RESUMEN
Steroid 5α-reductase plays a crucial role in catalyzing the conversion of testosterone to dihydrotestosterone, which is involved in many androgen-dependent disorders. Leaf-hexane extract from Tectona grandis L.f. has shown promise as a 5α-reductase inhibitor. The objectives of this current study were to isolate and identify 5α-reductase inhibitors from T. grandis leaves and to use them as the bioactive markers for standardization of the extract. Three terpenoid compounds, (+)-eperua-8,13-dien-15-oic acid (1), (+)-eperua-7,13-dien-15-oic acid (2), and lupeol (3), were isolated and evaluated for 5α-reductase inhibitory activity. Compounds 1 and 2 exhibited potent 5α-reductase inhibitory activity, while 3 showed weak inhibitory activity. An HPLC method for the quantitative determination of the two potent inhibitors (1 and 2), applicable for quality control of T. grandis leaf extracts, was also developed. The ethanolic extract showed a significantly higher content of 1 and 2 than found in the hexane extract, suggesting that ethanol is a preferable extraction solvent. This study is the first reported isolation of 5α-reductase inhibitors (1 and 2) from T. grandis leaves. The extraction and quality control methods that are safe and useful for further development of T. grandis leaf extract as an active ingredient for hair loss treatment products are also reported.
Asunto(s)
Lamiaceae , Verbenaceae , 3-Oxo-5-alfa-Esteroide 4-Deshidrogenasa , Inhibidores de 5-alfa-Reductasa/farmacología , Colestenona 5 alfa-Reductasa , Cromatografía Líquida de Alta Presión , Inhibidores Enzimáticos/farmacología , Hexanos , Extractos Vegetales/farmacologíaRESUMEN
Four new depsidones, mollicellins V-Y (1-4), together with eight known depsidones (5-12) were isolated from the endophytic fungus, Chaetomium brasiliense, detached from stems of Thai rice. Their structures were determined by extensive spectroscopic methods. Mollicellins X, H, and F (3, 8 and 10) showed potent cytotoxicity against the human oral epidermoid carcinoma (KB) cell line, and mollicellin F (10) also showed a potent cytotoxicity against the human hepatocellular carcinoma (HepG2) cell line. Besides, mollicellin B (11) exhibited cytotoxicity against the colorectal adenocarcinoma (HT-29) cell line. Moreover, most of the isolated depsidones displayed potent antibacterial activity against Gram-positive bacteria, Bacillus cereus and Bacillus subtilis, and several of them showed moderate activity against Methicillin-resistant Staphylococcus aureus (MRSA) and clinical isolates of S. aureus. In addition, a few of them also showed moderate activity against a Gram-negative bacteria Pseudomonas aeruginosa.
Asunto(s)
Antineoplásicos , Chaetomium , Staphylococcus aureus Resistente a Meticilina , Oryza , Antibacterianos/química , Antineoplásicos/química , Chaetomium/química , Depsidos , Humanos , Lactonas , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Sordariales , Staphylococcus aureus , TailandiaRESUMEN
A phytochemical investigation of the stems and leaves of Piper wallichii led to the isolation of two new compounds, an aryl alkanone, piwalkanone (1) and a dioxoaporphine alkaloid, piwallidione (2), together with nine known compounds, a dioxoaporphine alkaloid, cepharadione A (3); two aristolactams, piperolactam A (4) and stigmalactam (5); a piperidine, piperine (6); four isobutylamides, piperlonguminine (7), pellitorine (8), N-isobutyl-2E,4E-octadecadienamide (9), and guineensine (10); and a tyramine, N-trans-feruloyltyramine (11). Their structures were elucidated on the basis of spectroscopic evidence (IR, 1H NMR, 13C NMR and 2 D NMR) and MS. Compounds 2 and 3 showed inhibitory activities against pathogenic bacteria, Bacillus cereus, Bacillus subtilis and Staphylococcus aureus.
Asunto(s)
Piper , Antibacterianos/farmacología , Estructura Molecular , Piper/química , Extractos Vegetales , Hojas de la PlantaRESUMEN
Two new aromadendrin rhamnosides, cissusfoliate A (1) and 3-epi-cissusfoliate A (2) together with seven known compounds (3-9) were isolated from the roots of Cissus rheifolia Planch. Their structures were determined by extensive spectroscopic methods. The absolute configurations of compounds 1-5 were assigned by combination of the J coupling constant values of H-2 and H-3 and the comparison of their experimental ECD spectra with those reported in literature. Compounds 1, 3 and 5-8 showed antioxidant effects on ORAC, ATBS and DPPH assays as well as antibacterial activity against six pathogenic bacterial strains. Their cytotoxicity against Hela, KB, MCF-7, HepG2 and HT-29 cell lines were also evaluated.
Asunto(s)
Cissus , Antibacterianos/farmacología , Estructura Molecular , Raíces de PlantasRESUMEN
Phytochemical investigation of the roots of Walsura trichostemon, a Thai medicinal plant, provided a new tirucallane, 3-epimesendanin S 12-acetate (1), together with four known compounds, 3-epimesendanin S (2), meliasenin G (3), ß-sitosterol (4) and ß-sitosterol glucoside (5). Their structures were characterized by intensive spectroscopy including 1 D and 2 D NMR, UV, IR and MS spectrometric analysis. The isolated compounds were evaluated for antibacterial and acetylcholinesterase inhibitory activities. Compounds 1-2 showed antibacterial activity against Bacillus cereus and Bacillus subtilis with MIC values ranging from 16-128 µg/mL. In addition, compound 3 was active against Pseudomonas aeruginosa and Escherichia coli with MIC values of 64 and 128 µg/mL, respectively.
Asunto(s)
Antibacterianos , Meliaceae , Triterpenos , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Meliaceae/química , Pruebas de Sensibilidad Microbiana , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Raíces de Plantas/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacologíaRESUMEN
Three undescribed spirosteroids, asparacemosones A-C, an undescribed spiro-21-norsteroid, asparacemosone D, along with seven known compounds were isolated from Thai herbal plant Asparagus racemosus Willd. roots. Their structures were elucidated by spectroscopic analysis including NMR, UV, IR and mass spectrometry. The absolute configurations of asparacemosones A, B, and D were determined by single crystal X-ray diffraction using CuKα radiation. Among the isolated compounds, the norlignan nyasol and three acetylenic norlignans demonstrated potent α-glucosidase inhibition, with IC50 values ranging from 0.003 to 0.004 µM which is 5 × 104 fold more potent than the standard acarbose.
Asunto(s)
Asparagus , alfa-Glucosidasas , Extractos Vegetales , Raíces de PlantasRESUMEN
A new xanthoquinodin B9 (1), together with two known xanthoquinodins, xanthoquinodin A1 (2) and xanthoquinodin A3 (3), three epipolythiodioxopiperazines, chetomin (4), chaetocochin C (5) and dethio-tetra(methylthio)chetomin (6), and four other compounds, chrysophanol (7), emodin (8), alatinone (9), and ergosterol (10) were isolated from the endophytic fungus Chaetomium globosum 7s-1, isolated from Rhapis cochinchinensis (Lour.) Mart. All isolated structures were established based on their spectroscopic data analyses. Compounds 1-6 showed antibacterial activity against Gram positive bacteria with MICs ranging from 0.02 pM to 10.81 µM. Compounds 1-6 also exhibited cytotoxicity against KB, MCF-7 and NCI-H187 cancer cell lines (IC50 0.04-18.40 µM). However, they were cytotoxic towards a normal cell line (Vero cell) with IC50 values ranging from 0.04 to 3.86 µM.
Asunto(s)
Antibacterianos/aislamiento & purificación , Antineoplásicos/aislamiento & purificación , Chaetomium/química , Cromonas/aislamiento & purificación , Citotoxinas/aislamiento & purificación , Piperazina/aislamiento & purificación , Animales , Antibacterianos/química , Antibacterianos/farmacología , Antineoplásicos/química , Antineoplásicos/farmacología , Línea Celular Tumoral , Chlorocebus aethiops , Cromonas/química , Citotoxinas/química , Citotoxinas/farmacología , Disulfuros/aislamiento & purificación , Ergosterol/química , Ergosterol/aislamiento & purificación , Humanos , Alcaloides Indólicos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Piperazina/química , Piperazinas/aislamiento & purificación , Células VeroRESUMEN
Chromatographic separation of fruits and flowers of the Thai medicinal plant, Miliusa velutina, resulted in the isolation of five new rare homogentisic acid derivatives, miliusanal (1) and miliusanones A-D (2-5), together with fifteen known secondary metabolites (6-20). Their structures were determined through the use of extensive spectroscopic data. The absolute configurations of homogentisic acid derivatives 2-7 were identified using NOESY data and a comparison of experimental and calculated ECD spectral data. Compounds 2, 3, 6, and 7 showed antimalarial activity with IC50 values in the range of 3.3-5.2⯵g/mL. Compound 6 also showed activity against Mycobacterium tuberculosis with an MIC value of 50⯵g/mL. Compounds 1-3, 6 and 7 exhibited cytotoxicity againt KB, MCF-7, NCI-H187 and Vero cell lines with IC50 values in the range of 5.8-40.4⯵g/mL. In addition, compounds 1, 2 and 6 showed moderate antibacterial activities against three Gram-positive bacteria (Bacillus cereus, Staphylococcus aureus, and Methicillin resistant S. aureus) with MICs in the range of 32-64⯵g/mL.
Asunto(s)
Annonaceae/química , Antibacterianos/farmacología , Antineoplásicos Fitogénicos/farmacología , Ácido Homogentísico/farmacología , Animales , Antibacterianos/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Chlorocebus aethiops , Flores/química , Frutas/química , Bacterias Grampositivas/efectos de los fármacos , Ácido Homogentísico/aislamiento & purificación , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Mycobacterium tuberculosis/efectos de los fármacos , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Tailandia , Células VeroRESUMEN
Three new carbazole alkaloids, harmandianamines A-C (1-3), together with fifteen known compounds (4-18) were isolated from the twigs of Clausena harmandiana. The structures were elucidated by spectroscopic methods, including UV, IR, NMR, and MS. The antibacterial activity against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphylococcus aureus TISTR 1466 and methicillin-resistant S. aureus (MRSA) SK1 of some isolated compounds was also evaluated. Compound 6 exhibited significant antibacterial activity against MRSA SK1 with an MIC value of 0.25 µg/mL which higher than that of standard drug, vancomycin (MIC value=1 µg/mL) whereas compounds 14 and 5 showed strong activity with MIC values of 4 and 8 µg/mL, respectively. Only compound 14 showed strong antibacterial activity against S. aureus TISTR 1466 with an MIC value of 4 µg/mL.
Asunto(s)
Antibacterianos/farmacología , Bacterias/efectos de los fármacos , Carbazoles/farmacología , Clausena/química , Alcaloides Indólicos/farmacología , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Extractos Vegetales/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Carbazoles/química , Carbazoles/aislamiento & purificación , Alcaloides Indólicos/química , Alcaloides Indólicos/aislamiento & purificación , Resistencia a la Meticilina/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Extractos Vegetales/química , Vancomicina/farmacologíaRESUMEN
Four new carbazole alkaloids, clausenawallines C-F (1-4), along with 18 known compounds (5-22) were isolated from the roots of Clausena wallichii. Compounds 3, 9, and 22 exhibited significant antibacterial activity against methicillin-resistant Staphylococcus aureus SK1 (MRSA SK1) and Staph. aureus TISTR 1466 with MIC values in the range 4-16 µg/mL, whereas compound 4 showed the highest cytotoxicity against oral cavity cancer (KB) and small-cell lung cancer (NCI-H187) with IC(50) values of 10.2 and 4.5 µM, respectively.
Asunto(s)
Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Carbazoles/aislamiento & purificación , Carbazoles/farmacología , Clausena/química , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Alcaloides/química , Antibacterianos/química , Antineoplásicos Fitogénicos/química , Carbazoles/química , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Raíces de Plantas/química , Staphylococcus aureus/efectos de los fármacos , TailandiaRESUMEN
Two new compounds, garciniacowol (1) and garciniacowone (2) along with 15 knowncompounds were isolated from the stem barks of Garcinia cowa. Their structures weredetermined by intensive spectroscopic methods. The structure of 1 was a symmetrical dimericdihydrobenzopyran derivative, whereas the framework of 2 was a triprenyl caged-xanthoneprecursor. The antibacterial activities against Escherichia coli TISTR 780, Salmonellatyphimurium TISTR 292, Staphylococcus aureus TISTR 1466, and methicillin-resistant S. aureus(MRSA) SK1 of the isolated compounds were also evaluated. Compounds 2 and 9 exhibitedgood antibacterial activity against MRSA SK1 with the same minimum inhibitory concentration(MIC) value of 2 µg/mL. Moreover, compound 2 also showed good antibacterial activityagainst S. aureus with an MIC value of 2 µg/mL.