Synthesis and evaluation of water-soluble resveratrol and piceatannol via BGLation

• Published in: Bioorganic & medicinal chemistry letters Vol. 22; no. 15; pp. 5051 - 5054
• Main Authors: Nemoto, Hisao, Katagiri, Ayato, Kamiya, Masaki, Matsushita, Tsuyoshi, Hattori, Hatsuhiko, Matsumura, Kosuke, Itou, Tomohiro, Kawamura, Tomoyuki, Kita, Toshiyuki, Nishida, Hana, Arakaki, Naokatu
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.08.2012; Elsevier
• Subjects: Biological and medical sciences; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Fat-reducing; Glycerol; Glycerol - chemical synthesis; Glycerol - chemistry; Life Sciences & Biomedicine; Medical sciences; Mitochondria; Mitochondria - metabolism; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Physical Sciences; Resveratrol; Science & Technology; Solubility; Stilbenes - chemical synthesis; Stilbenes - chemistry; structure-activity relationships; Water - chemistry; Water-solubility; Water-solubility; Glycerol; Mitochondria; Fat-reducing; Resveratrol; MECHANISM; H+-ATP SYNTHASE; CASCADE-TYPE; SOLUBILITY; BRANCHED OLIGOGLYCEROL; P-BORONOPHENYLALANINE; CARBORANE; SURFACE; BEARING; DERIVATIVES; Evaluation; Lipids; Antioxidant; Stilbene derivatives; Water soluble compound; Polyphenol; Phytoalexin; Water solubility; Phenols; Chemical synthesis; Physicochemical properties
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2012.06.019

Synthesis of four water-soluble resveratrol and piceatannol derivatives bearing symmetrically branched glyceryl trimer (BGL003) with a non-biocleavable linkage, and their biological evaluation as a mitochondrial fusion-inducing agent with cellular fat-reducing effect from cells, is described. The effect of Piceatannol–BGL003 conjugate was as high as that of original stilbenoids.