RESUMEN
Chemical investigation of two Irciniidae sponges collected by hand (SCUBA) from Australian near shore waters, afforded six new examples of a rare class of sesterterpene lactam; ircinialactams B (1), G (2), H (5), and I (6), and 8-hydroxyircinialactams C (3) and G (4); together with the new biosynthetically related lactone, ircinialactone A (7). Also isolated were seven biosynthetically related known Irciniidae metabolites; ircinialactams A (8) and C (9), (7E,12E,20Z,18S)-variabilin (10), (7Z,12Z,20Z,18S)-variabilin (11), (7E,12Z,20Z,18S)-variabilin (12), (7Z,12E,20Z,18S)-variabilin (13) and irciniafuran A (14). The structure elucidation of 1-14 was achieved by detailed spectroscopic analysis, and consideration of a plausible biosynthetic relationship linking Irciniidae sesterterpene ß-furans, lactams and lactones.
Asunto(s)
Lactamas/química , Poríferos/química , Sesterterpenos/química , Animales , Lactamas/aislamiento & purificación , Estructura Molecular , Nueva Gales del Sur , Proteínas/química , Sesterterpenos/aislamiento & purificaciónRESUMEN
Activity-guided fractionation of an EtOAc-soluble partition of the MeOH extract from the root bark of Berberis vulgaris L. (barberry), using a hydroxyl radical-scavenging assay, led to the isolation and identification of three phenolic compounds of a previously known structure, N-(p-trans-coumaroyl)tyramine, cannabisin G and (+/-)-lyoniresinol. Of these, cannabisin G and (+/-)-lyoniresinol exhibited antioxidant activity in this bioassay. Furthermore, it was found that cannabisin G showed cytoprotective activity in cultured MCF-7 cells modulated by hydrogen peroxide.
Asunto(s)
Anisoles/farmacología , Antioxidantes/farmacología , Berberis/química , Ácidos Cumáricos/farmacología , Naftalenos/farmacología , Fenoles/farmacología , Anisoles/análisis , Antioxidantes/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Fraccionamiento Químico , Cromatografía Líquida de Alta Presión , Ácidos Cumáricos/análisis , Citoprotección , Depuradores de Radicales Libres , Humanos , Radical Hidroxilo , Naftalenos/análisis , Estrés Oxidativo/efectos de los fármacos , Fenoles/análisis , Fitoterapia , Extractos Vegetales/química , Extractos Vegetales/farmacología , Raíces de Plantas/químicaRESUMEN
Activity-guided fractionation of hexanes- and CHCl 3-soluble extracts of Amomum aculeatum leaves, collected in Indonesia, led to the isolation of three new dioxadispiroketal-type ( 3- 5) and two new oxaspiroketal-type ( 6 and 7) derivatives. Nine semisynthetic derivatives ( 1a- 1h and 2a) of the parent compounds, aculeatins A ( 1) and B ( 2), were prepared. All isolates and semisynthetic compounds were tested against a small panel of human cell lines. Of these, aculeatin A ( 1; ED 50 0.2-1.0 microM) was found to be among the most cytotoxic of the compounds tested and was further evaluated in an in vivo hollow fiber assay; it was found to be active against MCF-7 (human breast cancer) cells implanted intraperitoneally at doses of 6.25, 12.5, 25, and 50 mg/kg. However, when 1 was tested using P388 lymphocytic leukemia and human A2780 ovarian carcinoma in vivo models, it was deemed to be inactive at the doses used.
Asunto(s)
Alcanos , Amomum/química , Antineoplásicos Fitogénicos , Plantas Medicinales/química , Compuestos de Espiro , Alcanos/síntesis química , Alcanos/química , Alcanos/aislamiento & purificación , Alcanos/farmacología , Animales , Antineoplásicos Fitogénicos/síntesis química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Ciclohexanonas , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Humanos , Leucemia P388 , Compuestos de Espiro/síntesis química , Compuestos de Espiro/química , Compuestos de Espiro/aislamiento & purificación , Compuestos de Espiro/farmacologíaRESUMEN
Two new indole alkaloids, polyneuridine-N-oxide (1) and 17-hydroxy-10-methoxy-yohimbane (2), together with seven known alkaloids were isolated from the roots of Ochrosia acuminata collected in Savu, Indonesia. 9-Methoxyellipticine (3) and ellipticine (4) were responsible for the antitumor activities of the extract. The structures of all compounds were elucidated using MS and NMR methods.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Alcaloides Indólicos/aislamiento & purificación , Ochrosia/química , Plantas Medicinales/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Elipticinas/química , Elipticinas/aislamiento & purificación , Elipticinas/farmacología , Alcaloides Indólicos/química , Alcaloides Indólicos/farmacología , Indonesia , Espectrometría de Masas , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Raíces de Plantas/químicaRESUMEN
A new indole alkaloid, akuammiginone (1), and a new glycosidic indole alkaloid, echitamidine-N-oxide 19-O-beta-d-glucopyranoside (2), together with the five known alkaloids, echitaminic acid (3), echitamidine N-oxide (4), N(b)-demethylalstogustine N-oxide (5), akuammicine N-oxide (6), and N(b)-demethylalstogustine (7), were isolated from the trunk bark of Alstonia scholaris collected in Timor, Indonesia. The structures of all compounds were elucidated by spectroscopic methods. This is the first report of compounds 3-5and 7 in A. scholaris. Some NMR assignments of the known compounds were revised.
Asunto(s)
Alstonia/química , Antimaláricos/aislamiento & purificación , Alcaloides Indólicos/aislamiento & purificación , Plantas Medicinales/química , Animales , Antimaláricos/química , Antimaláricos/farmacología , Alcaloides Indólicos/química , Alcaloides Indólicos/farmacología , Indonesia , Concentración 50 Inhibidora , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Corteza de la Planta/química , Plasmodium falciparum/efectos de los fármacosRESUMEN
Three new alkaloids, the two pyrrolidine type alkaloids (1 and 2) and 6E-pandanamine (3), together with five known alkaloids (4-8), were isolated from the leaves of Pandanus amaryllifolius collected in West Java, Indonesia. All the new alkaloids have two alpha-methyl alpha,beta-unsaturated gamma-lactone moieties, while compound 2 also has an additional seven-membered ring, which has not been encountered before in Pandanus alkaloids. Two different extraction methods, namely, a solvent partitioning extraction and acid-base treatment, were tested, giving secondary and tertiary amines, respectively. Spectroscopic and chemical studies showed that the tertiary amines isolated from the acid-base treatment were artifacts formed during the extraction process. This finding suggests that the use of conventional acid-base treatment in isolating Pandanus alkaloids should be reviewed since it can introduce artifacts.