RESUMEN
Two sulfur-containing heterodimers of a cytochalasan and a macrolide, sucurchalasins A and B (1 and 2), and four known cytochalasan monomers (3-6), as well as four known macrolide derivatives (7-10), were obtained from the endophytic fungus Aspergillus spelaeus GDGJ-286. Sucurchalasins A and B (1 and 2) are the first cytochalasan heterodimers formed via a thioether bridge between cytochalasan and curvularin macrolide units. Their structures were elucidated by detailed analysis of NMR, LC-MS/MS, and X-ray crystallography. In bioassays, 1 and 2 exhibited cytotoxic effects on A2780 cells, with IC50 values of 3.9 and 8.3 µM, respectively. They also showed antibacterial activities against E. faecalis and B. subtilis with MIC values of 3.1 and 6.3 µg/mL, respectively.
RESUMEN
Eighteen new oleanane-type triterpenoids were isolated from the stems of Sabia limoniacea, including sabialimon A (1), a triterpenoid with an unprecedented 6/6/6/7/7 pentacyclic skeleton and seventeen undescribed triterpenoids, sabialimons B-R (2 - 18), along with six previously described analogs (19 - 24). Their structures were fully elucidated via extensive spectroscopic analysis including 1D and 2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), experimental electronic circular dichroism measurements and X-ray crystallographic studies. Compound 1 is the first triterpenoid that possesses a rare ring system (6/6/6/7/7) with an oxygen-bearing bridge between C-17 and C-18 and a hemiketal form at C-17, which is generated a larger ring by the degradation of C-28 and D/E-ring expansion. Biological evaluation revealed that sabialimon I (9), sabialimon K (11), sabialimon P (16) and 11,13(18)-oleanadien-28-hydroxymethyl 3-one (20) exhibited significantly inhibitory activities against nitric oxide (NO) release with IC50 values of 29.65, 23.41, 18.12 and 26.64 µM, respectively, as compared with the positive control (dexamethasone, IC50 value: 40.35 µM). Furthermore, sabialimon P markedly decreased the secretion of TNF-α, iNOS, IL-6 and NF-κB and inhibited the expression of COX-2 and NF-κB/p65 in LPS-induced RAW264.7 cells in a dose-dependent manner.
Asunto(s)
Ácido Oleanólico , Ratones , Animales , Células RAW 264.7 , Ácido Oleanólico/farmacología , Ácido Oleanólico/química , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/análogos & derivados , Estructura Molecular , Relación Estructura-Actividad , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Óxido Nítrico/metabolismo , Lipopolisacáridos/farmacología , Lipopolisacáridos/antagonistas & inhibidores , Relación Dosis-Respuesta a Droga , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Óxido Nítrico Sintasa de Tipo II/metabolismo , Ciclooxigenasa 2/metabolismoRESUMEN
Two new open-chain cytochalasins, xylarchalasins A and B (1 and 2), together with six known analogues (3-8), were isolated from the endophytic fungus Xylaria sp. GDGJ-77B from the Chinese medicinal plant Sophora tonkinensis. Their structures were elucidated on the basis of comprehensive spectroscopic analysis. Compound 2 displayed moderate antibacterial activities against Bacillus subtilis and Escherichia coli with MIC values of 25 and 12.5 µg/mL, respectively.
RESUMEN
One new cyclopentapeptide, cycloaspeptide H (1), featuring a serine residue, along with seven known compounds (2-8), was isolated from the endophytic fungus Penicillium virgatum GDGJ-227. The planar structure of 1 was elucidated by a comprehensive analysis of NMR and MS spectroscopic spectra, and the absolute configuration was determined by single-crystal X-ray diffraction (Cu Kα) analysis. Compounds 7 and 8 displayed antibacterial activities against Bacillus subtilis and Enterobacter aerogenes with MIC values ranging from 12.5 to 50 µg/mL.
RESUMEN
Three new andrastin derivatives, 10-formyl andrastone A (1), 10-demethylated andrastone A (2) and andrastin G (3), together with four known andrastin analogues (4-7) were isolated from an endophytic fungus Penicillium vulpinum. Their structures were determined by 1 D, 2 D NMR, and the absolute configurations were further determined by experimental and calculated ECD spectra. Compound 5 exhibited significant antibacterial activity against Bacillus paratyphosus B with an MIC value of 6.25 µg·mL-1. Compounds 2 and 6 showed remarkable inhibitory activities against Bacillus megaterium with the MIC value of 6.25 µg·mL-1, respectively.
Asunto(s)
Penicillium , Antibacterianos/química , Hongos , Estructura Molecular , Penicillium/químicaRESUMEN
A systematic chemical exploration of the marine-derived fungus Penicillium janthinellum led to the isolation of four indole-diterpenoid derivatives (1-4), including new penijanthines C and D (1 and 2), and a pair of new steroidal epimers, penijanthoids A and B (5 and 6). The calculated ECD spectra and Snatzke's method for the new compound 1 were carried out to determine its absolute configuration. The absolute configuration of 3 was established by X-ray diffraction and calculated ECD methods for the first time. DP4plus approach was used to elucidate the absolute configurations of the C-25 epimeric steroids 5 and 6. 25-Epimeric 5 and 6 represent the first examples of steroids forming a five-membered lactone between C-23 and C-27 from marine fungi. Compounds 1, 2, 5, and 6 displayed significant anti-Vibrio activity (Minimum inhibitory concentration, MIC values ranging from 3.1 to 50.0 µM) against three pathogenic Vibrio spp.
RESUMEN
Two new cyclopentapeptides, xylapeptide A (1) with an uncommon L-pipecolinic acid moiety, and xylapeptide B (2) having a common L-proline residue were identified from an associated fungus Xylaria sp. isolated from the Chinese medicinal plant Sophora tonkinensis. Their planar structures were elucidated by a comprehensive analysis of NMR and MS spectroscopic spectra. The absolute configurations were determined by Marfey's method and single-crystal X-ray diffraction (Cu Kα) analysis. Xylapeptide A (1) is the first example of cyclopentapeptide with L-Pip of terrestrial origin and showed strong antibacterial activity against Bacillus subtilis and B. cereus with MIC value of 12.5 µg/mL.
Asunto(s)
Antibacterianos/química , Bacillus/efectos de los fármacos , Péptidos Cíclicos/química , Xylariales/química , Antibacterianos/farmacología , Bacillus cereus/efectos de los fármacos , Bacillus subtilis/efectos de los fármacos , Cristalografía por Rayos X , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Péptidos Cíclicos/farmacología , Sophora/microbiología , Xylariales/aislamiento & purificaciónRESUMEN
One new hydroanthraquinone dimer with a rare C-9-C-7' linkage, nigrodiquinone A (1), and four known anthraquinone monomers 2-5, were isolated from a fungus Nigrospora sp. obtained from the zoanthid Palythoa haddoni collected in the South China Sea. The structure of 1 was established through extensive NMR spectroscopy, and the absolute configuration was elucidated by comparing computed electronic circular dichroism (ECD) and optical rotations (OR) with experimental results. All the compounds were evaluated for antiviral activity, and 1 was also evaluated for antibacterial activity. Compound 4 displayed mild antiviral activity against coxsackie virus (Cox-B3) with the IC50 value of 93.7 µM, and 5 showed an IC50 value of 74.0 µM against respiratory syncytial virus (RSV).
Asunto(s)
Antraquinonas/aislamiento & purificación , Antibacterianos/aislamiento & purificación , Antivirales/aislamiento & purificación , Ascomicetos/química , Antraquinonas/química , Antraquinonas/farmacología , Antibacterianos/química , Antibacterianos/farmacología , Antivirales/química , Antivirales/farmacología , China , Dicroismo Circular , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Océanos y Mares , Rotación ÓpticaRESUMEN
A new compound, illiciumflavane acid (1), along with 13 known compounds (2-14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC50 values of 4.63 µM and 9.17 µM, respectively.
Asunto(s)
Flavonoides/aislamiento & purificación , Frutas/química , Illicium/química , Antineoplásicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Dicroismo Circular , Cisplatino/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Flavonoides/química , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Rotación ÓpticaRESUMEN
Four new lignans, strebluslignanol F (1), (7'R,8'S,7â³R,8â³S)-erythro-strebluslignanol G (2), isomagnaldehyde (3) and isostrebluslignanaldehyde (4), along with 12 known lignans (5-16) were isolated from the ethyl acetate-soluble part of MeOH extract of the root of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans were evaluated for their anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line. The most active lignans, (7'R,8'S,7â³R,8â³S)-erythro-strebluslignanol G, magnolol, isomagnolol and isolariciresinol, exhibited significant anti-HBV activities with IC50 values of 1.58, 2.03, 10.34 and 3.67 µM, respectively, for HBsAg with no cytotoxicity, and of 3.24, 3.76, 8.83 and 14.67 µM, respectively, for HBeAg with no cytotoxicity. (7'R,8'S,7â³R,8â³S)-erythro-Strebluslignanol G and magnolol showed significant anti-HBV activities to inhibit the replication of HBV DNA with the IC50 values of 9.02 and 8.67 µM, respectively.
Asunto(s)
Antivirales/farmacología , Virus de la Hepatitis B/efectos de los fármacos , Lignanos/farmacología , Moraceae/química , Extractos Vegetales/farmacología , Raíces de Plantas/química , Antivirales/química , Antivirales/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Células Hep G2 , Humanos , Lignanos/química , Lignanos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Relación Estructura-ActividadRESUMEN
A new lignan, (7'R,8'R)-threo-strebluslignanol-2-O-beta-D-glucopyranoside, along with 8 known compounds (2-9) were isolated from the water-soluble part of the MeOH extract of the heartwood of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR (1H NMR, 13C NMR), 2D NMR (HMQC, HMBC, and NOESY), and HRMS. The stereochemistry at the chiral centers was determined using the CD spectrum, as well as analyses of coupling constants and optical rotation data. In the preliminary bioassay, the isolated compounds did not show anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line.
Asunto(s)
Moraceae/química , Extractos Vegetales/análisis , Virus de la Hepatitis B/efectos de los fármacos , Lignanos/análisis , Lignanos/química , Lignanos/farmacología , Espectroscopía de Resonancia Magnética , Solubilidad , Agua/químicaRESUMEN
Seven compounds, (7'S,8'S)-trans-streblusol A, (7'R,8'S)-erythro-streblusol B, (7'S,8'S)-threo-streblusol B, 8'R-streblusol C, streblusquinone, (8R,8'R)-streblusol D, and streblusol E, along with 15 known compounds (8-22) were isolated from the n-butanol-soluble part of the MeOH extract of stem bark of Streblus asper. Their structures were elucidated through application of extensive spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans and allylbenzene derivatives were evaluated for their anti-HBV activities in vitro using the HBV transfected Hep G2.2.15 cell line. The most active compounds, magnolol and 9-ß-xylopyranosyl-isolariciresinol, exhibited significant anti-HBV activities with IC(50) values of 2.03 and 6.58µM for secretion of HBsAg, with no cytotoxicity, and of 3.76 and 24.86µM for secretion of HBeAg, with no cytotoxicity.
Asunto(s)
Antivirales/aislamiento & purificación , Antivirales/farmacología , Virus de la Hepatitis B/efectos de los fármacos , Moraceae/química , Corteza de la Planta/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Células Hep G2 , Antígenos de Superficie de la Hepatitis B/metabolismo , Antígenos e de la Hepatitis B/metabolismo , Humanos , Concentración 50 Inhibidora , Metanol/químicaRESUMEN
Four new bisabolane-type sesquiterpenoids, aspergiterpenoid A (1), (-)-sydonol (2), (-)-sydonic acid (3), and (-)-5-(hydroxymethyl)-2-(2',6',6'-trimethyltetrahydro-2H- pyran-2-yl)phenol (4) together with one known fungal metabolite (5) were isolated from the fermentation broth of a marine-derived fungus Aspergillus sp., which was isolated from the sponge Xestospongia testudinaria collected from the South China Sea. Four of them (1-4) are optically active compounds. Their structures and absolute configurations were elucidated by using NMR spectroscopic techniques and mass spectrometric analysis, and by comparing their optical rotations with those related known analogues. Compounds 1-5 showed selective antibacterial activity against eight bacterial strains with the MIC (minimum inhibiting concentrations) values between 1.25 and 20.0 µM. The cytotoxic, antifouling, and acetylcholinesterase inhibitory activities of these compounds were also examined.
Asunto(s)
Antibacterianos/aislamiento & purificación , Aspergillus/metabolismo , Poríferos/microbiología , Sesquiterpenos/aislamiento & purificación , Animales , Antibacterianos/farmacología , Aspergillus/química , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
The extracts from leaves, heartwood, barks and roots of the Streblus asper were investigated for anti-HBV activities, separately. The results suggested that the MeOH extracts of the heartwood, barks, and roots exhibited good anti-HBV activities. Further investigations displayed that ethyl acetate and n-butanol soluble parts of their MeOH extracts showed more significant anti-HBV activities. Moreover, a new lignan, together with 11 known compounds, was isolated from n-butanol-soluble part of MeOH extract of the roots of S. asper. The structures were elucidated by spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC) and HR-EI-MS experiments. Compounds 1-3 were evaluated for their anti-HBV activities. Honokiol showed significant anti-HBV activity with IC(50) values of 3.14µM and 4.74µM for HBsAg and HBeAg with no cytotoxicity respectively, while lamivudine (3TC, positive control) exhibited weak anti-HBV activity with IC(50) values of 11.81µM and 25.80µM for HBsAg and HBeAg respectively.
Asunto(s)
Antivirales/uso terapéutico , Compuestos de Bifenilo/uso terapéutico , Virus de la Hepatitis B/efectos de los fármacos , Hepatitis B/tratamiento farmacológico , Lignanos/uso terapéutico , Moraceae/química , Fitoterapia , Extractos Vegetales/uso terapéutico , Antivirales/aislamiento & purificación , Antivirales/farmacología , Compuestos de Bifenilo/aislamiento & purificación , Compuestos de Bifenilo/farmacología , Células Hep G2 , Hepatitis B/virología , Humanos , Concentración 50 Inhibidora , Lamivudine/aislamiento & purificación , Lamivudine/farmacología , Lignanos/aislamiento & purificación , Lignanos/farmacología , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Raíces de Plantas/química , Estructuras de las PlantasRESUMEN
Three new lignans, erythro-strebluslignanol (1), threo-7'-methoxyl strebluslignanol (2) and erythro-7'-methoxyl strebluslignanol (3), together with twelve known compounds were isolated from the n-butanol and chloroform fractions of the heartwood of Streblus asper. Their structures were elucidated through extensive spectroscopic methods, including MS and 2D NMR experiments (HMQC and HMBC). The stereochemistry at the chiral center was determined using CD spectra, as well as analysis of coupling constants and optical rotation data, respectively. Primary bioassays showed that 6-hydroxyl-7-methoxyl-coumarin (5) and ursolic acid (10) showed anti-HBV activities, with IC(50) values of 29.60 µM and 89.91 µM for HBsAg at no cytotoxicity, and IC(50) values of 46.41 µM and 97.61 µM for HBeAg at no cytotoxicity, respectively.
Asunto(s)
Antivirales/farmacología , Virus de la Hepatitis B/efectos de los fármacos , Lignanos/farmacología , Moraceae/química , Extractos Vegetales/farmacología , Antivirales/química , Antivirales/aislamiento & purificación , Bioensayo , Compuestos de Bifenilo/química , Compuestos de Bifenilo/aislamiento & purificación , Compuestos de Bifenilo/farmacología , Línea Celular , Supervivencia Celular , Cumarinas/química , Cumarinas/aislamiento & purificación , Cumarinas/farmacología , Antígenos de Superficie de la Hepatitis B/efectos de los fármacos , Antígenos e de la Hepatitis B/efectos de los fármacos , Humanos , Concentración 50 Inhibidora , Lignanos/química , Lignanos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Triterpenos/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Madera/química , Ácido UrsólicoRESUMEN
The various fractions of the barks of Cyclocarya paliurus were systematically tested for hypoglycemic effects in alloxan-induced diabetic rats. The results showed that the chloroform fraction of the 75% EtOH extract of the barks of this plant exhibited significant blood sugar reducing activity, most of which were significantly higher than that of positive-drug metformin hydrochloride. A new compound, together with nine known compounds, was isolated from the most active fraction. The structure elucidation was based on spectroscopic methods, including two-dimensional NMR experiments (¹H-¹H COSY, HMQC, and HMBC). All of the isolates were evaluated for their α-glycosidase and glycogen phosphorylase inhibitory activities.
Asunto(s)
Diabetes Mellitus Experimental/tratamiento farmacológico , Inhibidores Enzimáticos/uso terapéutico , Glucógeno Fosforilasa/antagonistas & inhibidores , Hipoglucemiantes/uso terapéutico , Juglandaceae/química , Lactonas/aislamiento & purificación , Fitoterapia , Animales , Diabetes Mellitus Experimental/enzimología , Inhibidores Enzimáticos/aislamiento & purificación , Inhibidores Enzimáticos/farmacología , Glucosidasas/antagonistas & inhibidores , Hipoglucemiantes/aislamiento & purificación , Hipoglucemiantes/farmacología , Lactonas/química , Lactonas/farmacología , Metformina/farmacología , Corteza de la Planta , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/uso terapéutico , Ratas EndogámicasRESUMEN
The title compound, C(21)H(30)O, was isolated from the soft coral Sinularia sp. The mol-ecule contains four alicyclic rings, all trans-fused, among which three six-membered rings are in different distorted chair conformations while a five-membered ring assumes an envelope form.
RESUMEN
Four compounds, apicidin (1), N-methylharman (2), cylo (Phe-Tyr) (3) and indole-3-acetic acid (4) were isolated from the mangrove endophytic fungus ZZF42 from the South China Sea. Their structures were elucidated by spectral data. Compound 1 was first isolated from the marine fungus. Compound 2 was firstly isolated from marine microorganism. Compound 1 exhibited selective in vitro cytotoxicity towards KB ahd KBv200 with IC50 values of less than 0.78 microg/ml.
Asunto(s)
Alcaloides/aislamiento & purificación , Hongos/química , Péptidos Cíclicos/aislamiento & purificación , Rhizophoraceae/microbiología , Alcaloides/química , Alcaloides/farmacología , Antineoplásicos/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , China , Hongos/metabolismo , Humanos , Ácidos Indolacéticos/química , Ácidos Indolacéticos/aislamiento & purificación , Ácidos Indolacéticos/farmacología , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Estructura Molecular , Neoplasias Nasofaríngeas/patología , Péptidos Cíclicos/química , Péptidos Cíclicos/farmacologíaRESUMEN
In order to study the serological characteristics and genetic background of Bel subtypes, A, B and H antigens on the surface of red blood cells of the proband as well as his family and the anti-A, anti-B antibodies in their serum samples were detected by hemagglutination test; the A, B, H substances in saliva were determined by inhibitory agglutination test. The results indicated that the proband, his mother and his daughter all were identified to be Bel phenotype; his two sisters were identified to be ABel phenotype; his father, son and spouse were identified to be A, B and B phenotype respectively. It is concluded that the Bel subtype exists as family genetic characteristics in China.
Asunto(s)
Sistema del Grupo Sanguíneo ABO/genética , Tipificación y Pruebas Cruzadas Sanguíneas , Adulto , China , Cartilla de ADN , Femenino , Genotipo , Humanos , Masculino , LinajeRESUMEN
Two new metabolites named 6-oxo-de-O-methyllasiodiplodin (1) and (E)-9-etheno-lasiodiplodin (2), with three known compounds lasiodiplodin (3), de-O-methyllasiodiplodin (4), and 5-hydroxy-de-O-methyllasiodiplodin (5), were isolated from the mycelium extracts of a brown alga endophytic fungus (No. ZZF36) obtained from the South China Sea. Their structures were elucidated using spectroscopic methods, mainly 1D and 2D NMR. Additionally, the structure of compound 1 was confirmed by single crystal X-ray diffraction analysis. The antimicrobial activities of lasiodiplodins, and the 13-acetyl and 12,14-dibromo derivatives of lasiodiplodin were tested for the first time and the results were compared to each other.