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Efficient preparation of catechin thio conjugates by one step extraction/depolymerization of pine (Pinus pinaster) bark procyanidins.
J Agric Food Chem. 2005 Oct 05; 53(20):7760-5.JA

Abstract

The skin penetrating antioxidant cysteamine derivative of (-)-epicatechin as well as other thio conjugates were efficiently obtained with high yields from pine (Pinus pinaster) bark by simultaneous one pot extraction and depolymerization using water and cysteamine hydrochloride. The influence of the concentration of bark, acid, and cysteamine, as well as the reaction time on the total conversion, was studied. The total conversion into the epicatechin and catechin conjugates was as high as 47 g/kg pine bark with 1666 g cysteamine/kg bark and 28 g/kg with 166 g cysteamine/kg bark. A fast cleanup step by absorption/desorption on XAD-16 greatly facilitated further purification of the active major component. At a pilot scale, 4beta-(2-aminoethylthio)epicatechin (1) (conversion 263 g, purity 35% by reversed phase high-performance liquid chromatography/weight) was obtained from 17 kg of pine bark after simultaneous extraction/depolymerization followed by cleanup with the polymeric resin in approximately 10 h. The results show that pine (P. pinaster) bark is a suitable source of flavanols for the preparation of active thio derivatives. Conditions are given for the fast and efficient preparation of the conjugates.

Authors+Show Affiliations

Institute for Chemical and Environmental Research (IIQAB-CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain.No affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16190628

Citation

Selga, Ariadna, and Josep Lluís Torres. "Efficient Preparation of Catechin Thio Conjugates By One Step Extraction/depolymerization of Pine (Pinus Pinaster) Bark Procyanidins." Journal of Agricultural and Food Chemistry, vol. 53, no. 20, 2005, pp. 7760-5.
Selga A, Torres JL. Efficient preparation of catechin thio conjugates by one step extraction/depolymerization of pine (Pinus pinaster) bark procyanidins. J Agric Food Chem. 2005;53(20):7760-5.
Selga, A., & Torres, J. L. (2005). Efficient preparation of catechin thio conjugates by one step extraction/depolymerization of pine (Pinus pinaster) bark procyanidins. Journal of Agricultural and Food Chemistry, 53(20), 7760-5.
Selga A, Torres JL. Efficient Preparation of Catechin Thio Conjugates By One Step Extraction/depolymerization of Pine (Pinus Pinaster) Bark Procyanidins. J Agric Food Chem. 2005 Oct 5;53(20):7760-5. PubMed PMID: 16190628.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient preparation of catechin thio conjugates by one step extraction/depolymerization of pine (Pinus pinaster) bark procyanidins. AU - Selga,Ariadna, AU - Torres,Josep Lluís, PY - 2005/9/30/pubmed PY - 2005/11/1/medline PY - 2005/9/30/entrez SP - 7760 EP - 5 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 53 IS - 20 N2 - The skin penetrating antioxidant cysteamine derivative of (-)-epicatechin as well as other thio conjugates were efficiently obtained with high yields from pine (Pinus pinaster) bark by simultaneous one pot extraction and depolymerization using water and cysteamine hydrochloride. The influence of the concentration of bark, acid, and cysteamine, as well as the reaction time on the total conversion, was studied. The total conversion into the epicatechin and catechin conjugates was as high as 47 g/kg pine bark with 1666 g cysteamine/kg bark and 28 g/kg with 166 g cysteamine/kg bark. A fast cleanup step by absorption/desorption on XAD-16 greatly facilitated further purification of the active major component. At a pilot scale, 4beta-(2-aminoethylthio)epicatechin (1) (conversion 263 g, purity 35% by reversed phase high-performance liquid chromatography/weight) was obtained from 17 kg of pine bark after simultaneous extraction/depolymerization followed by cleanup with the polymeric resin in approximately 10 h. The results show that pine (P. pinaster) bark is a suitable source of flavanols for the preparation of active thio derivatives. Conditions are given for the fast and efficient preparation of the conjugates. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/16190628/Efficient_preparation_of_catechin_thio_conjugates_by_one_step_extraction/depolymerization_of_pine__Pinus_pinaster__bark_procyanidins_ L2 - https://doi.org/10.1021/jf0509815 DB - PRIME DP - Unbound Medicine ER -
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