2″,4″-O-Diacetylquercitrin, a Novel Advanced Glycation End-Product Formation and Aldose Reductase Inhibitor from Melastoma sanguineum

• Published in: Chemical & pharmaceutical bulletin Vol. 61; no. 6; pp. 662 - 665
• Main Authors: Lee, Ik-Soo, Kim, Il Soon, Lee, Yun Mi, Lee, Youngseop, Kim, Joo-Hwan, Kim, Jin Sook
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.06.2013; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan
• Subjects: advanced glycation end-product; Aldehyde Reductase - antagonists & inhibitors; Aldehyde Reductase - metabolism; Animals; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; Enzyme Inhibitors - metabolism; flavonoid; Flavonoids - chemistry; Flavonoids - isolation & purification; Flavonoids - metabolism; Glycation End Products, Advanced - antagonists & inhibitors; Glycation End Products, Advanced - metabolism; Lens, Crystalline - enzymology; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Melastoma sanguineum; Melastomataceae - chemistry; Molecular Conformation; Pharmacology & Pharmacy; Physical Sciences; Plant Components, Aerial - chemistry; Protein Binding; rat lens aldose reductase; Rats; Science & Technology; DIABETIC COMPLICATIONS; GLYCOSIDES; WALL; STRUCTURAL REQUIREMENTS; advanced glycation end-product; PROTEIN GLYCATION; LEAVES; Melastonia sanguineum; FLAVONOIDS; flavonoid; rat lens aldose reductase; ERIGERON-ANNUUS
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.c12-00877

A new flavonoid, 2,″4″-O-diacetylquercitrin (1), along with six known flavonoids (2–7) were isolated from the aerial parts of Melastoma sanguineum. The structure of the new flavonoid was established by extensive spectroscopic studies and chemical evidence. The inhibitory effects of isolated compounds (1–7) on advanced glycation end-products (AGEs) formation and rat lens aldose reductase (RLAR) in vitro were examined. Of the tested compounds, compound 1 was the strongest inhibitor of AGEs, with an IC50 of 11.46±0.44 µ m . In the RLAR assay, all tested compounds exhibited greater inhibitory effects on RLAR than that of a positive control, 3,3-tetramethyleneglutaric acid (IC50=28.8±1.5 µ m ); compound 1 exhibited the strongest RLAR-inhibitory activity, with an IC50 of 0.077±0.003 µ m .