RESUMO
A tropical small tree, Callicarpa saccata, is known to have a symbiotic relationship with ants. It has sac-like structures at the base of the leaves that are inhabited by ants. No other species has been determined to be a myrmecophyte among the ca. 140 species of this genus. However, our recent field investigation discovered that two other species on Borneo (C. barbata and C. teneriflora) have hollow stems, which seem to be inhabited by ants. We observed the morphological features of these species in relation to their usage by ants, and became convinced that they are mymecophytic species. The molecular phylogenetic analyses using ITS and chloroplast regions suggest that C. saccata and C. teneriflora are closely related, but the differences in the myrmecophytic features of these species should be noted.
Assuntos
Formigas/fisiologia , Lamiaceae/anatomia & histologia , Lamiaceae/fisiologia , Filogenia , Animais , Sequência de Bases , Teorema de Bayes , Bornéu , Folhas de Planta/anatomia & histologia , Caules de Planta/anatomia & histologiaRESUMO
Two novel zierane-type sesquiterpenes, named melicodenones A and B (1 and 2, resp.), and three new guaiane-type sesquiterpenes, named melicodenones C-E (3-5), were isolated from the root of Melicope denhamii (Seem.) T. G. Hartley together with zierone (6). Their structures were established by extensive NMR-spectroscopic analyses. Compounds 1-6 were tested for cytotoxicity using human colon cancer DLD-1 cells, and melicodenone A (1) was found to exhibit moderate activity.
Assuntos
Rutaceae/química , Sesquiterpenos de Guaiano/química , Sesquiterpenos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Raízes de Plantas/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/toxicidadeRESUMO
Two new isoflavonoids, eryvarins V and W (1 and 2, resp.), and a new chromen-4-one derivative, eryvarin X (3), along with three known isoflavonoids, 4-6, were isolated from the roots of Erythrina variegata. Their structures were established by spectroscopic analyses. Compound 1 is a rare naturally occurring isoflavanone which possesses a OH group at C(3). Among the new compounds 1-3, 2 exhibited a potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains.
Assuntos
Antibacterianos/farmacologia , Cromonas/farmacologia , Erythrina/química , Isoflavonas/farmacologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Raízes de Plantas/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Cromonas/química , Cromonas/isolamento & purificação , Relação Dose-Resposta a Droga , Isoflavonas/química , Isoflavonas/isolamento & purificação , Testes de Sensibilidade Microbiana , Conformação Molecular , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
Phytochemical investigation of an acetone extract of Upuna borneensis (Dipterocarpaceae) resulted in the isolation of two new resveratrol tetramers, upunaphenols O (1) and P (2). The structures were elucidated by spectroscopic analysis including NMR experiments.
Assuntos
Benzofuranos/química , Dipterocarpaceae , Extratos Vegetais/química , Caules de Planta/química , Estilbenos/química , Estilbenos/isolamento & purificação , Benzofuranos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Estrutura Molecular , ResveratrolRESUMO
Investigation of the chemical constituents in the stem of Upuna borneensis (Dipterocarpaceae) resulted in the isolation of three new resveratrol derivatives, upunaphenols L (1), M (2) (resveratrol tetramers with a C(6)-C(3) unit) and N (3) (resveratrol tetramer with a C(1) unit). The structures have the same partial structure as vaticanol B (4). Upunaphenols L and M are new complex polyphenol compounds, lignostilbene. Their structures were determined by spectroscopic analysis including two dimensional NMR. Upunaphenol M was found to be an artifact generated by silica gel catalyzed methanolysis of 1.
Assuntos
Antineoplásicos Fitogênicos/química , Dipterocarpaceae/química , Flavonoides/química , Fenóis/química , Caules de Planta/química , Estilbenos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Polifenóis , Resveratrol , Análise Espectral , Estilbenos/isolamento & purificação , Estilbenos/farmacologiaRESUMO
Three new resveratrol oligomers, cotylelophenol C (1) (resveratrol tetramer) and cotylelosides A (2) and B (3) (O-glucosides of resveratrol trimer), together with four known glucosides of resveratrol oligomers (vaticasides A, B, C, D) and piceid, were isolated from an acetone soluble part of stem of Cotylelobium lanceolatum (Dipterocarpaceae). The structures of new compounds were determined by spectral data analysis. The characteristic properties observed in the NMR spectra of 1 were also discussed.
Assuntos
Ericales/química , Estilbenos/química , Glucosídeos/química , Glucosídeos/isolamento & purificação , Isomerismo , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Conformação Molecular , Resveratrol , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Ultravioleta , Estilbenos/isolamento & purificação , Relação Estrutura-AtividadeRESUMO
Four new resveratrol derivatives, upunaphenols B (1), C (4), D (5) (resveratrol tetramer) and E (6, resveratrol dimer with a C6-C1 unit), together with nine known resveratrol oligomers and resveratrol were isolated from an acetone soluble part of stem of Upuna borneensis (Dipterocarpaceae). The structures of new compounds were determined by spectral analysis including 1D and 2D NMR experiments.
Assuntos
Ericales/química , Estilbenos/química , Cromatografia em Camada Fina , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Conformação Molecular , Resveratrol , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria UltravioletaRESUMO
Two new resveratrol (= 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol) trimers, cotylelophenols A (1) and B (2), were isolated from the stem of Cotylelobium lanceolatum (Dipterocarpaceae), together with ten known resveratrol oligomers (3-12). The structures of the isolates were established on the basis of spectroscopic analyses, including a detailed NMR spectroscopic investigation of 1 under different conditions. Compound 1 is the first resveratrol trimer with a rearranged 4-hydroxyphenyl group. Four possible biogenetic pathways towards resveratrol oligomers are proposed (Scheme).
Assuntos
Ericales/química , Estilbenos/química , Estrutura Molecular , ResveratrolRESUMO
Five new resveratrol (=5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol) tetramers, upunaphenols H-J (1-3) and trans-(4) and cis-upunaphenol K (5), were isolated from the stem of Upuna borneensis (Dipterocarpaceae). Their structures were elucidated on the basis of 1D- and 2D-NMR as well as FAB-MS data. Compounds 1-3 bear a rare biphenyl bond in their frameworks. Compounds 1 and 2 have an unprecedented nonacyclic fused ring system, and compounds 2 and 3 have symmetrical structures.
Assuntos
Ericales , Estilbenos/química , Estilbenos/isolamento & purificação , Estrutura Molecular , Casca de Planta , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Caules de Planta , ResveratrolRESUMO
Three acetophenone C-glycosides; 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-p-hydroxybenzoyl)-glucopyranoside, 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside, 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-cinnamoyl)-glucopyranoside, and two resveratrol O-glycosides; piceid 2'-O-p-hydroxybenzoate and, piceid 2'-O-E-ferulate, together with three known compounds were isolated from the acetone soluble part of stem of Upuna borneensis (Dipterocarpaceae). The structures of isolates were determined by spectral analysis including extensive 2D-NMR spectral analyses.
Assuntos
Acetofenonas/química , Ericales/química , Glucosídeos/química , Cromatografia em Agarose , Glucosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Caules de Planta/química , Análise EspectralRESUMO
Three new stilbene oligomers (1-3) were isolated from the stem bark of Vatica pauciflora. The structures of a resveratrol heptamer (pauciflorol D) (1), a resveratrol dimer (pauciflorol E) (2), and an indanone derivative (pauciflorol F) (3) were elucidated by means of spectroscopic data interpretation, especially HMBC and NOESY NMR experiments.
Assuntos
Ericales/química , Estilbenos/química , Estilbenos/isolamento & purificação , Indonésia , Modelos Moleculares , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química , Resveratrol , EstereoisomerismoRESUMO
Three new isoflavonoids, eryvarins M-O (1-3), two new 2-arylbenzofurans, eryvarins P and Q (4 and 5), and a new 3-aryl-2,3-dihydrobenzofuran, eryvarin R (6), together with three known compounds, were isolated from the roots of Erythrina variegata. The structures of these compounds were established by spectroscopic analysis. Eryvarin R (6) is an unusual 3-aryl-2,3-dihydrobenzofuran derivative with a formyl (CHO) group. Eryvarin Q (5) showed potent antibacterial activity against methicillin-resistant Staphylococcus aureus.
Assuntos
Erythrina , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de PlantasRESUMO
Four new phenolic derivatives, gnetofurans A-C (1-3) and dihydropinosylvindiol (4), were isolated from a methanol-soluble extract of the stems of Gnetum klossii, together with nine known compounds [gnetifolin F (5), isorhapontigenin, gnetulin, gnetins E and C, latifolol, gnetol, (-)-epsilon-viniferin, and trans-resveratrol]. The structures of the new compounds were determined by spectral data analysis.
Assuntos
Benzofuranos/isolamento & purificação , Gnetum/química , Benzofuranos/química , Indonésia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Caules de Planta/química , EstereoisomerismoRESUMO
Two 3-phenoxychromones, eryvarins F and G, were isolated from the roots of Erythrina variegata. Their structures were established to be 3-(2,4-dihydroxyphenoxy)-7-hydroxy-6,8-di(3,3-dimethylallyl)chromen-4-one and 3-(2,4-dihydroxyphenoxy)-8-(3,3-dimethylallyl)-2,2-dimethylpyrano[5,6:6,7]chromen-4-one on the basis of spectroscopic and chemical evidence. Eryvarins F and G are unusual 3-phenoxychromone derivatives with two isoprenoid groups.
Assuntos
Cromonas/química , Erythrina/química , Cromatografia em Gel/métodos , Cromonas/isolamento & purificação , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química , Terpenos/químicaRESUMO
Four stilbene derivatives, gnemonols K and L (resveratrol trimers), M (isorhapontigenin dimer), and gnemonoside K (glucoside of resveratrol trimer) together with eleven known stilbenoids and a lignan were isolated from the acetone, methanol and 70% methanol soluble parts of the root of Gnetum gnemon (Gnetaceae). The structures of the isolates were determined by spectral analysis. The antioxidant activity of the stilbenoids on lipid peroxide inhibition and super oxide scavenging activity were also investigated.
Assuntos
Antioxidantes/isolamento & purificação , Sequestradores de Radicais Livres/isolamento & purificação , Gnetum/química , Estilbenos/isolamento & purificação , Antioxidantes/química , Antioxidantes/farmacologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Indonésia , Peróxidos Lipídicos/antagonistas & inibidores , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Raízes de Plantas/química , Estilbenos/química , Estilbenos/farmacologia , Superóxidos/químicaRESUMO
Three stilbene trimers (gnemonols D, E, F) were isolated from the root of Gnetum gnemon. The structures were determined by spectroscopic analysis. In addition, the antioxidant activity of the compounds on lipid peroxide inhibition and super oxide scavenging activity were also investigated.
Assuntos
Gnetum/química , Estilbenos/química , Raízes de Plantas/química , Estilbenos/isolamento & purificaçãoRESUMO
An acetone extract of the stem of Gnetum latifolium Blume afforded the stilbene trimer (latifolol) together with five known stilbenoids (gnetin E, gnetin D, gnetin C, (-)epsilon -viniferin and resveratrol). Their structures were elucidated on the basis of spectral evidence, in particular by using 2D NMR methods.
Assuntos
Gnetum/química , Caules de Planta/química , Estilbenos/química , Estilbenos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Five new stilbene oligomers (gnemonols A, B and C, gnemonoside E and gnetal) were isolated together with 2b-hydroxyampelopsin F and gnetin E from Gnetum gnemon and G. gnemonoides. The structures of the compounds were elucidated on the basis of spectral evidence.
Assuntos
Benzofuranos , Cycadopsida/química , Estilbenos/isolamento & purificação , Conformação Molecular , Estilbenos/químicaRESUMO
In various fern species, a large amount of rbcL sequence variation has been reported, and it is possible that these species contain several reproductively isolated cryptic species. In our previous study on Asplenium nidus L., it was suggested that the plants growing in Mt. Halimun National Park, West Java, Indonesia, consist of several cryptic species based on the results of crossing experiments among rbcL sequence types. In this study, we examined allozyme polymorphisms of five rbcL sequence types found in West Java in order to test the hypothesis that the assemblages of A. nidus delimited based on the rbcL sequences are separate Mendelian populations and gene flow is disrupted by reproductive isolation from one another. The calculated fixation indices suggested that the individuals in each rbcL type are randomly crossing at least in the investigated localities. Nevertheless, these rbcL-based assemblages were genetically differentiated in allozymes that are encoded in their nuclear genomes, and it is also suggested that gene flow is disrupted even between sympatrically distributed pairs of rbcL sequence types. Therefore, our findings support the view that the five rbcL sequence types in West Java are potential cryptic species.