547.972The chemical analysis of the acetone extract of the dried leaves from Acacia pennatula yielded triacontanol, β-sitosterol palmitate, β-sitosterol, squalene, nonaprenol, norphytane, lupenone, lupeol, daphnetin and catechin, while from the methanol extract were isolated catechin, epigallocatechin, eriodictyol, β-sitosteryl-β-D-glucopyranoside, and stigmasteryl-β-D-glucopyranoside. The structures of all these natural products were established based on their IR, 1 H, and 13 C NMR and MS data.Several chemical studies have been performed on species of the Leguminosae family, one of the biggest and most important families of the vegetable kingdom [1]. Acacia is a genus belonging to this family and includes approximately 1.200 species. Of these, 64 species are located in Mexico, where some of them are used in the folkloric medicine for the treatment of cancer, gastrointestinal ailments, respiratory infections, diabetes, headache and paludism. A decoction from the aerial parts of A. pennatula (common name "algarrobo") is employed at Morelos, as a traditional medicine for the treatment of inflammation and cancer [2]. A. pennatula (Cham. & Schltdl.) Benth. is a shrub or tree growing up to 3 m high, found throughout the southern states of Mexico, and to our knowledge, no phytochemical investigation has been carried out on this species so far. In this analysis, from the dried leaves fourteen natural products were isolated: triacontanol [3], β-sitosterol palmitate [4], β-sitosterol, squalene [5], nonaprenol [6], meso-2,6,10,14-tetramethylpentadecane (norphytane, 1) [7], lupenone [8], lupeol [9], daphnetin [10], catechin [11], epigallocatechin [11], eriodictyol [12], 3-O-β-D-glucopyranosyl-β-sitosterol (daucasterol) [13], and stigmasteryl-β-D-glucopyranoside [14]. Compound 1 has been obtained from shark liver oil, herring oil, wool wax and zooplankton [15]; however, this is the first occasion that this natural product is isolated from a plant. The sterols, lupane triterpenes, and flavan-3-ols are compounds previously isolated from Acacia species [16], establishing that this species is chemically similar to other species of Acacia genus.
EXPERIMENTALGeneral Experimental Procedures. The acetone and methanol extracts from A. pennatula were fractioned by means of open CC (Merck Kiesel-gel 60 and Supelclean TM SPE LC-SI 6 mL Tubes), and TLC (ALUGRAM ® SIL G/UV 254 silicagel plates), using mixtures of n-hexane-acetone as eluent. In the TLC analysis, the compounds were visualized by UV light and spraying with a 1% solution of (NH 4 ) 4 Ce(SO 4 ) in 2N H 2 SO 4 ; IR spectra were recorded with a Bruker Vector 22 IR instrument in CHCl 3 solution; 1 H and 13 C NMR spectra were recorded in CDCl 3 on a Varian Unity 400 and Varian-Gemini 200 spectrometers, and the chemical shifts were expressed in parts per million (δ) relative to TMS as internal standard. Mass spectra