Terminaliachebula.PDFVIP

Issue in Honor of Prof. Sándor Antus ARKIVOC 2004 (vii) 83-105 The structural and conformational analyses and antioxidant activities of chebulinic acid and its thrice-hydrolyzed derivative, 2,4-chebuloyl-β-D-glucopyranoside, isolated from the fruit of Terminalia chebula Karel D. Klika,a Ammar Saleem,b Jari Sinkkonen,a Marja K?hk?nen,c Jyrki Loponen,b Petri T?htinen,a and Kalevi Pihlaja*a,b a Structural Chemistry Group, Department of Chemistry, University of Turku, Vatselankatu 2, FIN-20014 Turku, Finland. b Environmental Chemistry Group, Department of Chemistry, University of Turku, Vatselankatu 2, FIN-20014 Turku, Finland. c Division of Food Chemistry, Department of Applied Chemistry and Microbiology, University of Helsinki, D-Talo, Viikki, FIN-00014 Helsinki, Finland E-mail: kalevi.pihlaja@utu.fi Dedicated to Professor Sándor Antus on the occasion of his 60th birthday (received 02 Nov 03; accepted 29 Jan 04; published on the web 01 Feb 04) Abstract 1,3,6-Tri-O-galloyl-2,4-chebuloyl-β-D-glucopyranoside (chebulinic acid, 1) and its novel thrice- hydrolyzed derivative, 2,4-chebuloyl-β-D-glucopyranoside (galloyl-free chebulinic acid, 2), together with ellagic (3) and gallic acids (4), ethyl gallate (5), and luteolin (6), were isolated from the dried fruit of Terminalia chebula by bioactivity-guided fractionation of the extract. The compounds were variously identified on the basis of UV, MS, and NMR data. The latter proved 1 that the glucose unit in 1 adopts a well defined C4 chair conformation with all substituents in axial pos