RESUMEN
Two undescribed triterpenes, syzyfolium A (1) and syzyfolium B (2), together with twelve known compounds, terminolic acid (3), actinidic acid (4), piscidinol A (5), threo-dihydroxydehydrodiconiferyl alcohol (6), lariciresinol-4-O-ß-D-glucoside (7), icariol A2 (8), 14ß,15ß-dihydroxyklaineanone (9), garcimangosone D (10), (+)-catechin (11), myricetin-3-O-α-L-rhamnopyranoside (12), quercitrin (13), and 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-ß-D-glucopyranoside (14) were isolated from the leaves of Syzygium myrsinifolium. Their chemical structures were determined by IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 3 and 4 inhibited significantly α-glucosidase with IC50 values of 23.99 and 36.84, respectively, and compounds 1 and 2 inhibited significantly α-amylase with IC50 values of 35.48 and 43.65â µM, respectively.
Asunto(s)
Syzygium , Triterpenos , Syzygium/química , alfa-Glucosidasas , Extractos Vegetales/farmacología , Triterpenos/farmacología , alfa-Amilasas , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/químicaRESUMEN
One new indol, N-methoxymethyltryptophol (1), one new phenolic, (2 R)-2-(4-hydroxyphenyl)ethyl 2-hydroxy-3-phenylpropanoate (2) and fifteen known compounds (3-17) were isolated from the methanol extract of the fermentation of marine microalgae Aurantiochytrium sp. SC145. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis, HR-ESI-MS, quantum chemical calculation methods and by comparing their NMR data with those reported in the literature. All compounds were evaluated for their antimicrobial activities against microorganisms. Compounds 2, 3 and 11 significantly exhibited antimicrobial activities on all tested Gram-(+), Gram-(-) bacteria and the yeast C. albicans with MIC values ranging from 32 to 256 µg/mL.
Asunto(s)
Antiinfecciosos , Microalgas , Antiinfecciosos/química , Bacterias , Extractos Vegetales/química , Levaduras , Pruebas de Sensibilidad Microbiana , Antibacterianos/farmacología , Antibacterianos/químicaRESUMEN
A phytochemical investigation of the methanolic extract of the Macropanax membranifolius C.B. Shang leaves led to the isolation of three new flavans, (2R,3R)-4'-O-methylcatechin 5-O-ß-D-glucopyranoside (1), (2S,3S)-4'-O-methylcatechin 5-O-ß-D-glucopyranoside (2), (2S,3R)-4'-O-methylcatechin 5-O-ß-D-glucopyranoside (3), one new triterpene glycoside 3-O-ß-D-xylopyranosyl-(1â6)-[ß-D-xylopyranosyl-(1â2)]-ß-D-glucopyranosyl-oleanolic acid 28-O-ß-D-glucopyranoside (4), together with nine known compounds (5-13). Their chemical structures were elucidated based on HR-ESI-MS, NMR spectroscopic data. The absolute configurations of compounds 1-3 were established by electronic circular dichroism (ECD) spectra. At concentration of 20â µM, compounds 1-13 showed the percentages of dead cell in the range of 2.14 % to 33.61 % against KB, HepG2, HL60, P388, HT29, and MCF7 cancerous cell lines by SRB assay.
Asunto(s)
Antineoplásicos , Saponinas , Triterpenos , Saponinas/química , Glicósidos/química , Espectroscopía de Resonancia Magnética , Extractos Vegetales/farmacología , Extractos Vegetales/química , Triterpenos/farmacología , Triterpenos/química , Estructura MolecularRESUMEN
Three undescribed dihydrostilbene glycosides, 3,5-dihydroxyldihydrostilbene 4'-O-[6''-O-(4'''-hydroxylbenzoyl)]-ß-D-glucopyranoside (1), 3,5-dihydroxyldihydrostilbene 4'-O-(6''-O-galloyl)-ß-D-glucopyranoside (2), and 3,5-dihydroxyldihydrostilbene 4'-O-[6''-O-(3''',4'''-dimethoxyl)galloyl]-ß-D-glucopyranoside (3), and seven known compounds, kaempferol 3-O-ß-D-glucopyranoside (4), isoquercitrin (5), kaempferol 3-O-α-L-rhamnoside (6), quercitrin (7), (6S,9R)-roseoside (8), (-)-epicatechin 3-O-gallate (9), and (-)-epigallocatechin 3-O-gallate (10) have been isolated from the methanol extract of the leaves of Camellia sinensis var. assamica (J.W.Mast.) Kitam. (synnonym of Camellia assamica (Mast.) H.T.Chang) (Theaceae). Their structures were elucidated by spectroscopic methods (1 D-, 2 D-NMR) and mass spectra. All compounds were evaluated for cytotoxic activity against human oral cancer (CAL27) and human breast cancer (MDAMB231) cell lines. Compound 10 showed significant cytotoxic activity against CAL27 and MDAMB231 cell lines with IC50 values of 9.78 ± 0.25 and 3.27 ± 0.18 µM, respectively, compared to those of positive control, capecitabine (IC50 values of 8.20 ± 0.75 and 5.20 ± 0.89 µM).
Asunto(s)
Camellia sinensis , Camellia , Dihidrostilbenoides , Camellia sinensis/química , Glicósidos/química , Humanos , Hojas de la Planta/químicaRESUMEN
Two new sesquiterpenes and one new bis-sesquiterpene, named dysinidins C-E (1-3) along with three known sterols, dysideasterol F, 9α,l lα-epoxycholest-7-en-3ß,5α,6α-triol, and 9α,11α-epoxycholest-7-en-3ß,5α,6α,19-tetrol 6-acetate (4-6) were isolated from the Vietnamese marine sponge Dysidea fragilis (Montagu, 1814). Their structures were determined by 1D- and 2D-NMR spectroscopies and HR-ESI-MS, as well as by comparison with reported literature data. Compounds 4-6 were found to inhibit eight human cancer cell lines (KB, LU-1, HL-60, LNCaP, SK-Mel-2, HepG-2, MCF-7, and PC-3), with IC50 values ranging from 7.3 to 31.5 µM.
Asunto(s)
Antineoplásicos/aislamiento & purificación , Dysidea/química , Sesquiterpenos/aislamiento & purificación , Animales , Antineoplásicos/química , Línea Celular Tumoral , Colestenos/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Estructura Molecular , Sesquiterpenos/química , Esteroles/aislamiento & purificaciónRESUMEN
Using combined chromatographic methods, two new compounds, 6ß,9ß:9,13-diepoxymegastig-4-en-3ß-ol (1), 5a,6a-epoxy D:C-friedoolean-8-en-3ß-ol (2) were isolated from the methanol extract of the leaves of Glochidion obliquum Decne. Their structures were elucidated by 1D- and 2D-NMR spectra and in comparison with those reported in the literature.
Asunto(s)
Euphorbiaceae/química , Norisoprenoides/aislamiento & purificación , Triterpenos/aislamiento & purificación , Estructura Molecular , Norisoprenoides/química , Hojas de la Planta/química , Triterpenos/químicaRESUMEN
One new tirucallane-type triterpene glycoside, antidesoside (1), along with two biflavones, podocarpusflavone A (2) and amentoflavone (3) and two megastigmane glycosides, byzantionoside B (4), and (6S,9R)-roseoside (5) were isolated from the methanol extract of Antidesma bunius leaves. Their structures were determined by spectroscopic methods and in comparison with the published data. Compounds 1 - 3 were found to show strong inhibitory effect of NO production in BV2.cells and RAW264.7 macrophages LPS-stimulated, with IC50 values ranging from 8.5 to 26.9 µM.
Asunto(s)
Euphorbiaceae/química , Macrófagos/efectos de los fármacos , Microglía/efectos de los fármacos , Animales , Línea Celular , Glicósidos/química , Ratones , Óxido Nítrico , Hojas de la Planta/químicaRESUMEN
Two new sesquiterpenes, named dysinidins A-B (3, 4) along with two known sesquiterpenes, furodysinin lactone (1) and O-methyl urodysinin lactone (2), were isolated from the Vietnamese marine sponge Dysidea fragilis. Their structures were determined by ID- and 2D-NMR spectroscopies and HR ESI MS, as well as by comparison with reported literature data. None of compounds showed inhibitory growth of human lung cancer cell lines, A-549 and H-1975 (IC50 > 30 µM).
Asunto(s)
Dysidea/química , Sesquiterpenos/química , Animales , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , VietnamRESUMEN
CONTEXT: Traditional Chinese medicines have attracted increasing interest as potential sources of novel drugs with a wide range of biological and pharmacological activities. Annona glabra Linn (Annonaceae) is used in traditional medicine as an anticancer drug. Phytochemical investigation of this plant led to the isolation of acetogenins, ent-kauranes, peptides, and alkaloids. In addition, compounds exhibited anticancer, anti-HIV-reserve, and antimalaria. OBJECTIVE: Isolation, structure determination, and cytotoxic activity evaluation of compounds from the methanol extract from A. glabra fruits. MATERIALS AND METHODS: Using chromatographic methods to isolate compounds from the A. glabra methanol extract. The cytotoxic activity of compounds was evaluated by a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay. In addition, compounds which showed significant cytotoxic activity were chosen for further study apoptosis characteristics. RESULTS: One new, (2E,4E,1'R,3'S,5'R,6'S)-dihydrophaseic acid 1,3'-di-O-ß-d-glucopyranoside, and eight known compounds, (2E,4E,1'R,3'S,5'R,6'S)-dihydrophaseic acid 3'-O-ß-d-glucopyranoside (2), icariside D2 (3), icariside D2 6'-O-ß-d-xylopyranoside (4), 3,4-dimethoxyphenyl O-ß-d-glucopyranoside (5), 3,4-dihydroxybenzoic acid (6), blumenol A (7), cucumegastigmane I (8), and icariside B1 (9), were isolated from the fruits of A. glabra. Icariside D2 (3) was found to show significant cytotoxic activity on the HL-60 cell line with the IC50 value of 9.0 ± 1.0 µM and did not show cytotoxic activity on the Hel-299 normal cell line. The further test indicated that compound 3 induced apoptosis via alteration of expression of apoptosis-related proteins and decreased phosphorylation of AKT in HL-60 cells. DISCUSSION AND CONCLUSION: The results suggested that the constituents from A. glabra may contain effective compounds which can be used as anticancer agents.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Annona , Antineoplásicos Fitogénicos/toxicidad , Proliferación Celular/efectos de los fármacos , Citotoxinas/toxicidad , Frutas , Células HL-60 , Humanos , Extractos Vegetales/toxicidadRESUMEN
Three new ent-kaurane diterpenoids, 7ß,16α,17-trihydroxy-ent-kauran-19-oic acid (1), 7ß,17-dihydroxy-16α-ent-kauran-19-oic acid 19-O-ß-d-glucopyranoside ester (2), 7ß,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-ß-d-glucopyranoside ester (3) along with five known compounds, paniculoside IV (4), 16α,17-dihydroxy-ent-kaurane (5), 16ß,17-dihydroxy-ent-kaurane (6), 16ß,17-dihydroxy-ent-kauran-19-al (7), and 16ß,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01±0.01µM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39±0.12µM and 0.32±0.04µM, respectively.
Asunto(s)
Annona , Diterpenos de Tipo Kaurano/farmacología , Frutas , Macrófagos/efectos de los fármacos , Óxido Nítrico/antagonistas & inhibidores , Extractos Vegetales/farmacología , Animales , Diterpenos de Tipo Kaurano/química , Diterpenos de Tipo Kaurano/aislamiento & purificación , Lipopolisacáridos/toxicidad , Macrófagos/metabolismo , Ratones , Óxido Nítrico/biosíntesis , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificaciónRESUMEN
Two new isoflavone glycosides, dalspinosin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1) and caviunin 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), and two known compounds, caviunin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3) and caviunin (4) were isolated from the stems of Dalbergia vietnamensis. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparing with the NMR data reported in the literature.
Asunto(s)
Dalbergia/química , Glicósidos/química , Isoflavonas/química , Estructura MolecularRESUMEN
Four new cucurbitane-type triterpene glycosides, charantosides D-G (1-4) were isolated from a methanol extract of Momordica charantia fruits. The structures of these compounds were determined by chemical and spectroscopic methods to be (19R)-5 beta,19-epoxy-25-methoxycucurbita-6,23-diene-3 beta,19-diol 3-O-beta-D-glucopyranoside, (19R)-5 beta, 19-epoxy-25-methoxycucurbita-6,23-diene-3 beta,19-diol 3-O-beta-D-allopyranoside, 7 beta-methoxycucurbita-5,23E,25-triene-3 beta-ol 3-O-beta-D-allopyranoside, and 3 beta,7 beta-dihydroxycucurbita-5,23E,25-triene- 19-al 3-O-beta-D-allopyranoside.
Asunto(s)
Glicósidos/aislamiento & purificación , Momordica charantia/química , Triterpenos/aislamiento & purificación , Frutas/química , Glicósidos/química , Estructura Molecular , Triterpenos/químicaRESUMEN
A new ent-kaurane glycoside, annoglabasin H (1), and three known ent-kauranes, annoglabasin E (2), annoglabasin B (3), and 19-nor-ent-kaurent-4-ol-17-oic acid (4) were isolated from the fruits of Annona glabra. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparison with the NMR data reported in the literature. The cytotoxic activities of these compounds were evaluated on four human cancer cell lines, LU-1, MCF-7, SK-Mel2, and KB. Compound 1 exhibited significant cytotoxic activity on all tested human cancer cell lines with IC50 values ranging from 3.7 to 4.6 µM.
Asunto(s)
Annona/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Diterpenos de Tipo Kaurano/aislamiento & purificación , Línea Celular Tumoral , Diterpenos de Tipo Kaurano/química , Diterpenos de Tipo Kaurano/farmacología , Humanos , Espectroscopía de Resonancia MagnéticaRESUMEN
One new biscembranoid, petronigrione (1), and five known compounds, methyl tortuoate B (2), lobophytone U (3), lobophytone H (4), (24S)-ergostane 3beta, 5alpha, 6beta, 25 tetraol-25-monoacetate (5), and (24S)-ergostane-1beta, 3beta, 5alpha, 6beta, 25-pentaol-25-monoacetate (6), were isolated from the methanol extract of the marine sponge Petrosia nigricans. Their structures were established on the basis of spectral and chemical evidence. The cytotoxicity of all compounds was evaluated by MTT assay on four human cancer cell lines, HepG2, KB, LU-1, and MCF-7. Compounds 1 and 2 exhibited moderate cytotoxic activities on the four human cancer cell lines with IC50 values ranging of 20.7 - 28.9 microg/mL.
Asunto(s)
Antineoplásicos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Petrosia/química , Animales , Antineoplásicos/química , Diterpenos/química , Ensayos de Selección de Medicamentos Antitumorales , Células Hep G2 , Humanos , Células MCF-7 , Estructura MolecularRESUMEN
OBJECTIVE: To identify inhibitors of nitric oxide production and NF-κB activity from Chromolaena odorata (C. odorata). METHODS: The compounds isolated from the aerial parts of C. odorata by bioassay-guided fractionation were investigated for their inhibitory effects on the NO production and NF-κB activity in LPS-stimulated RAW264.7 cells. RESULTS: Six fatty acids (S)-coriolic acid (1), (S)-coriolic acid methyl ester (2), (S)-15,16-didehydrocoriolic acid (3), (S)-15,16-didehydrocoriolic acid methyl ester (4), linoleamide (5) and linolenamide (6) were isolated. All compounds inhibited the NO production at concentrations consistent with those required for NF-κB inhibition. Compound 2 was the most active with the IC(50) values of 5.22 and 5.73 µM. The addition of a double bond in the fatty chain decreased the inhibitory effects while the methyl esterification increased the activities. CONCLUSIONS: The fatty acid components in C. odorata with NF-κB inhibitory activity could explain the anti-inflammation property of this plant in traditional medicine. This study could also contribute to the better use of C. odorata for human health care.
Asunto(s)
Chromolaena/química , Ácidos Grasos/farmacología , Macrófagos/efectos de los fármacos , FN-kappa B/antagonistas & inhibidores , Óxido Nítrico/antagonistas & inhibidores , Extractos Vegetales/farmacología , Animales , Línea Celular , Ácidos Grasos/aislamiento & purificación , Ratones , Componentes Aéreos de las Plantas/químicaRESUMEN
One new megastigmane glycoside, ficalloside (1), and eleven known compounds, were isolated from methanol extract of Ficus callosa leaves by repeated column chromatography. Their structures were established on the basis of spectral and chemical evidence. The antioxidant activities of these compounds were measured using the oxygen radical absorbance capacity (ORAC) assay. Compound 8 exhibited potent antioxidant activity of 10.6 microM trolox equivalents at the concentration of 2 microM. At this concentration, compounds 4-7 and 9-12 showed significant antioxidant activity with ranging of 2.1-6.1 microM trolox equivalents.