RESUMO
OBJECTIVE: To investigate the chemical constituents in the roots of Angelica nitida. METHODS: The chemical constituents were isolated by silica gel,their structures were identified by spectral analysis. RESULTS: Nine compounds were isolated and identified as isoimperatorin(I), imperatorin(II), cnidilin(III), beta-sitosterol(IV), isopimpinellin(V), phellopterin(VI), neobyakangelicol(VII), (3S)-2,2-dimethyl-3,5-dihydroxy-8-hydroxylmethyl-3,4-dihydro-2H,6H-benzo[1,2-b: 5,4-b'] dipyran-6-one(VIll) and byakangelicin (IX). CONCLUSION: All the compounds are isolated from the plant for the first time.
Assuntos
Angelica/química , Medicamentos de Ervas Chinesas/química , Raízes de Plantas/química , Plantas Medicinais/química , China , Cumarínicos/química , Cumarínicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Furocumarinas/química , Furocumarinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
OBJECTIVE: To study the chemical constituents in roots of Angelica tianmuensis and A. megaphylla. METHODS: Compounds were isolated by column chromatography with silica gel, their structures were identified by spectral analysis. RESULTS: Another three compounds (ligustilone, 5-methoxyhamaudol, cimifugin) were obtained from the roots of Angelica tianmuensis, and another two compounds (ligustilone, angelol) were obtained from the roots of A. megaphylla. CONCLUSION: All the compounds are isolated in these two plants for the first time, and ligustilone is first found from Angelica L..
Assuntos
Angelica/química , Cromonas/isolamento & purificação , Cumarínicos/isolamento & purificação , Plantas Medicinais/química , Sesquiterpenos/isolamento & purificação , Angelica/classificação , Cromonas/química , Cumarínicos/química , Estrutura Molecular , Raízes de Plantas/química , Sesquiterpenos/químicaRESUMO
BACKGROUND: Osthol is a natural coumarin and lead compound that has been developed into commercial fungicides in China. Natural coumarins comprise five major subtypes: simple coumarins, linear furanocoumarins, angular furanocoumarins, linear pyranocoumarins and angular pyranocoumarins. Studies pertaining to the antifungal activities of linear pyranocoumarins are few, and no reports exist for the antifungal activities of angular pyranocoumarins. In order to discover more antifungal natural coumarins, we synthesised a series of simple natural coumarins and isolated several plant-based furanocoumarins and pyranocoumarins using previously described methods. The compounds were biologically evaluated against some plant fungal pathogens. RESULTS: Several of the 35 coumarins evaluated here exhibited strong activities against specific fungal species, including compound 25 (Pd-D-V, a linear pyranocoumarin), compound 26 (libanorin, an angular furanocoumarin) and compound 34 (disenecioyl khellactone, an angular pyranocoumarin). Compound 25 exhibited a high activity against Sclerotinia sclerotiorum (EC50 = 13.2 µg mL-1 ); compound 34 displayed a strong antifungal activity against Botrytis cinerea (EC50 = 11.0 µg mL-1 ). CONCLUSION: This study demonstrates that several natural coumarins (one linear pyranocoumarin and one angular pyranocoumarin in particular) exhibit strong antifungal activities. These results call for further studies, where these coumarins can be examined as potential lead compounds for developing novel antifungal agents. © 2016 Society of Chemical Industry.
Assuntos
Cumarínicos/química , Fungicidas Industriais/química , Controle Biológico de Vetores/métodos , Relação Estrutura-Atividade , China , Testes de Sensibilidade Microbiana , Doenças das Plantas/microbiologia , Plantas/microbiologiaRESUMO
DNA barcodes have been increasingly used in authentication of medicinal plants, while their wide application in materia medica is limited in their accuracy due to incomplete sampling of species and absence of identification for materia medica. In this study, 95 leaf accessions of 23 species (including one variety) and materia medica of three Pharmacopoeia-recorded species of Angelica in China were collected to evaluate the effectiveness of four DNA barcodes (rbcL, matK, trnH-psbA and ITS). Our results showed that ITS provided the best discriminatory power by resolving 17 species as monophyletic lineages without shared alleles and exhibited the largest barcoding gap among the four single barcodes. The phylogenetic analysis of ITS showed that Levisticum officinale and Angelica sinensis were sister taxa, which indicates that L. officinale should be considered as a species of Angelica. The combination of ITS + rbcL + matK + trnH-psbA performed slight better discriminatory power than ITS, recovering 23 species without shared alleles and 19 species as monophyletic clades in ML tree. Authentication of materia medica using ITS revealed that the decoction pieces of A. sinensis and A. biserrata were partially adulterated with those of L. officinale, and the temperature around 80 °C processing A. dahurica decoction pieces obviously reduced the efficiency of PCR and sequencing. The examination of two cultivated varieties of A. dahurica from different localities indicated that the four DNA barcodes are inefficient for discriminating geographical authenticity of conspecific materia medica. This study provides an empirical paradigm in identification of medicinal plants and their materia medica using DNA barcodes.
Assuntos
Angelica/classificação , Angelica/genética , Código de Barras de DNA Taxonômico/métodos , Materia Medica/isolamento & purificação , Filogenia , Plantas Medicinais/classificação , Plantas Medicinais/genética , China , Análise por Conglomerados , DNA de Plantas/química , DNA de Plantas/genética , DNA Espaçador Ribossômico/química , DNA Espaçador Ribossômico/genética , Levisticum/classificação , Levisticum/genética , Dados de Sequência Molecular , Análise de Sequência de DNA , TemperaturaRESUMO
Four novel furanocoumarin glucosides, candinosides A, B, C and D (1-4), were isolated from the roots of Heracleum candicans Wall. Their structures were established using chemical and spectral methods.
Assuntos
Furocumarinas/química , Glucosídeos/química , Heracleum/química , Extratos Vegetais/química , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Three new spirotrifuranocoumarins, canditririns C-E (1-3), a new spirotetrafuranocoumarin, canditetrarin A (4), and a new tetrafuranocoumarin, canditetrarin B (5), were isolated from the roots of Heracleum candicans Wall. Their structures were established using spectral methods.
Assuntos
Furocumarinas/química , Heracleum/química , Extratos Vegetais/química , Raízes de Plantas/química , Cumarínicos/química , Furocumarinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Two new ester coumarins, candinols B and C (1 and 2), and three new coumarin dimers, candibirins F-H (3-5), were isolated from the roots of Heracleum candicans Wall. Their structures were established by using chemical and spectral means.
Assuntos
Heracleum , Extratos Vegetais/química , Raízes de Plantas/química , Extratos Vegetais/isolamento & purificaçãoRESUMO
Five new coumarins, (+)-peujaponisin (1) and multivittans A-D (2-5), were isolated from the roots of Ligusticum multivittatum Franch., and their structures were established by spectral means.
Assuntos
Cumarínicos/isolamento & purificação , Ligusticum/química , Cumarínicos/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Raízes de PlantasRESUMO
Two new alkyl coumarins, isophellodenol C (1) and candinol A (2); four new spirobifuranocoumarins, candibirins B-E (3-6); and two trifuranocoumarins, canditririns A and B (7 and 8), were isolated from the roots of Heracleum candicans Wall. Their structures were established using chemical and spectral means.
Assuntos
Cumarínicos/isolamento & purificação , Heracleum/química , Extratos Vegetais/química , Cumarínicos/química , Raízes de Plantas , Análise Espectral/métodosRESUMO
Two new isocoumarins, angelicoins A and B, were isolated from the roots of Pleurospermum angelicoides, and their structures were established by spectral means.
Assuntos
Apiaceae/química , Cumarínicos/química , China , Cromatografia em Camada Fina , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Raízes de Plantas/química , Espectrofotometria InfravermelhoRESUMO
Four new coumarins (1-4) were isolated from the roots of Heracleum yunngningense HAND.-MASS. Their structures were established by spectral analyses.
Assuntos
Cumarínicos/química , Cumarínicos/isolamento & purificação , Heracleum , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de PlantasRESUMO
Four new bisabolane-type sesquiterpenes, liginvolones A-D (1-4), a new coumarin, 4'-octanoyloxyosthenol (5), and 20 known constituents were isolated from Ligusticum involucratum. Their structures were elucidated on the basis of spectroscopic analyses and chemical methods.
Assuntos
Cumarínicos/química , Cumarínicos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Ligusticum/química , Plantas Medicinais/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/químicaRESUMO
Four new guaianolides, sinodielides E-H (1-4), were isolated from the root of Sinodielsia yunnanensis WOLFF. Their structures were established by spectral evidence.
Assuntos
Plantas Medicinais/química , Sesquiterpenos de Guaiano/química , China , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Raízes de Plantas/química , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Candibirin A [systematic name: 9,9'-(1,4-dioxane-2,5-diyldimethylenedioxy)di(7H-furo[3,2-g]chromen-7-one)], a new furanocoumarin dimer, was isolated from Heracleum candicans WALL. (1)H NMR and MS spectra had indicated that the title compound was a dimer of heraclenin or heraclenol, but the linkage structure and its chirality were undetermined. The dioxane linkage, having the R,R configuration, has now been elucidated from dimethyl sulfoxide-solvated crystals, C(32)H(28)O(10).2C(2)H(6)OS. Candibirin A is thus a dimerization product from heraclenin formed by reaction at the epoxy group. Dimethylformamide-solvated crystals, C(32)H(28)O(10).C(3)H(7)NO, adopt a different conformation, with a folded structure that differs from the extended structure in the dimethyl sulfoxide solvate. However, the puckering of the dioxane linker unit is very similar in the two conformers. This result shows that the rotation of the ether bonds, in the linker between the furanocoumarin and dioxane moieties, causes the conformational flexibility of (I).
Assuntos
Analgésicos não Narcóticos/química , Heracleum/química , Cristalografia por Raios X , Dimetil Sulfóxido , Medicina Herbária , Ligação de Hidrogênio , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Modelos Moleculares , Conformação Molecular , SolventesRESUMO
Four new guaianolides, sinodielides A-D (1-4), were isolated from Sinodielsia yunnanensis WOLFF together with a known polyacetylene, falcarindiol, and two known coumarins, bergapten and scopoletin. Their structures were established by spectral and X-ray analyses.