RESUMEN
The young leaves of Phyllanthus acidus (Euphorbiaceae) are commonly used as edible vegetables in Indonesia, Thailand, and India, and their water infusions as dieting aids for people trying to remain slim. However, it is regarded as a poisonous plant in Malaya, and current researches are insufficient to provide a conclusion on its toxicity and safety under large doses. In this study, we firstly found that the refined nonpolar extracts of P. acidus leaves showed significant cytotoxic effect against BEAS-2B and L02 normal cell lines with IC50 values of 2.15 and 1.64 mg/mL, respectively. Further bioactivity-guided isolation produced four new rare dichapetalins (pacidusins A-D) from the most active fraction. Their structures including absolute configurations were elucidated by extensive spectroscopic data and X-ray diffraction analysis. All the isolated dichapetalins exhibited moderate cytotoxicity against, BEAS-2B and L02 normal cell lines with IC50 values ranging from 12.44 to 22.55 µM, as well as five human cancer cell lines with IC50 values ranging from 3.38 to 22.38 µM. Furthermore, the content of the main dichapetalins in the leaves were determined by analytical HPLC, which showed that the leaves contained a very high amount of the four isolated dichapetalins with a total yield of 0.488 mg/g of dry plant material. These toxic dichapetalins may lead to adverse health effects in higher doses. Our findings indicate that the dichapetalin containing leaves may not be suitable for consumption in large quantities as food, but demonstrate their potency as anti-cancer agents for new drug discovery.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Phyllanthus/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Relación Estructura-ActividadRESUMEN
The actinomycete genus Streptomyces is characterized by producing bioactive secondary metabolites, including antibiotics. In this study, chemical and biological investigations were carried out on Streptomyces strain 4205 isolated from the paddy soil, leading to the identification and characterization of 10 albocycline-type macrolides, among which 4 compounds were new, namely albocyclines A-D (1-4). The structures of 1-10 were identified according to the 1D- and 2D-NMR spectroscopic data. Furthermore, compounds 1-10 were evaluated for antimicrobial activity. Compounds 5-7 displayed antimicrobial activities against Candidaalbicans ATCC 90028 with the same MIC value of 10.0â mg/mL and the IC50 values of 1.5, 1.0, and 1.0â mg/mL, respectively. Thus, the research on Streptomyces sp. is of vital significance for developing new antibiotic agents.
Asunto(s)
Antibacterianos/farmacología , Streptomyces/química , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antifúngicos/farmacología , Aspergillus fumigatus/efectos de los fármacos , Bacterias/clasificación , Bacterias/efectos de los fármacos , Candida albicans/efectos de los fármacos , Espectroscopía de Resonancia Magnética con Carbono-13 , Cryptococcus neoformans/efectos de los fármacos , Medios de Cultivo , Fermentación , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Concentración 50 Inhibidora , Lactonas/química , Lactonas/aislamiento & purificación , Lactonas/farmacología , Pruebas de Sensibilidad Microbiana , Microbiología del Suelo , Espectrometría de Masa por Ionización de Electrospray , Relación Estructura-ActividadRESUMEN
Sixty-three amide alkaloids, including three new, piperflaviflorine A (1), piperflaviflorine B (2), and sarmentamide D (4), and two previously synthesized ones, (1E,3S)-1-cinnamoyl-3- hydroxypyrrolidine (3) and N-[7'-(4'-methoxyphenyl)ethyl]-2-methoxybenzamide (5), were isolated from the aerial parts of Piper flaviflorum and Piper sarmentosum. Their structures were elucidated by detailed spectroscopic analysis and, in case of 3, by single-crystal X-ray diffraction. Most of the isolates were tested for their antifungal and antibacterial activities. Ten amides (6-15) showed antifungal activity against Cryptococcus neoformans ATCC 90â113 with IC50 values in the range between 4.7 and 20.0 µg/mL.
Asunto(s)
Alcaloides/farmacología , Amidas/farmacología , Antifúngicos/farmacología , Cryptococcus neoformans/efectos de los fármacos , Estructura Molecular , Piper/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Amidas/química , Amidas/aislamiento & purificación , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Difracción de Rayos XRESUMEN
Chinese ripe pu-erh tea is produced by aerobic microbial fermentation of green tea. To clarify the microbial degradation of tea polyphenols, Japanese commercial green tea was mixed with Chinese ripe pu-erh tea, which retains microorganisms, and fermented for 5 d. Chromatographic separation yielded a novel water-soluble yellow pigment termed theagalloflavic acid. Spectroscopic and chemical evidence suggested that this pigment was produced by oxidative ring cleavage of hexahydroxydiphenoyl esters. In addition, two new oxygenated lignin metabolites, (+)-5,5'-dihydroxypinoresinol and 5-hydroxydihydrodehydrodiconiferyl alcohol, were also isolated together with known degradation products of quercetin and tea catechins.
Asunto(s)
Taninos Hidrolizables/metabolismo , Lignanos/metabolismo , Fenoles/metabolismo , Té/química , Aerobiosis , Fermentación , Taninos Hidrolizables/química , Lignanos/química , Estructura Molecular , Oxidación-Reducción , Fenoles/química , Té/metabolismoRESUMEN
Seven steroidal saponins including two new furostanol glycosides were isolated from the rhizomes of Polygonatum prattii collected from Panzhihua, Sichuan province of China. The new compounds were determined as 26-O-ß-d-glucopyranosyl-(25R)-3ß,22ξ-dihydroxy-furost-5-en-7-one (pratioside G) and 26-O-ß-D-glucopyranosyl-(25R)-22ξ-hydroxy-furost-5-en-3ß-O-ß-D-glucopyranosyl-(1â2)-ß-D-glucopyranosyl-(1â2)-[ß-D-xylopyranosyl-(1â3)]-ß-D-glucopyranosyl-(1â4)-ß-D-galactopyranoside (pratioside H), on the basis of detailed spectroscopic and chemical analysis.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Fitosteroles/aislamiento & purificación , Polygonatum/química , Rizoma/química , Saponinas/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Fitosteroles/química , Saponinas/químicaRESUMEN
Two new compounds, (Z,R)-1-phenylethylcinnamate (1) and (1R,2R,3R,6S)-pipoxide (2) were isolated from the aerial part of Piper hainanense, along with 12 known compounds, including nine benzene derivatives (4-11), one isobutylamide (12), and two polyoxygenated cyclohexene derivatives (13-14). Their structures were elucidated on the basis of the HRESIMS, 1D and 2D NMR spectroscopic analyses, and ECD in cases of 2 and 3. The absolute configuration of ellipeiopsol B (3) was determined for the first time. All these compounds 1-14 were reported from the titled plant for the first time. Most of the isolates were tested for their cytotoxicities against five human cancer cell lines. Four of which, 2, 3, 9, 14 showed moderate bioactivities. Among them, the new compound 2 showed potential cytotoxicity against SMMC-7721, MCF-7, and SW-480 with IC50 values of 9.7, 15.0, and 13.2 µM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Cinamatos/aislamiento & purificación , Cinamatos/farmacología , Ciclohexenos/aislamiento & purificación , Ciclohexenos/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Piper/química , Antineoplásicos Fitogénicos/química , Cinamatos/química , Ciclohexenos/química , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Triterpenos/químicaRESUMEN
The roots of Panax notoginseng, an important Chinese medicinal plant, have been used traditionally in both the raw and processed forms, due to the different chemical constituents and bioactivities found. Thirty-eight dammarane-type triterpenoid saponins were isolated from the steam-processed roots of P. notoginseng, including 18 new substances, namely, notoginsenosides SP1-SP18 (1-18). The structures of 1-18 were determined on the basis of spectroscopic analysis and acidic hydrolysis. The absolute configuration of the hydroxy group at C-24 in 1-4, 19, and 20 was determined in each case by Mo2(AcO)4-induced circular dichroism. The new compounds were found to feature a diversity of highly oxygenated side chains, formed by hydrolysis of the C-20 sugar moiety followed by dehydration, dehydrogenation, epoxidation, hydroxylation, or methoxylation of the main saponins in the raw roots. The new saponins 1, 2, 6-8, 14, and 17 and the known compounds 20-27 showed promoting effects on the differentiation of PC12 cells, at a concentration of 10 µM.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Panax notoginseng/química , Plantas Medicinales/química , Saponinas/aislamiento & purificación , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Animales , Diferenciación Celular/efectos de los fármacos , Medicamentos Herbarios Chinos/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Células PC12 , Raíces de Plantas/química , Ratas , Saponinas/química , Saponinas/farmacología , Triterpenos/química , DamaranosRESUMEN
Nineteen new highly oxygenated norbisabolane sesquiterpenoids, phyllanthacidoid acid methyl ester (1), and C-T (4-21), were isolated from Phyllanthus acidus Skeels, together with two known ones, phyllanthusols A (2) and B (3), whose sugar moiety was revised as glucosamine-N-acetate, rather than the previously assigned mannosamine-N-acetate. Compounds 2 and 3 were renamed respectively as phyllanthacidoids A (2) and B (3) to avoid confusion. All of the isolates except for 1 are glycosides, whose saccharide moieties possess a pentaoxy cyclohexane (scyllo quercitol) connecting with glucosamine-N-acetate or glucosyl moieties, which are first examples in natural products. Phyllanthacidoids N-R (15-19) with 8R configurations and/or 5,8-diketal skeleton, are unprecedented structures among norbisabolane sesquiterpenoids. Phyllanthacidoids S (20) and T (21) have the unusual tricyclo [3.1.1.1] oxygen bridge skeleton formed by a diketal system, of which the relative configurations of the aliphatic chain were assigned on the basis of heteronuclear coupling constants. The absolute configurations of compounds (1-21) were established by means of calculated electronic circular dichroism (ECD) and coupling constants. Compounds 1-5, 7-9, 10, and 14 displayed potential anti-hepatitis B virus (HBV) activities, with IC50 values of 0.8-36 µM against HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg), and the results indicated that the 5-ketal group and sugar moieties had contributions to the selectivity of HBsAg and HBeAg.
Asunto(s)
Antivirales/química , Antivirales/aislamiento & purificación , Antivirales/farmacología , Benzofuranos/química , Benzofuranos/farmacología , Disacáridos/química , Disacáridos/farmacología , Glicósidos/química , Antígenos de Superficie de la Hepatitis B/química , Antígenos e de la Hepatitis B/química , Virus de la Hepatitis B/química , Virus de la Hepatitis B/efectos de los fármacos , Phyllanthus/química , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Compuestos de Espiro/química , Compuestos de Espiro/farmacología , Benzofuranos/aislamiento & purificación , Disacáridos/aislamiento & purificación , Antígenos de Superficie de la Hepatitis B/inmunología , Antígenos e de la Hepatitis B/inmunología , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Teoría Cuántica , Compuestos de Espiro/aislamiento & purificación , EstereoisomerismoRESUMEN
During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1G8 (18) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6G8 (68) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory. The sesquiterpenoid glycoside dimers 69 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 ± 0.97 and 5.68 ± 1.75 µM towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively.
Asunto(s)
Antivirales/química , Glicósidos/química , Virus de la Hepatitis B/efectos de los fármacos , Phyllanthus emblica/química , Sesquiterpenos/química , Antivirales/aislamiento & purificación , Antivirales/farmacología , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Células Hep G2 , Antígenos de Superficie de la Hepatitis B/análisis , Antígenos e de la Hepatitis B/análisis , Virus de la Hepatitis B/fisiología , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Extractos Vegetales/química , Raíces de Plantas/química , Teoría Cuántica , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Terpenos/química , Terpenos/aislamiento & purificación , Terpenos/farmacologíaRESUMEN
Six new bisbenzylisoquinoline alkaloids (1-6) and seven known compounds (8-14) were isolated from the tubers of Stephania epigaea, in addition to the major alkaloid, cepharanthine (7). The structures of 1-6 were elucidated by combined spectroscopic data analysis and chemical methods, with their configurations determined from their optical rotation values and confirmed using circular dichroism. Compounds 1-6 belong to the oxyacanthine type of bisbenzylisoquinoline alkaloids and have a rare methylenedioxy substituent. Compound 1, a dimer composed of benzylisoquinoline and seco-aristolactam units, represents a new type of bisbenzylisoquinoline alkaloid, while compounds 3-6 are bisbenzylisoquinoline N-oxides. These compounds were evaluated for their in vitro cytotoxicities against six human cancer cell lines (A-549, ECA109, HL-60, MCF-7, SMMC-7721, and SW480). Cepharanthine (7), the major component of S. epigaea, exhibited cytotoxicity against all of these cancer cell lines except ECA109, while its known analogue, 10, displayed cytotoxicity against all six cancer cell lines.
Asunto(s)
Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Bencilisoquinolinas/aislamiento & purificación , Bencilisoquinolinas/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Stephania/química , Alcaloides/química , Antineoplásicos Fitogénicos/química , Bencilisoquinolinas/química , Dicroismo Circular , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Espectroscopía de Resonancia por Spin del Electrón , Células HL-60 , Humanos , Isoquinolinas/farmacología , Estructura Molecular , Tubérculos de la Planta/químicaRESUMEN
Balanophora involucrata HOOK.f. & THOMSON (Balanophoraceae) is a parasite plant often growing on the roots of leguminous plants. The whole herb has been used medicinally for the treatment of irregular menstruation, cough, hemoptysis, traumatic injury and bleeding, dizziness and gastralgia in Yunnan Province, China. The 2,2-diphenyl-2-picrylhydrazyl (DPPH) assay on the 60% aq. acetone extract of the fresh whole plant of B. involucrata showed considerable radical-scavenging activity (SC50 15.3 µg/ml). Further purification on the extract led to the isolation of one new phenolic glycoside, sieboldin-3'-ketocarboxylic acid (1), and one new cyanogenic glycoside, proacacipetalin 6'-O-ß-D-glucopyranoside (2), together with 26 known compounds including three 4"-O-galloyl and 2",3"-O-(S)-hexahydroxydiphenoyl (HHDP) derivatives of dihydrochalcone glucosides, seven hydrolyzable tannins, and alkane glycosides. The cyanogenic compound isolated from the Balanophoraceae family for the first time might be a signal molecule between B. involucrata and its hosts. The free-radical-scavenging activity of the isolated compounds was also examined by DPPH assay.
Asunto(s)
Balanophoraceae/química , Depuradores de Radicales Libres/química , Glicósidos/química , Fenoles/química , Depuradores de Radicales Libres/aislamiento & purificación , Glicósidos/aislamiento & purificación , Raíces de Plantas/químicaRESUMEN
Eleven flavonoids including one new flavonol glycoside, quercetin-3-O-(2-α-L-rhamnopyranosyl)-ß-D-glucuronopyranosyl methyl ester (1), were isolated for the first time from the fruits of Phyllanthus acidus (L.) Skeels (Phyllanthaceae). Their structures were determined by extensive spectroscopic data. The known flavonoids, quercetin-3-O-ß-D-glucuronide methyl ester (3), quercetin-3-O-(2''-α-L-rhamnopyranosyl-6''-O-α-L-rhamno pyranosyl)-ß-D-glucopyranoside (5), myricetin (9), and 6-methoxy-naringenin (11) were isolated for the first time from the genus Phyllanthus. Flavonoids 4, 6 and 9 (IC50 = 6.01, 6.32, and 7.84 µM, respectively) showed stronger α-glucosidase inhibitory activities than the positive control, acarbose (IC50 = 306.45 µM). The fruits of P. acidus might be further developed as an anti-diabetic food supplement.
Asunto(s)
Phyllanthus , Quercetina , Quercetina/análisis , Frutas/química , Phyllanthus/química , Flavonoides/química , GlucosidasasRESUMEN
Camellia taliensis (W. W. Smith) Melchior, belonging to the genus Camellia sect. Thea., is mainly distributed from northern Myanmar to western and southwestern Yunnan province of China, and its leaves have been used to make various teas by the locals of its growing regions. The chemical constituents of C. taliensis are significantly related to those of cultivated tea plants, C. sinensis and C. sinensis var. assamica. The HPLC-ESI-MS analysis of black tea prepared from the leaves of C. taliensis showed a rich existence of polyphenols. Further comprehensive chemical study led to the separation and recognition of 32 compounds (1-32), including one new hydrolyzable tannin, 1-O-galloyl-4,6-tetrahydroxydibenzofurandicarboxyl-ß-D-glucopyranose (1), and one new natural product (24). The known compounds referred to seven hydrolyzable tannins (2-8), 10 flavonols and glycosides (9-18), and 14 simple phenolics (19-32). Their structures were elucidated by comprehensive spectroscopic analyses. Among them, 20 compounds (2, 3, 6, 7, 8, 15, 17, 18, 20-22, 24-32) were isolated from black tea for the first time. Most isolates displayed obvious antioxidant activities on DPPH and ABTS+ assays, and the hydrolyzable tannins 1, 3-5, 7, and 8 exhibited stronger inhibitory activities on α-glycosidase than quercetin and acarbose (IC50 = 5.75 and 223.30 µM, respectively), with IC50 values ranging from 0.67 to 2.01 µM.
RESUMEN
Panax notoginseng (PN) is a well-known traditional Chinese medicine, with dammarane-type triterpenoid saponins characterized as major component and active ingredients, together with amino acids, flavonoids, polysaccharides, and polyacetylenes. The roots of PN are susceptible to root rot disease, which causes a huge loss and changes in the chemical components of this precious resource. In this study, sub-fractions of rot PN root extracts were preliminarily found to have admirable cytotoxicity on two human cancer cells. Further bioassay-guided isolation discovered nine new non-triterpenoids, including two novel N-methylacetamido-1-oxotetrahydropyrimidine alkaloids (1, 2), five 2H-furanones or 2H-pyranones (3-7), and two polyacetylenic alcohols (8, 9). Their structures were illuminated by extensive spectroscopic data, calculated ECD, and X-ray diffraction analysis. Among them, 3-7 were considered to be transformed from panaxatriol through the intermediates (8, 9). The new alkaloids (1, 2) displayed noteworthy cytotoxicity against five human cancer cells with IC50 values ranging from 14 to 24 µM. In silico target prediction and molecular docking studies showed that 1 and 2 may interact with EGFR, and were verified by the experimental inhibitory effect on EGFR tyrosine kinase.
RESUMEN
Two new sulfur-containing triterpenoid saponins, asprellanosides A (1) and B (2), were isolated from the roots of Ilex asprella, together with 10 known compounds (3-12). An in vitro anti-HSV-1 activity test of the isolates (1-4, 6-7, and 9-12) showed that only asprellanoside A (1) and oblonganoside H (6) exhibited anti-HSV-1 activity with TIC values of 0.14 and 0.18 mM, respectively.
Asunto(s)
Antivirales/farmacología , Medicamentos Herbarios Chinos/farmacología , Herpesvirus Humano 1/efectos de los fármacos , Ilex/química , Saponinas/farmacología , Triterpenos/farmacología , Antivirales/química , Antivirales/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicina Tradicional China , Modelos Moleculares , Estructura Molecular , Raíces de Plantas/química , Saponinas/química , Saponinas/aislamiento & purificación , Triterpenos/química , Triterpenos/aislamiento & purificaciónRESUMEN
Three new phenolic compounds, eucalmaidin F (1), (3S)-5-guaiacyl-3-hydroxypentanoic acid (2), and 8-ß-C-glucopyranosyl-5,7-dihydroxy-2-isobutylchromone (3), were isolated from the branches of E. maideni, together with 30â known compounds, including four phenylpropanoids, three lignans, four phloroglucinol glucosides, five dihydroflavonoids, seven simple phenolic compounds, six terpenoids, and glycerol. The new structures were established by spectroscopic studies (MS, and 1D- and 2D-NMR), chemical degradation, and modified Mosher's method. Compounds 3, guaiacylglycerol, 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one, caffeic acid, (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid, (7'S,8R,8'R)-lyoniresinol, (+)-lyoresinol 3α-O-α-L-rhamnopyranoside, garcimangosone, phlorocetophenone 2'-glucopyranoside, (+)-taxifolin 3α-O-α-L-rhamnopyranoside, (+)-aromadendrin, (+)-taxifolin, resveratrol, piceatannol, 3,4,5-trihydroxyphenol. Tachiaside, gallic acid, macrocapals A und G, and oleuropeic acid were evaluated for their cytotoxicities against five human cancer cell lines. Resveratrol, piceatannol, gallic acid, and macrocapal G exhibited moderate inhibitory effects on human myeloid heukemia HL-60 cell, with IC(50) values of 22.05, 22.05, 7.75, and 31.93â µM, respectively; and only macrocapal G showed inhibitory effect on hepatocellular carcinoma SMMC-7721 cell, with an IC(50) value of 26.75â µM.
Asunto(s)
Cromonas/química , Eucalyptus/química , Flavonas/química , Fenoles/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Cromonas/aislamiento & purificación , Cromonas/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Flavonas/aislamiento & purificación , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Conformación Molecular , Fenoles/aislamiento & purificación , Fenoles/farmacología , Tallos de la Planta/químicaRESUMEN
Phyllaciduloids E (1) and F (2), two new cleistanthane diterpenoids, were isolated from the leaves of Phyllanthus acidus (L.) Skeels (Phyllanthaceae). Their planar structures were established by spectroscopic analysis and comparison with literature values. The relative configurations of phyllaciduloids E and F were confirmed by DFT-NMR chemical shift calculations and subsequent CP3 probability methods. Phyllaciduloids E and F were evaluated for their cytotoxicity. However, no significant activities were detected at concentrations up to 40 µM.[Formula: see text].
Asunto(s)
Diterpenos , Phyllanthus , Diterpenos/análisis , Diterpenos/farmacología , Estructura Molecular , Phyllanthus/química , Extractos Vegetales/análisis , Hojas de la Planta/químicaRESUMEN
Six diterpenoids including three ent-kauranes (1-2, 4) and three cleistanthanes (3, 5-6) were isolated from the roots and stems of Phyllanthus acidus (L.) Skeels. Of them, (16S)-ent-16,17,18-tri-hydroxy-19-nor-kaur-4-en-3-one (1), phyllanthone A (2), and 6-hydroxycleistanthol (3) are new compounds, while the ent-kaurane diterpenoids were reported from the titled plant for the first time. Their structures were elucidated on the basis of the extensive spectroscopic analyses. Compounds 2 and 4-6 displayed cytotoxic potential with IC50 values ranging from 1.96 to 29.15 µM. They also showed moderate anti-inflammatory activities (IC50 = 6.30-12.05 µM). Particularly, the new ent-kaurane 2 displayed cytotoxic potential against HL-60 (IC50 = 2.00 µM) and MCF-7 (IC50 = 3.55 µM) cells, and anti-inflammatory activity (IC50 = 6.47 µM).
Asunto(s)
Diterpenos de Tipo Kaurano/toxicidad , Diterpenos/toxicidad , Phyllanthus/química , Extractos Vegetales/toxicidad , Alcaloides/química , Alcaloides/aislamiento & purificación , Alcaloides/toxicidad , Línea Celular Tumoral , Diterpenos/química , Diterpenos de Tipo Kaurano/química , Humanos , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/síntesis química , Raíces de Plantas/química , Tallos de la Planta/químicaRESUMEN
Pentagalloylglucose (PGG) is a natural polyphenolic compound with broad-spectrum anti-viral activity, however, the mechanisms underlying anti-viral activity remain undefined. In this study, we investigated the effects of PGG on anti-viral activity against Herpes simplex virus type 1 (HSV-1) associated with autophagy. We found that the PGG anti-HSV-1 activity was impaired significantly in MEF-atg7-/- cells (autophagy-defective cells) derived from an atg7-/- knockout mouse. Transmission electron microscopy revealed that PGG-induced autophagosomes engulfed HSV-1 virions. The mTOR signaling pathway, an essential pathway for the regulation of autophagy, was found to be suppressed following PGG treatment. Data presented in this report demonstrated for the first time that autophagy induced following PGG treatment contributed to its anti-HSV activity in vitro.
Asunto(s)
Antivirales/farmacología , Autofagia , Herpesvirus Humano 1/efectos de los fármacos , Taninos Hidrolizables/farmacología , Fagosomas/efectos de los fármacos , Animales , Proteína 7 Relacionada con la Autofagia , Línea Celular , Proteínas de Unión al ADN/genética , Humanos , Ratones , Ratones Noqueados , Proteínas Asociadas a Microtúbulos/genética , Fagosomas/virología , Factores de Transcripción/genéticaRESUMEN
Influenza A virus (IAV) infection is a major public health threat leading to significant morbidity and mortality. The emergence of drug-resistant virus strains highlights the urgent need to develop novel antiviral drugs with alternative modes of action. Pentagalloylglucose (PGG), a naturally occurring polyphenolic compound, possesses a broad spectrum of biological activities. In this study, we found that PGG has anti-influenza-virus activity, and investigated its possible mechanism(s) of action in vitro. Both pre-incubation of virus prior to infection and post-exposure of infected cells with PGG significantly inhibited virus yields. Influenza-virus-induced hemagglutination of chicken red blood cells was inhibited by PGG treatment, suggesting that PGG can inhibit IAV infection by interacting with the viral hemagglutinin. PGG did not affect viral protein synthesis or nuclear transport of viral nucleoprotein (NP) but greatly reduced plasma membrane accumulation of NP protein at the late stage of the replication cycle. Furthermore, PGG significantly reduced virus budding and progeny virus release from infected cells. This study revealed for the first time that PGG can inhibit IAV replication with a dual mode of action and offers new insights into its underlying mechanisms of antiviral action.