Phyllanthus emblica L. (Euphorbiaceae) is a shrub or tree growing in subtropical and tropical areas of the People's Republic of China, India, Indonesia, and the Malay Peninsula. The whole plant, especially the fruit has been used as an antiinflammatory and antipyretic drug in many local traditional medicines: Chinese herbal medicine, Tibetan medicine, and Ayurvedic medicine.1) Several reports about this plant have shown that the fruits are rich in vitamin C, mucic acid, and tannins.2-6) In our previous work, 7,8) a novel highly oxygenated norbisabolane together with its methyl ester and three ester glycosides were isolated from the roots of the plant along with 15 tannins and related compounds. As part of our continuing studies on the plant, we report herein the isolation and structural elucidation of new phenolic constituents, L-malic acid 2-O-(1), mucic acid 2-O-(5), mucic acid 1,4-lactone 2-O-(6), 5-O-(8), 3-O-(10), 3,5-di-O-(11) gallates, and their methyl esters (2-4, 7, 9) from the fruit juice of P. emblica.
Results and DiscussionA 60% aqueous acetone extract of the powdered form of fruit juice of P. emblica was subjected to MCI gel CHP 20P column chromatography to afford five fractions. Fraction 1 obtained by elution with H 2 O was further chromatographed successively over Sephadex LH-20, MCI gel CHP20P, Toyopearl HW-40F, and Cosmosil 75C 18 OPN to afford compounds 1-11 and three known compounds. By comparison of the physical and spectral data with those of authentic samples, the known compounds were identified as gallic acid, chebulic acid, 9) and 1-O-galloyl-b-D-glucose, 10) respectively. Compound 1 was obtained as a white amorphous powder and showed a dark blue coloration with ferric chloride reagent. Its molecular formula was assigned as C 11 H 10 O 9 on the basis of the 13 C-NMR spectral data, the negative-ion 2-O-(1), mucic acid 2-O-(5), mucic acid 1,4-lactone 2-O-(6), 5-O-(8), 3-O-(10), and 3,5-di-O-(11) gallates, were isolated from the fruit juice of Phyllanthus emblica together with their methyl esters (2-4, 7, 9), and their structures were determined by spectral and chemical methods. Compounds 5, 6, and 8, the major phenolic constituents of the juice, were present as an equilibrium mixture in aqueous solution.