RESUMEN
Piper longum L.(PL) is considered one of the most important species traditionally used for treating various ailments and has indicated the presence of alkaloids, flavonoids, and steroids. In this study, we isolated the chemical compounds of PLleaves,andmeasuredNO, IL-6, iNOS, as well as COX-2 protein levels. In addition, molecular docking analysis were used to further understand anti-inflammation effect of the compounds. We identified one new alkaloid named piperlongumine A (1) with ten known compounds (2-11). The new compound (1) and two other alkaloids 2E)-3-(4-hydroxy-3-methoxyphenyl)-1-(pyrrol-1-yl)propanone (7) and piperchabamide A (8) significantlyreduced NO production in LPS-stimulated RAW 264.7 cells with the IC50 values of 0.97 ± 0.05 mM, 0.91 ± 0.07mM, 1.63 ± 0.14 mM, respectively. Moreover, at concentration of 2 mM, compound 1 inhibited approximately 98 ± 0.64 % of IL-6 secretion, and decreased iNOS and COX-2 protein level by about 96 and 19 folds compared to LPS treatment alone, respectively. Furthermore, compounds 1, 7, and 8 were predicted to bind and inhibit IL-6, TNF-a, and iNOS, with compound 1 showing the highest binding energy of -7.09 kcal/mol. This study provides new insights for potential anti-inflammatory drug design and warrants further investigation.
RESUMEN
BACKGROUND: Dryopteris erythrosora (D.C. Eaton) Kuntze is a species of fern in the family of Dryopteridaceae, which is distributed throughout East Asia. The genus Dryopteris has been used as traditional medicine, especially to treat hepatitis and protect liver. However, only few studies of chemical constituents of D. erythrosora have been conducted so far. OBJECTIVE: In this study, we investigated the phytochemical constituents of D. erythrosora. MATERIALS AND METHODS: The 80% methanol extract of the aerial part of D. erythrosora was used for the isolation of phenolic compounds. The isolated compounds were elucidated by various spectroscopic methods including nuclear magnetic resonance and mass spectrometry. RESULTS: The present phytochemical investigation on the aerial part of D. erythrosora led to the isolation of two new phenolic glycosides, 1 and 2, as well as nine known flavonoids including two flavones (3 and 4) and seven flavonols (5-11). CONCLUSION: In this study, two new phenolic glycosides together with nine known flavonoids were isolated from the aerial part of D. erythrosora. Among them, compounds 4, 8, and 11 were isolated for the first time in Dryopteridaceae family from the present investigation. These results helped us to enrich our understanding of the chemical constituents of D. erythrosora and to identify compounds 1 and 2 which could be potential chemotaxonomic markers for the species. SUMMARY: The genus Dryopteris has been used as traditional medicine, especially to treat hepatitis and protect liverTwo new phenolic glycosides were isolated from D. erythrosoraNine known flavonoids (3-11) were isolated from D. erythrosoraCompounds 4, 8, and 11 were isolated for the first time in Dryopteridaceae family. Abbreviations used: HPLC: High-performance liquid chromatography; Q-TOF LC/MS: Quadrupole-time-of-flight liquid chromatography/mass spectrometry; NMR: Nuclear magnetic resonance; TMS: Tetramethylsilane.
RESUMEN
Two new diterpenes, lobocompactols A (1) and B (2), and five known compounds (3-7) were isolated from the methanol extract of the soft coral Lobophytum compactum using combined chromatographic methods and identified based on NMR and MS data. Each compound was evaluated for cytotoxic activity against A549 (lung) and HL-60 (acute promyelocytic leukemia) human cancer cell lines. Among them, compound 5 exhibited strong cytotoxic activity against the A549 cell line with an IC(50) of 4.97 ± 0.06 µM. Compounds 3, 4, and 7 showed moderate activity with IC(50) values of 23.03 ± 0.76, 31.13 ± 0.08, and 36.45 ± 0.01 µM, respectively. The cytotoxicity of 5 on the A549 cells was comparable to that of the positive control, mitoxantrone (MX). All compounds exhibited moderate cytotoxicity against the HL-60 cell line, with IC(50) values ranging from 17.80 ± 1.43 to 59.06 ± 2.31 µM. Their antioxidant activity was also measured using oxygen radical absorbance capacity method, compounds 1 and 2 exhibiting moderate peroxyl radical scavenging activity of 1.4 and 1.3 µM Trolox equivalents, respectively, at a concentration of 5 µM.
Asunto(s)
Antozoos/química , Antioxidantes/farmacología , Diterpenos/farmacología , Esteroles/farmacología , Animales , Antioxidantes/aislamiento & purificación , Línea Celular Tumoral , Diterpenos/aislamiento & purificación , Humanos , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Modelos Moleculares , Esteroles/aislamiento & purificaciónRESUMEN
By bioactive-guided fractionation of methanol extract of the Ficus microcarpa leaves, one new C-glucosylflavone, ficuflavoside (1), one new megastigmane glycoside, ficumegasoside (8), and twelve known compounds including flavonoids (2-6), phenylpropanoids (7), megastigmanes (9-11) and sterol derivatives (12-14) were isolated. Their chemical structures were elucidated by mass, 1D, and 2D NMR spectroscopies. The antioxidant activities of these compounds were measured using the oxygen radical absorbance capacity methods. Compounds 1-6 exhibited potent antioxidant activities of 6.6-9.5µM Trolox equivalents at the concentration of 2.0µM. The results indicated 2, 3, and 5 having meaningful reducing capacity of copper (I) ions concentration of 6.1-8.4µM.
Asunto(s)
Antioxidantes/química , Antioxidantes/farmacología , Ficus/química , Flavonoides/química , Flavonoides/farmacología , Especies Reactivas de Oxígeno/metabolismo , Antioxidantes/aislamiento & purificación , Cromanos/farmacología , Flavonoides/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Hojas de la Planta/químicaRESUMEN
One new monoterpenoid glycoside, myresculoside (1), and eleven known compounds, were isolated from methanol extract of Myrica esculenta leaves by repeated column chromatography. The effects of these compounds on angiotensin I-converting enzyme (ACE) inhibition were investigated. Compounds 3 and 4 showed the most potent ACE inhibition with rates of 29.97% and 25.63% at concentration of 100 µM, respectively. Compounds 5, 6, and 11 showed weak activity with inhibitory rates of 0.07-1.41% at concentration of 100 µM.
Asunto(s)
Inhibidores de la Enzima Convertidora de Angiotensina/química , Glicósidos/química , Monoterpenos/química , Myrica/química , Peptidil-Dipeptidasa A/química , Inhibidores de la Enzima Convertidora de Angiotensina/aislamiento & purificación , Glicósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Conformación Molecular , Monoterpenos/aislamiento & purificación , Peptidil-Dipeptidasa A/metabolismo , Hojas de la Planta/químicaRESUMEN
Chromatographic separation resulted in the identification of one new squalene derivative, named lobophytene (1), three cembranoid diterpenes (2-4), and two sterols (5 and 6) from the Vietnamese marine soft coral Lobophytum sp. Their structures were identified on the basis of extensive spectroscopic data and comparison of those with reported data. Compounds 1 and 2 showed significant cytotoxic activities against lung (A549) and colon (HT-29) cell lines with IC(50) values of 8.2 and 5.6 microM for 1; 5.1 and 1.8 microM for 2, respectively.
Asunto(s)
Antozoos/química , Antineoplásicos , Animales , Antozoos/crecimiento & desarrollo , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Humanos , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Estructura Molecular , Espectrometría de Masa por Ionización de Electrospray , Espectroscopía Infrarroja por Transformada de Fourier , VietnamRESUMEN
The chemical study of Momordica charantia fruits led to the isolation of three new cucurbitane triterpene glycosides, momordicosides U, V, and W (1-3). The structures of these compounds were determined to be (19R, 23R)-5beta, 19-epoxy-19-methoxycucurbita-6,24-diene-3beta, 23-diol 3-O-beta-D-allopyranoside (1), (23R)-5beta, 19-epoxycucurbita-6,24-diene-3beta, 23-diol 3-O-beta-D-allopyranoside (2), and (19R)-5beta, 19-epoxy-19,25-dihydroxycucurbita-6,23(E)-diene-3beta-ol 3-O-beta-D-glucopyranoside (3), by chemical and spectroscopic methods.
Asunto(s)
Glicósidos/aislamiento & purificación , Momordica charantia/química , Triterpenos/aislamiento & purificación , Conformación de Carbohidratos , Glicósidos/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masa por Ionización de Electrospray , Triterpenos/químicaRESUMEN
Two new 2-C-beta-D-glucopyranosyl benzoic acid derivatives named mallonanosides A (1) and B (2) were isolated from the methanolic extract of the leaves of Mallotus nanus along with five known flavonoids, kaempferin (3), juglanin (4), quercitrin (5), myricitrin (6), and rhoifolin (7). Their structures were established on the basis of spectral and chemical evidence. Their antioxidant activities were shown to depend on the number of hydroxyl groups, and the location and species of sugar moiety.
Asunto(s)
Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Depuradores de Radicales Libres/aislamiento & purificación , Depuradores de Radicales Libres/farmacología , Ácido Gálico/análogos & derivados , Glucósidos/aislamiento & purificación , Glucósidos/farmacología , Mallotus (Planta) , Ácido Vanílico/análogos & derivados , Antioxidantes/química , Flavonoides/química , Depuradores de Radicales Libres/química , Ácido Gálico/química , Ácido Gálico/aislamiento & purificación , Ácido Gálico/farmacología , Glucósidos/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Especies Reactivas de Oxígeno/antagonistas & inhibidores , Relación Estructura-Actividad , Ácido Vanílico/química , Ácido Vanílico/aislamiento & purificación , Ácido Vanílico/farmacologíaRESUMEN
Three new lupane triterpene glycosides, acankoreosides J-L ( 1- 3), were isolated from the leaves of Acanthopanax koreanum. Based on the spectroscopic data, the chemical structures were determined as 3 alpha-hydroxy-20-oxo-30-norlupane-23,28-dioic 28- O- alpha- L-rhamnopyranosyl-(1 --> 4)- beta- D-glucopyranosyl-(1 --> 6)- beta- D-glucopyranosyl ester ( 1); 3 alpha,20,29-trihydroxylupane-23,28-dioic 28- O- alpha- L-rhamnopyranosyl-(1 --> 4)- beta- D-glucopyranosyl-(1 --> 6)- beta- D-glucopyranosyl ester ( 2); and (20S)-3 alpha-hydroxy-29,29-dimethoxylupane-23,28-dioic 28- O- alpha- L-rhamnopyranosyl-(1 --> 4)- beta- D-glucopyranosyl-(1 --> 6)- beta- D-glucopyranosyl ester ( 3). Compounds 1- 3 were evaluated for their cytotoxicity and showed moderate activity against four cell lines, A549 (lung), HL-60 (leukemia), MCF-7 (breast), and U937 (leukemia), with IC (50) values of 23.4, 36.5, 22.6, and 18.5 microM for 1; 6.8, 18.6, 23.1, and > 100 microM for 2; and 28.9, 21.8, 11.0, and 27.5 microM for 3, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/uso terapéutico , Eleutherococcus/química , Glicósidos/uso terapéutico , Neoplasias/tratamiento farmacológico , Extractos Vegetales/uso terapéutico , Triterpenos/uso terapéutico , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Humanos , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Hojas de la Planta , Triterpenos/aislamiento & purificación , Triterpenos/farmacologíaRESUMEN
Two new C(29) sterols with a cyclopropane ring at C-25 and C-26, petrosterol-3,6-dione (1) and 5alpha,6alpha-epoxy-petrosterol (2), along with petrosterol (3), were isolated from the Vietnamese marine sponge Ianthella sp. The structures of the new compounds were elucidated by comprehensive spectroscopic analyses. Compounds 1-3 showed cytotoxic activities on A549, HL-60, MCF-7, SK-OV-3, and U937 cancer cell lines with IC(50) in the range of 8.4-22.6 microM, whereas compounds 1-3 exhibited only weak cytotoxic activities on HT-29 cell. After HL-60 cells were treated with the compounds, several apoptosis events like chromatin condensation and the increase of the population of sub-G1 hypodiploid cells were observed. These data supported that the compounds might have potential for leukemia treatment.