New Cytotoxic Lupane Lactones from Kokoona ochracea

• Published in: Journal of natural products (Washington, D.C.) Vol. 54; no. 5; pp. 1353 - 1359
• Main Authors: Ngassapa, Olipa D, Soejarto, Djaja D, Che, Chun-Tao, Pezzuto, John M, Farnsworth, Norman R
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-09-1991; Glendale, AZ American Society of Pharmacognosy
• Subjects: AGENTES ANTINEOPLASTICOS; Animals; ANTINEOPLASTIC AGENTS; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; BARK PRODUCTS; Biological and medical sciences; CARCINOMA; CARCINOME; CELASTRACEAE; CELL CULTURE; CELL LINES; CULTIVO DE CELULAS; CULTURE DE CELLULE; CYTOTOXIC COMPOUNDS; CYTOTOXICITY; Drug Screening Assays, Antitumor; FITOTOXICIDAD; General pharmacology; Humans; LACTONAS; LACTONE; LACTONES; LEUCEMIA; LEUCEMIE; LEUKAEMIA; LEUKEMIA; Leukemia P388 - drug therapy; Magnetic Resonance Spectroscopy; Medical sciences; MEDICAMENT CYTOSTATIQUE; MOLECULAR CONFORMATION; Molecular Structure; OCHRACEOLIDES; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; PHYTOTOXICITE; PHYTOTOXICITY; PRODUIT A BASE D'ECORCE; STEMS; STRUCTURE; SUBSTANCE TOXIQUE; SUSTANCIAS TOXICAS; TALLO; TIGE; TOXIC SUBSTANCES; Triterpenes - chemistry; Triterpenes - isolation & purification; Triterpenes - pharmacology; TROZOS DE CORTEZA; Tumor Cells, Cultured; Cell culture; Molecular structure; Pharmacognosy; Celastraceae; P388-Leukemia; Cytotoxicity; Lactone; Extract; Malignant hemopathy; In vitro; Stem; Sensitivity resistance; Structure activity relation; Dicotyledones; KB cell line; Angiospermae; Plant origin; Isolation; Spermatophyta; Tumor cell
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np50077a019

Three new compounds, ochraceolides A, B, and C, were isolated from nonpolar extracts derived from Kokoona ochracea stem bark. Based on spectroscopic data, their structures were determined to be the closely related lupane lactones: 3-oxolup-20(29)-en-30,21 alpha-olide, 20,29-epoxy-3-oxolupan-30,21 alpha-olide, and 3,6-dioxolup-20(29)-en-30,21 alpha-olide. Compounds 1 and 3 exhibited significant cytotoxic activity with cultured P-388 cells (ED50 values of 0.26 and 0.53 microgram/ml, respectively) but were at least tenfold less active with a variety of human tumor cell lines. Compound 2 was weakly active with cultured P-388 and KB-3 cells (ED50 values of 7.8 and 5.2 micrograms/ml, respectively), but no significant activity was observed with other human cancer cell types (ED50 values of more than 20 micrograms/ml).