ABSTRACT
Bioassay-directed fractionation of the methyl ethyl ketone extract of Chiloscyphus rivularis yielded five new sesquiterpenes, 12-hydroxychiloscyphone (2), chiloscypha-2,7-dione (3), 12-hydroxychiloscypha-2,7-dione (4), chiloscypha-2,7,9-trione (5), and rivulalactone (6) in addition to the known sesquiterpenes, 4-hydroxyoppositan-7-one (7), chiloscyphone (1), and isointermedeol (8). The structure and stereochemistry of rivulalactone, a novel trinorsesquiterpene, was confirmed by its synthesis starting from 1. Compound 2 showed selective bioactivity in our yeast-based DNA-damaging assay and cytotoxicity to human lung carcinoma cells.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Plants, Medicinal/chemistry , Sesquiterpenes/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , DNA Damage , Drug Screening Assays, Antitumor , Humans , Magnetic Resonance Spectroscopy , Oxidation-Reduction , Sesquiterpenes/pharmacology , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Tumor Cells, CulturedABSTRACT
Guided by cytotoxicity, ansamitocin P-3, a maytansinoid, was isolated in very low yield from two members of the moss family Thuidiaceae, Claopodium crispifolium (Hook.) Ren. & Card. and Anomodon attenuatus (Hedw.) Hueb. Ansamitocin P-3 showed potent cytotoxicity against the human solid tumor cell lines A-549, HT-29. A possible basis for the occurrence of this compound in mosses is discussed.
Subject(s)
Actinomycetales/analysis , Antibiotics, Antineoplastic , Maytansine/isolation & purification , Oxazines/isolation & purification , Breast Neoplasms/drug therapy , Chromatography , Colonic Neoplasms/drug therapy , Humans , Lung Neoplasms/drug therapy , Magnetic Resonance Spectroscopy , Maytansine/analogs & derivatives , Maytansine/therapeutic use , Molecular Structure , Tumor Cells, CulturedABSTRACT
The National Cancer Institute's record of "active plants" (extracts which showed a significant inhibitory effect in experimental tumor systems) was compared with plants reported in folklore to have medicinal or poisonous properties. The occurrence of active plants was found to be higher in plants reported in folk literature than in plants collected at random, suggesting a correlation between plants used in folklore and those with anticancer activity.
