765 0009-3130/12/4805-0765  2012 Springer Science+Business Media New York 1) Department of Pharmacetical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, 11451, Riyadh, Saudi Arabia, fax: +966 1 4676220, e-mail: msmarzouk@yahoo.co.uk; 2) Department of Pharmaceutical Sciences, College of Clinical Pharmacy (Girls), King Faisal University, P. O. Box 400, 31982, Hofuf, Saudi Arabia; 3) Department of Pharmacognosy, Faculty of Pharmacy, Helwan University, Ain-Helwan, Cairo, Egypt; 4) Department of Pharmacology, Division of Medical Sciences, National Research Centre, Dokki, 12622, Cairo, Egypt. Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2012, pp. 685–689. Original article submitted October 11, 2011. Chemistry of Natural Compounds, Vol. 48, No. 5, November, 2012 [Russian original No. 5, September–October, 2012] NOVEL BIFLAVONE DIGLYCOSIDES AND BIOLOGICAL ACTIVITY OF Jatropha multifida LEAVES M. S. Marzouk, 1* F. A. Moharram, 2 E. G. Haggag, 3 UDC 547.972 S. M. El-Batran, 4 I. I. Mahmoud, 3 and R. R. Ibrahim 3 Chromatographic separation of the 80% aqueous methanol extract (AME) of Jatropha multifida Linn. leaves has yielded three novel biapigenin di-C-glucosides, i.e., 6,6-di-C--glucopyranosyl-methylene-(8,8)- biapigenin ( 7 ), 3,6 -di- C- -glucopyranosyl-methylene-(6,8 )-biapigenin ( 8 ), and 6,6 -di- C- - glucopyranosyl-methylene-(3,8)-biapigenin (9), named jatrophenols I–III. In addition, seven known polyphenolic metabolites were identified as apigenin 7-O--neohespredoside (1), ferulic acid (2), quercetrin (3), vicinin-II (4), isoorientin (5), vitexin (6), and luteolin (10) for the first time from this species. The AME of the plant was reported for the first time to have significant analgesic, anti-inflammatory, and antihypertensive effects. Keywords: Jatropha multifida, HR-ESI-MS, biapigenin di-C-glucoside, analgesic, anti-inflammatory, antihypertensive. The genus Jatropha (Euphorbiaceae) comprises about 175 species, some of which are used in folk medicine remedies [1, 2]. The principal compounds that have been isolated from Jatropha species were mainly diterpenes [3–6], lignans [7], triterpenes [8], coumarins [9], tannins [10], and flavonoids [11], which were studied for their different biological activities such as hypotensive [12], antitumor [13], antioxidant [14], antibacterial [15], anti-inflammatory [16], and analgesic [11], and as a hemostatic agent [17]. Our previous report on J. curcas has led to the identification of compound 7 and its immunomodulatory activity in chicks [18]. Additionally, two studies were reported on the constitutive polyphenols of J. multifida [10, 18]. The present phytochemical and biological study was carried out on this species to throw light on the importance of this species that grows in the Benha Region in Egypt. The AME was chromatographed on a polyamide column followed by successive separation on Sephadex LH-20 and cellulose columns, affording ten pure compounds. Their structures were established as apigenin 7-O--D-neohespredoside (1), ferulic acid (2), quercetrin (3), three flavone C-glucosides vicinin-II (4), isoorientin (5), and vitexin (6) and luteolin (10) on the basis of their chromatographic properties, chemical and spectroscopic studies (UV, 1 H, 13 C NMR, and APT), and comparison with literature data of related compounds [19, 20]. In addition, we established the structures of the novel biflavone di-C-glucosides (jatrophenols I–III) as 6,6-di-C--glucopyranosyl-methylene-(8,8)-biapigenin (7), 3,6-di-C--glucopyranosyl-methylene-(6,8)- biapigenin (8), and 6,6-di-C--glucopyranosyl-methylene-(3,8)-biapigenin (9) by extensive spectroscopic studies, particularly 2D NMR ( 1 H– 1 H COSY, HMQC, and HMBC) and HR-ESI-MS. Compound 7 was identified before in our previous report on J. curcas, and full data on it (UV, 1D, 2D NMR, and HR-ESI-MS) were completely consistent with that published in [18], confirming its structure as 6,6-di-C-- 4 C 1 -glucopyranosyl-methylene-(8,8)-biapigenin (jatrophenol I). Compound 8 exhibited more or less the same chromatographic properties and UV spectral data as 7, which is a bi-apigenin glycoside with free hydroxyls at C-5 and C-7 of A-rings and C-4 of B-rings [18]. Compound 8 was tentatively identified as bi-apigenin di-C-hexoside with an extra methylene group, depending on its resistance to the conditions of normal acid hydrolysis and negative HR-ESI-MS spectrum, which showed a molecular ion peak at m/z 875.21892 corresponding exactly to the same molecular weight and molecular formula of 7.