RESUMEN
OBJECTIVE: To study the chemical constituents in the bark of Taxus chinensis var. mairei collected from southeast of China. METHODS: Chemical constituents were isolated and purified by column chromatography, Prep-TLC, and preparative HPLC. The structures were identified on the basis of 1D-and 2D-NMR spectral analysis. RESULTS: Twelve taxane diterpenoids were isolated from the bark of Taxus chinensis var. mairei grown in southeast of China. They were identified as: taxagifine (1), decinnamoyltaxagifine (2), 19-debenzoyl-19-acetyltaxinine M(3), 9-dihydro-13-acetyl-baccatin III (4), 7, 9-dideacetylbaccatin IV (5), 1,3-dihydro-taxinine (6), taxumairol C (7), taxezopidine J (8), 7-xylosyl-10-deacetyl-taxol A (9),10-deacetyltaxol (10), taxicin II (11), and 2alpha, 7beta, 10beta-triacetoxy-5alpha, 13alpha-dihydroxy-2 (3 --> 20) abeotaxa-4 (20), 11-dien-9-one (12). CONCLUSION: Compounds 1, 2, 4 - 6, 8, 9, 11 and 12 are obtained from this plant for the first time. Compound 7 is obtained from the bark of Taxus chinensis var. mairei for the first time.
Asunto(s)
Diterpenos/química , Corteza de la Planta/química , Plantas Medicinales/química , Taxus/química , China , Cromatografía Líquida de Alta Presión , Diterpenos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Taxoides/química , Taxoides/aislamiento & purificaciónRESUMEN
A new sesquiterpene, eudesm-11-ene-4alpha,7beta,9beta-triol, was isolated from the EtOH extract of aerial parts of Dichrocephala integrifolia. Its structure was determined on the basis of spectral analysis of 1D and 2D NMR data.
Asunto(s)
Asteraceae/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Sesquiterpenos de Eudesmano/químicaRESUMEN
OBJECTIVE: To study the chemical constituents in the needles of Taxus cuspidata collected from Japan. METHODS: Chemical constituents were isolated by column chromatography, TLC and preparative HPLC. The structures were identified on the basis of NMR spectral analysis. RESULTS: Six non-taxoids were isolated and identified as: 4-[(1E)-3-hydroxy-1-buten-1-yl]-3,5,5-trimethyl-2-cyclohexen-1-one (1), megastigm-5-ene-3, 9-diol (2), 6alpha-epoxy-7-megastigmen-9-one (3), 4-(4-hydroxyphenyl)-2-butanone (4), 12-hydroxy-alpha-cyperone (5), scutellarein-7-O-alpha-L-rhamnoside (6). CONCLUSION: Compounds 2 - 6 are isolated from Taxus genus for the first time. Compound 1 is obtained from Taxus cuspidata for the first time.
Asunto(s)
Taxus/química , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , TaxoidesAsunto(s)
Extractos Vegetales/farmacología , Estructuras de las Plantas/química , Salvia/química , Antiinfecciosos/farmacología , Antioxidantes/farmacología , Bacterias/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Humanos , Sesquiterpenos/química , Sesquiterpenos de Germacrano/química , Virus/efectos de los fármacosRESUMEN
A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3â20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7ß,9α,10ß-triacetoxytaxa-4(20),12-diene-2α,5α,11ß-triol (1) and 2α,7ß,10ß-triacetoxy-5α-hydroxy-2(3â20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.
Asunto(s)
Antineoplásicos/análisis , Extractos Vegetales/análisis , Taxoides/análisis , Taxus/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Neoplasias de la Mama/tratamiento farmacológico , Neoplasias de la Mama/patología , Línea Celular Tumoral , Femenino , Humanos , Espectroscopía de Resonancia Magnética , Masculino , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Hojas de la Planta/química , Neoplasias de la Próstata/tratamiento farmacológico , Neoplasias de la Próstata/patología , Taxoides/química , Taxoides/aislamiento & purificación , Taxoides/farmacología , Insuficiencia del Tratamiento , Neoplasias del Cuello Uterino/tratamiento farmacológico , Neoplasias del Cuello Uterino/patologíaRESUMEN
To determine the chemical constituents responsible for pharmacological effects of Inula britannica-F., three specific sesquiterpene lactones in Inula britannica were isolated from chloroform extract and identified, including britannilactone (BL), 1-O-acetylbritannilactone (ABLO), and 1,6-O,O-diacetylbritannilactone (ABLOO). Electrophoretic mobility shift assay (EMSA) was performed to detect the nuclear translocation of nuclear factor-kappaB (NF-kappaB) p65. The expressions of IkappaBalpha, pIkappaBalpha, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), IkappaB kinase alpha/beta (IKKalpha/beta) and NF-kappaB kinase (NIK) were detected by Western blot and RT-PCR. We found that acetyl side groups enhanced the inhibitory action of the agents on LPS/IFN-gamma-induced iNOS and COX-2 expression. Their inhibiting activity was positive correlation with the acetyl side group number. The effects of LPS/IFN-gamma were reversed by ABLOO, and BL without acetyl side groups showed only a weak inhibitory action. Further study indicated that ABLOO markedly inhibited the phosphorylation of IKKbeta down to based level, but not IKKalpha, corresponding with decreased in IkappaBalpha degradation and phosphorylation induced by LPS/IFN-gamma, resulting in the suppression of NF-kappaB nuclear translocation and activity. These results suggest that the acetyl moieties add to the lipophilicity, and consequently enhance cellular penetration, so that ABLOO possess the most anti-inflammatory effect and may be a potent lead structure for the development of therapeutic and cytokine-suppressing remedies valuable for the treatment of various inflammatory diseases.