Two fresh mexicanolide-type limonoids, carapanolides TCU (1C2), and three fresh phragmalin-type limonoids, carapanolides VCX (3C5), were isolated in the seed products of (andiroba). two brand-new uncommon 9,10-573.2704, calcd. for 573.2697) by HRFABMS, implying 12 over the levels of unsaturation. UV and IR spectra showed the current presence of hydroxylgroups in potential 3462 cm?1, ester groupings at potential 1727 cm?1 and -unsaturated -lactone at potential 230 nm (log 3.85). 1H- and 13C-NMR data indicated that eight from the 12 devices of unsaturation came from three carbon-carbon double bonds and three ester carbonyls, including a lactone carbonyl and ketone. Open in a separate window Number 1 Chemical constructions of Compounds 1C5. Therefore, the remaining examples of unsaturation required 1 to be pentacyclic. The 1H- and 13C-NMR spectra of 1 1 (Table 1) indicated the presence of four tertiary methyls (H 0.69, 0.86, 1.23, 1.27 (each s)), a 2-methyl propanoyl (H 1.25 and 1.27 (each 3H, d), 2.71 (1H, sept); C 19.1 and 19.2 (each q), 34.3 (d), 176.2 (s)), methyl ester (H 3.71 (s); C 52.2 (q), 173.6 (s)), four methylenes (C 20.7 (t), 32.9 (t), 33.7 (t), 45.0 (t)), four 683.2335, calcd. for 683.2340) by HRFABMS, implying 17 within the index of hydrogen deficiency. IR and UV spectra exposed the E7080 cell signaling presence of ester organizations and an -unsaturated -lactone at maximum 1748 and 1719 cm?1 and maximum at 226 nm (log 3.73). 1H- and 13C-NMR data indicated that eight out of the 17 devices of unsaturation came from three carbon-carbon double bonds and five ester carbonyls, including two lactone carbonyls. Consequently, the remaining examples of unsaturation required 3 to be non-acyclic. The 1H- and 13C-NMR spectra of 3 (Table 2) indicated the presence of two tertiary methyls (H 1.02, 1.14 (each s)), two acetyls (H 2.04 (s), 2.17 (s); C 20.8 (q), 21.8 (q), 169.1 (s), 170.1 (s)), an Hz) a673.2492, calcd. for 673.2496) by HRFABMS. IR and UV spectra exposed the presence of hydroxy organizations and ester organizations and an -unsaturated -lactone at maximum 3657, 1728 and 1698 cm?1 and maximum at 230 nm (log 3.73). The 1H- and 13C-NMR spectra of 4 (Table 2) indicated the presence of three tertiary methyl organizations (H 0.74, 1.32, 1.48 (each s)), an acetyl (H 2.09 (s); C 21.7 (q), 169.1 (s)), an 791.2765, calcd. for 791.2763) while determined by HRFABMS. The IR spectrum showed the presence of a hydroxyl at maximum 3352 cm?1 and ester organizations at maximum 1742 cm?1. 1H- and 13C-NMR spectra (Table 2) indicated the Nr4a3 presence of three methyls (H 1.10, 1.23, E7080 cell signaling 1.43 (each 3H, s)), three acetyl organizations (H 1.70, 2.18, 2.22 (each 3H, s)), a propanoyl group (H 1.09 (3H, t), 2.38 (2H, dq), C 172.5 (s)), a methoxycarbonyl group ((H 3.69 (3H, s), C 53.1 (q), 169.4 (s)), 0.05 and ** 0.01 in the NO inhibitory assay and # 0.05 and ## 0.01 in the cytotoxicity assay. 3. Experimental Section 3.1. General Methods Melting points were determined on a Yanagimoto micro-melting point apparatus and were uncorrected. Optical rotations were measured using a JASCO DIP-1000 digital polarimeter. IR spectra were recorded using a Perkin-Elmer 1720X FTIR spectrophotometer (Perkin-Elmer Inc., Wellesley, MA, USA). 1H- and 13C-NMR spectra were obtained on an Agilent vnmrs 600 spectrometer (Agilent Systems, Santa Clara, CA, USA) with standard pulse sequences, operating at 600 and 150 MHz, respectively. CDCl3 was used as the solvent and TMS as the internal standard. FABMS were recorded on a JEOL-7000 mass spectrometer (JEOL, Tokyo, Japan). Column chromatography was performed over silica gel (70C230 mesh, Merck, Darmstadt, Germany), while medium pressure liquid chromatography (MPLC) was carried out with silica gel (230C400 mesh, Merck). HPLC was operate on a JASCO PU-1586 device (JASCO, Tokyo, Japan) built with a differential refractometer (RI 1531). Fractions extracted from column chromatography had been supervised by TLC (silica gel 60 F254, Merck). 3.2. Place Material The essential oil of (2.03 kg) Carapa guianensis AUBLET (Meliaceae) was gathered in the Amazon, Brazil, in March 2013, and was supplied by Mr kindly. Akira Yoshino (who’s a representative from the NGO Green Center Love Amazon Task). A voucher specimen (CGS-01-2) was transferred in the Herbarium from the Lab of Therapeutic Chemistry, Osaka School of Pharmaceutical Sciences. 3.3. Isolation of Substances AUBLET (Meliaceae) (2.03 kg) was dissolved in CHCl3, as well as the CHCl3 solution was put through CC (silica gel 14 kg), affording 7 fractions: Fraction A (fraction (Fr.) Zero. 1C85, 1.512 kg) was eluted with +16.6 (0.1, CHCl3); HRFABMS (comparative strength (rel. int.)): 573 ([M + H]+, 100), 555 (11), 485 (20). ?18.1 (0.1, EtOH); HRFABMS E7080 cell signaling (rel. int.): 607.