RESUMEN
Bioassay-guided fractionation of a CH(2)Cl(2)-MeOH extract of the twigs of Coussarea paniculata using a yeast-based assay for potential DNA-damaging agents resulted in the isolation of three new lupane triterpenoids, 1-3, in addition to eight known triterpenoids, lupeol (4), lupeyl acetate (5), betulin (6), betulinic acid (7), 3-epi-betulinic acid (8), 3-epi-betulinaldehyde (9), oleanolic acid (10), and ursolic acid (11). The structures of the new compounds were established as lup-20(29)-en-3beta,25-diol (1), lup-20(29)-en-11alpha-ol-25,3beta-lactone (2), and 3-deoxybetulonic acid (3), on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversion.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Plantas Medicinales/química , Rubiaceae/química , Triterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Guyana , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Neoplasias Ováricas , Tallos de la Planta/química , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacología , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Bioassay-directed fractionation of the alkaloid portion of a CH(2)Cl(2)-MeOH extract of Tabernaemontana calcarea resulted in the isolation of the three new cytotoxic indole alkaloids, 1-3, and the 12 known alkaloids voacangine (4), isovoacangine (5), coronaridine (6), 11-hydroxycoronaridine (7), voacristine (8), 19-epi-voacristine (9), isovoacristine (10), ibogamine (11), 10-methoxyibogamine (12), 11-methoxyibogamine (13), heyneanine (14), and 19-epi-heyneanine (15). The structures of the new compounds 1-3 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic interpretation. All the compounds exhibited cytotoxic activity against the A2780 ovarian cancer cell line.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Alcaloides Indólicos/aislamiento & purificación , Plantas Medicinales/química , Tabernaemontana/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Humanos , Alcaloides Indólicos/química , Alcaloides Indólicos/farmacología , Madagascar , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Neoplasias Ováricas , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Bioassay-directed fractionation of a n-hexane extract of Couepia polyandra using an assay to detect inhibitors of the lyase activity of DNA polymerase beta resulted in the isolation of the new triterpene 3beta,16beta,23-triacetoxyolean-12-en-28-oic acid (1) and four known compounds, oleanolic acid, betulinic acid, stigmasterol, and beta-sitosterol. The structure of the new compound was established on the basis of extensive 1D and 2D NMR spectroscopic interpretation. All five compounds inhibited DNA polymerase beta lyase activity.
Asunto(s)
Chrysobalanaceae/química , ADN Polimerasa beta/antagonistas & inhibidores , Inhibidores Enzimáticos/aislamiento & purificación , Inhibidores Enzimáticos/farmacología , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/farmacología , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Secuencia de Bases , Inhibidores Enzimáticos/química , Liasas/antagonistas & inhibidores , México , Datos de Secuencia Molecular , Resonancia Magnética Nuclear Biomolecular , Ácido Oleanólico/química , Triterpenos Pentacíclicos , Corteza de la Planta/química , Tallos de la Planta/química , Triterpenos/química , Ácido BetulínicoRESUMEN
Bioassay-directed fractionation of a methyl ethyl ketone extract of the roots of Endlicheria aff. resulted in the isolation of four new neolignans (1-4) and eight known compounds, namely, canellin A (5), canellin C (6), 3'-methoxyguianin (7), (7S,8R,1'S,5'S,6'R)-Delta(2',8')-3',6'-dihydroxy-5'-methoxy-3,4-methylenedioxy-4'-oxo-8.1',7.5'-neolignan (8), armenin-B (9), dillapiole (10), 1-allyl-2,6-dimethoxy-3,4-methylenedioxybenzene (11), and omega-hydroxyisodillapiole (12). The structures of the new compounds (1-4) were established as (7S,8R,1'S,5'S,6'R)-Delta(2',8')-5',6'-dihydroxy-3'-methoxy-3,4-methylenedioxy-4'-oxo-8.1',7.5'-neolignan, (7S,8R,1'S,5'S,6'R)-Delta(2',8')-3',5',6'-trihydroxy-3,4-methylenedioxy-4'-oxo-8.1',7.5'-neolignan, 2,4-dimethoxy-5,6-methylenedioxy-1-(2-propenyl)benzene, and 2,6-dimethoxy-3,4-methylenedioxycinnamyl alcohol, respectively, on the basis of spectroscopic interpretation.
Asunto(s)
ADN Polimerasa beta/antagonistas & inhibidores , Inhibidores Enzimáticos/aislamiento & purificación , Lauraceae/química , Lignanos/aislamiento & purificación , Liasas/antagonistas & inhibidores , Plantas Medicinales/química , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Lignanos/química , Lignanos/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Perú , Raíces de Plantas/química , EstereoisomerismoRESUMEN
Bioassay-directed fractionation of the methanolic extract of the leaves and flowers of Viburnum odoratissimum resulted in the isolation of two new diterpenes, vibsanol A (1) and vibsanol B (2), together with two new triterpenoids, 6beta-hydroxylup-20(29)-en-3-oxo-27,28-dioic acid (3) and 6alpha-hydroxylup-20(29)-en-3-oxo-27,28-dioic acid (4). In addition, the known terpenoids vibsanins B and E, and 6alpha-hydroxylup-20(29)-en-3-oxo-28-oic acid, were also isolated. The structures of the new compounds were established by chemical and spectroscopic means. Vibsanol A (1) and compound 3 exhibited significant cytotoxicity against human gastric (NUGC) tumor cells.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Diterpenos/química , Diterpenos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , NADP/metabolismo , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Neoplasias Gástricas , Taiwán , Triterpenos/química , Triterpenos/farmacología , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Bioassay-guided fractionation of a CH(2)Cl(2)/MeOH extract of the wood of Vepris punctata resulted in the isolation of three new furoquinoline alkaloids, 5-methoxymaculine (1), 5,8-dimethoxymaculine (2), and 4,5,6,7,8-pentamethoxyfuroquinoline (3), in addition to the four known alkaloids flindersiamine (4), kokusaginine (5), maculine (6), and skimmianine (7). The structures of the new alkaloids 1-3 were established on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. All the isolated compounds were tested against the A2780 human ovarian cancer cell line, and all seven alkaloids showed weak cytotoxic activity.