiz-Márquez, D. B., Contreras-Esquivel, J. C., & Aguilar, C. N. (2021). Structural characterization of native and oxidized procyanidins (condensed tannins) from coffee pulp (Coffea arabica) using phloroglucinolysis and thioglycolysis-HPLC-ESI-MS. Food Chemistry, 340, 127830. https://doi.org/10.1016/j.foodchem.2020.127830
Wong-Paz JE, et al. Structural Characterization of Native and Oxidized Procyanidins (condensed Tannins) From Coffee Pulp (Coffea Arabica) Using Phloroglucinolysis and Thioglycolysis-HPLC-ESI-MS. Food Chem. 2021 Mar 15;340:127830. PubMed PMID: 32919355.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structural characterization of native and oxidized procyanidins (condensed tannins) from coffee pulp (Coffea arabica) using phloroglucinolysis and thioglycolysis-HPLC-ESI-MS. AU - Wong-Paz,Jorge E, AU - Guyot,Sylvain, AU - Aguilar-Zárate,Pedro, AU - Muñiz-Márquez,Diana B, AU - Contreras-Esquivel,Juan C, AU - Aguilar,Cristóbal N, Y1 - 2020/08/12/ PY - 2020/05/03/received PY - 2020/07/20/revised PY - 2020/08/11/accepted PY - 2020/9/13/pubmed PY - 2021/1/9/medline PY - 2020/9/12/entrez KW - Coffee KW - Flavonoids KW - Oxidation markers KW - Procyanidins-A type KW - Tannins KW - Thioglycolysis SP - 127830 EP - 127830 JF - Food chemistry JO - Food Chem VL - 340 N2 - Procyanidins from coffee pulp are responsible from the limited valorization of this by-product. Information about procyanidin structure is still scarce and imprecise. The aim of this work was to study the native and oxidized procyanidins from coffee pulp with respect to composition and structure. An aqueous acetone extract from coffee pulp was purified using Sephadex LH-20. Butanolysis, phloroglucinolysis and thioglycolysis coupled to HLPC-ESI-MS were applied for the characterization of the native and oxidized procyanidins. The purification allowed to recovery three fractions (aqueous, ethanolic and acetonic) and only acetone fraction showed a high concentration of procyanidins (98%, w/w). HPLC-ESI-MS of procyanidins-rich fraction without any reaction resulted in a UV-Vis chromatogram unresolved typical of the presence of procyanidins. The extracted ion chromatogram and MS2 analysis revealed the presence from dimers to pentamers of native procyanidins. Interestingly, by first time an A-type trimeric procyanidin (m/z of 863) was observed in coffee pulp. In our study, (-)-epicatechin was the constitutive unit of procyanidins with an aDP of 6.8 (oligomeric native procyanidins) according to the phloroglucinolysis assay. Two oxidation markers useful to characterization of oxidized procyanidins were observed in the procyanidins-rich fraction after thioglycolysis, a dimer A2-ext and a molecule that corresponds to a linkage between an extension and a terminal unit. Coffee pulp procyanidins were presented with only a minor class of oxidized procyanidins. As far as we know, this is the first study about characterization of the oxidized procyanidins from coffee pulp. SN - 1873-7072 UR - https://www.unboundmedicine.com/medline/citation/32919355/Structural_characterization_of_native_and_oxidized_procyanidins__condensed_tannins__from_coffee_pulp__Coffea_arabica__using_phloroglucinolysis_and_thioglycolysis_HPLC_ESI_MS_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0308-8146(20)31692-7 DB - PRIME DP - Unbound Medicine ER -