RESUMEN
The Caribbean island of Grenada furnishes the popular aphrodisiac drug Bois Bandé, which consists of the stem bark and the roots of Chione venosa (sw.) URBAN var. venosa (Rubiaceae), a native tree growing in the islands' rain forest. The phytochemical investigation of dichloromethane and methanolic-aqueous extracts of the bark and the roots yielded three acetophenone derivatives described for the first time in plants - ortho-hydroxy-acetophenone-azine (1), acetophenone-2-O-[beta-D-apiofuranosyl-(1''-->6')-O-beta-D-glucopyranoside] (2) and acetophenone-2-O-beta-D-glucopyranoside (3) - along with five known compounds, alpha-morroniside (4), sweroside (5), diderroside (6), daucosterol (7) and beta-sitosterol (8). Their structures were elucidated by 1D and 2D NMR analysis, UV-Vis and ESI-MS.
Asunto(s)
Acetofenonas/aislamiento & purificación , Rubiaceae/química , Terpenos/aislamiento & purificación , Acetofenonas/química , Estructura Molecular , Corteza de la Planta/química , Raíces de Plantas/química , Tallos de la Planta/química , Espectrometría de Masa por Ionización de Electrospray , Terpenos/químicaRESUMEN
Fourteen commercial samples of the popular Brazilian aphrodisiac Catuaba specified as bark drugs of Anemopaegma, Erythroxylum and Trichilia species were examined for identity and purity. Only a minority of the examined Catuaba samples contained the crude drugs claimed on the labels. More than half of the products were adulterated with different crude drugs. The majority of the samples contained a bark originating from Trichilia catigua. The TLC fingerprints confirmed the heterogeneity, in 50% of the samples tropane alkaloids of various concentrations were detected. TLC and HPLC methods for separation and identification of the tropane alkaloids were developed and their analytical data (RF values, retention times, ESI-MS) given. The structure elucidation of the two main alkaloids, catuabine D and its hydroxymethyl derivative, is presented. The 1H- and 13C-NMR assignments of these alkaloids are discussed with regard to literature data. Neither aqueous nor methanolic extracts of the Trichilia catigua reference material nor alkaloid-enriched fractions of commercial samples showed any effect on the rabbit corpus cavernosum in an in vitro test.
Asunto(s)
Afrodisíacos/farmacología , Fitoterapia , Extractos Vegetales/farmacología , Plantas Medicinales , Animales , Afrodisíacos/administración & dosificación , Afrodisíacos/química , Afrodisíacos/uso terapéutico , Brasil , Cromatografía Líquida de Alta Presión , Cromatografía en Capa Delgada , Espectroscopía de Resonancia Magnética , Masculino , Medicina Tradicional , Estructura Molecular , Erección Peniana/efectos de los fármacos , Corteza de la Planta , Extractos Vegetales/administración & dosificación , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , ConejosRESUMEN
From dichloromethane extracts of flowerheads of Achillea pannonica Scheele three sesquiterpenes were isolated and identified: 11,13-dehydrodesacetylmatricarin, (6E)-5-tigloxy-9-hydroxynerolidol and alpha-longipin-2-en-1-one. The structures were determined by MS, IR and NMR spectroscopic analyses, (6E)-5-Tigloxy-9-hydroxynerolidol is reported here for the first time. Additionally spathulenol, a compound of the essential oil was identified using GC-MS and GC-FTIR.
Asunto(s)
Achillea/química , Extractos Vegetales/química , Sesquiterpenos/química , Cromatografía en Capa Delgada , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Modelos Moleculares , Conformación Molecular , Sesquiterpenos/aislamiento & purificación , EspectrofotometríaRESUMEN
The investigation of a dichloromethane extract of flower heads of a Hungarian taxon of the Achillea millefolium group led to the isolation of three flavonoid aglycones, one triterpene, one germacranolide and five guaianolides. Their structures were elucidated by UV-VIS, EI- and CI-MS, 1H NMR and 13C NMR spectroscopic methods as well as by 2D-NMR studies and by selective 1D-NOE experiments. Besides apigenin, luteolin and centaureidin, beta-sitosterol, 3beta-hydroxy-11alpha,13-dihydro-costunolide, desacetylmatricarin, leucodin, achillin, 8alpha-angeloxy-leucodin and 8alpha-angeloxy-achillin were isolated. Both latter substances are reported here for the first time. Their NMR data were compared with those of the other guaianolides. The stereochemistry of 3beta-hydroxy-11alpha,13-dihydro-costunolide was discussed and compared with data of the literature.