RESUMO
Brunfelsia cabiesesiana J. G. Graham, sp. nov. (Solanaceae), a new species from montane cloud forests of Ucayali and Pasco Departments, Peru, is described and illustrated. The new species differs from all other members of the genus Brunfelsia by its cauline inflorescences. A key to the Peruvian species of Brunfelsia is presented.
Resumen Brunfelsia cabiesesiana J. G. Graham, sp. nov. (Solanaceae), descrita e ilustrada aquí, constituye una nueva especie de los bosques nublados de los departamentos de Ucayali y Pasco, Perú. La nueva especie difiere de todas las demás especies de Brunfelsia por sus inflorescencias caulinas. Se presenta aquí también una clave para las especies peruanas de Brunfelsia.
RESUMO
Cytotoxicity-based, bioassay-guided fractionation of the chloroform-soluble extracts of both the roots and leaves of Picramnia latifolia led to the isolation of two new anthrone C-glycosides, picramniosides G (1) and H (2), two new oxanthrone C-glycosides, mayosides D (3) and E (4), and a new benzanthrone natural product, 6,8-dihydroxy-10-methyl-7H-benz[de]anthracen-7-one (5), together with 10 known compounds, 6,8-dihydroxy-4-methyl-7H-benz[de]anthracen-7-one (6), nataloe-emodin (7), chrysophanein, chrysophanol, 1,5-dihydroxy-7-methoxy-3-methylanthraquinone, pulmatin, 7-hydroxycoumarin, 7-hydroxy-6-methoxycoumarin, beta-sitosterol, and beta-sitosterol glucoside. The structures of 1-5 were established by spectroscopic methods, including 1D and 2D NMR, HRMS, and CD data interpretation. The cytotoxic activity of all isolates was evaluated in a small panel of human cancer cell lines. Compound 7 exhibited significant in vitro cytotoxic activity in the tested cell lines, but no significant activity was observed with an in vivo hollow fiber model at doses of 6.25, 12.5, 25, and 50 mg/kg/injection.
Assuntos
Antracenos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Glicosídeos/isolamento & purificação , Plantas Medicinais/química , Antracenos/química , Antracenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Peru , Folhas de Planta/química , Estereoisomerismo , Células Tumorais CultivadasRESUMO
Bioactivity-directed fractionation of the methanolic extract of the stem and fruits of Senna obliqua led to the isolation of two known antimycobacterial natural products, quinquangulin (1) and rubrofusarin (2). Both compounds had minimum inhibitory concentrations (MICs) of 12.0 microg/mL against Mycobacteriatuberculosis in radiometric culture. This is the first report of antimycobacterial activity associated with naphthopyrone compounds. Their structures were determined by spectroscopic means including 1D and 2D NMR techniques and further confirmed by X-ray crystallographic analysis.
Assuntos
Antituberculosos/isolamento & purificação , Naftóis/isolamento & purificação , Plantas Medicinais/química , Pironas/isolamento & purificação , Senna/química , Antituberculosos/química , Antituberculosos/farmacologia , Cristalografia por Raios X , Testes de Sensibilidade Microbiana , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Naftóis/química , Naftóis/farmacologia , Peru , Pironas/química , Pironas/farmacologiaRESUMO
A new butenylflavanone, (2S)-5-hydroxy-7-methoxy-8-[(E)-3-oxo-1-butenyl]flavanone (1), and a new rotenoid, 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (2), as well as three active flavonoids of previously known structure, isoliquiritigenin (3), genistein (4), and chrysoeriol (5), along with nine known inactive compounds, alpha-toxicarol (6), sumatrol, 6a,12a-dehydro-alpha-toxicarol, 11-hydroxytephrosin, obovatin, marmesin, lupenone, benzyl benzoate, and benzyl trans-cinnamate, were isolated from an ethyl acetate-soluble extract of the stems of Tephrosia toxicaria, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structures of compounds 1 and 2 were elucidated by spectroscopic data interpretation. All isolates were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to determine quinone reductase induction. Selected compounds were tested in a mouse mammary organ culture assay to evaluate the inhibition of 7,12-dimethylbenz[a]anthracene (DMBA)-induced preneoplastic lesions.
Assuntos
Anticarcinógenos/isolamento & purificação , Cromonas/isolamento & purificação , Flavonoides/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Plantas Medicinais/química , Tephrosia/química , Animais , Anticarcinógenos/química , Anticarcinógenos/farmacologia , Carcinoma Hepatocelular , Cromonas/química , Cromonas/farmacologia , Flavonoides/química , Flavonoides/farmacologia , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Neoplasias Mamárias Experimentais , Camundongos , Estrutura Molecular , NAD(P)H Desidrogenase (Quinona)/metabolismo , Peru , Caules de Planta/química , Estereoisomerismo , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
A new cassane diterpene, dipteryxic acid (1), and a new isoflavonolignan, 5-methoxyxanthocercin A (2), as well as four known active compounds, isoliquiritigenin (3), 6,4'-dihydroxy-3'-methoxyaurone (4), sulfuretin (5), and (+/-)-balanophonin (6), and five known inactive compounds, butin, eriodictyol, 7-hydroxychromone, 7,3'-dihydroxy-8,4'-dimethoxyisoflavone, and (-)-lariciresinol, were isolated from an ethyl acetate-soluble extract of the seeds of Dipteryx odorata, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structures of compounds 1 and 2 were elucidated by spectroscopic data interpretation. Single-crystal X-ray diffraction analysis was used to confirm the relative stereochemistry of compound 1. Selected compounds (3-5) were evaluated in a mouse mammary organ culture assay, with isoliquiritigenin (3) found to exhibit 76% inhibition at a dose of 10 microg/mL.
Assuntos
Anticarcinógenos/isolamento & purificação , Diterpenos/isolamento & purificação , Fabaceae/química , Isoflavonas/isolamento & purificação , Lignanas/isolamento & purificação , Animais , Anticarcinógenos/química , Anticarcinógenos/farmacologia , Cristalografia por Raios X , Modelos Animais de Doenças , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Indução Enzimática , Concentração Inibidora 50 , Isoflavonas/química , Isoflavonas/farmacologia , Lignanas/química , Lignanas/farmacologia , Glândulas Mamárias Animais/efeitos dos fármacos , Camundongos , Conformação Molecular , Estrutura Molecular , NAD(P)H Desidrogenase (Quinona)/biossíntese , Ressonância Magnética Nuclear Biomolecular , Técnicas de Cultura de Órgãos , Peru , Sementes/química , Estereoisomerismo , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Activity-monitored fractionation of a CHCl(3)-soluble extract of Deprea subtriflora using a quinone reductase induction assay led to the purification of subtrifloralactones A-J (1-10), 10 novel C-18 norwithanolides based on a new C(27) skeleton. These compounds were characterized by spectroscopic and chemical studies, and single-crystal X-ray diffraction analysis was used to confirm the structures of 1 and 4. Compounds 1-10 were evaluated for their cancer chemopreventive activity in terms of their ability to induce quinone reductase activity with cultured murine hepatoma cells, and compounds 1 and 6 were found to be highly effective.
Assuntos
Lactonas/isolamento & purificação , Plantas Medicinais/química , Solanaceae/química , Animais , Anticarcinógenos , Carcinoma Hepatocelular , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Lactonas/química , Lactonas/farmacologia , Camundongos , Conformação Molecular , Estrutura Molecular , NAD(P)H Desidrogenase (Quinona)/metabolismo , Ressonância Magnética Nuclear Biomolecular , Peru , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Three new prenylated dihydrochalcones, (+/-)-nicolaioidesins A, B, and C (1-3), as well as a new natural product, 5-styrylfuran-2-carboxylic acid methyl ester (4), along with four known compounds, 2'-hydroxy-4',6'-dimethoxychalcone (5), (+/-)-5-hydroxy-7-methoxyflavanone (6), (+/-)-5-hydroxy-7,4'-dimethoxyflavanone, and panduratin A, were isolated from the roots of Renealmia nicolaioides, using a bioassay to determine the induction of quinone reductase (QR) activity with cultured Hepa lclc7 mouse hepatoma cells. Among these isolates, 5 and 6 induced QR activity, with observed concentrations to double activity (CD) values of 1.7 and 0.9 microg/mL, respectively, while the other constituents were not regarded as being active (CD >10 microg/mL). The chemical structures of 1-4 were elucidated by spectroscopic methods. A biogenetic pathway for the formation of (+/-)-nicolaioidins A-C (1-3) is proposed.