RESUMO
Three new diterpenoids, boesenmaxanes A-C (1-3), with an unprecedented core skeleton consisting of an unusual C-C bond between C-12 and an exo-cyclic methylene C-13, were isolated from the rhizome extracts of Boesenbergia maxwellii. The structures were elucidated by analysis of spectroscopic and X-ray diffraction data. Electronic circular dichroism spectra were used to determine the absolute configuration. All the isolates were evaluated for their cytotoxic effects, anti-HIV activity, and antimicrobial activity. Boesenmaxanes A and C (1 and 3) showed significant inhibitory activity in the syncytium reduction assay, with EC50 values of 55.2 and 27.5 µM, respectively.
Assuntos
Diterpenos/farmacologia , Zingiberaceae/química , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Linhagem Celular Tumoral , Diterpenos/isolamento & purificação , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Rizoma/química , TailândiaRESUMO
Context: Mitrephora sirikitiae Weeras., Chalermglin & R.M.K. Saunders (Annonaceae) is a plant endemic to Thailand. Its constituents and their biological activities are unknown.Objective: Isolation and identification of the compounds in the leaves and stems of M. sirikitiae and determination of their cytotoxicity.Materials and methods: Methanol extracts of the leaves and stems of M. sirikitiae were separated by chromatography, and spectroscopic methods were used to determine the structures of the components. The cytotoxicity of the extracts and pure compounds was evaluated using the sulforhodamine B assay with several cell lines. The cells were treated with the compounds at concentrations of 0.16-20 µg/mL for 48 or 72 h.Results: The investigation of the extracts of M. sirikitiae leaves and stems resulted in the isolation of a new lignan, mitrephoran, and 15 known compounds. Among these compounds, 2-(3,4-dimethoxyphenyl)-6-(3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane, ciliaric acid, 6-methoxymarcanine A, and stepharanine were isolated from this genus for the first time. The alkaloids liriodenine and oxoputerine exhibited strong cytotoxicity against all tested cells (IC50 values of 6.59-11.02 µM). In contrast, magnone A, 3',4-O-dimethylcedrusin, and 6-methoxymarcanine A inhibited the growth of some of the tested cells (IC50 values of 2.03-19.73 µM). Magnone A and 6-methoxymarcanine A showed low toxicity for Hek 293 cells (IC50 >20 µM).Discussion and conclusions: M. sirikitiae is a source of cytotoxic lignans and alkaloids. Among the cytotoxic compounds, magnone A and 6-methoxymarcanine A are potentially useful lead compounds for the further development of anticancer agents because of their selective inhibitory effects on cancer cell lines.
Assuntos
Annonaceae , Antineoplásicos Fitogênicos/toxicidade , Citotoxinas/toxicidade , Extratos Vegetais/toxicidade , Folhas de Planta , Células A549 , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Citotoxinas/isolamento & purificação , Relação Dose-Resposta a Droga , Células HEK293 , Células HT29 , Humanos , Células MCF-7 , Extratos Vegetais/isolamento & purificação , Ratos , Espectrometria de Massas por Ionização por Electrospray/métodos , TailândiaRESUMO
The chemical study on the heartwoods extract of Ventilago harmandiana (Rhamnaceae) resulted in the isolation of ten previously undescribed pyranonaphthoquinones (ventilanones A-J), an undescribed anthraquinone (ventilanone K), together with eight known anthraquinone derivatives. Their structures were elucidated by extensive analysis of their spectroscopic data. The absolute configuration of ventilanone A was established from single crystal X-ray crystallographic analysis of its p-bromobenzenesulfonate ester derivative using Cu Kα radiation. The absolute configurations of the other related compounds were identified by comparison of their ECD data with those of ventilanone A and related known compounds. Cytotoxic and anti-inflammatory activities of some of the isolated compounds were evaluated. Ventilanone A and ventilanone C exhibited moderate cytotoxicity against P-388â¯cell line. Ventilanone D exhibited significant anti-inflammatory activity while ventilanone A and ventilanone C showed moderate activity.
Assuntos
Antraquinonas/farmacologia , Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Edema/tratamento farmacológico , Naftoquinonas/farmacologia , Rhamnaceae/química , Animais , Antraquinonas/química , Antraquinonas/isolamento & purificação , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Camundongos , Modelos Moleculares , Estrutura Molecular , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Ratos , Relação Estrutura-Atividade , Células Tumorais CultivadasRESUMO
Three previously undescribed polyoxygenated cyclohexene derivatives named cherrevenol M (1), cherrevenol N (2), and cherrevenone (3), together with nine related known analogues 4-12 were isolated from the ethyl acetate fraction partitioned from the methanol extract of the aerial parts of Uvaria cherrevensis (Annonaceae). The determination of the structures and their relative configurations of the isolated compounds were established by spectroscopic techniques, electronic circular dichroism (ECD) analysis as well as comparison with the literature data. For cherrevenone (3), the relative and absolute configurations were also confirmed by using X-ray diffraction and ECD techniques, respectively. Compounds isolated except for compounds 8 and 10 were evaluated for their cytotoxic activity and cherrevenone (3) showed moderate cytotoxic activity against all cancerous cell lines except for ASK cell line with ED50 values ranging from 1.04⯱â¯0.13 to 10.09⯱â¯4.31⯵M.
Assuntos
Antineoplásicos Fitogênicos/farmacocinética , Cicloexenos/farmacologia , Uvaria/química , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Cicloexenos/isolamento & purificação , Humanos , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Ratos , TailândiaRESUMO
A rhodol-based fluorescent probe has been developed as a selective hydrazine chemosensor using levulinate as a recognition site. The rhodol levulinate probe (RL) demonstrated high selectivity and sensitivity toward hydrazine among other molecules. The chromogenic response of RL solution to hydrazine from colorless to pink could be readily observed by the naked eye, while strong fluorescence emission could be monitored upon excitation at 525â¯nm. The detection process occurred via a ring-opening process of the spirolactone initiated by hydrazinolysis, triggering the fluorescence emission with a 53-fold enhancement. The probe rapidly reacted with hydrazine in aqueous medium with the detection limit of 26â¯nM (0.83â¯ppb), lower than the threshold limit value (TLV) of 10â¯ppb suggested by the U.S. Environmental Protection Agency. Furthermore, RL-impregnated paper strips could detect hydrazine vapor. For biological applicability of RL, its membrane-permeable property led to bioimaging of hydrazine in live HepG2 cells by confocal fluorescence microscopy.
Assuntos
Técnicas Biossensoriais/métodos , Fluorescência , Corantes Fluorescentes/química , Hidrazinas/análise , Imagem Molecular/métodos , Espectrometria de Fluorescência/métodos , Xantonas/química , Células Hep G2 , Humanos , Limite de DetecçãoRESUMO
Eleven previously undescribed compounds, including four benzophenones (garciosones A-D), four xanthones (garciosones E-H) and three biphenyls (garciosines A-C), along with eighteen known compounds were isolated from the stems, leaves and twigs of Garcinia speciosa Wall. (Clusiaceae). Their structures were established by extensive spectroscopic analysis. For garciosines A-C, the structures were confirmed by single crystal X-ray diffraction analysis. Most of the isolated compounds were evaluated for their cytotoxic activity and anti-HIV-1 activity using the syncytium inhibition assay and HIV-1 reverse transcriptase (RT) assay. The known compounds, 4,6,3',4'-tetrahydroxy-2-methoxybenzophenone and macluraxanthone, displayed significant cytotoxic activity with the ED50 in the range of 1.85-11.76 µM. 1,5-Dihydroxyxanthone exhibited the most potent anti-HIV activity against syncytium formation with EC50 < 17.13 µM (SI > 25.28) and 2-(3,3-dimethylallyl)-1,3,7-trihydroxyxanthone was the most active compound in the HIV-1 reverse transcriptase assay with IC50 value of 58.24 µM. Structure-activity relationship of some isolated compounds were also discussed.
Assuntos
Fármacos Anti-HIV/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Benzofenonas/farmacologia , Compostos de Bifenilo/farmacologia , Garcinia/química , HIV-1/efeitos dos fármacos , Xantonas/farmacologia , Animais , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Benzofenonas/química , Benzofenonas/isolamento & purificação , Compostos de Bifenilo/química , Compostos de Bifenilo/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Infecções por HIV/tratamento farmacológico , Humanos , Camundongos , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Ratos , Relação Estrutura-Atividade , Xantonas/química , Xantonas/isolamento & purificaçãoRESUMO
Six new 14-membered ring cyclopeptide alkaloids, cambodines A-F (1-6), and two known compounds, frangufoline (7) and lotusanine B (8), were isolated from the root bark extract of Ziziphus cambodiana Pierre. Their structures and configurations were established based on 1D and 2D NMR, HRMS, ECD, and X-ray crystallographic data. Compounds 1 and 3 are rare 5(14)-type cyclopeptide alkaloids that possess an imidazolidin-4-one ring in the terminal unit. The cyclopeptides were tested for their in vitro antiplasmodial, antitubercular, and cytotoxic effects against three cancer cell lines. Compound 3 showed significant antiplasmodial activity against the malarial parasite Plasmodium falciparum, with an IC50 value of 6.09 µM.
RESUMO
Seven previously undescribed compounds, including three polycyclic polyprenylated acylphloroglucinols (garcinuntins A-C), three biphenyl derivatives (garcinuntabiphenyls A-C) and a lanostane triterpene (garcinuntine), along with thirteen known compounds were isolated from the root of Garcinia nuntasaenii Ngerns. & Suddee. Their structures were elucidated on the basis of spectroscopic techniques. For garcinuntins A-C, the absolute configurations were confirmed by the combination of single X-ray crystallography and ECD calculations. Anti-HIV activity using anti-HIV-1 reverse transcriptase and syncytium inhibition assays, and cytotoxic activity against a panel of cultured mammalian cancer cell lines of isolated compounds were investigated.
Assuntos
Fármacos Anti-HIV/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Compostos de Bifenilo/farmacologia , Garcinia/química , Transcriptase Reversa do HIV/antagonistas & inibidores , HIV-1/efeitos dos fármacos , Floroglucinol/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Compostos de Bifenilo/química , Compostos de Bifenilo/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HEK293 , Transcriptase Reversa do HIV/metabolismo , Humanos , Modelos Moleculares , Estrutura Molecular , Floroglucinol/análogos & derivados , Floroglucinol/isolamento & purificação , Raízes de Plantas/química , Relação Estrutura-AtividadeRESUMO
Five 12,20-epoxypregnane glycosides (1-3, 5, and 6) and two 11,12-seco-pregnane glycosides (4 and 7) with spirodilactone motifs, as well as spirodilactone cleavage products 8 and 9, were isolated from the stems of Hoya kerrii. The relative configurations of the three related skeletons were supported by ROESY experiments and X-ray crystallographic analyses. The isolates were evaluated for their anti-inflammatory activity based on the inhibition of NO production in RAW264.7 cells, and some showed IC50 values ranging from 12.6 to 96.5 µM. The most potent compound, 9a, was also examined for its anti-inflammatory mechanism against mRNA expression and was found to down-regulate mRNA expression of iNOS and COX-2 in a dose-dependent manner.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Apocynaceae/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Pregnanos/isolamento & purificação , Pregnanos/farmacologia , Animais , Anti-Inflamatórios/química , Cristalografia por Raios X , Ciclo-Oxigenase 2/efeitos dos fármacos , Ciclo-Oxigenase 2/metabolismo , Relação Dose-Resposta a Droga , Glicosídeos/química , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/metabolismo , Camundongos , Conformação Molecular , Estrutura Molecular , Óxido Nítrico/biossíntese , Óxido Nítrico Sintase Tipo II/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Caules de Planta/química , Pregnanos/química , TailândiaRESUMO
A rhodol cinnamate fluorescent chemosensor (RC) has been developed for selective detection of hydrazine (N2H4). In aqueous medium, the rhodol-based probe exhibited high selectivity for hydrazine among other molecules. The addition of hydrazine triggered a fluorescence emission with 48-fold enhancement based on hydrazinolysis and a subsequent ring-opening process. The chemical probe also displayed a selective colorimetric response toward N2H4 from colorless solution to pink, readily observed by the naked eye. The detection limit of RC for hydrazine was calculated to be 300nM (9.6ppb). RC is membrane permeable and was successfully demonstrated to detect hydrazine in live HepG2 cells by confocal fluorescence microscopy.
Assuntos
Técnicas Citológicas/métodos , Corantes Fluorescentes/química , Hidrazinas/análise , Espectrometria de Fluorescência/métodos , Xantonas/química , Células Hep G2 , HumanosRESUMO
Five new lanostanes, wallichinanes A-E (1-5) together with a known lanostane derivative 6 were isolated from the cytotoxic hexanes extract of fruits of Garcinia wallichii Choisy (Guttiferae). The structures of the isolated compounds were established by analysis of spectroscopic data, X-ray diffraction technique as well as comparison with the literature data. The cytotoxicity of all isolated compounds against a panel of cultured cancer cell lines was evaluated. Compound 4 exhibited good cytotoxicity with ED50 values ranging from 3.91 to 7.63µM.
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Garcinia/química , Lanosterol/análogos & derivados , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Frutas/química , Humanos , Lanosterol/química , Lanosterol/isolamento & purificação , Lanosterol/farmacologia , Modelos Moleculares , Neoplasias/tratamento farmacológico , Difração de Raios XRESUMO
Ten compounds including nine phenalenone derivatives (five bipolarides and four bipolarols) and a sesterterpene acid (bipolarenic acid), were isolated from a marine isolated of the fungus Lophiostoma bipolare (BCC25910), along with the known compounds, (-)-scleroderolide, (-)-sclerodin, and oxasetin. Chemical structures were elucidated based on NMR spectroscopic data and HRESIMS analysis. In addition, the absolute configurations of the phenalenones were resolved using specific rotations and chemical means, while the relative configuration of bipolarenic acid was confirmed by X-ray crystallographic analysis. The compounds were evaluated for biological activity against the Plasmodium falciparum K-1 strain, Candida albicans, and Bacillus cereus, and for cytotoxicity against both cancerous and non-cancerous cells.
Assuntos
Ascomicetos/química , Fenalenos/isolamento & purificação , Sesterterpenos/isolamento & purificação , Antibacterianos/química , Bacillus cereus/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Biologia Marinha , Testes de Sensibilidade Microbiana , Conformação Molecular , Estrutura Molecular , Fenalenos/química , Fenalenos/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Sesterterpenos/química , Sesterterpenos/farmacologia , TailândiaRESUMO
Six new naturally occurring polyoxygenated cyclohexene derivatives together with eight related known derivatives, two known alkaloids, and two known flavonoid derivatives were isolated from bioassay-guided fractionation of the ethyl acetate extract of the leaves and twigs of Dasymaschalon sootepense. The structure elucidation and determination of absolute configurations were established by various spectroscopic methods, X-ray diffraction techniques as well as comparison with the literature data. Several isolated compounds were evaluated for their cytotoxic, anti-HIV-1 RT and anti-inflammatory activities.
Assuntos
Alcaloides/química , Annonaceae/química , Fármacos Anti-HIV/química , Anti-Inflamatórios/química , Cicloexenos/química , Alcaloides/isolamento & purificação , Animais , Fármacos Anti-HIV/isolamento & purificação , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Cicloexenos/isolamento & purificação , HIV-1/efeitos dos fármacos , Humanos , Masculino , Camundongos , Estrutura Molecular , Folhas de Planta/química , Ratos , Ratos Sprague-Dawley , Inibidores da Transcriptase Reversa/química , Inibidores da Transcriptase Reversa/isolamento & purificaçãoRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: The rhizomes of Boesenbergia longiflora (Wall.) Kuntze have been traditionally used in treatment of inflammatory bowel disease, ulcerative colitis, aphthous ulcer and abscess. Our previous study indicated that CHCl3 fractions of Boesenbergia longiflora had potential on anti-inflammatory properties. In the present study, we investigated the active constituents of this plant for anti-inflammatory activity in order to support its traditional use. MATERIAL AND METHODS: The CHCl3 fraction was isolated using chromatographic techniques. Isolated compounds were tested using relevant in vitro anti-inflammatory assays against LPS-induced NO and TNF-α releases as well as their mechanisms in transcription levels in murine macrophage RAW264.7 cells. RESULTS: The isolation of the CHCl3 fraction from Boesenbergia longiflora rhizomes led to the isolation of three new daucane sesquiterpenes, which were identified as 8-hydroxy-dauca-9, 11-diene-7-one (longiferone A; 1), dauca-8, 11-diene-7-one (longiferone B; 2) and dauca-8, 11-diene-7, 10-dione (longiferone C; 3); together with four known flavonoids, six known diarylheptanoids as well as one sterol. The longiferone B (2) and longiferone C (3) showed anti-inflammatory activity against NO release with IC50 values of 21.0 and 31.3µM, respectively. Longiferone B (2) also suppressed the iNOS and COX-2 mRNA expression. Moreover, the flavonoids and diarylheptanoids inhibited NO and TNF-α production in a dose dependent manner. CONCLUSION: This study demonstrated that sesquiterpenes, diarylheptanoids and some methoxyflavonoids found in Boesenbergia longiflora are responsible for anti-inflammatory activity.
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Extratos Vegetais/farmacologia , Rizoma/química , Zingiberaceae/química , Animais , Anti-Inflamatórios não Esteroides/isolamento & purificação , Anti-Inflamatórios não Esteroides/uso terapêutico , Anti-Inflamatórios não Esteroides/toxicidade , Técnicas de Cultura de Células , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Ciclo-Oxigenase 2/biossíntese , Edema/tratamento farmacológico , Etnofarmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/enzimologia , Macrófagos/imunologia , Masculino , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/biossíntese , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/uso terapêutico , Extratos Vegetais/toxicidade , Ratos Wistar , Fator de Necrose Tumoral alfa/biossínteseRESUMO
A new sesquiterpene, 1-formamido-10(1â2)-abeopupukeanane (1), was isolated from the tubercle nudibranch Phyllidia coelestis Bergh, along with 2-formamidopupukeanane (2), which is reported here as a natural product for the first time. A rearrangement pathway toward the unprecedented tricyclo[4.4.0.0(2,8)]decane skeleton is proposed. Both compounds showed antiproliferative activity when targeting HeLa, MCF-7, KB, and HT-29 cancer cell lines in the range 0.05-10 µM.
Assuntos
Antineoplásicos/isolamento & purificação , Gastrópodes/química , Sesquiterpenos/isolamento & purificação , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células HT29 , Células HeLa , Humanos , Células KB , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , TailândiaRESUMO
Trinorcadalenes, parviflorals A and B (1 and 2), and four bis-trinorcadalenes, parviflorals C-F (3-6), together with the known trinorcadalenes, syriacusins A (7) and C (8), scopoletin (9) and stigmasterol were isolated from roots of Decaschistia parviflora. Their structures were established by spectroscopic techniques. The CD spectra of the bis-trinorcadalenes (3-6) established their absolute configurations at the binaphthyl axis. Further, structure 6 was confirmed by a single-crystal X-ray crystallographic analysis. Compounds 2 and 6 showed antimalarial activity against Plasmodium falciparum with IC50 values of 11.45 and 6.85 µM, respectively. Compounds 1, 5, 7 and 8 also exhibited weak antifungal activity against Candida albicans, with IC50 values in the range of 37.03-197.68 µM. Compounds 1-3 and 5-8 showed weak antimycobacterial activity against Mycobacterium tuberculosis with MIC values in the range of 54.30-192.13 µM. In addition, several of these compounds possessed cytotoxicity towards the cancer cell lines, KB, MCF7 and NCI-H187 with IC50 values in the range of 2.20-90.09 µM.
Assuntos
Candida albicans/efeitos dos fármacos , Malvaceae/química , Mycobacterium tuberculosis/efeitos dos fármacos , Neoplasias/tratamento farmacológico , Extratos Vegetais/química , Raízes de Plantas/química , Plasmodium falciparum/efeitos dos fármacos , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antimaláricos/química , Antimaláricos/isolamento & purificação , Antimaláricos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/uso terapêutico , Humanos , Concentração Inibidora 50 , Células KB , Células MCF-7 , Testes de Sensibilidade Microbiana , Estrutura Molecular , Fitoterapia , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêuticoRESUMO
Seven new lanostane-type triterpenes, hypocrellols A-G (1-7), and six new hopane-type triterpenes, 7ß,15α-dihydroxy-22(29)-hopene (8), 3ß,7ß-dihydroxy-22(29)-hopene (9), 3ß-acetoxy-15α-hydroxy-22(29)-hopene (10), 3ß,7ß,15α,22-tetrahydroxyhopane (11), 3ß-acetoxy-7ß,15α,22-trihydroxyhopane (12), and 7ß,15α,22-trihydroxyhopane (13), were isolated from the scale insect pathogenic fungus Hypocrella sp. BCC 14524. The structures of the new compounds were elucidated by analyses of the NMR spectroscopic and mass spectrometry data. The structure of 1 was confirmed by X-ray crystallography.
Assuntos
Antimaláricos/isolamento & purificação , Antineoplásicos/isolamento & purificação , Antituberculosos/isolamento & purificação , Hypocreales/química , Triterpenos/isolamento & purificação , Animais , Antimaláricos/química , Antimaláricos/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Antituberculosos/química , Antituberculosos/farmacologia , Chlorocebus aethiops , Cristalografia por Raios X , Resistência a Medicamentos , Ensaios de Seleção de Medicamentos Antitumorais , Testes de Sensibilidade Microbiana , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Plasmodium falciparum/efeitos dos fármacos , Estereoisomerismo , Tailândia , Triterpenos/química , Triterpenos/farmacologia , Células VeroRESUMO
Eight new sesquiterpene alkaloids (1-8) and four known sesquiterpene alkaloids (9-12) have been isolated from the roots of Maytenus mekongensis. Structures were determined using extensive spectroscopic methods. The relative configuration of 7-epi-mekongensine (2) was established by single-crystal X-ray crystallographic analysis. The alkaloids were evaluated for antiplasmodial activity against Plasmodium falciparum, K1 strain, and for cytotoxicity using a panel of cell lines.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antimaláricos/isolamento & purificação , Antimaláricos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Maytenus/química , Plasmodium falciparum/efeitos dos fármacos , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Alcaloides/química , Antimaláricos/química , Antineoplásicos Fitogênicos/química , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Estrutura Molecular , Sesquiterpenos/química , TailândiaRESUMO
Three new sesquiterpenes, named phomoarcherins A-C (1-3), and four known compounds, kampanol A (4), R-mevalonolactone, ergosterol, and ergosterol peroxide, were isolated from the endophytic fungus Phomopsis archeri. These structures were established on the basis of spectroscopic evidence. The structure and absolute configuration of 1 were confirmed by X-ray crystallographic analysis of its p-bromobenzoate derivative (1a). Compounds 1-4 showed cytotoxicity against five cholangiocarcinoma cell lines (0.1-19.6 µg/mL), while 1 and 2 exhibited weak cytotoxicity against the KB cell line with IC(50) values of 42.1 and 9.4 µg/mL, respectively. In addition, compound 2 showed antimalarial activity against Plasmodium falciparum with an IC(50) value of 0.79 µg/mL.
Assuntos
Antimaláricos/isolamento & purificação , Antimaláricos/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Antimaláricos/química , Antineoplásicos/química , Ascomicetos/química , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Ergosterol/análogos & derivados , Ergosterol/isolamento & purificação , Humanos , Concentração Inibidora 50 , Células KB , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Tailândia , Vanilla/microbiologiaRESUMO
Five new compounds, 2alpha-hydroxyjatropholone (1), 2beta-hydroxyjatropholone (2), 1,5-dioxo-2,3-dihydroxyrhamnofola-4(10),6,11(18),15-tetraene (3), 2-keto-5-hydroxyguai-3,11-diene (4), and a sesquiterpene-coumarin conjugate, jatrophadioxan (5), and nine known compounds have been isolated from the roots of Jatropha integerrima. The structures were established from spectroscopic data, and the relative configuration of 1 was confirmed by X-ray crystallography. Six diterpenes were evaluated for their antiplasmodial, antituberculosis, and cytotoxic activities.