RESUMEN
In our continuing activity-directed search for new antitumor compounds, using brine shrimp lethality (BST), mixtures of three additional pairs (1-6) of bis-THF ketolactone acetogenins were isolated from the ethanol extract of the bark of Annona bullata Rich. (Annonaceae). Compared with (2,4-cis and trans)-bullatacinone (7 and 8), these new compounds each have one more aliphatic OH group at a different position on the hydrocarbon chain, and, thus, were named (2,4-cis and trans)-10-hydroxybullatacinone (1 and 2), (2,4-cis and trans)-12-hydroxybullatacinone (3 and 4), and (2,4-cis and trans)-29-hydroxybullatacinone (5 and 6). These mixtures all showed potent activities in the brine shrimp lethality test (BST) and exhibited cytotoxicities comparable to those of adriamycin against human solid tumor cells in culture with selectivities exhibited especially toward the breast cancer cell line (MCF-7).
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/toxicidad , Furanos/aislamiento & purificación , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Acetilación , Animales , Antineoplásicos Fitogénicos/química , Artemia , Furanos/toxicidad , Humanos , Espectroscopía de Resonancia Magnética , Conformación Molecular , Extractos Vegetales/química , Relación Estructura-Actividad , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
The relative stereochemistries of bullatalicin [1] and bullatalicinone [2] were partially reassigned based on COSY and relayed COSY spectra. The structures of annonins VIII [3], IV [4], and XVI [5] were revised and concluded as bullatalicin [1], bullatanocin [6], and squamostatin A [7], respectively.
Asunto(s)
Antineoplásicos Fitogénicos/química , Furanos/química , Plantas Medicinales/química , Adenocarcinoma/tratamiento farmacológico , Antineoplásicos Fitogénicos/farmacología , Neoplasias de la Mama/tratamiento farmacológico , Carcinoma/tratamiento farmacológico , Neoplasias del Colon/tratamiento farmacológico , Furanos/farmacología , Humanos , Espectroscopía de Resonancia Magnética , Células Tumorales CultivadasRESUMEN
Using brine shrimp lethality to direct fractionation, extracts of the bark of Annona bullata Rich. (Annonaceae) have yielded 16 alpha-hydroxy-(-)-kauranoic acid as a bioactive plant constituent. This previously known diterpene showed significant (ED50 8.25 x 10(-2) micrograms/ml) and selective cytotoxicity against A-549 (lung) cells in our panel of human tumor cells.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Diterpenos/farmacología , Plantas Medicinales/análisis , Acetilación , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Decápodos , Diterpenos/análisis , Diterpenos/aislamiento & purificación , Ratones , Extractos Vegetales/análisis , Extractos Vegetales/farmacología , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Sylvaticin (I), a new tetrahydroxy annonaceous acetogenin with nonadjacent tetrahydrofuran rings, has been isolated from the dried fruits of Rollinia sylvatica St. Hil. (Annonaceae). This compound is extremely cytotoxic to human tumor cells and shows promising insect control properties.