Biological examination and novel biflavone di-C-glycosides from Jatropha multifida L. leaves

Many Jatropha species have been used as local or popular remedies [1]. Some extracts and compounds of different J. species were found to have anti-inflammatory, bronchodilator of tracheal muscles, antiarraythmic [2], and antihypertensive activities [3]. Also, several research programs are directed towards certain J. species to identify their antitumor active diterpenes and lignans [4–7]. This study aimed at the identification of polyphenols of J. multifida leaves and examination of some biological activities. Three novel biflavone di-C-glycosides have been identified as 6,6“-di-C-β-D-⁴C₁-glucopyranosyl-methylene-(8,8“)-biapigenin (jatrophenol I, 7), 3,6“-di-C-β-D-⁴C₁-glucopyranosyl-methylene-(6,8“)-biapigenin (jatrophenol II, 8), and 6,6“-di-C-β-D-⁴C₁-glucopyranosyl-methylene-(3,8“)-biapigenin (jatrophenol III, 9) on the basis of UV, HRESI-MS and NMR analyses. The total aq. 80% MeOH extract of J. multifida leaves was defatted under reflux with pet. ether (60–80°C) and then fractionated on polyamide column using H₂O-MeOH mixtures starting with H₂O up to pure MeOH. The mean frs. were then subjected to repeated column chromatography on cellulose, sephadex LH-20 and or polyamide with different convenient solvent systems e.g. aq. MeOH or MeOH, n-BuOH saturated with H₂O, BIW (n-BuOH-IsoprOH-H₂O, 4:1:5, organic layer) or MeOH/Me₂CO-H₂O (1:1). Together with the novel biflavones seven phenolic compounds have been identified as apigenin 7-O-β-D-neohespredoside (1), ferulic acid (2), quercetin (3), vicenin-II (4), isoorientin (5) vitexin (6), and luteolin (10) on the basis of comparison with the published data [8]. The investigated extract and that of J. integrima were found to be non-toxic up to the maximum soluble dose (LD₅₀ 4g/Kg b wt). In a dose dependant manner (at 20, 40mg/100g b. wt) from the two extracts, significant analgesic and anti-inflammatory effects in comparison to indomethacine were recorded and showed significant hypotensive effect at the same doses, as well.

References: [1] Baily, L.H (1953). The standard cyclopedia of harticulture. The Mcmillan Co., New york. [2] Ojewole, J.A.O. (1983). Fitoterapia 54: 153. [3] Abreu et al. (2003). Fitoterapia 74: 650. [4] Taylor, et al. (1983). J. Am. Chem. Soc. 105: 3177. [5] Endo, Y. et al. (1991). Tetrahedron Lett 32: 3083. [6] Ravendranath et al. (2003). Chem Pharm Bull 51: 870. [7] Das, B., Anjani, G. (1999). Phytochemistry 51: 115. [8] Harborne, J.B. (1984). Chapman & Hall Ltd, New York, pp. 49–50, 255.