Abstract The essential oils obtained by hydrodistillation from fresh leaves of Vitex agnus-castus and Ocimum campechianum, and from fresh inflorescences of Ocimum carnosum were analysed by GC-FID and GC-MS. The major components of V. agnus-castus essential oil were identified as 1,8-cineole (47.9%), terpinyl α-acetate (11.6%), sabinene (11.2%) and caryophyllene oxide (9.7%), while in the O. campechianum essential oil were eugenol (72.1%), β-elemene (6.8%), (E)-caryophyllene (6.4%) and bicyclogermacrene (5.2%). Linalool (79.0%), α-epi-cadinol (5.4%), terpinen-4-ol (3.2%) and 1,8-cineole (2.8%) were the major constituents in the O. carnosum essential oil. The essential oils were subsequently evaluated for their larvicidal and cytotoxic activities. Larval bioassay against Aedes aegypti of V. agnus-castus, O. campechianum and O. carnosum essential oils showed LC50 values of 97.55 ± 0.35, 81.45 ± 0.35 and 109.49 ± 0.35 μg/mL, respectively. The in vitro cytotoxic activities of the essential oils has been evaluated on breast adenocarcinoma (MCF-7), lung carcinoma (NCI-H292), pro-myelocytic leukemia (HL-60), and cervical adenocarcinoma (HEP-2) human cell lines, and pro-myelocytic leukemia cells lines (HL-60) were found to be the most sensitive to all the essential oils tested than the others. This is the first report on larvicidal and cytotoxic activities of these essential oils.
ABSTRACT The organic extracts from stems, roots and leaves of Tephrosia egregia Sandwith, Fabaceae, provided a new flavone, 5-hydroxy-8-(1",2"-epoxy-3"-hydroxy-3"-methylbutyl)-7-methoxyflavone (1), in addition to eleven known compounds: pongaflavone (2), praecansone B (3), 12a-hydroxyrotenone (4), praecansone A, 2',6'-dimethoxy-4',5'-(2",2"-dimethyl)-pyranochalcone, pongachalcone, maackiain, β-sistosterol and its glucoside, p-cumaric acid and cinnamic acid. The structures of all compounds were established on the basis of spectroscopic methods, mainly 1D and 2D NMR and HRESIMS, involving comparison with literature data. Cytotoxicity of compounds 1–4 was evaluated against AGP-01 (cancerous ascitic fluid), HCT-116 (colon adenocarcinoma), HL-60 (leukemia), PC-3 (prostate carcinoma), SF-295 (glioblastoma) and SKMEL 28 (melanoma) cell lines.
ABSTRACT Phytochemical investigation of Bauhinia acuruana Moric., Fabaceae, resulted in the isolation of sixteen constituents, including two new compounds 2'-hydroxy-2,3,5-trimethoxybibenzyl (1), (2R,3S)-2-(3,4'-dihydroxyphenyl)-5-methoxy-6-methylchroman-3,7-diol (2), together with fourteen known ones (3–16). The structures of the compounds were established by spectroscopic analysis including HR-ESI-MS, 1D and 2D NMR data, followed by comparison with previously reported data from the literature. Compounds 1, 2, 6, 7, 8 and 9 were evaluated for their cytotoxicity, which turned out to be marginal in a panel of six human cancer cell lines.
Stemodinol, a new natural compound, together with known compounds including jaceidin, stemodin, stemodinoside B, isocrenatoside, verbascoside, crenatoside, and isoverbascoside, were isolated from Stemodia maritima Linn. The antioxidant (DPPH method) and antimicrobial activities of stemodin, stemodinoside B, and crenatoside were investigated. Among the components tested, only crenatoside isolated from the roots showed a high antioxidant power. Stemodin and stemodinoside B exhibited antibacterial activities.
The chemical investigation of the stems and branches of Macroptilium lathyroides led to the isolation of a mixture of β-sitosterol and stigmasterol. The extracts from the roots allowed the isolation of lasiodiplodin, a mixture of stigmast-4-en-6β-ol-3-one and stigmast-4,22-dien-6β-ol-3-one, de-O-methyllasiodiplodin, genistein and lupinalbin A. The structures of the isolated compounds were assigned on the basis of their NMR data, including comparison of their spectral data with values described in the literature. The antibacterial activity of crude extracts from stems, branches and roots was evaluated. This is the first report involving the chemical investigation of this species.
A new diterpene, (5S*,8S*,9R*,10S*)-11β,12β-epoxy-9α-hydroxy-19(4→3) abeo-abieta-3,13-diene-19,18-olide, together with the known compounds stemodin, D-mannitol, betulinic acid, a mixture of 3β-O-β-D-glucopyranosyl-β-sitosterol and 3β-O-β-D-glucopyranosylstigmasterol and 5,7,4'-trihydroxy-3,8,3'-trimethoxyflavone were isolated from the leaves and stems of Stemodia maritima. Structural elucidation of all compounds was based on interpretation of spectral data, mainly NMR (1D and 2D) and MS, including comparison with values described in the literature.
Um novo diterpeno, (5S*,8S*,9R*,10S*)-11β,12β-epoxi-9α-hidróxi-19(4→3) abeo-abieta-3,13-dieno-19,18-olideo, e as substâncias conhecidas estemodina, D-manitol, ácido betulínico, uma mistura de 3β-O-β-D-glicopiranosil-β-sitosterol e 3β-O-β-D-glicopiranosilestigmasterol, e 5,7,4'-triidróxi-3,8,3'-trimetoxiflavona, foram isolados das folhas e talos de Stemodia maritima. A elucidação estrutural de todas as substâncias baseou-se na interpretação de dados espectrais, principalmente RMN (1D e 2D) e espectrometria de massa (EM), envolvendo comparação com valores descritos na literatura.
The aim of present study was to describe the chemical composition of the essential oils from the leaf and stem of Rollinia leptopetala R. E. Fries (Annonaceae) and to evaluate the larvicidal activities of these essential oils, of the methanol extract from roots of this plant and of the oxoaporphine alkaloid, liriodenine (1) against the third-instar of Aedes aegypti larvae. The methanol extract from the roots showed larvicidal activity with LC50 64.6 ± 1.5 ppm. Higher activity was observed for the isolated alkaloid liriodenine (1), LC50 3.6 ± 0.4 ppm. The essential oils from the leaves and stems, also exhibited larvicidal activity with LC50 104.7 ± 0.2 and 34.7 ± 0.3 ppm, respectively. These results suggest R. leptopetala as a source of natural larvicidal compounds. This is the first report about the chemical composition and larvicidal activity of the leaf and stem essential oils of R. leptopetala.
No presente trabalho descreve-se a composição química dos óleos essenciais de Rollinia leptopetala R.E. Fries (Annonaceae) e as atividades larvicidas dos óleos essenciais, do extrato metanólico das raízes desta espécie e do alcalóide oxoaporfinico, liriodenina (1), frente às larvas no terceiro estágio do mosquito Aedes aegypti. O extrato metanólico mostrou-se ativo com CL50 64,6 ± 1,5 ppm e uma forte atividade foi exibida para o composto (1), CL50 3,6 ± 0,4 ppm. Os óleos essenciais das folhas e galhos também mostraram atividade com CL50 104,7 ± 0,2 and 34,7 ± 0,3 ppm, respectivamente. Estes dados sugerem que R. leptopetala é fonte potencial de larvicidas naturais. A composição química do óleo essencial e as atividades descritas são comunicadas pela primeira vez.
The chemical investigation of the methanolic extract of the aerial part of Sebastiania macrocarpa allowed the isolation of the mixture of steroids β-sitosterol and stigmasterol, gallic acid, and scopoletin. The hexane extract of the roots allowed the isolation of the triterpene lupeol and of the macrociclic diterpene (+)-tonantzitlolone. The structures of all compounds isolated were identified on the basis of their spectral data and by comparison of their spectral data with values described in the literature. This is the first report involving the chemical investigation of this species.
The phytopatogenic fungus Lasiodiplodia theobromae, isolated from guava, was cultivated in rice for 32 days at room temperature. Extraction with CH2Cl2:MeOH (3:7), followed by chromatography fractionation of the extract provided ergosterol. From the fungus culture in Czapeck medium for 40 days at room temperature, were isolated isocoumarin cis-4-hydroxymeleine and an eremophilane-type sesquiterpene. The latter compound is being reported for the first time in the literature. Also, this is the first time that an eremophilane sesquiterpene is described for Lasiodiplodia genus.
O fungo fitopatogênico Lasiodiplodia theobromae, isolado de goiaba, foi cultivado em arroz por 32 dias à temperatura ambiente. Extração com CH2Cl2:MeOH (3:7), seguido de fracionamento cromatográfico do extrato forneceu o esteróide ergosterol. Da cultura fúngica em meio de Czapeck por 40 dias à temperatura ambiente, foram isolados a isocumarina cis-4-hidroximeleína e um sesquiterpeno do tipo eremofilano. O sesquiterpeno eremofilano está sendo descrito pela primeira vez na literatura. Este é o primeiro relato do isolamento de um sesquiterpeno eremofilano para o gênero Lasiodiplodia.
From fruits of Pterodon polygalaeflorus (Leguminosae) the new diterpene 6alpha-hydroxyvouacapane, the known diterpenoids vouacapane-6alpha,7beta,14beta,19-tetraol and methyl 6alpha,7beta-dihydroxyvouacapan-17b-oate and the flavonoid taxifolin were isolated. Structural determinations were accomplished by spectroscopic analysis, including two-dimensional NMR, chemical transformation of the new diterpene and comparison with literature data.
Dos frutos de Pterodon polygalaeflorus (Leguminosae) foram isolados o novo diterpeno 6alfa-hidroxivouacapano e os conhecidos diterpenóides 6alfa,7beta,14beta,19-tetraidroxivouacapano, 6alfa,7beta-diidroxivouacapan-17beta-oato de metila e o flavonóide taxifolina. As estruturas foram determinadas com base em análise espectroscópica, inclusive RMN bidimensional, transformação química do novo diterpeno e comparação com dados da literatura.