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Disaccharide anthocyanin delphinidin 3-O-sambubioside from Hibiscus sabdariffa L.: Candida antarctica lipase B-catalyzed fatty acid acylation and study of its color properties.
Food Chem. 2021 May 15; 344:128603.FC

Abstract

Enzymatic lipophilization is an important process to extend the use of anthocyanins in lipidic media. In this work delphinidin 3-O-sambubioside (Dp3sam) isolated from Hibiscus sabdariffa L. flower was esterified with octanoic acid using Candida antarctica lipase B. The physical-chemical properties of the new lipophilic pigment were studied by UV-vis spectroscopy. Dp3sam with chloride, acetate and formate as counter ions were employed to study the lipophilization reaction. The hydrolysis of the reagent was avoided with a formate counter ion and the expected product was achieved with a noteworthy change of solubility. 1D and 2D NMR characterization of Dp3sam-C8 confirmed that the lipophilization took place at the primary alcohol of the glucoside moiety. Overall, the Dp3sam-C8 ester presents a stabilization of the quinoidal base (blue color) at neutral or moderate alkaline pH, which foresees a potential use of this pigment as a broad kind of industries on lipo-soluble formulations.

Authors+Show Affiliations

Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Chihuahua 31125, Mexico.REQUIMTE/LAQV, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal.REQUIMTE/LAQV, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal.REQUIMTE/LAQV, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal.Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Chihuahua 31125, Mexico.Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Chihuahua 31125, Mexico.Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Chihuahua 31125, Mexico. Electronic address: esalas@uach.mx.REQUIMTE/LAQV, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal. Electronic address: luis.cruz@fc.up.pt.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

33234437

Citation

Marquez-Rodriguez, A S., et al. "Disaccharide Anthocyanin Delphinidin 3-O-sambubioside From Hibiscus Sabdariffa L.: Candida Antarctica Lipase B-catalyzed Fatty Acid Acylation and Study of Its Color Properties." Food Chemistry, vol. 344, 2021, p. 128603.
Marquez-Rodriguez AS, Guimarães M, Mateus N, et al. Disaccharide anthocyanin delphinidin 3-O-sambubioside from Hibiscus sabdariffa L.: Candida antarctica lipase B-catalyzed fatty acid acylation and study of its color properties. Food Chem. 2021;344:128603.
Marquez-Rodriguez, A. S., Guimarães, M., Mateus, N., de Freitas, V., Ballinas-Casarrubias, M. L., Fuentes-Montero, M. E., Salas, E., & Cruz, L. (2021). Disaccharide anthocyanin delphinidin 3-O-sambubioside from Hibiscus sabdariffa L.: Candida antarctica lipase B-catalyzed fatty acid acylation and study of its color properties. Food Chemistry, 344, 128603. https://doi.org/10.1016/j.foodchem.2020.128603
Marquez-Rodriguez AS, et al. Disaccharide Anthocyanin Delphinidin 3-O-sambubioside From Hibiscus Sabdariffa L.: Candida Antarctica Lipase B-catalyzed Fatty Acid Acylation and Study of Its Color Properties. Food Chem. 2021 May 15;344:128603. PubMed PMID: 33234437.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Disaccharide anthocyanin delphinidin 3-O-sambubioside from Hibiscus sabdariffa L.: Candida antarctica lipase B-catalyzed fatty acid acylation and study of its color properties. AU - Marquez-Rodriguez,A S, AU - Guimarães,M, AU - Mateus,N, AU - de Freitas,V, AU - Ballinas-Casarrubias,M L, AU - Fuentes-Montero,M E, AU - Salas,E, AU - Cruz,L, Y1 - 2020/11/13/ PY - 2020/08/27/received PY - 2020/10/06/revised PY - 2020/11/07/accepted PY - 2020/11/26/pubmed PY - 2021/2/2/medline PY - 2020/11/25/entrez KW - Chemical equilibria KW - Color stability KW - Disaccharide anthocyanin KW - Fatty acid KW - Lipophilization SP - 128603 EP - 128603 JF - Food chemistry JO - Food Chem VL - 344 N2 - Enzymatic lipophilization is an important process to extend the use of anthocyanins in lipidic media. In this work delphinidin 3-O-sambubioside (Dp3sam) isolated from Hibiscus sabdariffa L. flower was esterified with octanoic acid using Candida antarctica lipase B. The physical-chemical properties of the new lipophilic pigment were studied by UV-vis spectroscopy. Dp3sam with chloride, acetate and formate as counter ions were employed to study the lipophilization reaction. The hydrolysis of the reagent was avoided with a formate counter ion and the expected product was achieved with a noteworthy change of solubility. 1D and 2D NMR characterization of Dp3sam-C8 confirmed that the lipophilization took place at the primary alcohol of the glucoside moiety. Overall, the Dp3sam-C8 ester presents a stabilization of the quinoidal base (blue color) at neutral or moderate alkaline pH, which foresees a potential use of this pigment as a broad kind of industries on lipo-soluble formulations. SN - 1873-7072 UR - https://www.unboundmedicine.com/medline/citation/33234437/Disaccharide_anthocyanin_delphinidin_3_O_sambubioside_from_Hibiscus_sabdariffa_L_:_Candida_antarctica_lipase_B_catalyzed_fatty_acid_acylation_and_study_of_its_color_properties_ DB - PRIME DP - Unbound Medicine ER -