RESUMEN
Three new secolignans were found in the detailed chemical study of Peperomia blanda (Jacq.) Kunth collected from China. Detailed NMR data analysis, especially 1H NMR, 13C NMR and 2 D NMR, elucidates the structures of the three new secolignans.
Asunto(s)
Peperomia , Peperomia/química , Espectroscopía de Resonancia Magnética , ChinaRESUMEN
Seven undescribed polyketide compounds (1-4, 9-11) and six known polyketide compounds (5-8,12, 13) were isolated from Rhodiola tibetica endophytic Penicillium sp. HJT-A-10. The structural of seven undescribed polyketides metabolites were established on the basis of spectroscopic methods. The results of anti-inflammatory activity showed that compounds 1-8ï¼10-13 had significant inhibitory effects on LPS-induced NO production in RAW 264.7 cells.
Asunto(s)
Penicillium , Policétidos , Rhodiola , Penicillium/química , Estructura Molecular , Antiinflamatorios/químicaRESUMEN
Six new polyketone metabolites, compounds (1-6) and seven known polyketone compounds (7-13) were isolated from Rhodiola tibetica endophytic fungus Alternaria sp. The structural elucidation of five new polyketone metabolites were elucidated on the basis of spectroscopic including 2D NMR and HRMS and spectrometric analysis. Inhibition rate evaluation revealed that compounds 1(EC50 = 0.02 mM), 3(EC50 = 0.3 mM), 6(EC50 = 0.07 mM), 8(EC50 = 0.1 mM) and 9(EC50 = 0.04 mM) had inhibitory effect on the SARS-CoV-2 virus.
Asunto(s)
Alternaria/química , Antivirales/aislamiento & purificación , Antivirales/farmacología , Cetonas/aislamiento & purificación , Cetonas/farmacología , Polímeros/aislamiento & purificación , Polímeros/farmacología , SARS-CoV-2/efectos de los fármacos , Antivirales/química , Humanos , Cetonas/química , Estructura Molecular , Polímeros/químicaRESUMEN
Artemisinin (ART) is the most effective component in malaria treatment, however, the extremely low content restricts its clinical application. Therefore, it is urgent to increase the yield of ART. ART gradually accumulates with aging, small RNA (sRNA) and transcriptome analysis were applied on the leaves of 2-week-old (2 w) and 3-month-old (3 m) A. annua respectively. Among all the annotated sRNAs, 125 were upregulated and 128 downregulated in the 3 m sample compared to the 2 w one. Whereas 2183 genes were upregulated and 2156 downregulated. Notably, the level of miR156 and several annotated miRNAs gradually decreased while SPLs increased. In addition, the genes on ART biosynthesis pathway were significantly upregulated including ADS, CYP71AV1, ADH1, DBR2 and ALDH1, and so were the positive transcription factors like AaERF1, AaORA and AaWRKY1 indicating that age influences the ART biosynthesis by activating the expression of the synthesizing genes as well as positive transcription factors. This study contributes to reveal the regulatory effects of age on ART biosynthesis both in sRNA and transcription levels.
Asunto(s)
Artemisia annua/metabolismo , Artemisininas/metabolismo , Artemisininas/farmacología , Factores de Edad , Antimaláricos/metabolismo , Antimaláricos/farmacología , Vías Biosintéticas/genética , Expresión Génica/genética , Perfilación de la Expresión Génica/métodos , Regulación de la Expresión Génica de las Plantas/genética , MicroARNs/genética , Hojas de la Planta/metabolismo , Proteínas de Plantas/genética , Factores de Transcripción/metabolismo , Transcriptoma/genéticaRESUMEN
Two isopentenyl resorcinols, peperobtusin B and peperobtusin C, have been isolated from Peperomia tetraphylla. Their structures were determined on the basis of spectroscopic methods, especially 1H NMR, 13C NMR, 2D NMR, and HR-TOF-MS. Two compounds were evaluated for cytostatic activity against G2, A 549, Hela and HCT 116 cells, but cytostatic activity of both compounds is weak.
Asunto(s)
Peperomia , Células HeLa , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Resorcinoles/farmacologíaRESUMEN
It is reported that dihydroartemisinin could reduce the expression of phosphorylated adhesion kinase and matrix metalloproteinase-2, inhibit the growth, migration and invasion of ovarian cancer cells, promote the formation of Treg cells through TGF-beta/Smad signaling pathway, and play an immunosuppressive role; dihydroartemisinin could also inhibit the growth of lung cancer cells by inhibiting the expression of vascular endothelial growth factor(VEGF) receptor KDR. However, there are few studies on dihydroartemisinin in hepatocellular carcinoma cells. In order to preliminarily explore the effect of dihydroartemisinin on invasion and metastasis of hepatocellular carcinoma cells, CCK-8 method and crystal violet staining were used to detect the effect of dihydroartemisinin on the growth of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H. The effects of dihydroartemisinin on the invasion and metastasis of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H were studied by using cell wound healing and Transwell. Western blot was used to detect the protein expression of epidermal growth factor receptor(EGFR) and its downstream signaling pathway in cells treated with dihydroartemisinin for 48 hours. The results showed that dihydroartemisinin could inhibit the growth of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H at 25 µmol·L~(-1). As compared with the control group, the number of cell clones was significantly reduced, and the ability of cell migration and invasion was weakened. Western blot results showed that as compared with the control group, dihydroartemisinin group could down-regulate the protein expression of EGFR and its downstream signaling pathways p-AKT, p-ERK, N-cadherin, Snail and Slug, and up-regulate the expression of E-cadherin protein, thus affecting the migration, invasion and metastasis of hepatocellular carcinoma cells 7402 and MHCC97 H.
Asunto(s)
Artemisininas/farmacología , Carcinoma Hepatocelular/patología , Neoplasias Hepáticas/patología , Invasividad Neoplásica , Metástasis de la Neoplasia , Carcinoma Hepatocelular/tratamiento farmacológico , Línea Celular Tumoral , Movimiento Celular , Receptores ErbB/metabolismo , Humanos , Neoplasias Hepáticas/tratamiento farmacológico , Transducción de SeñalRESUMEN
Two new secolignans, 3,4-trans-3-hydroxymethyl-4-[bis(4-hydroxy-3- methoxyphenyl)methyl]butyrolactone (1) and 3,4-trans-3-hydroxymethyl-4- [bis(3,4-dimethoxyphenyl)methyl]butyrolactone (2) have been isolated from the roots of Urtica fissa E.Pritz. Their structures were determined on the basis of spectroscopic methods, especially 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS. The inhibitory effects on N1 and N2, two subtypes of neuraminidases (NAs), of these two compounds were assayed.
Asunto(s)
Lignanos/química , Raíces de Plantas/química , Urticaceae/química , Estructura MolecularRESUMEN
Euphorbia maculata is a medicinal plant of the Euphorbiaceae family, which can produce anti-inflammatory and cancer chemopreventive agents of triterpenoids. The present study reports on the bioactive triterpenoids of this plant. Two new lanostane-type triterpenoids, named (3S,4S,7S,9R)-4-methyl-3,7-dihydroxy-7(8â9) abeo-lanost-24(28)-en-8-one (1) and 24-hydroperoxylanost-7,25-dien-3ß-ol (2), together with 15 known triterpene derivatives, were isolated from Euphorbia maculata. The structures of the new compounds were determined on the basis of extensive spectroscopic data (UV, MS, ¹H and 13C-NMR, and 2D NMR) analysis. All tetracyclic triterpenoids (1â»11) were evaluated for their anti-inflammatory effects in the test of TPA-induced inflammation (1 µg/ear) in mice. The triterpenes exhibited significant anti-inflammatory activities.
Asunto(s)
Antiinflamatorios/química , Antiinflamatorios/farmacología , Euphorbia/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Triterpenos/química , Animales , Modelos Animales de Enfermedad , Edema/tratamiento farmacológico , Edema/patología , Femenino , Espectroscopía de Resonancia Magnética , Ratones , Estructura MolecularRESUMEN
Three new amino acid derivatives, oxalamido-L-phenylalanine methyl ester (1), oxalamido-L-leucine methyl ester (2), and lumichrome hydrolyzate (3), together with nine known compounds (4-12), were isolated from the solid culture of edible mushroom Pleurotus ostreatus. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations of 1 and 2 were established by the chiral synthesis and confirmed by circular dichroism (CD) analysis of their total synthesis products and natural isolates. All new compounds were evaluated for their antioxidant effects, antimicrobial activities, and cytotoxic activity. Compounds 1-3 showed weak antifungal activities against Candida albicans with minimum inhibitory concentration (MIC) value of 500 µg/ml.
Asunto(s)
Agaricales/química , Antioxidantes/aislamiento & purificación , Pleurotus/química , Antioxidantes/química , Antioxidantes/farmacología , Candida albicans/efectos de los fármacos , Flavinas/química , Flavinas/aislamiento & purificación , Leucina/análogos & derivados , Leucina/química , Leucina/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Fenilalanina/análogos & derivados , Fenilalanina/química , Fenilalanina/aislamiento & purificación , Fenilalanina/farmacologíaRESUMEN
Two new bisindolylbenzenoid alkaloids asterriquinol E (1) and asterriquinol F (2), together with four known compounds (3-6) were isolated from the fermentation products of the fungus Aspergillus sp. CBS-P-2. Their structures were established on the basis of extensive spectroscopic analysis, including HR-ESI-MS, UV, IR, 1D, and 2D NMR (HSQC, HMBC, and NOESY) methods. The stereochemical structure of 2 was confirmed via the CD data of the in situ formed [Rh2(OCOCF3)4] complex method. All of the isolated compounds were tested for inhibitory activity against LPS (lipopolysaccharide)-induced nitric oxide production in microglia.
Asunto(s)
Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Aspergillus/química , Alcaloides Indólicos/aislamiento & purificación , Alcaloides Indólicos/farmacología , Antiinflamatorios/química , China , Alcaloides Indólicos/química , Concentración 50 Inhibidora , Lipopolisacáridos/farmacología , Microglía/efectos de los fármacos , Estructura Molecular , Óxido Nítrico/biosíntesis , Resonancia Magnética Nuclear Biomolecular , Microbiología del SueloRESUMEN
Five new polyketides including three new butenolides (1-3), one new diphenyl ether (4), and one new benzophenone (5), together with eleven known compounds (6-16) were isolated from a wetland fungus Aspergillus flavipes PJ03-11. Their structures were elucidated on the basis of detailed spectroscopic analysis. All the isolated compounds were tested for their α-glucosidase inhibitory activities. The results showed that compounds 1-3, 6, 7, 11, 15 and 16 exhibited stronger inhibitory activities than acarbose. And the preliminary structure-activity relationships of aspulvinone and diphenyl ether compounds on the α-glucosidase inhibitory activity were reported.
Asunto(s)
4-Butirolactona/análogos & derivados , Aspergillus/química , Benzofenonas/química , Inhibidores de Glicósido Hidrolasas/química , Éteres Fenílicos/química , Policétidos/química , 4-Butirolactona/química , 4-Butirolactona/aislamiento & purificación , 4-Butirolactona/farmacología , Benzofenonas/aislamiento & purificación , Benzofenonas/farmacología , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/farmacología , Éteres Fenílicos/aislamiento & purificación , Éteres Fenílicos/farmacología , Policétidos/aislamiento & purificación , Policétidos/farmacología , Saccharomyces cerevisiae/enzimología , alfa-Glucosidasas/metabolismoRESUMEN
Two new compounds, (22E)-25-carboxy-8ß,14ß-epoxy-4α,5α-dihydroxyergosta-2,22-dien-7-one (1) and fusidione (3), along with two known compounds, 5α,8α-epidioxy ergosta-6,22-diene-3ß-ol (2) and microperfuranone (4), were isolated from the fermentation products of the marine-sourced fungus Acremonium fusidioides RZ01. The structures of compounds 1 and 3 were elucidated by extensive spectroscopic methods, especially 2D NMR, and their absolute configurations were suggested on the basis of the circular dichroism spectral analysis and the NOESY data. Both new compounds showed inhibitory activity against HL-60 cells with IC50 values being16.6 and 44.9 µmol·L-1, respectively.
Asunto(s)
Acremonium/química , Agua de Mar/microbiología , Acremonium/clasificación , Acremonium/aislamiento & purificación , Acremonium/metabolismo , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Proliferación Celular/efectos de los fármacos , Fermentación , Células HL-60 , Humanos , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
From the EtOH extract of the flowers of Camellia nitidissima Chi, a new acylated flavonoid glycoside, quercetin 7-O-(6"-O-E-caffeoyl)-ß-D-glucopyranoside (1), has been isolated, together with three known flavonoids: quercetin (2), quercetin 3-O-ß-D-glucopyranoside (3), and quercetin 7-O-ß-D-glucopyranoside (4). Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was shown to inhibit proliferation and to induce apoptosis of human lymphoma U937 cells.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Camellia/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Glucósidos/aislamiento & purificación , Glucósidos/farmacología , Quercetina/análogos & derivados , Antineoplásicos Fitogénicos/química , Apoptosis/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Flores/química , Glucósidos/química , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Quercetina/química , Quercetina/aislamiento & purificación , Quercetina/farmacología , Estereoisomerismo , Células U937RESUMEN
Three new secolignan glycosides {3,4-trans-4-[bis(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (1), {3,4-trans-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (2) and {3,4-cis-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (3) were isolated from the roots of Urtica fissa E. Pritz. Their structures were identified by spectral methods including 1D NMR, 2D NMR and HR-EI-MS.
Asunto(s)
Glicósidos/química , Raíces de Plantas/química , Urticaceae/química , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Two new 3-oxo-α-ionol glucoside isomers, (6R,9R)-3-oxo-α-ionol-9-O-ß-D-glucopyranosyl (1 â 2)-ß-D-glucopyranoside (1) and (6S,9R)-3-oxo-α-ionol-9-O-ß-D-glucopyranosyl (1 â 2)-ß-D-glucopyranoside (2) were isolated from the aerial parts of Urtica laetevirens Maxim. Their structures, including stereochemistry, were established by spectral analyses (HR-ESI-MS, NMR and CD). Also, 3-oxo-α-ionol glucosides were isolated from Urtica species for the first time.
Asunto(s)
Glucósidos/aislamiento & purificación , Urticaceae/química , Dicroismo Circular , Glucósidos/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masa por Ionización de Electrospray , EstereoisomerismoRESUMEN
Seven sinapine analogs (6a-6g) were synthesized using cinnamon acid or benzoic acid and their derivatives as starting materials, which obtained from substituted benzaldehyde and malonate. The structures of target compounds were characterized by IR, 1H NMR and elemental analysis. The effects of compounds 6a-6g on the smooth muscle of intestine isolated from rabbit were studied, and the experimental results showed that compounds 6a, 6d and 6g had diastolic action, while 6f had contractile action.
Asunto(s)
Colina/análogos & derivados , Intestinos/fisiología , Tono Muscular/efectos de los fármacos , Músculo Liso/fisiología , Animales , Colina/síntesis química , Colina/química , Colina/farmacología , Técnicas In Vitro , Estructura Molecular , Contracción Muscular/efectos de los fármacos , ConejosRESUMEN
Continuous research on the ethyl acetate extract of the fermentation broth of the marine fungus Y26-02 (Penicillium sp.) led to the purification of one known and three new compounds. Their structures were elucidated, respectively, as butyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (1), 4-hydroxyphenethyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (2), 3-hydroxybenzyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (3), and desoxypatulinic acid (4) on the basis of their spectroscopic and physico-chemical properties.
Asunto(s)
Penicillium/química , Piranos/aislamiento & purificación , Biología Marina , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Piranos/químicaRESUMEN
From the dried aerial parts of Acanthopanax senticosus, two new diketopiperazines, eleutherazines A (1) and B (2), were isolated. Their structures were elucidated on the basis of chemical and spectroscopic methods.
Asunto(s)
Dicetopiperazinas/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Eleutherococcus/química , Dicetopiperazinas/química , Medicamentos Herbarios Chinos/química , Estructura Molecular , Resonancia Magnética Nuclear BiomolecularRESUMEN
Two new aurantiamides named as cordyceamides A and B were isolated from the culture liquid of Cordyceps sinensis (BERK.) SACC., along with one known compound, aurantiamide acetate. Their structures were elucidated as N-benzoyl-L-tyrosinyl-L-phenylalaninol acetate and N-benzoyl-L-tyrosinyl-L-p-hydroxyphenylalaninol acetate by 1D, 2D-NMR techniques and comparison with literatures.