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Apigenin 7-O-B-glucoside from the leaves of Acanthus integrifolius T. Anders., Acanthaceae

The first investigation on chemical constituents of Acanthus integrifolius resulted in the isolation of apigenin-7-O- -glucoside from the leaves of this plant. Its chemical structure was determined by ESIMS, 1 H NMR, 13 C NMR, DEPT, HMBC and HMQC. | Journal of Chemistry Vol. 42 4 P. 496 - 498 2004 APIGENIN 7-O- -GLUCOSIDE FROM THE LEAVES OF ACANTHUS INTEGRIFQLIUS T. ANDERS. ACANTHACEAE Received 18th-Sept.-2003 PHAN MINH GIANG PHAN TONG SON Faculty of Chemistry College of Natural Science Vietnam National University Hanoi SUMMARY The first investigation on chemical constituents of Acanthus integrifolius resulted in the isolation of apigenin-7-O-ft-glucoside from the leaves of this plant. Its chemical structure was determined by EsIMS 1H nMr 13C nMr dept HMBC and HMQC. Acanthus integrifolius T. Anders. Acanthaceae local name ắc Ó is a shrub growing to the height of 1 - 2 m and possessing white flowers 1 . The leaves of A. integrifolius Folium Acanthi are used in the treatment of pain and rheumatism 2 . Our first phytochemical investigation on A. integrifolius was prompted by the need to identify the compounds responsible for anti-inflammatory therapeutic effects of this plant. Successive liquid-liquid fractionation of the aqueous MeOH extract of the leaves of A. integrifolius by solvents with increasing polarity gave n-hexane- CH2Cl2- ethyl acetate-and n-BuOH-soluble fractions. The n-hexane soluble fraction contained mainly phytosterols as indicated in a TLC analysis and was not further investigated. Two-time column chromatography of the ethyl acetate soluble fraction on lipophilic Sephadex LH-20 gave apigenin-7-O- -glucoside 1 with 95 purity. We reported herein the structure elucidation of this flavone glucoside. The 1H-NMR spectrum of 1 in DMSO-d6 contained two distinctive groups of resonances. Those at Ỗ 7.96 2H and 6.95 2H both as d J 9 Hz 6.87 1H s 6.84 1H and 6.45 1H both as d J 2.2 Hz represented the flavone Figure 1 Chemical structure of apigenin 7-O- -glucoside 1 nucleus protons the 13C NMR chemical shifts of this moiety were consistent with the identification of 1 as a derivative of apigenin 3 . The second group appearing between Ỗ 3.1 and 5.06 comprised the resonances of a glucosidic moiety. The .