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1.
J Nat Prod ; 85(8): 2100-2103, 2022 08 26.
Artículo en Inglés | MEDLINE | ID: mdl-35968659

RESUMEN

To study the chemical constituents from the ripe fresh fruits of Syzygium samarangense (wax apple) and their potential health effects, a phytochemical investigation was undertaken. A new δ-lactone derivative, syzysamalactone (1), along with a known biogenetically related δ-lactone derivative, 6-pentyl-α-pyrone (2), were isolated from the fresh ripe fruits of S. samarangense. Syzysamalactone (1) is an unusual 11-carbon δ-lactone derivative, and its chemical structure and absolute configuration were elucidated by spectroscopic data analysis. A plausible biogenetic pathway for 1 was also proposed. Furthermore, the potential neuroprotective effects of compounds 1 and 2 were assessed. As a result, compounds 1 and 2 displayed notable neuroprotective effects with EC50 values of 0.29 ± 0.03 and 1.28 ± 0.06 µM, respectively, using the SH-SY5Y human neuroblastoma cell line. This is the first report of δ-lactone derivatives showing significant neuroprotective activities.


Asunto(s)
Neuroblastoma , Fármacos Neuroprotectores , Syzygium , Carbono/metabolismo , Frutas/química , Humanos , Lactonas/metabolismo , Lactonas/farmacología , Estructura Molecular , Neuroblastoma/tratamiento farmacológico , Fármacos Neuroprotectores/metabolismo , Fármacos Neuroprotectores/farmacología , Syzygium/química
2.
J Org Chem ; 86(24): 17722-17726, 2021 12 17.
Artículo en Inglés | MEDLINE | ID: mdl-34817178

RESUMEN

A unique prenylated bicarbazole alkaloid, clausanisumine (1), and two biogenetically related known monomer carbazole alkaloids, mukonal (2) and 3-methylcarbazole (3), were isolated from the fruits of Clausena anisum-olens. Clausanisumine (1) was an uncommon prenylated bicarbazole alkaloid, possessing an unprecedented carbon skeleton, which was composed of a simple carbazole alkaloid and a prenylated carbazole alkaloid. The chemical structure of 1 was established by a combination of comprehensive spectral methods. A plausible biosynthetic pathway of 1 was also proposed. Additionally, the potential anti-HIV activities of all isolates 1-3 in vitro were evaluated. Compound 1 exhibited remarkable anti-HIV-1 reverse transcriptase effects showing an EC50 value of 18.58 nM. The discovery of the prenylated bicarbazole alkaloid from C. anisum-olens with notable anti-HIV activity would be meaningful to discovering and developing new anti-HIV drugs.


Asunto(s)
Alcaloides , Fármacos Anti-VIH , Clausena , Alcaloides/farmacología , Fármacos Anti-VIH/farmacología , Carbazoles/farmacología , Frutas , Estructura Molecular
3.
Zhongguo Zhong Yao Za Zhi ; 46(10): 2519-2526, 2021 May.
Artículo en Zh | MEDLINE | ID: mdl-34047099

RESUMEN

The chemical constituents from the stems and leaves of Morinda citrifolia were isolated and purified by column chromatography methods with silica gel, ODS, Sephadex LH-20 and preparative high performance liquid chromatography(HPLC). The structures of the isolated compounds were identified by physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in literature. 17 compounds were isolated from the 90% ethanol extract of the stems and leaves of M. citrifolia, and were identified as 9,10-dihydroxy-4, 7-megastigmadien-3-one(1), 5,12-epoxy-6,9-hydroxy-7-megastigmen-3-one(2), fukinone(3), ß-eudesmol(4), sarmentol F(5), 4, 5-dihydroblumenol A(6), 3-hydroxy-ß-ionone(7), aristol-8-en-1-one(8), ergosta-7-en-3ß-ol(9), ergosta-7-ene-3ß,5α,6ß-triol(10),(22E)-5α,8α-epidioxyergosta-6,22-dien-3ß-ol(11), olivil(12), 4-epi-larreatricin(13), chushizisin Ⅰ(14), rabdosia acid A(15), glycerol monolinoleate(16) and(9Z,12Z,15Z)-2,3-dihydroxypropyl octadeca-trienoate(17). All compounds were isolated from M. citrifolia for the first time. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their inhibitory activities on the proliferation of synoviocytes in vitro using MTS met-hod. Compounds 1-11 showed significant anti-rheumatoid arthritis activities, displaying the inhibitory effects on the proliferation of MH7 A synovial fibroblast cell with the IC_(50) values ranging from(38.69±0.86) to(203.45±1.03) µmol·L~(-1).


Asunto(s)
Morinda , Sinoviocitos , Proliferación Celular , Cromatografía Líquida de Alta Presión , Estructura Molecular
4.
Bioorg Chem ; 105: 104388, 2020 12.
Artículo en Inglés | MEDLINE | ID: mdl-33130343

RESUMEN

A phytochemical investigation on the stems and leaves of Wikstroemia chuii resulted in the isolation of three new daphnane diterpenes, wikstroechuins A-C (1-3), together with eight known analogues (4-11). The structures of new daphnane diterpenes (1-3) were determined on the basis of extensive spectroscopic methods and the known daphnane diterpenes (4-11) were identified by comparing their observable spectroscopic data with those reported spectral data in the literature. The anti-inflammatory effects as well as anti-HIV activities in vitro of all isolated daphnane diterpenes 1-11 were assessed. As a consequence, daphnane diterpenes 1-11 displayed remarkable inhibitory activities on NO (nitric oxide) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells showing IC50 values in the range of 0.12 ± 0.03 to 10.58 ± 0.16 µM. Meanwhile, daphnane diterpenes 1-11 displayed significant anti-HIV-1 reverse transcriptase (RT) effects showing EC50 values ranging from 0.09509 to 8.62356 µM. These research results indicated that the discovery of these new daphnane diterpenes with remarkable anti-inflammatory and anti-HIV activities from W. chuii, especially these new ones, could be extremely meaningful to the discovery of new anti-inflammatory agents and anti-HIV drugs as well as their potential practical values in the health and pharmaceutical products.


Asunto(s)
Fármacos Anti-VIH/farmacología , Antiinflamatorios no Esteroideos/farmacología , Diterpenos/farmacología , Inhibidores de la Transcriptasa Inversa/farmacología , Wikstroemia/química , Animales , Fármacos Anti-VIH/química , Fármacos Anti-VIH/aislamiento & purificación , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Diterpenos/química , Diterpenos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , VIH/efectos de los fármacos , Transcriptasa Inversa del VIH/antagonistas & inhibidores , Transcriptasa Inversa del VIH/metabolismo , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Ratones , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Hojas de la Planta/química , Células RAW 264.7 , Inhibidores de la Transcriptasa Inversa/química , Inhibidores de la Transcriptasa Inversa/aislamiento & purificación , Relación Estructura-Actividad
5.
Nat Prod Res ; 37(9): 1456-1462, 2023 May.
Artículo en Inglés | MEDLINE | ID: mdl-34894893

RESUMEN

The phytochemical investigation on the fruits of Morinda citrifolia led to the isolation and characterization of a new anthraquinone, moricitrifone (1), along with seven known anthraquinones (2-8). The chemical structure of 1 was elucidated by extensive spectral analyses. The known compounds (2-8) were identified by comparing their spectral data with those reported in the literature. The antiproliferative activities of all isolated anthraquinones (1-8) against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 were evaluated in vitro. Compounds 1-8 exhibited remarkable antiproliferative activities with IC50 values ranging from 0.26 ± 0.05 to 16.58 ± 0.18 µM, which were comparable to those of doxorubicin.


Asunto(s)
Morinda , Humanos , Morinda/química , Estructura Molecular , Frutas/química , Extractos Vegetales/química , Antraquinonas/química
6.
Nat Prod Res ; 36(10): 2526-2533, 2022 May.
Artículo en Inglés | MEDLINE | ID: mdl-33949253

RESUMEN

A phytochemical investigation on the fruits of Artocarpus heterophyllus led to the isolation and characterisation of a new prenylated coumarin, artoheteronin (1), together with six known analogues (2-7). The chemical structure of 1 was elucidated using extensive spectral methods and the known compounds (2-7) were identified by comparing their spectral data with those reported in the literature. All known compounds (2-7) were isolated from the genus Artocarpus for the first time. The anti-inflammatory and anti-HIV activities of all isolated prenylated coumarins (1-7) were assessed in vitro. As a result, compounds 1-7 displayed notable inhibitory effects against nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro with the IC50 values in range of 0.58 ± 0.06 to 6.29 ± 0.12 µM. Meanwhile, compounds 1-7 exhibited notable anti-HIV-1 reverse transcriptase (RT) activities possessing EC50 values in the range of 0.18 to 9.12 µM.


Asunto(s)
Artocarpus , Animales , Antiinflamatorios/química , Artocarpus/química , Cumarinas/química , Frutas/química , Ratones , Estructura Molecular , Células RAW 264.7
7.
Nat Prod Res ; 36(12): 3078-3084, 2022 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-34304659

RESUMEN

Eight cadinane-type sesquiterpenes, including a new cadinane-type sesquiterpene, named as mappianiodene (1), and seven known analogues (2-8), were isolated and identified from the stems and leaves of Mappianthus iodoides. The chemical structure and absolute configurations of 1 was elucidated by extensive spectral methods and the known compounds were identified by comparing their experimental spectral data with the reported spectral data in the literature. The anti-inflammatory and anti-HIV activities of those isolated cadinane-type sesquiterpenes were tested. As a result, cadinane-type sesquiterpenes 1-8 displayed notable inhibitory effects on NO (nitric oxide) production with IC50 values equivalent to that of the hydrocortisone. Moreover, compounds 1-8 exhibited pronounced anti-HIV-1 reverse transcriptase (RT) activities with the EC50 values in range of 0.17 to 9.28 µM.


Asunto(s)
Magnoliopsida , Sesquiterpenos , Antiinflamatorios/farmacología , Magnoliopsida/química , Estructura Molecular , Óxido Nítrico , Hojas de la Planta , Sesquiterpenos Policíclicos , Sesquiterpenos/química , Sesquiterpenos/farmacología
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