RESUMEN
Aphadilactones A-D (1-4), four diastereoisomers possessing an unprecedented carbon skeleton, were isolated from the Meliaceae plant Aphanamixis grandifolia. Their challenging structures and absolute configurations were determined by a combination of spectroscopic data, chemical degradation, fragment synthesis, experimental CD spectra, and ECD calculations. Aphadilactone C (3) with the 5S,11S,5'S,11'S configuration showed potent and selective inhibition against the diacylglycerol O-acyltransferase-1 (DGAT-1) enzyme (IC50 = 0.46 ± 0.09 µM, selectivity index > 217) and is the strongest natural DGAT-1 inhibitor discovered to date. In addition, compounds 1-4 showed significant antimalarial activities with IC50 values of 190 ± 60, 1350 ± 150, 170 ± 10, and 120 ± 50 nM, respectively.
Asunto(s)
Antimaláricos/farmacología , Diacilglicerol O-Acetiltransferasa/antagonistas & inhibidores , Diterpenos/farmacología , Inhibidores Enzimáticos/farmacología , Meliaceae/química , Plasmodium falciparum/efectos de los fármacos , Antimaláricos/química , Antimaláricos/aislamiento & purificación , Diacilglicerol O-Acetiltransferasa/metabolismo , Dimerización , Diterpenos/química , Diterpenos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Humanos , Conformación Molecular , Pruebas de Sensibilidad Parasitaria , Proteínas Recombinantes/metabolismo , Relación Estructura-ActividadRESUMEN
The paper is to report the establishment of three methods for determination of methyl salicylate-2-O-beta-D-galactopyranoside (1-4)-beta-D-glucopyranoside (MSG) by HPLC, UV or potentiometric titration. The results determined by the three methods turned out to be of no significant difference (P>0.05). The method was chosen according to MSG difference test demands.
Asunto(s)
Antiinflamatorios/análisis , Cromatografía Líquida de Alta Presión/métodos , Glicósidos/análisis , Potenciometría/métodos , Salicilatos/análisis , Espectrofotometría Ultravioleta/métodos , Antiinflamatorios/química , Glicósidos/química , Estructura Molecular , Reproducibilidad de los Resultados , Salicilatos/química , Sensibilidad y EspecificidadRESUMEN
Five new ring A-seco triterpenoids, dysoxyhainic acids F-J (1-5), along with a known ring A-seco triterpenoid koetjapic acid (6) were isolated from the twigs and leaves of Dysoxylum hainanense. Their structures were established on the basis of extensive spectroscopic analysis. Antimicrobial activity of all the compounds against fungi and bacteria were tested. Compounds 2-4 and 6 exhibited significant antimicrobial activity against Gram-positive bacteria, and the antibacterial SAR (structure-activity relationship) was also briefly discussed.
Asunto(s)
Antibacterianos/química , Meliaceae/química , Triterpenos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Bacterias Grampositivas/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Hojas de la Planta/química , Relación Estructura-Actividad , Triterpenos/aislamiento & purificación , Triterpenos/farmacologíaRESUMEN
Three new limonoids (toonaciliatins N-P, 1-3)and four new pimaradiene-type diterpenoids(toonacilidins A-D, 4-7) were isolated from the leaves and twigs of Toona ciliata Roem. var. yunnanensis.Their structures were elucidated on the basis of spectroscopic methods. Toonacilidin B(5)showed moderate inhibitory activity against H. pylori-SS1 with an MIC of 50 µg/mL.
Asunto(s)
Antiinfecciosos/química , Diterpenos/química , Helicobacter pylori/efectos de los fármacos , Limoninas/química , Meliaceae/química , Extractos Vegetales/química , Antiinfecciosos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Limoninas/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura MolecularRESUMEN
Ten new limonoids, namely, mesendanins A-J (1-10), together with 14 known compounds, have been isolated from the leaves and twigs of Melia toosendan. Their structures were established on the basis of spectroscopic data analysis.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Limoninas/aislamiento & purificación , Melia/química , Medicamentos Herbarios Chinos/química , Limoninas/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Tallos de la Planta/químicaRESUMEN
Two new sesquiterpenes, sarcandralactones A (1) and B (2), and five new dimeric sesquiterpenoids, sarcandrolides A-E (3-7), along with 10 known compounds were isolated from the whole plants of Sarcandra glabra. Their structures were elucidated on the basis of spectroscopic analysis. Some of the new isolates exhibit significant cytotoxicities when tested against a small panel of tumor cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Magnoliaceae/química , Sesquiterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Células HL-60 , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
Lactuca sativa L. var. augustana has a basmati rice-like odor with a green note in the background. This typical odor is due to the release of 2-acetyl-1-pyrroline (2-AP) after heating, which is confirmed by volatile analysis. Recent metabolomic and genomic studies of different rice varieties highlighted that the presence of 2-AP was linked to the accumulation of γ-aminobutyraldehyde; genome-wide association studies also indicated that acyltransferases were involved. These results prompted us to analyze nonvolatile compound precursors in L. sativa L. var. augustana (celtuce) to search for compound derivatives with a 4,5-dioxohexan alkyl amine-like structure. Hypothetical synthetic compounds were prepared from a reductive amination between 4,5-dioxohexanal and glycine, alanine, aspartic acid, and glutamic acid to give 2-(2-acetylpyrrolidin-1-yl) alkanoic acid. We proved that 2-(2-acetylpyrrolidin-1-yl) propionic acid is present in L. sativa, which, when thermally treated, released 2-AP. Other 2-AP precursors occurring in this plant are discussed.
Asunto(s)
Lactuca/química , Extractos Vegetales/química , Pirroles/química , Genoma de Planta , Lactuca/genética , Espectrometría de Masas , Odorantes/análisisRESUMEN
OBJECTIVE: To select a proper Ganoderma luciderm strain for the fruiting body production. METHOD: The strains were cultivated on the agar media and in the liquid media, respectively. Then the strains were inoculated onto the solid medium made from agricultural products (such as wheat bran, corn powder, wood meal, etc.) and cultured for a certain period. RESULT: Strains, which were easier to produce polyporic tissues at the vegetative growth stage, would be more quickly to form fruiting body with high quality and yield of the spores. CONCLUSION: Appearance of the polyporic tissues at the mycelium vegetative growth stage could be used as a marker for the strain selection for the G. luciderm substituted cultivation.
Asunto(s)
Cuerpos Fructíferos de los Hongos/crecimiento & desarrollo , Ganoderma/crecimiento & desarrollo , Micelio/crecimiento & desarrollo , Reactores Biológicos , Medios de Cultivo , Triticum , Zea maysRESUMEN
Three highly oxygenated new diterpenes, trigochinins A-C (1-3) were isolated from Trigonostemon chinensis. Their structures with the absolute configuration were determined by a spectroscopic method, X-ray crystallography, and CD analysis. This study suggested the revision of the C-6 stereochemistry of trigonothyrins A-C reported quite recently. Compound 3 showed significant inhibition against MET tyrosine kinase activity with a IC(50) value of 1.95 microM.
Asunto(s)
Diterpenos/química , Euphorbiaceae/química , Inhibidores de Proteínas Quinasas/química , Cristalografía por Rayos X , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Modelos Moleculares , Conformación Molecular , Hojas de la Planta/química , Tallos de la Planta/química , Inhibidores de Proteínas Quinasas/aislamiento & purificación , Inhibidores de Proteínas Quinasas/farmacología , Proteínas Tirosina Quinasas/antagonistas & inhibidores , Proteínas Tirosina Quinasas/metabolismo , EstereoisomerismoRESUMEN
Trigochilides A (1) and B (2), two highly modified daphnane-type diterpenoids with 12-carbon-containing polyketide appendages at C-16 forming a macro-lactone with C-3, were isolated from the twigs and leaves of Trigonostemon chinensis. Their structures were elucidated by spectroscopic analysis. Trigochilides A (1) showed modest cytotoxicity against two tumor cell lines.
Asunto(s)
Antineoplásicos/uso terapéutico , Diterpenos/uso terapéutico , Ensayos de Selección de Medicamentos Antitumorales , Euphorbiaceae/química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Diterpenos/clasificación , Medicamentos Herbarios Chinos/química , Células HeLa , Humanos , Células K562 , Lactonas/farmacología , Hojas de la Planta/química , Relación Estructura-Actividad , Células Tumorales CultivadasRESUMEN
Five new alkaloids, gelseganines A-D (1-4) and humantenine N(4)-oxide (5), were isolated from the stems and leaves of Gelsemium elegans. Compounds 1-4 represent a rare class of monoterpenoid indole alkaloids that bear an N(4)-iridoid unit. The structures of 1-5 were determined by spectroscopic analysis, single-crystal X-ray diffraction, and chemical correlation, and their absolute configurations were elucidated by CD analysis. A plausible biogenetic pathway for alkaloids 1-5 was also postulated.
Asunto(s)
Gelsemium/química , Iridoides/química , Alcaloides de Triptamina Secologanina/química , Dicroismo Circular , Iridoides/aislamiento & purificación , Estructura Molecular , Hojas de la Planta/química , Tallos de la Planta/química , Plantas Medicinales/química , Alcaloides de Triptamina Secologanina/aislamiento & purificaciónRESUMEN
Two novel rearranged oleanane-type triterpenes, dysoxyhainanin A ( 1) possessing a unique 1,3- cyclo-2,3- seco A ring with a formamido-containing appendage and dysoxyhainanin B ( 2) featuring an unprecedented 1,2-dinor-3,10:9,10- bisseco skeleton, were isolated from Dysoxylum hainanense. Dysoxyhainanin A ( 1) exhibited significant antibacterial activity against Gram-positive bacteria.