RESUMO
AIMS: To characterize antifungal principles from the methanol extract of Magnolia obovata and to evaluate their antifungal activities against various plant pathogenic fungi. METHODS AND RESULTS: Four neolignans were isolated from stem bark of M. obovata as antifungal principles and identified as magnolol, honokiol, 4-methoxyhonokiol and obovatol. In mycelial growth inhibition assay, both magnolol and honokiol displayed more potent antifungal activity than 4-methoxyhonokiol and obovatol. Both magnolol and honokiol showed similar in vivo antifungal spectrum against seven plant diseases tested; both compounds effectively suppressed the development of rice blast, tomato late blight, wheat leaf rust and red pepper anthracnose. 4-Methoxyhonokiol and obovatol were highly active to only rice blast and wheat leaf rust respectively. CONCLUSIONS: The extract of M. obovata and four neolignans had potent in vivo antifungal activities against plant pathogenic fungi. SIGNIFICANCE AND IMPACT OF THE STUDY: Neolignans from Magnolia spp. can be used and suggested as a novel antifungal lead compound for the development of new fungicide and directly as a natural fungicide for the control of plant diseases such as rice blast and wheat leaf rust.
Assuntos
Antifúngicos/farmacologia , Fungos/efeitos dos fármacos , Lignanas/farmacologia , Magnolia/química , Extratos Vegetais/farmacologia , Compostos Alílicos , Antifúngicos/química , Antifúngicos/isolamento & purificação , Compostos de Bifenilo , Cromatografia em Camada Fina , Lignanas/química , Lignanas/isolamento & purificação , Testes de Sensibilidade Microbiana , Micélio/efeitos dos fármacos , Éteres Fenílicos , Casca de Planta/química , Doenças das Plantas , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificaçãoRESUMO
A new lanostane-type terpenoid, lucidenic acid SP1 (1), was isolated from a CHCl(3)-soluble fraction of Ganoderma lucidum spores together with four other known compounds (2 - 5). The structure of lucidenic acid SP1 was determined to be 3 beta,7 beta-dihydroxy-4,4,14 alpha-trimethyl-11,15-dioxo-5 alpha-chol-8-en-24-oic acid by spectroscopic means including 2D-NMR. Twelve triterpenes (1-12) isolated from G. lucidum spores were investigated in vitro for their anticomplementary activity. Compounds 1 - 5 were inactive, whereas ganoderiol F (8), ganodermanondiol (9) and ganodermanontriol (10) showed a strong anticomplement activity against the classical pathway (CP) of the complement system with IC(50) values of 4.8, 41.7, and 17.2 microM, respectively. The potency of these triterpene alcohols (8-10) in inhibiting CP activity was improved when the number of hydroxymethyl groups on the side chain moiety is increased. On the other hand, the ganoderic acids 1-7, which contain a carboxyl group in the side chain, and lucidumols A and B (11, 12) had little activity on this system.
Assuntos
Proteínas Inativadoras do Complemento/farmacologia , Lanosterol/isolamento & purificação , Reishi , Triterpenos/isolamento & purificação , Ativação do Complemento/efeitos dos fármacos , Proteínas Inativadoras do Complemento/química , Medicamentos de Ervas Chinesas , Hemólise/efeitos dos fármacos , Hemólise/imunologia , Humanos , Lanosterol/análogos & derivados , Lanosterol/química , Lanosterol/farmacologia , Espectroscopia de Ressonância Magnética , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Further studies on leaves of Annona montana led to isolation of one iso-acetogenin, montanacin G, three pairs of acetogenins, montanacin H-J and 34-epi-montanacin H-J, together with four known acetogenins, gigantetrocins A and B, annonacin and cis-annonacin. Montanacin G belongs to the iso-acetogenin group with a terminal 2,4-trans-ketolactone unit. Montanacin H-J and 34-epi-montanacin H-J contain the rare gamma-hydroxy-gamma-methyl-gamma-lactone moiety. The cytotoxic activities of these compounds, together with previously reported acetogenins, montanacins B and C, were examined against Meth-A and LLC tumor cell lines in vitro.
Assuntos
4-Butirolactona/análogos & derivados , Annonaceae , Furanos/química , Extratos Vegetais/química , 4-Butirolactona/química , 4-Butirolactona/isolamento & purificação , 4-Butirolactona/farmacologia , Animais , Divisão Celular/efeitos dos fármacos , Álcoois Graxos/química , Álcoois Graxos/isolamento & purificação , Álcoois Graxos/farmacologia , Furanos/isolamento & purificação , Furanos/farmacologia , Espectroscopia de Ressonância Magnética , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Árvores/química , Células Tumorais CultivadasRESUMO
In the search for novel anti-human immunodeficiency virus type 1 (anti-HIV-1) agents from natural sources, 49 MeOH extracts of Korean plants were screened for their inhibitory effects against RNA-dependent DNA polymerase (RT) and ribonuclease H (RNase H) activities of HIV-1 reverse transcriptase and HIV-1 protease, and anti-HIV-1 activity. Regarding the HIV-1 reverse transcriptase, Agrimonia pilosa (whole plant), Cornus kousa (stem and leaf), Limonium tetragonum (root) and Mallotus japonicus (stem) showed significant inhibitory activity on RT activity with 50% inhibitory activity (IC(50)) of 8.9, 6.3, 7.5 and 11.9 microg/mL, respectively, whereas Agrimonia pilosa was also active against RNase H activity (IC(50) = 98.4 microg/mL). Four plants, namely Agrimonia pilosa (whole plant), Atractylodes japonica (root), Clematis heracleifolia (whole plant) and Syneilesis palmata (whole plant), were appreciably active (<35%) against recombinant HIV-1 protease at a concentration of 100 microg/mL. Crinum asiaticum var. japonicum (root) showed significant anti-HIV-1 activity (ED(50) = 12.5 microg/mL) with a favourable SI value of 16.
Assuntos
Fármacos Anti-HIV/farmacologia , HIV-1/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/farmacologia , Protease de HIV/metabolismo , Transcriptase Reversa do HIV/antagonistas & inibidores , Medicina Herbária , Humanos , Coreia (Geográfico) , Plantas Medicinais/classificação , Ribonuclease H/antagonistas & inibidores , Ribonuclease H/metabolismoRESUMO
A new pyrrolophenanthridone alkaloid, criasiaticidine A (1), was isolated from the bulbs of Crinum asiaticum var. japonicum, together with pratorimine (2), lycorine (3) and 4'-hydroxy-7-methoxyflavan (4). The structure of the new alkaloid was determined to be 4,5-etheno-9,10-dihydroxy-6-phenanthridone by spectroscopic means. The cytotoxicity of the isolated compounds 1-4 was evaluated in vitro against Meth-A (mouse sarcoma) and Lewis lung carcinoma (mouse lung carcinoma) tumor cell lines. Furthermore, 3 was examined for in vivo antitumor activity with LLC tumor cells.
Assuntos
Alcaloides/química , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Fenantrenos/farmacologia , Plantas Medicinais/química , Animais , Cromatografia Líquida , Feminino , Indicadores e Reagentes , Japão , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Transplante de Neoplasias , Neoplasias Experimentais/tratamento farmacológico , Fenantrenos/química , Raízes de Plantas/química , Espectrofotometria Ultravioleta , Células Tumorais CultivadasRESUMO
Three new kaempferol glycosides, called crassirhizomosides A (1), B (2) and C (3), were isolated from the rhizome of Dryopteris crassirhizoma (Aspidiaceae), together with the known kaempferol glycoside, sutchuenoside A (4). The structures of 1-3 were determined as kaempferol 3-alpha-L-(2,4-di-O-acetyl)rhamnopyranoside-7-alpha-L-rhamnopyranoside, kaempferol 3-alpha-L-(3,4-di-O-acetyl)rhamnopyranoside, and kaempferol 3-alpha-L-(2,3-di-O-acetyl)rhamnopyranosside-7-alpha-L-rhamnopyranoside, respectively, by chemical and spectroscopic means. Inhibitory effects of 1-4 and kaempferol on human immunodeficiency virus reverse transcriptase-associated DNA polymerase (RNA-dependent DNA polymerase and DNA-dependent DNA polymerase) and RNase H activities were investigated.
Assuntos
Flavonoides , Glicosídeos/química , HIV-1/enzimologia , Quempferóis , Plantas Medicinais/química , Quercetina/química , Quercetina/farmacologia , Inibidores da Transcriptase Reversa/química , Inibidores da Transcriptase Reversa/farmacologia , Carboidratos/análise , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Hidrólise , Espectroscopia de Ressonância Magnética , Metanol , Inibidores da Síntese de Ácido Nucleico , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Quercetina/análogos & derivados , Quercetina/isolamento & purificação , RNA Polimerase I/antagonistas & inibidores , Inibidores da Transcriptase Reversa/isolamento & purificação , Ribonuclease H/antagonistas & inibidores , Solventes , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
One new triterpene, 3beta-hydroxy-29-norcycloart-24-one (1), and four new lignans, caruilignans (2-5), together with six known compounds were isolated from the aerial part of Artemisia caruifolia BUCH.-HAM. ex TOXB. Their structures were determined by various spectroscopic means. Most of the isolated lignans were moderately cytotoxic to Meth-A cells with ED50 values of 5-10 microg/ml, but not to Lowis lung carcinoma (LLC) cells. An oxime derivative of 1 showed more potent cytotoxic activity against Meth-A and LLC cells than the original triterpene 1.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Artemisia/química , Lignanas/isolamento & purificação , Plantas Medicinais , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Divisão Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Lignanas/química , Lignanas/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Triterpenos/química , Triterpenos/farmacologia , Células Tumorais CultivadasRESUMO
From the stem-bark of Juglans mandshurica, two new naphthalenyl glucopyranosides, 1,4,8-trihydroxynaphthalene 1-O-[alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside] (1) and 1,4,8-trihydroxynaphthalene 1-O-beta-D-[6'-O-(3",5"-dihydroxy-4"-methoxybenzoyl)]glucopyranosi de (4), and two new alpha-tetralonyl glucopyranosides, 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(3",5"-dihydroxy-4"-methoxybenzoyl)]glucopyranosi de (7) and 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(3",4",5"-trihydroxybenzoyl)]glucopyranoside (8), were isolated together with three known naphthalenyl glucopyranosides (2, 3 and 5), one alpha-tetralonyl glucopyranoside (6), four flavonoids (9-12), and two galloyl glucopyranosides (13, 14). Amongst the isolated compounds, 1,2,6-trigalloylglucopyranose (13) and 1,2,3,6-tertagalloylglucopyranose (14) exhibited the most potent inhibition of reverse transcriptase (RT) activity with IC50 values of 0.067 and 0.040 microM, respectively, while the latter compound also inhibited ribonuclease H (RNase H) activity with an IC50 of 39 microM, comparable in potency to illimaquinone used as a positive control. 1,4,8-Trihydroxy-naphthalene 1-O-beta-D-glucopyranoside (2), 1,4,8-trihydroxynaphthalene 1-O-beta-D-[6'-O-(4"-hydroxy-3",5"-dimethoxybenzoyl)]glucopyranoside (3) and 8 showed moderate inhibition against both enzyme activities, and inhibitory potency of 2 against RNase H activity (IC50 = 156 microM) was slightly greater than that against the RT activity (IC50 = 290 microM). The inhibitory potencies of 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(4"-hydroxy-3",5"-dimethoxybenzoyl)] glucopyranoside (6), 7 and 8 against RT activity increased accompanied by an increase in the number of free hydroxyls on the galloyl residues, as represented by the IC50 values of > 500, 330 and 5.8 microM, respectively.
Assuntos
Inibidores Enzimáticos/farmacologia , Transcriptase Reversa do HIV/antagonistas & inibidores , Plantas Medicinais/química , Inibidores da Transcriptase Reversa/farmacologia , Ribonuclease H/antagonistas & inibidores , Cromatografia Líquida , Dicroísmo Circular , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Hidrólise , Coreia (Geográfico) , Espectroscopia de Ressonância Magnética , Hibridização de Ácido Nucleico , Epiderme Vegetal/química , Caules de Planta/química , Inibidores da Transcriptase Reversa/química , Inibidores da Transcriptase Reversa/isolamento & purificação , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
With the aim of finding novel anti-human immunodeficiency virus agents from natural products, 93 MeOH extracts of Korean plants were screened for their inhibitory activities against HIV-1 protease. The most potent inhibition was shown by the root of Rodiola rosea with 70.4% inhibition at a concentration of 100 microg/mL.
Assuntos
Inibidores da Protease de HIV/farmacologia , Protease de HIV/efeitos dos fármacos , HIV-1/enzimologia , Medicina Tradicional , Extratos Vegetais/farmacologia , Plantas Medicinais/química , Cromatografia Líquida de Alta Pressão , Inibidores da Protease de HIV/isolamento & purificação , Humanos , Coreia (Geográfico) , Extratos Vegetais/isolamento & purificaçãoRESUMO
The methanol extracts of the leaves of Crataegus pinnatifida showed potent inhibitory activities against HIV-1 protease at a concentration of 100 micrograms/ml. The subsequent fractionation and isolation of the extract gave two active compounds. Their structures were identified as uvaol (1) and ursolic acid (2) by spectral data. These active compounds inhibit HIV-1 protease with IC50 values of 5.5 and 8.0 microM, respectively.
Assuntos
Fármacos Anti-HIV/farmacologia , Inibidores da Protease de HIV/farmacologia , Rosales/química , Triterpenos/farmacologia , Fármacos Anti-HIV/química , Inibidores da Protease de HIV/química , HIV-1/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Folhas de Planta/química , Triterpenos/química , Ácido UrsólicoRESUMO
Two triterpenoid compounds, ursolic acid and uvaol, were isolated from Crataegus pinnatifida Bunge leaves. Ursolic acid inhibits chitin synthase II from S. cerevisiae with an IC50 value of 0.84 microgram/ml and the inhibition appears to be selective for chitin synthase II, whereas uvaol has no inhibitory activity up to 280 micrograms/ml. Oleanolic acid, alpha-hederin hydrate, and betulic acid inhibited the chitin synthase II activity under the same conditions with an IC50 of 5.6, 64.3, and 98.7 micrograms/ml, respectively.
Assuntos
Quitina Sintase/antagonistas & inibidores , Inibidores Enzimáticos/farmacologia , Rosales/química , Triterpenos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Saccharomyces cerevisiae/enzimologia , Triterpenos/química , Triterpenos/isolamento & purificação , Ácido UrsólicoRESUMO
Two diterpenoid compounds, agastanol (1) and agastaquinone (2), were isolated from the roots of Agastache rugosa (Labiatae). Compound 1 and 2 showed significant inhibitory effects against human immunodeficiency virus type 1 (HIV-1) protease activity with IC50 values of 360 and 87 microM, respectively.