Three new triterpenes, 3,4-seco-3,11β-epoxyfriedel-4(23)-en-3β-ol (1), friedelan-3α,11β diol (2), 7β,26-epoxyfriedelan-3a,7a-diol (3), a mixture of two new triterpenes 3α-hydroxyfriedelan-29-yl palmitate (4) and 3α-hydroxyfriedelan-29-yl stearate (5) and eleven known compounds were obtained from the hexane extract of Maytenus quadrangulata leaves. The structures and the relative stereochemistry of the new triterpenes were established through 1D/2D nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS), and Fourier transform infrared (FTIR) spectral data. The hexane extract and isolated compounds were submitted to the cytotoxicity assays against leukemia (THP-1 and K562), ovarian (TOV-21G) and breast cancer (MDA-MB-231) cell lines. Compounds 1, 2 and 11β-hydroxyfriedelan-3-one (15) displayed high cytotoxicity and selectivity against leukemic cells when compared to positive control cytarabine (for THP-1) and imatinib (for K562). Furthermore, compound 2 showed similar cytotoxicity and an enhanced selectivity towards ovarian and breast cells in comparison to positive control etoposide.

Maytenus distichophylla is a medicinal species used in Northeast of Brazil. The hexane (HE), chloroform (CE), ethyl acetate (EAE) and methanol (ME) extracts and compounds from its roots were evaluated for their protective activity against Staphylococcus aureus and Candida albicans. The cytotoxicity for chronic myeloid leukemia (K562), acute monocytic leukemia (THP-1), and peripheral blood mononuclear cells of normal individuals (PBMC) cells was established by MTT method using etoposide as standard. The in vivo toxicity of samples was determined using Caenorhabditis elegans model. From HE and CE were isolated: friedelan-3-one (1), b-sitosterol (2), 3-oxo-olean-9(11),12-diene (3), a mixture of pristimerin (4) and 11a-hydroxylup-20(29)-en-3-one (5), 30-hydroxylup-20(29)-en-3-one (6), friedelane-3,7-dione (7), tingenone (8) and triacylglycerol (9). The structures of 1-9 were confirmed by spectral data. All samples reduced the viability of S. aureus and present no effect against C. albicans. The HE, CE, mixture of 4/5 and 8 reduced 75% of S. aureus viability. Cytotoxic effect for K562 and THP-1 cells was caused by compounds 1, 2 and 8. All samples displayed selectivity for leukemic cells and low toxicity to PBMC cells, suggesting their potential as anticancer agents. Extracts and compounds were non-toxic to L1 larvae of C. elegans. However, most of them reduced significantly young adult worm’s survival, being considered as potential nematicides.

Two new compounds, caryopristimerin and 2α,3α,22β-trihydroxy-21-oxo-29-nor-friedelan-24-oic acid, were isolated from the hexane/ethyl ether extract of Salacia crassifolia roots. Caryopristimerin represents the first example of a homo Diels-Alder adduct of a sesquiterpene and a triterpene, and the new 29-nor-friedelane displays a highly oxygenated A ring with a carboxylic group at the unusual C-5 position. The new compounds were elucidated by infrared (IR), high-resolution-atmospheric pressure chemical ionization-mass spectrometry (HR-APCI-MS), 1D/2D nuclear magnetic resonance (NMR) and single crystal X-ray diffraction analysis. Additionally, the known compounds 3-oxo-29-hydroxyfriedelane, pristimerin, tingenone and netzahualcoyonol are herein reported for the first time as constituents of S. crassifolia. Their structures were established by spectroscopic analysis.

The new triterpene friedelan-1,3,21-trione, the known compounds friedelan-3-one, 3β-friedelinol, 3,4-seco-friedelan-3-oic acid, 28-hydroxyfriedelan-3-one, friedelan-3-oxo-28-al, friedelan-3,21-dione, 30-hydroxyfriedelan-3-one, a mixture of 30-hydroxyfriedelan-3-one/21α-hydroxyfriedelan-3-one, 21β-hydroxyfriedelan-3-one, gutta-percha, squalene, and a mixture of palmitic/stearic/oleic acids were isolated from the hexane extracts of leaves and branches of T. micrantha. Their chemical structures were established by Fourier transform infrared spectroscopy (FTIR), gas chromatography (GC), 1D/2D nuclear magnetic resonance (NMR) and comparison with the literature data. All compounds were described for T. micrantha and the genus Tontelea for the first time. The branch and leaf extracts displayed anti-Zika virus activity at the lowest tested concentration of 15.6 µg mL-1, mainly virucidal effect, and presented no cytotoxicity to Vero cells. Furthermore, the ethyl acetate and methanolic leaf extracts demonstrated the best activities at the concentration of 31.2 and 15.6 µg mL-1 at the viral adsorption and penetration stages, respectively. These results showed that these extracts may be promising candidates for the Zika virus treatment.

Psychotria viridis is one of the species that produces N,N-dimethyltryptamine. Its decoction together with other species, such as Banisteriopsis caapi, produces ayahuasca, a beverage used for ritualistic and medicinal purposes. The goal of this study was to understand how environmental factors and cultivation methods influenced the content of N,N-dimethyltryptamine in P. viridis. Over all four seasons, leaf samples were collected from 25 different locations in 14 Brazilian states, and Federal District. Environmental parameters, micro and macronutrients, plant characteristics, information on farming methods were correlated with N,N-dimethyltryptamine content, determined by gas chromatography coupled to mass spectrometry (GC-MS). Greatest effects on the N,N-dimethyltryptamine amount were associated with seasonality, altitude, latitude and biome type. A positive correlation between N and Mg content and N,N-dimethyltryptamine levels was statistically established. By regression analysis, the adequate foliar nutrient levels that would result in the concentration of N,N-dimethyltryptamine in cultivated plants similar to that of Amazonian P. viridis were equated.

ABSTRACT Diarrhea is an infectious disease caused by bacterial, virus, or protozoan, and dengue is caused by virus, included among the neglected diseases in several underdeveloped and developing countries, with an urgent demand for new drugs. Considering the antidiarrheal potential of species of Maytenus genus, a phytochemical investigation followed by antibacterial activity test with extracts of branches and heartwood and bark of roots from Maytenus gonoclada were conducted. Moreover, due the frequency of isolation of lupeol from Maytenus genus the antiviral activity against Dengue virus and cytotoxicity of lupeol and its complex with β-cyclodextrins were also tested. The results indicated the bioactivity of ethyl acetate extract from branches and ethanol extract from heartwood of roots of M. gonoclada against diarrheagenic bacteria. The lupeol showed potent activity against Dengue virus and low cytotoxicity in LLC-MK2 cells, but its complex with β-cyclodextrin was inactive. Considering the importance of novel and selective antiviral drug candidates the results seem to be promising.

ABSTRACT The phytochemical study of the extract leaves from Maytenus distichophylla Mart. and Salacia crassifolia (Mart. ex Schult.) G. Don, Celastraceae, resulted in the isolation of 3-oxofriedelane, 3β-hydroxyfriedelane, 3β,24-dihydroxyfriedelane, 3-oxo-28,29-dihydroxyfriedelane, two mixtures of pentacyclic triterpenes (α-amyrin with β-amyrin and 3β-stearyloxy-urs-12-ene with 3β-stearyloxy-olean-12-ene), 3β-palmityloxy-urs-12-ene, the steroid β-sitosterol and its glycosylated derivative β-glucosyl-β-sitosterol, tritriacontanoic acid and the natural polymer gutta percha. The chemical structures of these constituents were established by IR, 1H and 13C NMR spectral data. Crude extracts, the mixtures of triterpenes and the isolated constituents were subjected to in vitro acetylcholinesterase inhibitory evaluation. Acetylcholinesterase inhibitory effect was observed for crude chloroform extract leaves from M. distichophylla (100%) and S. crassifolia (97.93 ± 5.63%) and for the triterpenes 3β,24-dihydroxyfriedelane (99.05 ± 1.12%), 3-oxo-28,29-dihydroxyfriedelane (90.59 ± 3.76%) and 3β-palmityloxy-urs-12-ene (97.93 ± 1.47%). The percent inhibitions induced by these natural products were very similar to those produced by physostigmine (93.94 ± 2.10%) a standard acetylcholinesterase inhibitor. Therefore, these results open perspectives for the use of these species as source of compounds with similar physostigmine pharmacological effect.

ABSTRACT The phytochemical study of hexane, chloroform and methanol extracts from leaves of Psychotria viridis resulted in the identification of: the pentacyclic triterpenes, ursolic and oleanolic acid; the steroids, 24-methylene-cycloartanol, stigmasterol and β-sitosterol; the glycosylated steroids 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol; a polyunsaturated triterpene, squalene; the esters of glycerol, 1-palmitoylglycerol and triacylglycerol; a mixture of long chain hydrocarbons; the aldehyde nonacosanal; the long chain fat acids hentriacontanoic, hexadecanoic and heptadenoic acid; the ester methyl heptadecanoate; the 4-methyl-epi-quinate and two indole alkaloids, N,N-dimethyltryptamine (DMT) and N-methyltryptamine. The chemical structures were determined by means of spectroscopic (IR, 1H and 13C NMR, HSQC, HMBC and NOESY) and spectrometric (CG-MS and LCMS-ESI-ITTOF) methods. The study of biologic properties of P. viridis consisted in the evaluation of the acetylcholinesterase inhibition and cytotoxic activities. The hexane, chloroform, ethyl acetate and methanol extracts, the substances 24-methylene-cycloartanol, DMT and a mixture of 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol showed cholinesterase inhibiting activity. This activity induced by chloroform and ethyl acetate extracts was higher than 90%. The methanol and ethyl acetate extracts inhibit the growth and/or induce the death of the tumor cells strains B16F10 and 4T1, without damaging the integrity of the normal cells BHK and CHO. DMT also demonstrated a marked activity against tumor cell strains B16F10 and 4T1.

The composition of essential oils from flowers of Solanum stipulaceum Roem & Schult collected in May and September was studied for the first time. Effects of g-radiation on volatile constituents were investigated by gas chromatography (GC) with flame ionization detector (FID). In addition, the antileukemic activity was studied by a 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide (MTT) colorimetric assay against human cell lines HL-60 and THP-1. The main constituents of the essential oil of flowers collected in May were β-caryophyllene (25.8%), γ-gurjunene (11.9%), and β-gurjunene (8.2%), whereas the essential oil of flowers collected in September was mainly composed of β-caryophyllene (26.5%), caryophyllene oxide (11.0%), and γ-gurjunene (10.0%). The main components of essential oil from flowers collected in September were not significantly affected by γ-radiation at lower doses than 10.0 kGy. No cytotoxic activity in leukemic cell lines was observed for non-irradiated samples. However, irradiated samples exhibited slightly cytotoxic activity.

The phytochemical study of hexane extract from leaves of Salacia crassifolia resulted in the isolation of 3β-palmitoxy-urs-12-ene, 3-oxofriedelane, 3β-hydroxyfriedelane, 3-oxo-28-hydroxyfriedelane, 3-oxo-29-hydroxyfriedelane, 28,29-dihydroxyfriedelan-3-one, 3,4-seco-friedelan-3-oic acid, 3β-hydroxy-olean-9(11):12-diene and the mixture of α-amirin and β-amirin. β-sitosterol, the polymer gutta-percha, squalene and eicosanoic acid were also isolated. The chemical structures of these constituents were established by IR, 1H and 13C NMR spectral data. Crude extracts and the triterpenes were tested against Entamoeba histolytica, Giardia lamblia and Trichomonas vaginalis and no activity was observed under the in vitro assay conditions. The hexane, chloroform, ethyl acetate and ethanol crude extracts, and the constituent 3,4-seco-friedelan-3-oic acid and 28,29-dihydroxyfriedelan-3-one showed in vitro antimicrobial activity against Salmonella typhimurium, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Streptococcus sanguinis and Candida albicans.

The phytochemical study of hexane/ethyl ether (1:1) extract of the roots of M. imbricata, Celastraceae, resulted in the isolation and characterization of six known triterpenes: 11α-hydroxylup-20(29)-en-3-one, previously isolated from this species besides, 3β,11α-di-hydroxylup-20(29)-ene, 3,7-dioxofriedelane, 3-oxo-29-hydroxyfriedelane, tingenone and 6-oxo-tingenol. The chemical structures of these triterpenes were established by spectrometric data (IR, ¹H and 13C NMR) and through comparison with literature data. The hexane/ethyl ether (1:1), ethyl acetate and methanol extracts, and 11α-hydroxylup-20(29)-en-3-one, tingenone and 6-oxo-tingenol, showed antimicrobial properties on in vitro assays. All extracts and triterpenes, except 3β,11α-di-hydroxylup-20(29)-ene, presented toxicity demonstrated by the larvicidal effect test using Artemia salina.

The phytochemical investigation on the aereal parts of Lychnophora pinaster Mart., Asteraceae, was carried to isolation of triterpenes. 3-O-Acetyl-lupeol (1), 3-O-acetyl-pseudotaraxasterol (2), and 3-O-acetyl-α-amyrin (3) were isolated from hexanic extract and 4,4-dimethyl-cholesta-22,24-dien-5-ol (4), α-amyrin (5), and lupeol (6) were isolated from hexanic/dichlorometanic extract of the leaves. Compounds Δ7-bauerenyl acetate (7), friedelin (8), stigmasterol (9), and sitosterol (10) were isolated from the hexanic/dichlorometanic extract of the stems. The steroids 9 and 10 were also isolated from the hexanic/dichlorometanic extract of the flowers. Triterpenes 1, 3, 4, and 7 are described for the first time in the genus Lychnophora. The apolar fractions of the leaf and stem extracts and some isolated triterpenes showed low trypanocidal activity. Moreover, apolar fractions of the leaf and stem extracts and 5 showed antibacterial action against Staphylococcus aureus.

Six pentacyclic triterpenes were isolated from hexane extract of stems of Maytenus salicifolia Reissek, Celastraceae: 30-hydroxyfriedelan-3-one (1), 3,16-dioxofriedelane (2), friedeline (3), lupeol (4), betuline (5) and lup-20(29)-en-3,30-diol (6). The structure each one was established on the basis of detailed ¹H and 13C NMR spectral investigation and by comparison with the respective literature values. For compound 1, the complete 2D NMR (HMBC, HMQC and NOESY) spectral data were herein reported for the first time. Compounds 1, 2, 5 and 6 were isolated for the first time from this plant. Antioxidant activity is described for some extracts from species of the Celastraceae family, then, the extracts from aerial parts of M. salicifolia were evaluated in relation to antioxidant potential using the DPPH method. Compared to quecertin, the AcEt extract (EAF) from leaves, AcEt (EAPF) and MeOH (EMPF) from pulp fruit and AcEt (EAT) and MeOH (EMT) from stems showed significant antioxidant property.

Seis triterpenos pentacíclicos isolados dos galhos de Maytenus gonoclada (Celastraceae), incluindo todos os dados de RMN do novo composto 3-oxo-12α,29-diidroxifriedelano são aqui relatados. A estereoquímica do novo friedelano foi estabelecida por dados de RMN bidimensional (HSQC, HMBC e NOESY), e sua massa molecular confirmada por espectrometria de massas (ESI). Testes de atividade antimicrobiana usando método de difusão em disco e de macrodiluição foram realizados contra as bactérias Escherichia coli, Citrobacter freundii e Bacillus cereus, e contra o fungo Candida albicans. O triterpeno 3-oxo-12α-hidroxifriedelano mostrou resultado positivo contra C. albicans.

Six pentacyclic triterpenes were isolated from branches of Maytenus gonoclada (Celastraceae) and all NMR data of a new compound 3-oxo-12α,29-dihydroxyfriedelane are herein reported. The stereochemistry of the new friedelane was established by bidimensional NMR (HSQC, HMBC and NOESY) data, and its molecular weight confirmed by ESI mass spectrometry. Antimicrobial activity assays using the method of disk diffusion and macrodilution were carried out against the bacteria Escherichia coli, Citrobacter freundii, and Bacillus cereus, and against the fungi Candida albicans. The triterpene 3-oxo-12α-hydroxyfriedelane showed positive result against C. albicans.

A grande variedade de angiospermas apontou a necessidade do desenvolvimento de sistemas de classificação botânica apoiada pela fitoquímica, bioquímica e outras. Recentemente, técnicas de análise utilizadas para o isolamento e caracterização de metabólitos secundários vêm sendo empregadas como métodos auxiliares rápidos e eficientes para identificação e classificação de espécies vegetais. M. salicifolia é popularmente conhecida no Brasil, como "cafezinho". O chá obtido a partir de folhas frescas é usado topicamente para aliviar pruridos e sintomas alergiformes. Este trabalho apresenta a utilização do CCD em sílica gel e espectrofotometria no UV / Vis como métodos auxiliares na identificação botânica de M. salicifolia. Os resultados demonstraram que este processo pode ser usado na diferenciação de plantas do mesmo gênero, assim como detectar variações químicas entre indivíduos de uma mesma espécie.

The great variety of angiosperms shows the need to development of botanical classification systems supported by phytochemistry, biochemistry and others. Recently, techniques of analysis used for the isolation and characterization of secondary metabolites have been employed as auxiliary quick and efficient methods for the identification and classification of plant species. M. salicifolia is popularly known in Brazil, as "small coffee" and decoct obtained from its fresh leaves is topically used to alleviate itches and other skins allergic symptoms. This work presents the use of TLC and UV/Vis spectrophotomety processes to be applied like an auxiliary method in botanical taxonomy. The results demonstrate that this process can be used in differentiation of the same genera species, and in the selection of chemical variations between individuals of the same species.