RESUMEN
Phytochemical investigation on the fruiting bodies of the medicinal fungus Ganoderma lingzhi led to the isolation of a new norsteroid, namely ganonorsterone A (1), together with one known steroid, cyathisterol (2). The structure and absolute configuration of compound 1 were assigned by extensive analysis of MS, NMR data, and quantum-chemical calculations including electronic circular dichroism (ECD) and calculated 13C NMR-DP4+ analysis. Bioassay results showed that compound 1 displayed moderate inhibition on NO production in RAW 264.7 macrophages.
Asunto(s)
Ganoderma , Óxido Nítrico , Ganoderma/química , Ratones , Células RAW 264.7 , Animales , Estructura Molecular , Óxido Nítrico/biosíntesis , Óxido Nítrico/antagonistas & inhibidores , Macrófagos/efectos de los fármacos , Cuerpos Fructíferos de los Hongos/químicaRESUMEN
One new 6a,11a-dehydropterocarpan derivative, 6-O-methyl-anhydrotuberosin (1), one new 6a-hydroxypterocarpan, (6aR,11aR,11bR)-hydroxytuberosone (7), and seven known compounds including two 6a,11a-dehydropterocarpans (2 and 4), two coumestans (3 and 5), one isoflavonoid (6) and two other phenolic compounds (8 and 9) were isolated from the roots of Pueraria lobata. The structures of the isolated compounds were elucidated with spectroscopic and spectrometric methods (1 D and 2DNMR, HRESIMS). Compounds 1, 2, 4-5 showed potent LSD1 inhibitory activities with IC50 values ranging from 1.73 to 4.99 µM. Furthermore, compound 2 showed potent cytotoxicity against gastric cancer cell lines MGC-803 and BGC-823, and lung cancer cell lines H1299 and H460.
Asunto(s)
Isoflavonas , Pueraria , Pueraria/química , Línea Celular , Fenoles , Histona Demetilasas/análisis , Raíces de Plantas/química , Isoflavonas/farmacología , Isoflavonas/químicaRESUMEN
ABSTACTA chemical investigation of the whole plant of traditional Chinese medicine, Chrysanthemum indicum L., led to the discovery of six guaianolide-type sesquiterpenoids 1-6 with a 1,10-splited skeleton. The structure of the new compound 1 was established by extensive analysis of UV, IR, MS, NMR and ECD data. Compounds 3-6 are mutually stereoisomers with four chiral centers and their absolute configurations were determined by comparison of ECD spectra. The anti-inflammatory effects of these isolates on lipopolysaccharide (LPS)-induced nitric oxide (NO) were investigated in RAW 264.7 cells. Results showed that most of the compounds displayed NO production inhibitory activities with IC50 values ranged from 3.54 to 8.17 µM.
Asunto(s)
Chrysanthemum , Sesquiterpenos , Animales , Lipopolisacáridos/farmacología , Ratones , Estructura Molecular , Óxido Nítrico , Células RAW 264.7 , Sesquiterpenos/farmacologíaRESUMEN
Xylarilongipins A (1) and B (2), two diterpenes each with an unusual cage-like bicyclo[2.2.2]octane moiety, along with their biosynthetic precursor hymatoxin L (3), were isolated from the culture broth of the fungicolous fungus Xylaria longipes HFG1018 inhabiting in the medicinal fungus Fomitopsis betulinus. The structures and absolute configurations of the three compounds were established by extensive spectroscopic analysis and single-crystal X-ray diffraction analysis. Xylarilongipin A (1) displayed moderate inhibitory activity against the cell proliferation of concanavalin A-induced T lymphocytes and lipopolysaccharide-induced B lymphocytes with IC50 values of 13.6 and 22.4 µM, respectively. Additionally, the biosynthetic pathways for compounds 1-3 are discussed. This work not only corroborates the structure of the 9,16-cyclo-(18-nor-)isopimarane skeleton by single-crystal X-ray diffraction analysis for the first time, but also provides new insights into the biosynthetic origin of the unusual diterpene skeletons.
Asunto(s)
Compuestos Bicíclicos con Puentes/farmacología , Diterpenos/farmacología , Inmunosupresores/farmacología , Compuestos Bicíclicos con Puentes/química , Compuestos Bicíclicos con Puentes/toxicidad , Línea Celular Tumoral , Diterpenos/química , Diterpenos/toxicidad , Humanos , Inmunosupresores/química , Inmunosupresores/toxicidad , Xylariales/químicaRESUMEN
Eighteen new nor-isopimarane diterpenes, xylarinorditerpenes A-R (1-18), along with two previously reported compounds, 14α,16-epoxy-18-norisopimar-7-en-4α-ol (19) and the labdane-type diterpene agatadiol (20), were isolated from cultures of the fungicolous fungus Xylaria longipes HFG1018 isolated from the wood-rotting basidiomycete Fomitopsis betulinus. The structure elucidation and relative configuration assignments of 1-18 were accomplished by interpretation of spectroscopic data and through computational methods. The absolute configurations of 1, 4, and 16 were determined by single-crystal X-ray diffraction. Compounds 1-16 possess an 18- or 19-nor-isopimarane skeleton, and compounds 17 and 18 possess an 18,19-dinor-isopimarane skeleton. Compounds 2-5, 9, 14, 19, and 20 showed immunosuppressive activity but were devoid of cytotoxicity against the cell proliferation by concanavalin A-induced T lymphocytes and lipopolysaccharide-induced B lymphocytes, with IC50 values varying from 1.0 to 27.2 µM and from 16.1 to 51.8 µM, respectively.
Asunto(s)
Abietanos/química , Ascomicetos/química , Diterpenos/química , Inmunosupresores/química , Xylariales/química , Basidiomycota , Proliferación Celular/efectos de los fármacos , Cristalografía por Rayos X , Diterpenos/farmacología , Inmunosupresores/farmacología , Estructura Molecular , Polyporales/químicaRESUMEN
Irpexolidal (1), a triterpenoid with an unprecedented carbon skeleton, along with its biogenetic-related compound irpexolide A (2), were isolated from the fruiting bodies of the medicinal fungus Irpex lacteus. Irpexolidal features a 6/5/6/5/6/5-fused polycyclic skeletal system which arises from the eburicane-type triterpene by a 6,7- seco-6,8- cyclo pattern. The structures of 1 and 2 were established by means of extensive spectroscopic techniques, ECD calculation, and DP4+ probability based on GIAO NMR chemical shift calculations. The plausible biosynthetic pathways for compounds 1 and 2 were proposed. Their biological activities were evaluated.
Asunto(s)
Carbono/química , Cuerpos Fructíferos de los Hongos/química , Triterpenos/química , Vías Biosintéticas , Espectroscopía de Resonancia MagnéticaRESUMEN
Five new triterpenoids, irpeksins A-E (1-5), were isolated from fruiting bodies of the medicinal fungus Irpex lacteus. The structures as well as absolute configurations of the new compounds were established via extensive spectroscopic analysis, computational methods, and Cotton effects. Compounds 1-4 are featured by a scaffold of 1,10- seco- and ring B aromatic eburicane (24-methyllanostane), and compound 5 is characterized by a scaffold of 1,10-9,11- diseco- and ring B aromatic eburicane, which represents unprecedented cleavage patterns in the lanostane family. Compounds 1-5 showed significant inhibitory activity against NO production in LPS-activated RAW 264.7 macrophage cells with IC50 values varying from 2.2 to 19.6 µM.
Asunto(s)
Óxido Nítrico/antagonistas & inhibidores , Polyporales/química , Triterpenos/farmacología , Animales , Ascomicetos , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Células RAW 264.7 , Triterpenos/químicaRESUMEN
Matsutakone (1), a novel sterol with an unprecedented polycyclic ring system, together with a new norsteroid matsutoic acid (2) were isolated from the fruiting bodies of Tricholoma matsutake. Their structures and absolute configurations were assigned by extensive spectroscopic analyses and computational methods. Bioassay results showed that compounds 1 and 2 exhibited inhibitory activities against acetylcholinesterase (IC50 20.9 µM for 1).
Asunto(s)
Acetilcolinesterasa/metabolismo , Inhibidores de la Colinesterasa/farmacología , Noresteroides/farmacología , Esteroles/farmacología , Tricholoma/química , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Eritrocitos/enzimología , Humanos , Conformación Molecular , Noresteroides/química , Noresteroides/aislamiento & purificación , Esteroles/química , Esteroles/aislamiento & purificación , Relación Estructura-ActividadRESUMEN
Studies of the fermentation broth of fungus Antrodiella gypsea led to the isolation of a new bisabolane-type sesquiterpenoid that was named gypseatriol (1), together with the known compound 2,10-dodecadiene-1,6,7-triol (2). The structure of this new metabolite was assigned by analysis of 2D NMR and HR-EI-MS. Absolute configuration was assigned by single crystal X-ray diffraction analysis. Compound 1 was evaluated for its antifungal activity on Candida albicans.
Asunto(s)
Basidiomycota/química , Sesquiterpenos/aislamiento & purificación , Coriolaceae , Cristalografía por Rayos X , Fermentación , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
Four new polycylic alkaloids, lucidimine A-D, were isolated from the fruiting bodies of Ganoderma lucidum. Their chemical structures were established based on 1D and 2D NMR data as well as HREIMS/HRESIMS analyses.
Asunto(s)
Alcaloides/aislamiento & purificación , Reishi/química , Alcaloides/química , Cuerpos Fructíferos de los Hongos/química , Estructura Molecular , Resonancia Magnética Nuclear BiomolecularRESUMEN
Two new triterpenoids, (24E)-9α,11α-epoxy-3ß-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 â 12)abeo-lanosta-8,22,24-trien-26,23-olide (2) were isolated from dried fruiting bodies of fungus Ganoderma lucidum. The structures of these two new compounds were elucidated on the basis of extensive spectroscopic analyses. Compound 1 possessed a lanostane skeleton, while compound 2 was based on a rare 14 (13 â 12)abeo-lanostane skeleton with a 26,23-olide moiety. Both of them were evaluated for their antifungal and cytotoxic activities. Neither of them displayed obvious inhibition on Candida albicans and five human cancer cell lines.
Asunto(s)
Ganoderma/química , Triterpenos/aislamiento & purificación , Candida albicans/efectos de los fármacos , China , Ensayos de Selección de Medicamentos Antitumorales , Cuerpos Fructíferos de los Hongos/química , Células HL-60 , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
Cultivation and extraction of the fungus Stereum hirsutum (Willd.) Pers. yielded 12 isopentenyl benzene derivatives, including six previously undescribed derivatives, named stereuins A-F. Their structures were established based on NMR and mass spectroscopy analyses, supplemented by comparison with previously reported data. Stereuins A-C are unique benzoate derivatives containing fatty acid subunits. Stereuins D and E feature a valylene group and a 6/6/6 ring system. In vitro, stereuin A significantly promoted neurite outgrowth. Several compounds exhibited antibacterial activity against Staphylococcus aureus. Stereuin F has an IC50 value of 5.2 µg/mL against S. aureus, comparable to the positive control, penicillin G sodium (1.4 µg/mL).
RESUMEN
Nine pyrrole alkaloid derivatives, including four new ones (1-4), were isolated from the wild mushroom Lentinula edodes for the first time. Their chemical structures were determined using UV-Vis spectroscopy, IR spectroscopy, MS, NMR spectroscopy, and single-crystal X-ray diffraction techniques. Compound 1, a previously unreported bicylo-pyrrole aldehyde homologue, was found to be a major component, approximately 8.2 µg g -1 in the dry powder of L. edodes. Compound 1 showed cytotoxicity against SMMC-772 (IC50 15.8 µM) without any cytotoxic effect on LO2, a normal hepatic cell line; compounds 1 and 2 displayed weak immunosuppressive activities by inhibiting the proliferation of induced T cells; compound 3 showed inhibition activity on the proliferation of HaCaT cell line (IC50 25.4 µM) and weak antioxidant activity at a concentration of 50 µM.
RESUMEN
A total of nine new phenolic amides (1-9), including four pairs of enantiomeric mixtures (3-5 and 8), along with ten known analogues (10-19) were identified from the fruits of Lycium barbarum using bioassay-guided chromatographic fractionation. Their structures were elucidated by comprehensive spectroscopic and spectrometric analyses, chiral HPLC analyses, and quantum NMR, and electronic circular dichroism calculations. Compounds 5-7 are the first example of feruloyl tyramine dimers fused through a cyclobutane ring. The activity results indicated that compounds 1, 11, and 13-17 exhibited remarkable inhibition against α-glucosidase with IC50 of 1.11-33.53 µM, 5-150 times stronger than acarbose (IC50 = 169.78 µM). Meanwhile, compounds 4a, 4b, 5a, 5b, 13, and 14 exerted moderate agonistic activities for peroxisome proliferator-activated receptor (PPAR-γ), with EC50 values of 10.09-44.26 µM. Especially,compound 14 also presented inhibitory activity on dipeptidyl peptidase-4 (DPPIV), with an IC50 value of 47.13 µM. Furthermore, the banding manner of compounds 14 and 17 with the active site of α-glucosidase, DPPIV, and PPAR-γ was explored by employing molecular docking analysis.
Asunto(s)
Lycium , alfa-Glucosidasas , alfa-Glucosidasas/análisis , Frutas/química , Lycium/química , Receptores Activados del Proliferador del Peroxisoma , Agonistas de PPAR-gamma , Amidas , Simulación del Acoplamiento Molecular , Fenoles/análisis , Espectroscopía de Resonancia Magnética , Dipeptidil-Peptidasas y Tripeptidil-Peptidasas/análisis , Estructura Molecular , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/químicaRESUMEN
Eight previously undescribed lanostane triterpenoids and nine known ones were identified from the fruiting bodies of Ganoderma lingzhi S.H. Wu, Y. Cao & Y.C. Dai. Their structures were determined based on spectroscopic data and quantum chemical calculations. Structurally, ganoderane GL-1, featuring a hydrogenated tetramethyls-phenanthraquinone, represents the first example in lanostane nor-triterpenoid group. Biologically, ganoderanes GL-2 and GL-3, distinguished by the presence of a rare "1,11-epoxy" moiety, exhibited significant inhibition against nitric oxide production induced by lipopolysaccharide in RAW264.7 macrophage cells, while ganoderanes GL-4 and GL-8 exhibited bifunctional activities of anti-proliferation and anti-inflammation.
Asunto(s)
Agaricales , Ganoderma , Triterpenos , Triterpenos/farmacología , Triterpenos/química , Estructura Molecular , Cuerpos Fructíferos de los Hongos/química , Ganoderma/química , Antiinflamatorios/farmacología , Antiinflamatorios/química , Esteroides/análisisRESUMEN
Six new flavonols, including four glucosylated flavonols (dysosmaflavonoid A-D), one phenylpropanoid-substituted flavonol (dysosmaflavonoid E), and one phenyl-substituted flavonol (dysosmaflavonoid F), together with five known analogues, were isolated from the roots and rhizomes of Dysosma versipellis. Their structures were elucidated by comprehensive analysis of their NMR, IR, UV, HRESIMS, and HPLC data. The antioxidant activities of all isolated compounds were examined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. Compounds 2, 3, 5-8, and 12 exhibited significant DPPH scavenging capacity with IC50 values of 33.95, 39.02, 31.17, 32.79, 31.85, 30.48, and 23.75 µM, respectively, in comparison with Trolox (IC50, 15.80 µM). Compound 12 displayed more potent DPPH radical scavenging activity than prenylated and (or) glucosided derivatives (2-4, or 10). The preliminary structure-activity relationship showed that the catechol structure in flavonol is essential for DPPH radical scavenging effect.
Asunto(s)
Berberidaceae , Flavonoles , Flavonoles/farmacología , Flavonoles/química , Estructura Molecular , Antioxidantes/farmacología , Antioxidantes/química , Berberidaceae/química , Relación Estructura-Actividad , Depuradores de Radicales Libres/química , Compuestos de Bifenilo , Picratos/químicaRESUMEN
Investigation into the chemical diversity of Nardostachys chinensis Batal led to the discovery of three new (1-3) and one known (4) iridoid glycosides. Their structures were established through spectroscopic methods including 1 D and 2 D NMR experiments and HRESIMS analysis. Inhibitory effects of 1-4 on nitric oxide production were investigated in lipopolysaccaride (LPS)-mediated RAW 264.7 cells, and they displayed IC50 values in the range 7.8-15.2 µM.
Asunto(s)
Nardostachys , Animales , Glicósidos/farmacología , Glicósidos Iridoides/farmacología , Espectroscopía de Resonancia Magnética , Ratones , Nardostachys/química , Óxido Nítrico , Células RAW 264.7RESUMEN
Eighteen linear triquinane sesquiterpenoids (LTSs), including seventeen previously undescribed ones (hirsutuminoids A-Q), were isolated from the fermentation of the fungus Stereum hirsutum (Willd.) Pers. The structures and absolute configurations of the isolates were characterized by extensive spectroscopic analysis (1D, 2D NMR, and HRMS data), together with comparing the experimental and calculated data of both electronic circular dichroism and NMR data, as well as X-ray crystallography. Based on the literature survey and efforts on constructing the absolute configurations of these LTSs in this study, one empirical rule about the orientations of substitutions at C-2/C-3/C-7/C-9 was summarized. Anti-inflammatory and cytotoxic bioassays showed that only hirsutuminoid B inhibited the nitric oxide (NO) production in RAW 264.7 macrophages with an IC50 value, 18.9 µM.
Asunto(s)
Basidiomycota , Sesquiterpenos , Basidiomycota/química , Cristalografía por Rayos X , Estructura Molecular , Óxido Nítrico , Sesquiterpenos/químicaRESUMEN
Ochracines F-L (1-7), seven previously undescribed chamigrane and cadinane sesquiterpenoids, together with four known chamigranes were isolated from cultures of the wood-decaying fungus Steccherinum ochraceum HFG119. Ochracines F-L were structurally characterized by extensive analysis of HRMS and NMR spectroscopic data. The relative configurations were assigned through a combination of NOE correlations and J-based configuration analysis (JBCA), while the absolute configurations were determined by X-ray single-crystal diffraction, and calculated methods (ECD, [α], 13C NMR). All the new isolates were evaluated for their cytotoxicity against five human cancer cell lines HL-60, SMMC-7721, A549, MCF-7, and SW-480, and inhibitory activity on NO production in RAW 264.7 macrophages.
RESUMEN
Two new monoterpene indole alkaloid glycosides nutanoside A-B (1-2), two new phenolic glycoside esters nutanester A-B (6-7), together with five known compounds (3-5, 8-9) were isolated from the ethanol extract of Gardneria nutans Siebold & Zuccarini. Their structures were established on the basis of extensive spectroscopic analysis and TDDFT/ECD calculations. Compounds 1 and 2 are two rare monoterpene indole alkaloids with the glucosyl moiety located at C-12 and represent the first two examples of enantiomer of ajmaline type monoterpene indole alkaloids. Compounds 3, 4 and 6 displayed significant inhibitory effects on NO production in over-activated BV2 microglial cells, with the IC50 values of 2.29, 6.36, and 8.78 µM, respectively. Compounds 1, 5, 7 could significantly inhibit the mRNA expression of inflammatory factors TNF-α and IL-6 induced by LPS in BV2 microglial cells at the effective concentration. Moreover, compound 3 exhibited stronger cytotoxicities against U87 and HCT116 cell lines than taxol with IC50 values of 10.58 and 14.60 µM, respectively.