Xylopia laevigata, popularly known as "meiú" and "pindaíba", is a medicinal plant used in the folk medicine of the Brazilian Northeast for several purposes. The chemical constituents of the essential oil from leaves of X. laevigata, collected from wild plants growing at three different sites of the remaining Atlantic forest in Sergipe State (Brazilian Northeast), were analyzed by GC/FID and GC/MS. The effect of the essential oil samples was assessed on tumor cells in culture, as well on tumor growth in vivo. All samples of the essential oil were dominated by sesquiterpene constituents. A total of 44 compounds were identified and quantified. Although some small differences were observed in the chemical composition, the presence of γ-muurolene (0.60-17.99%), δ-cadinene (1.15-13.45%), germacrene B (3.22-7.31%), α-copaene (3.33-5.98%), germacrene D (9.09-60.44%), bicyclogermacrene (7.00-14.63%), and (E)-caryophyllene (5.43-7.98%) were verified as major constituents in all samples of the essential oil. In the in vitro cytotoxic study, the essential oil displayed cytotoxicity to all tumor cell lines tested, with the different samples displaying a similar profile; however, they were not hemolytic or genotoxic. In the in vivo antitumor study, tumor growth inhibition rates were 37.3-42.5%. The treatment with the essential oil did not significantly affect body weight, macroscopy of the organs, or blood leukocyte counts. In conclusion, the essential oil from the leaves of X. laevigata is chemically characterized by the presence of γ-muurolene, δ-cadinene, germacrene B, α-copaene, germacrene D, bicyclogermacrene, and (E)-caryophyllene as major constituents and possesses significant in vitro and in vivo anticancer potential.

Essential oils from leaves of Xylopia frutescens (XFMJ) and two specimens of Xylopia laevigata (XLMC and XLSI) were obtained by hydrodistillation using a Clevenger-type apparatus, and analyzed by GC-MS and GC-FID. Sesquiterpenes dominated the essential oils. The main constituents of XFMJ were (E)-caryophyllene (24.8%), bicyclogermacrene (20.8%), germacrene D (17.0%), -elemene (7.9%), and (E)--ocimene (6.8%). XLMC contained significant quantities of germacrene D (18.9%), bicyclogermacrene (18.4%), -elemene (9.5%), -selinene (9.2%), (E)-caryophyllene (8.5%), germacrene B (5.7%) and -muurolene (5.7%), while germacrene D (27.0%), bicyclogermacrene (12.8%), (E)-caryophyllene (8.6%), -muurolene (8.6%), -cadinene (6.8%), and germacrene B (6.0%) were the main components of XLSI. The essential oils had trypanocidal activity against the Y strain of Trypanosoma cruzi, with IC 50 values lower than 30 µg.mL-1 and 15 µg.mL-1 against epimastigote and trypomastigote forms of T. cruzi, respectively, and were also able to reduce the percentage in vitro of T. cruzi-infected macrophages and the intracellular number of amastigotes at concentrations that were non-cytotoxic to macrophages.

The phytochemical investigation of the stem bark of Annona pickelii yielded four steroids (β-sitostenone, β-sitosterol, stigmasterol and campesterol), three lignans (eudesmin, magnolin and yangambin), twelve alkaloids (liriodenine, lysicamine, atherospermidine, anonaine, analobine, asimilobine, discretamine, stepholidine, coclaurine, orientaline, juziphine and stepharine), and a benzenoid (2-methoxybenzoic acid). These compounds support their recent reclassification from Rollinia to Annona , and that it is a typical species of the family Annonaceae. Significant antifungal and antioxidant activities were found for the methanol crude extract as well as for the lignans eudesmin, magnolin, yangambin and the alkaloid discretamine. In addition, several items of NMR data for the alkaloids were reviewed and unequivocally described in this work. ]]>

The phytochemical investigation of the hexane extract which was obtained from the leaves of Xylopia laevigata (Annonaceae) produced six terpenes. Among these, five diterpenes named abieta-7,13-dien-3-one, ent-7β-acetoxy-16β-hydroxy-kaurane, 4-epi-cupressic acid, powerol, and labdorffianic acid B, and one oxygenated sesquiterpene, spathulenol. This is the first time these isolated diterpenes from X. laevigata have been described. The different structures belong to the abietane, kaurane, and labdane diterpenoids, and are indicative of the chemical diversity found in X. laevigata. Moreover, the diterpene ent-7β-acetoxy-16β-hydroxykaurane is reported herein for the first time as a natural product, and 4-epi-cupressic acid, powerol, and labdorffianic acid B are reported for the first time in the Annonaceae family. The structures of the isolated compounds were established by extensive analyses using 1D and 2D NMR spectroscopy in combination with MS. The cytotoxic activities of compounds abieta-7,13-dien-3-one, spathulenol, 4-epi-cupressic acid, and powerol were evaluated against tumor and non-tumor cell lines, in which spathulenol was found to be the most active, mainly against K562 with an IC 50 value of 17.20 µmol L-1 .