Sesquiterpenoid and Phenolic Glucoside Gallates from Lagerstroemia balansae

Abstract

Three new compounds, including a sesquiterpenoid glucoside gallate, 2Z,4E,1′R,2′S,4′R,6′S-dihydrophaseic acid 4′-O-(6′′-O-galloyl)-β-D-glucopyranoside (1), two new phenolic glucoside gallates, 4-hydroxy-3,5-dimethoxybenzoic acid 4-O-(6′-O-galloyl)-β-D-glucopyranoside (2) and 3,4-dimethoxyphenol 1-O-(6′-O-galloyl)-β-D-glucopyranoside (3), together with eight known compounds (4–11), have been isolated from the stems of Lagerstroemia balansae. Their structures were elucidated on the basis of chemical and spectroscopic evidences.

Key words

Lagerstroemia balansae - Lythraceae - 2Z,4E,1′R,2′S,4′R,6′S-dihydrophaseic acid 4′-O-(6′′-O-galloyl)-β-D-glucopyranoside - 4-hydroxy-3,5-dimethoxybenzoic acid 4-O-(6′-O-galloyl)-β-D-glucopyranoside - 3,4-dimethoxyphenol 1-O-(6′-O-galloyl)-β-D-glucopyranoside

References

• 1 Corry D B, Tuck M L. Protection from vascular risk in diabetic hypertension.  Curr Hypertens Rep. 2000;  2 154-159
• 2 Stratton I M, Adler A I, Neil H A W, Matthews D R, Manley S E, Cull C A, Hadden D, Turner R C, Holman R R. Association of glycaemia with macrovascular and microvascular complications of type 2 diabetes (UKPDS35): prospective observational study.  BMJ. 2000;  321 405-409
• 3 Goke B, Herrmann-Rinke C. The evolving role of α-glucosidase inhibitors.  Diabetes Metab Rev. 1998;  14 S31-S38
• 4 Perry L M. The medicinal plants of the East and Southeast Asia. Cambridge: The MIT Press; 1980: 248
• 5 Hayashi T, Maruyama H, Kasai R, Hattori K, Takasuga S, Hazeki O, Yamasaki K, Tanaka T. Ellagitannins from Lagerstroemia speciosa as activators of glucose transport in fat cells.  Planta Med. 2002;  68 173-175
• 6 Judy W V, Hari S P, Stogsdill W W, Judy J S, Naguib Y M, Passwater R. Antidiabetic activity of a standardized extract (glucosol) from Lagerstroemia speciosa leaves in type 2 diabetics. A dose-dependence study.  J Ethnopharmacol. 2003;  87 115-117
• 7 Miura T, Itoh Y, Kaneko T, Ueda N, Ishida T, Fukushima M, Matsuyama F, Seino Y. Corosolic acid induces GLUT4 translocation in genetically type 2 diabetic mice.  Biol Pharm Bull. 2004;  27 1103-1105
• 8 Liu X Q, Kim J K, Li Y S, Li J, Liu F, Chen X Z. Tannic acid stimulates glucose transport and inhibits adipocyte differentiation in 3T3-L1 cells.  J Nutr. 2005;  135 165-171
• 9 del Refugio Ramos M, Jerz G, Villanueva S, Lopez-Dellamary F, Waibel R, Winterhalter P. Two glucosylated abscisic acid derivates from avocado seeds (Persea americana Mill. Lauraceae cv. Hass).  Phytochemistry. 2004;  65 955-962