RESUMEN
Colossolactone J (1), an undescribed lanostane triterpenoid was isolated from a natural fruiting body of Ganoderma colossus using silica gel column chromatography and preparative HPLC. Its structure was elucidated on the basis of the spectroscopic method. The absolute configuration was determined by the combination of the modified Mosher's method and detailed NMR data analysis.
RESUMEN
Antitubercular lanostane triterpenoids isolated from mycelial cultures of the basidiomycete Ganoderma australe were structurally modified by semisynthesis. One of the synthetic compounds, named GA003 (9), showed more potent activity against Mycobacterium tuberculosis H37Ra than the lead natural lanostane (1). GA003 was also significantly active against the virulent strain (H37Rv) as well as extensively drug-resistant tuberculosis strains.
Asunto(s)
Antituberculosos/química , Antituberculosos/farmacología , Ganoderma/química , Triterpenos/química , Animales , Antituberculosos/toxicidad , Chlorocebus aethiops , Ganoderma/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Mycobacterium tuberculosis/efectos de los fármacos , Relación Estructura-Actividad , Triterpenos/síntesis química , Triterpenos/farmacología , Células VeroRESUMEN
Three previously undescribed limonoids, fulvifomins A-C, together with two known compounds, 6-deoxydetigloyl-swietenine acetate and methyl angolensate, were isolated from fruiting bodies of the wood-rot fungus Fulvifomes xylocarpicola (Hymenochaetaceae), growing on the mangrove tree Xylocarpus granatum (Meliaceae). The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data, and X-ray crystallographic analysis (for fulvifomin A). A number of similar limonoids have been isolated from higher plants of the family Meliaceae, including X. granatum. The present study represents a unique evidence that the associated basidiomycete also contains these limonoids. Fulvifomin B exhibited moderate antimalarial and antitubercular activites.
Asunto(s)
Basidiomycota , Limoninas , Meliaceae , Cuerpos Fructíferos de los Hongos , Limoninas/farmacología , Estructura Molecular , Árboles , MaderaRESUMEN
Ten previously undescribed lanostane-type triterpenoids (1-10), together with 15 known lanostanes, were isolated from artificially cultivated fruiting bodies of the basidiomycete Ganoderma sp. BCC 21329. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data and by application of the modified Mosher's method. Compounds 1, 3, 5, and 7 showed moderate antimalarial activity (IC50 3.8-7.6 µg ml-1).
Asunto(s)
Antimaláricos/aislamiento & purificación , Cuerpos Fructíferos de los Hongos/química , Ganoderma/química , Triterpenos/aislamiento & purificación , Antimaláricos/química , Antimaláricos/farmacología , Espectroscopía de Resonancia Magnética , Estructura Molecular , Plasmodium falciparum/efectos de los fármacos , Relación Estructura-Actividad , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
The wood-rot basidiomycete Ganoderma colossus has been chemically investigated. Comparative analyses of the natural fruiting body, artificially cultivated fruiting bodies, and mycelial cultures resulted in the isolation, in total, of 13 new highly modified lanostanes, ganocolossusins A-H (1-8) and ganodermalactones T-X (9-13), together with 23 known compounds (14-36). There were significant overlaps of the same compounds among the three different states of the fungal materials. Ganocolossusin D (4) displayed the most potent antimalarial activity against Plasmodium falciparum K1 (multi-drug-resistant strain) with an IC50 value of 2.4 µM, while it was noncytotoxic to Vero cells at 50 µg/mL.
Asunto(s)
Cuerpos Fructíferos de los Hongos/química , Micelio/química , Polyporaceae/química , Triterpenos/aislamiento & purificación , Madera/microbiología , Espectroscopía de Resonancia Magnética con Carbono-13 , Estructura Molecular , Plasmodium falciparum/efectos de los fármacos , Espectroscopía de Protones por Resonancia Magnética , Espectrometría de Masa por Ionización de Electrospray , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
In a continuation of our research into antitubercular lanostane triterpenoids from submerged cultures of Ganoderma species, three strains, Ganoderma orbiforme BCC 22325, Ganoderma sp. BCC 60695, and Ganoderma australe BCC 22314, have been investigated. Fourteen new lanostane triterpenoids, together with 35 known compounds, were isolated. Antitubercular activities of these mycelium-associated Ganoderma lanostanoids against Mycobacterium tuberculosis H37Ra were evaluated. Taken together with the assay data of previously isolated compounds, structure-activity relationships of the antitubercular activity are proposed. Most importantly, 3ß- and 15α-acetoxy groups were shown to be critical for antimycobacterial activity. The most potent compound was (24E)-3ß,15α-diacetoxylanosta-7,9(11),24-trien-26-oic acid (35).
Asunto(s)
Antituberculosos/aislamiento & purificación , Antituberculosos/farmacología , Cuerpos Fructíferos de los Hongos/química , Ganoderma/aislamiento & purificación , Lanosterol/análogos & derivados , Micelio/química , Mycobacterium tuberculosis/química , Antituberculosos/química , Ganoderma/química , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Estructura Molecular , Relación Estructura-ActividadRESUMEN
Nine alliacane sesquiterpenoids, inonoalliacanes A-I, were isolated from culture broth of the basidiomycete Inonotus sp. BCC 22670. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The absolute configuration of inonoalliacane F was determined by application of the modified Mosher's method. Inonoalliacane A, the most abundant sesquiterpene constituent, exhibited moderate antibacterial activity against Bacillus cereus, whereas inonoalliacane B showed antiviral activity against herpes simplex virus type 1.
Asunto(s)
Antibacterianos/aislamiento & purificación , Basidiomycota/química , Sesquiterpenos/aislamiento & purificación , Antibacterianos/química , Antibacterianos/farmacología , Bacillus cereus/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos/química , TailandiaRESUMEN
The structure of a C2-symmetric epidithiodiketopiperazine alkaloid, SCH 64874, was determined by semisynthesis. The relative stereochemistry of the ß-hydroxy carboxylic acid chain having three chiral centers was determined by comparison of the NMR data of the four possible diastereomeric ß-hydroxy carboxylic acid fragments with those of SCH 64874. Condensation of the (-)-deacetylaranotin core with two enantiomeric ß-hydroxy carboxylic acids revealed the relative stereochemistry of SCH 64874. The relative stereochemistry of the ß-keto carboxylic acid chain of the analogous alkaloid hirsutellomycin was determined in a stepwise manner. The C4'-C6' syn relationships were predicted by comparing the NMR data of the corresponding ester fragments with that of hirsutellomycin. The relative stereochemistry of the whole molecule, including the epimerizable C2' stereocenter, was determined by introduction of four possible side chains into the bisdethiodi(methylthio)deacetylaranotin core. We found that the stereochemistry of C2' converged with that of the thermodynamically stable form influenced by the core structure.
Asunto(s)
Alcaloides/síntesis química , Ácidos Carboxílicos/química , Dicetopiperazinas/síntesis química , Piperazinas/síntesis química , Alcaloides/química , Dicetopiperazinas/química , Estructura Molecular , Piperazina , Piperazinas/química , EstereoisomerismoRESUMEN
Two new hirsutane sesquiterpenes, marasmiellins A (1) and B (2), were isolated from cultures of the basidiomycete Marasmiellus sp. BCC 22389. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The absolute configuration of marasmiellin B was determined by application of the modified Mosher's method.
RESUMEN
Sixteen new lanostane triterpenoids (1-16), together with 26 known compounds (17-42), were isolated from cultures of the basidiomycete Ganoderma sp. BCC 16642. Antitubercular activities of these Ganoderma lanostanoids against Mycobacterium tuberculosis H37Ra were evaluated, and structure-activity relationships are proposed.
Asunto(s)
Antituberculosos/aislamiento & purificación , Antituberculosos/farmacología , Ganoderma/química , Lanosterol/análogos & derivados , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Antituberculosos/química , Cuerpos Fructíferos de los Hongos/química , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Estructura Molecular , Mycobacterium tuberculosis/efectos de los fármacos , Resonancia Magnética Nuclear Biomolecular , Relación Estructura-Actividad , Tailandia , Triterpenos/químicaRESUMEN
Sterostreins F-O (1-10), 10 illudalanes and norilludalanes, were isolated from cultures of the Basidiomycete Stereum ostrea BCC 22955. Their structures were elucidated by analyses of the NMR spectroscopic and mass spectrometry data. Sterostreins M (8), N (9), and O (10) are pyridine-containing illudalanes.
Asunto(s)
Basidiomycota/química , Basidiomycota/crecimiento & desarrollo , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Técnicas de Cultivo , Espectroscopía de Resonancia MagnéticaRESUMEN
Seven new lanostane-type triterpenes, hypocrellols A-G (1-7), and six new hopane-type triterpenes, 7ß,15α-dihydroxy-22(29)-hopene (8), 3ß,7ß-dihydroxy-22(29)-hopene (9), 3ß-acetoxy-15α-hydroxy-22(29)-hopene (10), 3ß,7ß,15α,22-tetrahydroxyhopane (11), 3ß-acetoxy-7ß,15α,22-trihydroxyhopane (12), and 7ß,15α,22-trihydroxyhopane (13), were isolated from the scale insect pathogenic fungus Hypocrella sp. BCC 14524. The structures of the new compounds were elucidated by analyses of the NMR spectroscopic and mass spectrometry data. The structure of 1 was confirmed by X-ray crystallography.
Asunto(s)
Antimaláricos/aislamiento & purificación , Antineoplásicos/aislamiento & purificación , Antituberculosos/aislamiento & purificación , Hypocreales/química , Triterpenos/aislamiento & purificación , Animales , Antimaláricos/química , Antimaláricos/farmacología , Antineoplásicos/química , Antineoplásicos/farmacología , Antituberculosos/química , Antituberculosos/farmacología , Chlorocebus aethiops , Cristalografía por Rayos X , Resistencia a Medicamentos , Ensayos de Selección de Medicamentos Antitumorales , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Mycobacterium tuberculosis/efectos de los fármacos , Resonancia Magnética Nuclear Biomolecular , Plasmodium falciparum/efectos de los fármacos , Estereoisomerismo , Tailandia , Triterpenos/química , Triterpenos/farmacología , Células VeroRESUMEN
The insect pathogens in the genus Torrubiella s. lat. were recently divided into new genera based on molecular phylogenetic characters. Isolates collected at various locations in Thailand, were tested for their productivity of a hopane-type triterpene, zeorin (6α,22-dihydroxyhopane), when cultured in potato dextrose broth under static conditions. Among the 49 strains of Torrubiella s. lat. species, Conoideocrella luteorostrata (ten strains) and C. tenuis (seven strains), all collected on scale insects (Hemiptera), produced zeorin, whereas another six strains of Orbiocrella petchii (which was recently removed from Torrubiella) failed in the detection of this secondary metabolite. All other Torrubiella s. lat. (26 strains), collected on other insect hosts including leafhoppers (eight strains), Lepidoptera (one strain), and spiders (17 strains), produced no detectable zeorin. Paecilomyces cinnamomeus (nine strains), the anamorph of C. luteorostrata, also produced zeorin. These results correspond with the recent taxonomic reclassification based on multigene phylogeny.
Asunto(s)
Hypocreales/química , Micelio/química , Filogenia , Triterpenos/análisis , Animales , Hemípteros/microbiología , Paecilomyces/químicaRESUMEN
A novel cyclodepsipeptide, cordycommunin (1), and two dihydroisocoumarins (2 and 3) were isolated from the insect pathogenic fungus Ophiocordyceps communis BCC 16475. The absolute configurations of the amino acid residues of 1 were addressed by application of Marfey's method. Cordycommunin (1) showed growth inhibition of Mycobacterium tuberculosis H37Ra with an MIC value of 15 microM. This compound also exhibited weak cytotoxicity to KB cells with an IC50 of 45 microM, while it was inactive against BC, NCI-H187, and Vero cell lines at a concentration of 88 microM (50 microg/mL).
Asunto(s)
Antituberculosos/aislamiento & purificación , Antituberculosos/farmacología , Cordyceps/química , Depsipéptidos/aislamiento & purificación , Depsipéptidos/farmacología , Mycobacterium tuberculosis/efectos de los fármacos , Animales , Antituberculosos/química , Chlorocebus aethiops , Depsipéptidos/química , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Concentración 50 Inhibidora , Células KB , Pruebas de Sensibilidad Microbiana , Estructura MolecularRESUMEN
The scale insect pathogens Hypocrella s. lat. and their Aschersonia anamorphs, collected at various locations in Thailand, were surveyed for their productivity of three hopane triterpenes, zeorin (6alpha,22-dihydroxyhopane), dustanin (15alpha,22-dihydroxyhopane), and 3beta-acetoxy-15alpha,22-dihydroxyhopane, when cultured in a liquid medium (potato-dextrose broth) under static conditions. Among 53 strains of Aschersonia species, 48 strains (91 %) produced at least one of these compounds. Hypocrella and Moelleriella species (43 strains) also frequently produced these triterpenoids; only two strains lacked all of these triterpenes. The results demonstrate that hopane triterpenes may be suitable for use as chemotaxonomic markers for Hypocrella and Moelleriella species and their Aschersonia anamorphs.