RESUMO
Juglans regia L. (walnut) green husks are an important fraction of waste resulting from the walnut production, thus representing an interesting natural matrix to explore as a source of bioactive compounds. In this work, the hydroethanolic extract of walnut green husks was studied considering the phytochemical composition and the biological activity using different cell model assays, most of them evaluated for the first time for this matrix. From the HPLC-DAD-ESI/MSn analysis, sixteen compounds were identified, being the extract mostly composed of naphthalene derivatives (including tetralone derivatives) and less abundant in phenolic compounds (hydroxycinnamic acids and flavonols). The cytotoxic potential of the extract was assessed against tumour (MCF-7, NCI-H460, HeLa and HepG2) and non-tumour (PLP2) cell lines. Moreover, the antioxidant activity of the extract was evaluated by inhibition of the oxidative haemolysis (OxHLIA) and the formation of thiobarbituric acid reactive substances (TBARS), and the anti-inflammatory potential by the inhibition of the NO production by the RAW264.7 cell culture. The antibacterial effects of the extract were also evaluated against Gram-negative and Gram-positive bacteria. The results obtained represent a stepping stone for the development of future applications using walnut green husks as a source of added value compounds with bioactive potential.
Assuntos
Antibacterianos/farmacologia , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Juglans/química , Nozes/química , Compostos Fitoquímicos/farmacologia , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Bactérias/efeitos dos fármacos , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Humanos , Testes de Sensibilidade Microbiana , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Suínos , Tetralonas/química , Tetralonas/isolamento & purificação , Tetralonas/farmacologiaRESUMO
Five new α-tetralone glycosides, juglanbiosides A-E (1-5), together with an α-tetralone derivative (15) and nine known 1,4-naphthoquinones (6-14) were isolated from the 95% EtOH extract of green walnut husks of Juglans mandshurica Maxim. Their structures were elucidated by comprehensive spectroscopic methods (1H, 13C NMR, DEPT, HSQC, HMBC, CD, HR-ESI-MS). In vitro cytotoxicities of all the isolated compounds were evaluated against BGC-823, HCT-15 and K562 cancer cell lines.[Formula: see text].
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Glicosídeos/farmacologia , Juglans/química , Nozes/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Estrutura Molecular , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Naftoquinonas/farmacologia , Extratos Vegetais/química , Análise Espectral , Tetralonas/química , Tetralonas/isolamento & purificação , Tetralonas/farmacologiaRESUMO
Enantioselective open tubular capillary electrochromatography with carboxymethyl-ß-cyclodextrin conjugated gold nanoparticles as stationary phase was developed. This novel open tubular column was fabricated through layer-by-layer self-assembly of gold nanoparticles on a 3-mercaptopropyl-trimethoxysilane-modified fused-silica capillary and subsequent surface functionalization of the gold nanoparticles through self-assembly of 6-mercapto-ß-cyclodextrin. The 6-mercapto-ß-cyclodextrin was firstly synthesized and determined by extensive spectroscopic data. Scanning electron microscopy, energy dispersive X-ray analysis spectroscopy, and electroosmotic flow experiments were carried out to characterize the prepared open tubular column. Then, the separation effectiveness of the open tubular column was verified by two pairs of É-tetralones derivatives enantiomers and two pairs of basic drug enantiomers (tramadol hydrochloride and zopiclone) as mode analytes. Factors that influence the enantioseparation were optimized, and under the optimized conditions, satisfactory separation results were obtained for the four enantiomers: compound A, compound B, tramadol hydrochloride, and zopiclone with resolutions of 3.79, 1.56, 1.03, 1.60, respectively. For the combination of gold nanoparticles and negatively charged carboxymethyl-ß-cyclodextrin, the open tubular column exhibited wider separation range for neutral and basic drugs. Moreover, the repeatability and stability of the column were studied through the run-to-run and day-to-day investigations.
Assuntos
Compostos Azabicíclicos/isolamento & purificação , Eletrocromatografia Capilar/métodos , Ouro/química , Nanopartículas Metálicas/química , Piperazinas/isolamento & purificação , Tetralonas/isolamento & purificação , Tramadol/isolamento & purificação , beta-Ciclodextrinas/química , Compostos Azabicíclicos/química , Estrutura Molecular , Tamanho da Partícula , Piperazinas/química , Estereoisomerismo , Propriedades de Superfície , Tetralonas/química , Tramadol/químicaRESUMO
Three new tetralol analogs, myrochromanols A-C (1-3), together with 11 known trichothecenes (4-14), were isolated from a soil fungus Myrothecium verrucaria HL-P-1. The structures of the three new compounds were elucidated by extensive spectroscopic analysis including HRESIMS, NMR, and ECD calculation. All of the new compounds were tested for their anti-inflammatory activity and cytotoxicity. Compounds 1 and 3 inhibited lipopolysaccharide (LPS)-induced NO production in BV2 cells with IC50 values of 26.04 and 25.80 µM, respectively.
Assuntos
Anti-Inflamatórios/farmacologia , Hypocreales/metabolismo , Microbiologia do Solo , Tetralonas/isolamento & purificação , Células HL-60 , Humanos , Tetralonas/química , Tetralonas/farmacologiaRESUMO
Juglonols A-C (1-3), three new juglone derivatives possessing a hydroxyethyl side chain, were isolated from an organic extract of the immature exocarps of Juglans mandshurica together with five known tetralones (4-8). Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. The new juglone derivatives exhibited inhibitory activities towards a panel of bacteria and fungi, as well as cancer cell lines. In contrast, the known tetralone homologues (4-8) appeared to be much less efficacy.
Assuntos
Anti-Infecciosos/isolamento & purificação , Juglans/química , Naftoquinonas/farmacologia , Extratos Vegetais/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Anti-Infecciosos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Linhagem Celular , Humanos , Estrutura Molecular , Naftoquinonas/isolamento & purificação , Naftoquinonas/toxicidade , Extratos Vegetais/farmacologia , Análise Espectral/métodos , Tetralonas/isolamento & purificação , Tetralonas/farmacologiaRESUMO
Two new tetralone glycosides, 4(S)-5-methoxy juglanoside A (1), 4(S)-5-methoxy juglanoside D (2), together with ten known compounds (3-12) have been isolated from the green walnut husks of Juglans mandshurica Maxim. Their structures were elucidated on the basis of their ESI-MS, 1 D and 2 D NMR spectroscopic data. In addition, all compounds were evaluated for their cytotoxic activities against the cancer BGC-823 (human gastric carcinoma), HCT-15 (human colorectal carcinoma) and K562 (human chronic myeloid leukemia) cell lines. The results showed aglycones of naphthoquinones had stronger cytotoxic activities than glycosides of tetralone.
Assuntos
Detecção Precoce de Câncer , Glicosídeos/isolamento & purificação , Juglans/química , Antineoplásicos Fitogênicos/química , Linhagem Celular Tumoral , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Estrutura Molecular , Naftoquinonas/farmacologia , Nozes/química , Extratos Vegetais/química , Análise Espectral , Tetralonas/química , Tetralonas/isolamento & purificação , Tetralonas/farmacologiaRESUMO
A methanolic extract of Juglans regia L. leaves was fractioned by various chromatographic techniques yielding a total of 40 metabolites belonging to megastigmane, tetralone, phenylpropanoid, neolignane and juglone glycosides. Ten unknown megastigmane glucoside derivatives (juglanionosides A-K, 1-10) and six unknown tetralone glucoside derivatives (juglanosides J-O, 11-16) together with 24 known compounds - among them 16 described for the first time in Juglans - were isolated. As characteristic structural feature, the previously undescribed compounds showed acylation of the sugar units with sinapic, ferulic, coumaric, benzoic or salicylic acid. Their chemical structures were elucidated on the basis of 1D and 2D NMR techniques, HRESIMS as well as CD spectroscopy. Absolute stereochemistry was revealed by mild alkaline hydrolysis and comparison of CD and polarimetric data to literature values.
Assuntos
Juglans/química , Norisoprenoides/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Folhas de Planta/química , Tetralonas/isolamento & purificação , Conformação Molecular , Norisoprenoides/química , Compostos Fitoquímicos/química , Tetralonas/químicaRESUMO
Phytochemical research of different polarity extracts from green Juglans regia L. pericarps from Greece afforded 32 compounds: four pentacyclic triterpenes (1 - 4), three sesquiterpenes (5 - 7), four tetralones (8 - 11), two naphthoquinones (12 and 13), seven phenolic acids (14 - 20), one diarylheptanoid (21), one neo-lignan (22), seven flavonoids (23 - 29), two phenylethanoids (30 and 31) and one hydrolysed tannin (32). Compounds 4 and 29 are isolated for the first time from the species, while compounds 3, 7, 20, 22, 23, 24, 25, 26, 28, 30 are reported for the first time in Juglandaceae. Chemotaxonomic significance of isolated compounds into Junglandaceae family is thoroughly discussed.
Assuntos
Juglans/química , Juglans/classificação , Grécia , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Tetralonas/química , Tetralonas/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
As a candidate for bioherbicide, 4,8-dihydroxy-1-tetralone (4,8-DHT) was isolated from Caryospora callicarpa epicarp and its two enantiomers, S-(+)-isosclerone and R-(-)-regiolone, were separated by chiral high-performance liquid chromatography (HPLC) on a Chiralcel OD column with chiral stationary phase (CSP)-coated cellulose-tris(3,5-dimethylphenylcarbamate). Then, the phytotoxicity of 4,8-DHT and its enantiomers toward the seeds germination and seedling growth of the five tested plant species, including lettuce (Latuca sativa), radish (Raphanus sativus), cucumber (Cucumis sativus), onion (Allium cepa), and wheat (Triticum aestivum), were investigated and the results indicated a hormesis at low concentration of 4,8-DHT and its enantiomers, but a retardant effect at high concentration. Between the two enantiomers of 4,8-DHT, the S-(+)-isosclerone was more toxic to seeds germination and seedling growth of the five tested plant species than the R-(-)-regiolone, and also the phytotoxicity of S-(+)-isosclerone varied with different plants. For example, S-(+)-isosclerone was the most active to seedling growth of lettuce, indicating that S-(+)-isosclerone had specific effects on different organisms. Thus, all of the chirality and concentration of 4,8-DHT, as well as the affected plant species, need to be taken into consideration in the development and utilization of 4,8-DHT.
Assuntos
Coccídios/química , Produtos Agrícolas/efeitos dos fármacos , Produtos Agrícolas/crescimento & desenvolvimento , Herbicidas/toxicidade , Tetralonas/toxicidade , Cucumis sativus/efeitos dos fármacos , Cucumis sativus/crescimento & desenvolvimento , Germinação/efeitos dos fármacos , Herbicidas/isolamento & purificação , Lactuca/efeitos dos fármacos , Lactuca/crescimento & desenvolvimento , Cebolas/efeitos dos fármacos , Cebolas/crescimento & desenvolvimento , Raphanus/efeitos dos fármacos , Raphanus/crescimento & desenvolvimento , Plântula/efeitos dos fármacos , Estereoisomerismo , Tetralonas/isolamento & purificação , Triticum/efeitos dos fármacos , Triticum/crescimento & desenvolvimentoAssuntos
Antibióticos Antineoplásicos/isolamento & purificação , Cladosporium/metabolismo , Rhizophoraceae/microbiologia , Tetralonas/isolamento & purificação , Antibióticos Antineoplásicos/química , Antibióticos Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Dicroísmo Circular , Dimerização , Humanos , Espectroscopia de Ressonância Magnética , Tetralonas/química , Tetralonas/farmacologiaRESUMO
The aqueous extract from Carya cathayensis Sarg. exocarp was centrifuged, filtered, and separated into 11 elution fractions by X-5 macroporous resin chromatography. A phenolic compound, 4,8-dihydroxy-1-tetralone (4,8-DHT) was isolated from the fractions with the strongest phytotoxicity by bioassy-guided fractionation, and investigated for phytotoxicity on lettuce (Latuca sativa L.), radish (Raphanus sativus L.), cucumber (Cucumis sativus L.), onion (Allium cepa L.) and wheat (Triticum aestivum L.). The testing results showed that the treatment with 0.6 mM 4,8-DHT could significantly depress the germination vigor of lettuce and wheat, reduce the germination rate of lettuce and cucumber, and also inhibit radicle length, plumule length, and fresh weight of seedlings of lettuce and onion, but could significantly promote plumule length and fresh weight of seedlings of cucumber (p < 0.05). For the tested five plants, the 4,8-DHT was the most active to the seed germination and seedling growth of lettuce, indicating that the phytotoxicity of 4,8-DHT had the selectivity of dosage, action target (plant type) and content (seed germination or seedling growth).
Assuntos
Carya/química , Extratos Vegetais/farmacologia , Tetralonas/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Germinação/efeitos dos fármacos , Lactuca/efeitos dos fármacos , Lactuca/crescimento & desenvolvimento , Ressonância Magnética Nuclear Biomolecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Tetralonas/química , Tetralonas/isolamento & purificação , Tetralonas/toxicidadeRESUMO
Bioassay-guided phytochemical investigation of Zygogynum calothyrsum using the human colon carcinoma cell lines COLO205 and KM12 led to the isolation of three new drimane-type sesquiterpenoids, 1ß-p-hydroxy-E-cinnamoyldrimeninol (1), 1ß-p-hydroxy-E-cinnamoyl-5α-hydroxydrimeninol (2), and methyl ether of 1ß-p-hydroxy-E-cinnamoyl-12α-methoxydrimeninol (3). Also isolated was the known 1ß-p-coumaroyloxypolygodial (4) together with two new tetralones, 3'-deoxyisozygolone A (5) and calothyrlone A (9), three known tetralones, isozygolone A (6), zygolone A (7), and 4'-O-methylzygolone A (8), and a known cinnamolide (10). Compounds 1, 7, and 8 demonstrated higher cytotoxicity against COLO205 (GI50 18, 17, and 11 µM, respectively) and KM12 (GI50 14, 14, and 17 µM, respectively) than the other compounds.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Neoplasias do Colo/tratamento farmacológico , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Tetralonas/isolamento & purificação , Tetralonas/farmacologia , Winteraceae/química , Antineoplásicos Fitogênicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Sesquiterpenos/química , Estereoisomerismo , Tetralonas/químicaRESUMO
Cultivation of the fungal strain Annulohypoxylon ilanense, an endophytic fungus isolated from the wood of medicinal plant Cinnamomum species, resulted in the isolation of one new furanoid derivative, ilanefuranone (1), one new pyrrole alkaloid, ilanepyrrolal (2), and one new biarylpropanoid derivative, ilanenoid (3), together with 22 known compounds, of which one α-tetralone analog, (-)-(4R)-3,4-dihydro-4,6-dihydroxynaphthalen-1(2H)-one (4) was isolated for the first time from a natural source. The structures were elucidated on the basis of physicochemical evidence, in-depth NMR spectroscopic analysis, and high-resolution mass spectrometry, and the antimycobacterial activities were also evaluated.
Assuntos
Antituberculosos/química , Cinnamomum/microbiologia , Furanos/química , Guaiacol/análogos & derivados , Pirróis/química , Saccharomycetales/química , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antituberculosos/isolamento & purificação , Antituberculosos/farmacologia , Furanos/isolamento & purificação , Furanos/farmacologia , Guaiacol/química , Guaiacol/isolamento & purificação , Guaiacol/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Conformação Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Plantas Medicinais/microbiologia , Pirróis/isolamento & purificação , Pirróis/farmacologia , Saccharomycetales/isolamento & purificação , Tetralonas/química , Tetralonas/isolamento & purificação , Tetralonas/farmacologiaRESUMO
The methanolic extract of Ammannia multiflora (Lythraceae) showed significant bioenhancing activity with the antibiotic nalidixic acid. Bioassay-guided fractionation of MeOH extract resulted in the isolation of a novel compound, 2,5-bis-(3,3'-hydroxyaryl)tetrahydrofuran, named as ammaniol (5), along with 9 other known compounds (1-4, 6-10). Furthermore, compound 4-hydroxy- α-tetralone (1) was converted into five semisynthetic acyl derivatives, 1A-1E, which were evaluated along with compounds 1, 5, 6, 9, and 10 for their bioenhancing activity in combination with nalidixic acid against the two strains, CA8000 and DH5 α, of Escherichia coli. The results showed that the methanolic extract of A. multiflora and compounds 1 and 9 possessed significant bioenhancing activity and reduced the dose of nalidixic acid fourfold while compounds 5, 6, 10 and semisynthetic derivatives 1A- 1E reduced the dose of nalidixic acid twofold. Compound 5 was also tested for antimycobacterial activity against Mycobacterium H37Rv and was found to show moderate activity (MIC 25 µg/mL) against this pathogen.
Assuntos
Anti-Infecciosos/farmacologia , Escherichia coli/efeitos dos fármacos , Furanos/farmacologia , Lythraceae/química , Mycobacterium tuberculosis/efeitos dos fármacos , Ácido Nalidíxico/farmacologia , Extratos Vegetais/farmacologia , Tetralonas/farmacologia , Anti-Infecciosos/isolamento & purificação , Antituberculosos/isolamento & purificação , Antituberculosos/farmacologia , Sinergismo Farmacológico , Furanos/isolamento & purificação , Interações Ervas-Drogas , Extratos Vegetais/química , Tetralonas/química , Tetralonas/isolamento & purificaçãoRESUMO
OBJECTIVE: To investigate the chemical constituents of Carya cathayensis and their antitumor bioactivity. METHODS: The compounds were isolated by Sephadex LH-20 and silica gel column chromatography. Their structures were identified by physicochemical properties and spectroscopic analysis. Then their cytotoxic activity was studied. RESULTS: Five compounds were elucidated as chrysophanol (1), physcion (2), beta-sitosterol (3), pinostrobin(4), 4,8-dihydroxy-1-tetralone (5). CONCLUSION: Compounds 2 and 5 are isolated from Carya cathayensis for the first time. In the MTT antitumor experiments, the compounds 1,4 and 5 have the cytotoxic activity to KB cell.
Assuntos
Carya/química , Medicamentos de Ervas Chinesas/farmacologia , Emodina/análogos & derivados , Tetralonas/isolamento & purificação , Antraquinonas/química , Antraquinonas/isolamento & purificação , Antraquinonas/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Emodina/química , Emodina/isolamento & purificação , Flavanonas/química , Flavanonas/isolamento & purificação , Flavanonas/farmacologia , Frutas/química , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Casca de Planta/química , Tetralonas/química , Tetralonas/farmacologiaRESUMO
A novel alpha-tetralonyl derivative, juglanone, was isolated from the fresh unripe fruits of Juglans mandshurica. Its structure was determined by spectroscopic analyses and from chemical evidence. Juglanone exhibited significant antioxidant activity in assays for 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity and superoxide dismutase-like activity with IC(50) values of 10.1 and 9.0 microM, respectively. It also showed moderate cytotoxic activity against HL-60 human myeloid leukemia with an IC(50) value of 19.7 microM.
Assuntos
Antioxidantes/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Frutas , Juglans , Tetralonas/isolamento & purificação , Antioxidantes/química , Medicamentos de Ervas Chinesas/química , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Células HL-60 , Humanos , Juglans/química , Tetralonas/químicaRESUMO
Further chemical investigation of the whole plants of Gentiana loureirii led to the isolation and characterization of three new compounds, cyclic 4-O-beta-D-glucopyranosylcaffeic acid dimer (1), a new alpha-tetralone, 4-hydroxy-6-methyl-alpha-tetralone 4-O-beta-D-glucopyranoside (2), and 3beta,30-dihydroxy-12-ursen-28-oic acid 28-O-beta-D-glucopyranosyl ester (3), along with five known compounds. To the best of our knowledge, compound 1 is the first cyclic phenolic acid glycoside dimer.
Assuntos
Medicamentos de Ervas Chinesas/química , Gentiana/química , Glicosídeos/análise , Hidroxibenzoatos/análise , Terpenos/análise , Tetralonas/análise , Glucosídeos/análise , Glucosídeos/isolamento & purificação , Glicosídeos/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Modelos Moleculares , Estrutura Molecular , Terpenos/isolamento & purificação , Tetralonas/isolamento & purificaçãoRESUMO
Tubercularia sp. TF5 is an endophytic fungal strain isolated from the medicinal plant Taxus mairei. Previously, taxol has been detected in the fermentation products of this strain. However, it lost the capability of producing taxol after long-term laboratory culture. Herein, we tried to reactivate the production of taxol by protoplast mutations and genome shuffling. The protoplasts of Tub. sp. TF5 were prepared from its mycelia, and mutated by UV and NTG. The mutant strains regenerated from the mutated protoplasts were selected and classified into four groups on the basis of their phenotypes, the profile of their metabolites analyzed by TLC, MS, and bioassay data. Then, genome shuffling was subsequently carried out with eight mutant strains, with two representatives from each protoplast mutant group, and genome shuffling mutant strains were obtained and screened using the same screening procedure. Although taxol has not been detected in any mutant, two important mutants, M-741 and G-444 were selected for metabolites isolation and determination due to their phenotypes, and differences in TLC analysis result from TF5 and other mutants. Three new sesquiterpenoids, namely tuberculariols A-C (1-3), and a known dihydroisocoumarin (4) were obtained from M-741. Eighteen novel compounds were isolated from G-444, including five new sesquiterpenoids (5-9), two new dihydroisocoumarins (10, 11), one new tetralone (12), together with 10 known compounds (13-20, 1, and 2). The compounds isolated from the M-741 and G-444 were different in structure types and substitutions from those of TF5 (15, 21-29). The results showed, for the first time, that protoplast mutations and genome shuffling are efficient approaches to mining natural products from endophytic fungi. Understanding the mechanisms of unlocking the biosynthesis of new metabolites will facilitate the manipulation of the secondary metabolism in fungi.
Assuntos
Embaralhamento de DNA , DNA Fúngico/genética , Genoma Fúngico , Hypocreales/genética , Hypocreales/metabolismo , China , Cromatografia em Camada Fina , Citocalasinas/isolamento & purificação , Citocalasinas/metabolismo , DNA Fúngico/química , Diterpenos/isolamento & purificação , Diterpenos/metabolismo , Fermentação , Instabilidade Genômica , Hifas/enzimologia , Espectrometria de Massas , Mutação , Paclitaxel/metabolismo , Plantas Medicinais/metabolismo , Protoplastos/metabolismo , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/metabolismo , Tetralonas/isolamento & purificação , Tetralonas/metabolismo , Raios UltravioletaRESUMO
One new tetralone, monaspurpurone (1), was isolated from the EtOH extract of a yellow mutant of the fungus Monascus purpureus BCRC 38113 (Eurotiaceae) grown on rice, along with five known compounds, ß-sitosteryl palmitate (2), ergosterol (3), ankaflavin (4), monascin (5) and p-nitrophenol (6). They were characterised on the basis of spectral analysis and comparison with literature data. All the isolates were also evaluated for the scavenging properties towards the DPPH in TLC autographic and spectroscopic assays.
Assuntos
Sequestradores de Radicais Livres/isolamento & purificação , Monascus/química , Oryza/microbiologia , Tetralonas/isolamento & purificação , Compostos de Bifenilo , Cromatografia em Camada Fina , Ergosterol/análise , Ergosterol/química , Ergosterol/isolamento & purificação , Flavinas/análise , Flavinas/química , Flavinas/isolamento & purificação , Sequestradores de Radicais Livres/análise , Sequestradores de Radicais Livres/química , Compostos Heterocíclicos com 3 Anéis/análise , Compostos Heterocíclicos com 3 Anéis/química , Compostos Heterocíclicos com 3 Anéis/isolamento & purificação , Estrutura Molecular , Nitrofenóis/análise , Nitrofenóis/química , Nitrofenóis/isolamento & purificação , Palmitatos/análise , Palmitatos/química , Palmitatos/isolamento & purificação , Picratos , Sitosteroides/análise , Sitosteroides/química , Sitosteroides/isolamento & purificação , Análise Espectral , Tetralonas/análise , Tetralonas/químicaRESUMO
Callianthones A ( 1) and B ( 2), a pair of new isomeric alpha-tetralones, together with a known alpha-tetralone ( 3) and four known flavonoids ( 4 - 7) were isolated from the 50 % EtOH extract of Pyrola calliantha. The structures and absolute configurations of the two new isomers were established to be (2 S,4 R) - and (2 S,4 S)-2,4-dihydroxy-2,7-dimethyl-3,4-dihydronaphthalen-1(2 H)-one ( 1 and 2, respectively) on the basis of spectral analysis, including 2 D NMR, model studies, and CD spectra.