RESUMEN
From the 80% acetone extract of "Cimicifugae Rhizoma" (a mixture of Cimicifuga dahurica and C. heracleifolia used medicinally), seven new fukiic acid derivatives (1-7) and a new phenylethanoid derivative (8) were isolated along with eight known compounds (9-16). Fukinolic acid (9) and cimicifugic acids A-J (10-16, 5-7) showed stronger hyaluronidase inhibitory activities than the positive control, rosmarinic acid.
Asunto(s)
Ácidos Cafeicos/aislamiento & purificación , Ácidos Cafeicos/farmacología , Cimicifuga/química , Hialuronoglucosaminidasa/antagonistas & inhibidores , Fenilacetatos/aislamiento & purificación , Fenilacetatos/farmacología , Fenilpropionatos/aislamiento & purificación , Fenilpropionatos/farmacología , Plantas Medicinales/química , Succinatos/aislamiento & purificación , Succinatos/farmacología , Ácidos Cafeicos/química , Cinamatos/química , Depsidos/química , Japón , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Fenilacetatos/química , Fenilpropionatos/química , Rizoma/química , Succinatos/química , Ácido RosmarínicoRESUMEN
Chemical investigation of the aerial parts of Cimicifuga simplex afforded four new fukinolic acid analogues, cimicifugic acids K-N (1-4), and 10 known compounds, and C. japonica afforded three new fukinolic acid analogues, cimicifugic acids K-M (1-3), a new phenolic glycoside, shomaside F (5), and 10 known compounds. Cimicifugic acids K-N showed more potent hyaluronidase inhibitory activities than rosmarinic acid.
Asunto(s)
Ácidos Cafeicos/aislamiento & purificación , Cimicifuga/química , Hialuronoglucosaminidasa/antagonistas & inhibidores , Fenoles/aislamiento & purificación , Fenilacetatos/aislamiento & purificación , Plantas Medicinales/química , Ácidos Cafeicos/química , Cinamatos/farmacología , Depsidos/farmacología , Japón , Estructura Molecular , Fenoles/química , Fenilacetatos/química , Ácido RosmarínicoRESUMEN
Cimicifugoside, a triterpenoid isolated from Cimicifuga simplex, which has been used as a traditional Chinese medicine due to its anti-inflammatory, analgesic or anti-pyretic action, was examined for inhibition of nucleoside transport and synergistic potentiation of methotrexate cytotoxicity. Cimicifugoside inhibited uptake of uridine, thymidine and adenosine in human leukemia U937 cells with the low nanomolar IC(50) values, but did not affect that of uracil, leucine or 2-deoxyglucose at
Asunto(s)
Cimicifuga , Lanosterol/análogos & derivados , Metotrexato/efectos adversos , Metotrexato/metabolismo , Nucleósidos/antagonistas & inhibidores , Nucleósidos/metabolismo , Triterpenos/metabolismo , Antiinflamatorios no Esteroideos/efectos adversos , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Células Cultivadas , Cimicifuga/efectos de los fármacos , Sinergismo Farmacológico , Humanos , Células K562 , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/metabolismo , Metotrexato/química , Transporte de Proteínas/efectos de los fármacos , Transporte de Proteínas/fisiología , Triterpenos/química , Triterpenos/aislamiento & purificación , Células U937RESUMEN
We evaluated the antioxidant activity of natural compounds in water-soluble and lipid-soluble phases and found that ferulic acid, quercetin and caffeic acid showed stronger activity in the water-soluble phase. Various fractions isolated from Bidens pilosa showed this activity mainly in the water-soluble phase. Antioxidant activity in the lipid-soluble phase of propolis depended on the lipophilic extraction.
Asunto(s)
Antioxidantes/farmacología , Ácidos Cafeicos/farmacología , Ácidos Cumáricos/farmacología , Medicamentos Herbarios Chinos/química , Radicales Libres/antagonistas & inhibidores , Lípidos , Própolis/química , Quercetina/farmacología , Agua , Antioxidantes/aislamiento & purificación , Bidens , Ácidos Cafeicos/aislamiento & purificación , Ácidos Cumáricos/aislamiento & purificación , Quercetina/aislamiento & purificación , SolubilidadRESUMEN
1-Deoxynojirimycin is a glycosidase-inhibitory alkaloid obtained from several plants and microorganisms. Administration experiments using [1-(13C)] glucose in the higher plant Commelina communis and 13C NMR spectroscopic analyses of products suggested that 1-deoxynojirimycin was biosynthesized through a different route compared with that in Streptomyces and Bacilli microorganisms.
Asunto(s)
1-Desoxinojirimicina/metabolismo , Bacillus/metabolismo , Commelina/metabolismo , Streptomyces/metabolismo , 1-Desoxinojirimicina/química , Commelina/química , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Twelve N-caffeoylamino acids and N-cinnamoylamino acids were synthesized and their vasorelaxation activity against norepinephrine (NE)-induced contraction of rat aorta was examined. The following structure-activity relationships were found. 1) On the benzene ring, the caffeoyl structure is effective for vasorelaxation, while the cinnamoyl structure reduced vasorelaxation activity. 2) Four to six carbons are more effective as the carbon chain connecting the acylamino and carboxyl terminal groups. N-Caffeoyl-beta-alanine and N-caffeoyltranexamic acid were used to investigate the action mechanism of vasorelaxing activities. It is believed that these compounds antagonize NE-induced vasocontraction by inhibiting receptor-operated calcium channels.
Asunto(s)
Ácidos Cafeicos/farmacología , Cinamatos/farmacología , Músculo Liso Vascular/efectos de los fármacos , Vasodilatación/efectos de los fármacos , Vasodilatadores/farmacología , Animales , Aorta/efectos de los fármacos , Ácidos Cafeicos/síntesis química , Canales de Calcio/efectos de los fármacos , Cinamatos/síntesis química , Técnicas In Vitro , Masculino , Norepinefrina/antagonistas & inhibidores , Ratas , Ratas Wistar , Relación Estructura-Actividad , Vasoconstricción/efectos de los fármacos , Vasodilatadores/síntesis químicaRESUMEN
Some Glycyrrhiza species grown in several domestic research gardens of medicinal plants were collected by the Osaka University of Pharmaceutical Sciences and were cultivated to compare their morphological properties. HPLC profile analysis was performed and index compounds of MeOH extracts of aerial parts and EtOAc extracts of subterranean parts were determined. Glycyrrhizin contents and growth rates of the underground parts of some types of Glycyrrhiza uralensis and Glycyrrhiza glabra were compared and four excellent types were selected as candidates for cultivation. One of them was due to Kanzo-Yashiki (Enzan, Yamanashi prefecture), where G. uralensis was cultivated in the Edo period. Alkaloidal constituents of G. uralensis and G. glabra were also investigated and anabasine (an insecticide) and a new tricyclic alkaloid were obtained.
Asunto(s)
Glycyrrhiza/química , Glycyrrhiza/clasificación , Alcaloides/análisis , Cromatografía Líquida de Alta Presión , Glycyrrhiza/genética , Glycyrrhiza/crecimiento & desarrollo , Ácido Glicirrínico/análisisRESUMEN
Cimigenol (1) and 39 related compounds were screened as potential antitumor promoters by examining the ability of the compounds to inhibit Epstein-Barr virus early antigen (EBV-EA) activation (induced by 12-O-tetradecanoylphorbol-13-acetate) in Raji cells. Structure-activity relationship analysis indicated that compound 1 showed the highest activity and also exhibited significant inhibitory effects on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test. These data suggest that 1 and the related compounds might be valuable anti-tumor promoters.