Synthesis and antioxidant activity of novel amphipathic derivatives of tea polyphenol

• Published in: Bioorganic & medicinal chemistry letters Vol. 8; no. 14; pp. 1801 - 1806
• Main Authors: Tanaka, Takashi, Kusano, Rie, Kouno, Isao
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 21-07-1998; Elsevier
• Subjects: Antioxidants - chemical synthesis; Antioxidants - pharmacology; Biological and medical sciences; Catechin - analogs & derivatives; Catechin - chemical synthesis; Catechin - chemistry; Catechin - pharmacology; General and cellular metabolism. Vitamins; General pharmacology; Lipid Bilayers; Lipid Peroxidation - drug effects; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Tea - chemistry; Amphipathic compound; Organic hydroxysulfide; Lipids; Antioxidant; Organic carbamate; Bilayer; Flavonoid; Radical scavenger; Free radical; Organic sulfide; Chemical modification; Polyphenol; Penetration; Structure activity relation; Oxidation; Inhibition; Hemisynthesis; Peroxidation
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(98)00311-4

Hydrophobic derivatives of a tea polyphenol have been synthesized. 6, 8-Bis(octylthiomethyl)-epigallocatechin 3-
O-gallate, 6, 8-bis(octylthiomethyl)-4β-(2-hydroxyethylthio)epigallocatechin 3-
O-gallate and epigallocatechin 3-
O-[4-
O-(
N-octadecylcarbamoyl)gallate] showed strong inhibition activity against lipid peroxidation of liposome caused by both lipid-soluble and water-soluble radical generators.
Hydrophobic Derivatives of epigallocatechin 3-
O-gallate having alkyl chains have been synthesized. Compounds having one or two alkyl chains showed strong antioxidant activity against both lipid-soluble and water-soluble radicals.