Two new polyunsaturated 3,4-epoxy-heneicosane derivatives named as epoxy-lobophorene A and epoxy-lobophorene B were isolated from the brown alga Lobophora variegata, in addition to nine known compounds. The structures of the new compounds were elucidated using a combination of 1D/2D nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). The isolated compounds were submitted to antiproliferative assays against the human colon cancer cell line HCT-116, human metastatic prostate cancer PC-3M, murine metastatic melanoma B16-F10 and murine fibroblast cell line L929 and also tested as antibacterial. Both 3,4-epoxy lobophorene A and 3,4-epoxy lobophorene B depicted moderate antiproliferative effect against cell lines. None of them showed antibacterial activity.

Two unreported ergostane-type sterols 24(R)-7α-hydroperoxy-ergost-5-en-3β-ol and 6β-carboxyl-24(R)-(8→6)-abeo-ergostan-3β,5β-diol, along with seven known ones were isolated from the hexane and alcohol extracts from the zoanthids Palythoa caribaeorum and Palythoa variabilis. The structures of the new compounds were determined using spectroscopic techniques, including 1D and 2D nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectrometry (HRESIMS), and comparison with data previously published. 6β-Carboxyl-24(R)-(8→6)-abeo-ergostan-3β,5β-diol showed moderate cytotoxicity against colon cancer cells (HCT-116) as previously described for others abeo-sterol derivatives.

One new alkaloid, 2α-10bα-dihydroxy-9-O-demethylhomolycorine, in addition to seven others known alkaloids, and 5-(hydroxymethyl)furfural, piscidic acid and eucomic acid, were isolated from the bulbs of Hippeastrum solandriflorum. The structures of all compounds were determined using nuclear magnetic resonance (NMR) spectroscopic techniques: 1H NMR and 13C NMR, heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), nuclear Overhauser effect spectroscopy (NOESY), and also the high-resolution electrospray ionization mass spectrometry (EI-HRMS). The cytotoxic activity of all alkaloids was evaluated against three human cancer cell lines (HCT-116, HL-60, OVCAR8 and SF-295) showing IC50 values ranging from 0.01 to 35.7 µM.

The chemical investigation of hexane and ethanol extracts from the aerial parts of Vernonia scorpioides resulted in the isolation and characterization of a new polyacetylene lactone, rel-4-dihydro-4β-hydroxy-5a-octa-2,4,6-triynyl-furan-2-(5H)-one, along with the new ethyl 3,4-dihydroxy-6,8,10-triynyl-dodecanoate, and seven known compounds: taraxasteryl acetate, lupeyl acetate, lupeol, lupenone, β-sitosterol, stigmasterol and luteolin. The structure of all compounds was determined by spectrometric techniques (HR-ESI-MS, ¹H and 13C NMR and IV) and comparison with published spectral data.

The chemical investigation of the stem EtOH extract of S. buddleifolium resulted in the isolation of terpenoids, amides, lignans and a steroidal alkaloid. Based on HRMS, IR and ¹H and 13C NMR data analysis, the structures of the isolated compounds were identified as: 13-hydroxysolavetivone, betulinic acid, N-trans-caffeoyltyramine, N-trans-feruloyldopamine, N-trans-p-cumaroyltyramine, N-trans-feruloyltyramine, N-trans-feruloyl3'-O-methoxydopamine, alangilignoside C, isolariciresinol, polistachiol, (+)-(8R,7'S,8'S)-3α-O-(β-D-glucopiranosyl)-lioniresinol, (-)-(8S,7'R,8'R)-3α-O-(β-D-glucopiranosyl)-lioniresinol and solamargine. The occurrence of terpenoids and amides is common in Solanum, unlike lignans which are rare. The isolated lignans described in this work are reported for the first time in the genus Solanum.

A investigação química das raízes de Cordia polycephala resultou no isolamento de duas novas naftoquinonas terpenoídicas, 6-[10-(12,12-dimetil-13α-(22-metil-21-butenoilóxi)-16-metenilciclohexil)etil]-naftaleno-1,4-diona e (6-[10-(12,12-dimetil-13α-(tigloilóxi)-16-metenilciclohexil)etil]-naftaleno-1,4-diona, designadas de cordiaquinonas N (1) e O (2), respectivamente. As cordiaquinonas já conhecidas, B (3), L (4) e E (5), foram também isoladas. Suas estruturas foram elucidadas após detalhada análise dos dados de RMN ¹H e 13C (1D e 2D) e EMAR (espectrometria de massas de alta resolução). Todas as cordiaquinonas (1-5) foram avaliadas contra quatro linhagens de células cancerígenas: HCT-8 (colo), HL-60 (leucemia), MDA-MB-435 (melanoma) e SF295 (glioblastoma), mostrando IC50 na faixa de 1,2 a 11,1 mmol L-1. As novas cordiaquinonas 1 e 2 foram as mais ativas contra todas as linhagens de câncer, enquanto 3 foi mais seletiva para células leucêmicas (IC50 2,2 µmol L-1).

The chemical investigation of roots of Cordia polycephala resulted in the isolation of two new terpenoid naphtoquinones, 6-[10-(12,12-dimethyl-13α-(22-methyl-21-butenoyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione and (6-[10-(12,12-dimethyl-13α-(tigloyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione, named as cordiaquinone N (1) and O (2), respectively. The known cordiaquinones B (3), L (4) and E (5) were also isolated. Their structures were elucidated after detailed 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HRESIMS) data analysis. All cordiaquinones (1-5) were evaluated against four human cancer cell lines: HCT-8 (colon), HL-60 (leukemia), MDA-MB-435 (melanoma) and SF295 (glioblastoma), showing IC50 values in the range of 1.2 to 11.1 mmol L-1. The new cordiaquinones 1 and 2 were the most active against all cancer cell lines, while compound 3 was selective to leukemia HL-60 cells (IC50 2.2 mmol L-1).

Dois novos furanoflavonoides, 5-hidróxi-2’’-isopropenil-3-metoxifurano-(2",3":7,8)-flavona e 5-hidróxi-2’’-(1-hidróxi-1-metiletil)-3-metoxifurano-(2",3":7,8)-flavona, juntamente com treze compostos conhecidos, foram isolados das cascas das raízes de Lonchocarpus obtusos (Leguminosae). As estruturas de todos os compostos isolados foram determinadas usando métodos espectrométricos tais como RMN 1D e 2D (COSY, HSQC e HMBC) e EMAR, além da comparação com dados espectrais descritos na literatura para compostos de estruturas semelhantes.

Two new furanoflavonoids, 5-hydroxy-2’’-isopropenyl-3-methoxyfurane-(2",3":7,8)-flavone and 5-hydroxy-2’’-(1-hydroxy-1-methylethyl)-3-methoxyfurane-(2",3":7,8)-flavone, along with thirteen other known compounds, were isolated from the root barks of Lonchocarpus obtusus (Leguminosae). The structures of all compounds were determined by spectrometric methods such as 1D and 2D NMR (COSY, HSQC and HMBC) and HREISMS beside comparison with spectral data for similar compounds.

A new flavone named 3,4',5,6-tetramethoxy-[2'',3'':7,8]furanoflavone besides the known flavonoids (2S,3R,4S)-3,4,5,8-tetramethoxy-[2'',3'':6,7]-furanoflavan, 3,6-dimethoxy-2'',2''-dimethylcromene-[2'',3'':7,8] -flavone, 3,5,6-trimethoxy-[2'',3'':7,8]-furanoflavone, 2,4',4,5-tetramethoxy-[2'',3'':6,7]-furanodihydroaurone, (2R,3S,4S)-3,4,5,6-tetramethoxy-[2'',3'':7,8]-furanoflavan and 3',4'-methylenodioxy-5,6-dimethoxy-[2'',3'':7,8]-furanoflavone were isolated from the root barks of Lonchocarpus campestris. The complete ¹H and 13C NMR assignments of the new furan flavonoid was performed using 1D and 2D pulse sequences, including COSY, HMQC and HMBC experiments.

Two glycoalkaloids: solamargine and solasonine; three flavonoids: tiliroside, 7-O-α-L-ramnopyranosyl-kaempferol and 3-O-[ß-D-glucopyranosyl-(1→6)-α-L-ramnopyranosyl]-7- O-α-L-ramnopyranosyl-kaempferol, in addition to the tripeptide Leu-Ile-Val, the aminoacid proline and the eicosanoic acid were isolated from Solanum asperum (Solanaceae). The structures of all compounds were determined by interpretation of their spectra (IR, MS, ¹H and 13C NMR) and comparison with the literature data. All compounds, except the glycoalkaloids, are being reported for the first time for S. asperum. Solasonine showed strong activity (MIC < 0.24 μg/mL) against four filamentous fungi species of the genera Microsporum and Trichophyton.

Este trabalho descreve a composição química dos óleos essenciais e o isolamento de onze substâncias de Eupatorium ballotifolium Kunth, Asteraceae. Os óleos essenciais foram obtidos por hidrodestilação, analisados por CG-EM e avaliados quanto às suas atividades frente à enzima acetilcolinesterase. O rendimento dos óleos foi de 0,11% para as folhas e 0,03% para os talos. Os principais constituintes dos óleos foram os sesquiterpenos β-cariofileno (24,9 e 22,2%), espatulenol (17,7 e 12,4%) e epóxi-allo-aromadendreno (23,0 e 23,6%). Do extrato hexânico da parte aérea foi isolada a mistura de β-sitosterol e estigmasterol, incluindo suas formas glicosiladas, e os triterpenos acetato de taraxasterila e taraxasterol, enquanto, do extrato etanólico foram isolados os flavonóides nepetina and 3-O-glicosil-quercetina. Do extrato hexânico das raízes foram isolados os triterpenos epi-friedelanol e damara-20,24-dien-3β-ol e do extrato etanólico a cumarina 11-hidroxi-11,12-di-hidroobliquina. As estruturas de todos os compostos foram determinadas usando técnicas espectroscópica tais como IV, EM e RMN ¹H e 13C.

This work describes the chemical composition of the essential oils and the isolation of eleven substances from Eupatorium ballotifolium Kunth, Asteraceae. The essential oils were obtained by hydrodistillation, analyzed by GC/MS and evaluated towards the acetylcholinesterase enzyme. The oils yield was of 0.11% for the leaves and 0.03% for the stems. The main constituents of the oils were the sesquiterpenes β-caryophyllene (24.9 and 22.2%), spathulenol (17.7 and 12.4%) and epoxy-allo-aromadendrene (23.0 and 23.6%). From the hexane extract of the aerial part were isolated a mixture of sitosterol and stigmasterol, its glucosides, and the triterpenes taraxasteryl acetate and taraxasterol, while from the ethanol extract were obtained the flavonoids nepetin and 3-O-glucoside-quercetin. The triterpenes epi-friedelanol and dammara-20,24-dien-3β-ol were obtained from the hexane extract of roots, while the coumarin 11-hydroxy-11,12-di-hydroobliquine was obtained from the ethanol extract. The structures of all compounds were determinate based on spectroscopic methods such as IR, MS and ¹H and 13C NMR

The phytochemical investigation of the ethanol extract from the aerial parts of Blainvillea rhomboidea (Asteraceae) resulted in the isolation and characterization of 8β-tigloyloxy-grazielia acid, together with the flavonoids derrone, acacetin, luteolin and luteolin 7-methyl ether, and p-(1-methyl-ethan-1-ol)-phenol. The structures of all compounds were determined by spectroscopic methods (¹H and 13C NMR and HREIMS) and comparison with published spectral data. The flavonoids luteolin and 7-O-metyl-luteolin, isolated from the active dichloromethane fraction, showed moderate cytotoxic activity.

The chemical composition of the essential oils, obtained by hidrodistillation, from leaves of two Vernonia species (V. remotiflora and V. brasiliana), was determined by GC-FID and GC-MS. Both essential oils were predominantly constituted by sesquiterpenes (92.0 - 93.4%). The main constituents of the oil from V. brasilana were (E)-caryophyllene (36.7%), germacrene D (35.5%), and α-humulene (11.7%), while (E)-caryophyllene (42.2%) and bicyclogermacrene (20.0%) were the major ones in the oil from V. remotiflora. Although with moderate activity both oils showed acetylcholinesterase and antibacterial activities.

The chemical composition of the essential oils from leaves and fruits of Triphasia trifolia was analyzed by GC-FID and GC-MS. The major constituents of oil obtained from leaves were sabinene (35.4%) and myrcene (34.1%), while the prevalent compounds in oil from fruits were sabinene (37.2%), beta-pinene (23.95) and gamma-terpinene (16.3%). Both oils showed moderate antimicrobial activity. The fruit decoction was also investigated leading to the isolation of the coumarins isopimpinelin, (R)-byakangelicin and (S)-mexoticin. From leaves were isolated the coumarins (R)-byakangelicin, aurapten, (S)-mexoticin, isosibiricin, isomerazin and coumurrayin and the flavonoid vitexin. All coumarins showed cholinesterase inhibition on TLC tests.

The chemical investigation of the hexane and ethanol extracts from aerial parts of Vernonia chalybaea conducted to the isolation and characterization of a new aliphatic tetrahydroxyl ether, along with a series of known compounds such as 4 α,10 α-epoxyaromadendrane, friedelin, taraxasteryl acetate, pseudotaraxasteryl acetate, lupeyl acetate, lupeol, α-amiryn, β-amiryn, β-sitosterol, stigmasterol, 2,3-dimethyl-1,2,3-tri-hydroxybuthanol, angophorol, angophorol-7-O-glucoside, angophorol-7-O-rutinoside, 3,7-dimethoxy-5,3',4'-trihydroxyflavone and acacetin. The structures of all compounds were determined by spectroscopic analysis and comparison with published spectral data.

Os óleos essenciais das folhas de Cordia leucomalloides e Cordia curassavica foram obtidos por hidrodestilação e suas composições químicas determinadas por uma combinação de CG-EM e CG-DIC. Como resultado, vinte e três componentes foram identificados em ambos os óleos, representando 98,6 e 91,2% da composição volátil. O óleo essencial de C. leucomalloides foi caracterizado por uma alta percentagem de sesquiterpenos (90,6%), sendo delta-cadineno (17,4%), (E)-cariofileno (15,7%), biciclogermacreno (12,5%) e germacreno D (11,2%) os majoritários. Por outro lado, o óleo de C. curassavica mostrou proporções similares de monoterpenos (47,3%) e sesquitepenos (43,9%), entre os quais alfa-pineno (20,5%), beta-pineno (13,1%), (E)-cariofileno (12,4%) e biciclogermacreno (13,8%) foram os compostos predominantes. O potencial larvicida dos dois óleos foi avaliado contra larvas no terceiro estágio do mosquito Aedes aegypti. Os resultados mostraram que ambos os óleos apresentaram atividade biológica significativa, particularmente o óleo essencial de C. leucomalloides, o qual foi capaz de matar 98,7% das larvas numa concentração de 100 ppm.

The essential oils obtained from the leaves of Cordia leucomalloides and Cordia curassavica were obtained by hydrodistillation and their chemical compositions determined by a combination of GC-MS and GC-FID. Twenty-three components were tentatively identified in both oils representing 98.6 and 91.2% of the volatile content. The oil of C. leucomalloides was characterized by a large percentage of sesquiterpenes (90.6%), being delta-cadinene (17.4%), (E)-caryophyllene (15.7%), bicyclogermacrene (12.5%) and germacrene D (11.2%) the major ones. On the other hand, the oil of C. curassavica showed similar proportions of monoterpenes (47.3%) and sesquiterpenes (43.9%) among which <FONT FACE=Symbol>a-</FONT>pinene (20.5%), beta-pinene (13.1%), (E)-caryophyllene (12.4%) and bicyclogermacrene (13.8%) were the predominant compounds. The larvicidal potential of the two oils were evaluated against the third-instar of Aedes aegypti larvae. The results showed that both oils exhibited significant activity, particularly the oil of C. leucomalloides which was able to kill 98.7% of the larvae in the concentration of 100 ppm.