Chemical composition of Croton laevigatus

Abstract

The tree Croton laevigatus Vahl. (Euphorbiaceae) is distributed mainly in China in the provinces of Yunnan, Guangdong, and Hainan. Roots and leaves of the plant are usually used by the Dai people as a traditional drug for treating fractures, malaria, stomach ache, and wounds received from falling [1]. Phytochemical studies of C. laevigatus have not yet been reported with the exception of diterpenoids with interesting skeletons [2,3].Air-dried ground leaves (20 kg) were extracted with MeOH (3 u 80 L) in order to obtain the crude extract (2120 g) after evaporation in vacuo. The extract was suspended in H 2 O (8.0 L) and fractionated successively with petroleum ether, CHCl 3 , and n-BuOH (3 u 8.0 L). The petroleum-ether extract (673 g) was chromatographed over a column of silica gel with elution by petroleum ether:EtOAc mixtures (1:0, 9:1, 4:1, 3:2, 0:1) to afford compounds 1 (3 g) and 5 (10 g). The BuOH fraction was chromatographed over a column of silica gel with gradient elution by CHCl 3 :CH 3 OH mixtures (50:1o0:1) to afford 2 (50 mg), 3 (5 mg), 4 (20 mg), and 6 (20 mg).PMR and 13 C NMR spectra were used to identify 1-4. Compounds 5 and 6 were identified by direct comparison with authentic samples as E-sitosterol and daucosterol, respectively. 3c-(4cc-Hydroxy-3cc,5cc-dimethoxyphenyl)propylbenzoate (1), brown oil, C 18 H 20 O 5 . EI-MS (m/z, %): 316 (90) [M] + , 194 (100), 179 (23), 167 (52), 163 (53), 105 (75), 77 (92). The PMR and 13 C NMR spectra were published [4]. Dihydrodehydrodiconiferyl alcohol E-D-glucoside (2), yellow semi-solid compound, C 26 H 34 O 11 . ESI-MS (m/z, +-ions): 545.2 [M + Na] + , 383.1 [M + Na -glucose] + , 365.1 [M + Na -glucose -H 2 O] + . The PMR and 13 C NMR spectra were published [5]. Myrsinionoside C (3), yellow semi-solid compound, C 19 H 36 O 7 . ESI-MS (m/z, +-ions): 400.2 [M + Na] + . The PMR and 13 C NMR spectra were published [6]. Alangionoside J (4), yellow semi-solid compound, C 19 H 36 O 7 . ESI-MS (m/z, +-ions): 400.2 [M + Na] + . The PMR and 13 C NMR spectra were published [7].All compounds were isolated from C. laevigatus for the first time whereas 2-4 were isolated for the first time from a plant of the genus Croton. ACKNOWLEDGMENTS

Acetylcholinesterase Inhibitors from Croton sylvaticus Ethyl Acetate Leaf Extract and their Mutagenic Effects

“…To the best of our knowledge this is the first report of this compound as natural product. Closely related phenyl propanoid analogues: namely 3'-(4''hydroxyphenyl)propyl benzoate and 3'-(4'' hydroxy-3'',5''dimethoxyphenyl)-propyl benzoate were recently reported from Croton laevigatus and C. hutchinsonianus [11,12].…”