New terpenoid constituents from Eunicea pinta.
The secondary metabolite composition of the gorgonian octocoral Eunicea pinta from San Andrés Island, Colombia, is described for the first time. This investigation has resulted in the isolation of eight new gamma-cembranolide-type diterpenes, namely, compounds 3-10, and a new saponin, 13, possessing a pregnene-derived aglycon. In addition, two previously known alpha-methylene-gamma-lactone cembranolides, euniolide (1) and succinolide (2), were also isolated. Their structures were determined on the basis of the results of spectroscopic analysis, X-ray diffraction analysis, and chemical conversions. The discovery of cembranolides 3-10 has prompted us to conclude that the structures proposed earlier for several uprolide-type cembranolides need revision and that a minor stereochemical correction is also in order for succinolide. Cytotoxicity of compounds 3, 4, and 13 toward various cancer cell lines and results of an antimycobacterial screening for 2, 4, and 13 also are described.
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002289:Carcinoma, Non-Small-Cell Lung; D003063:Cnidaria / Q000737:chemistry*; D003105:Colombia; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007680:Kidney Neoplasms; D008175:Lung Neoplasms; D008968:Molecular Conformation; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013601:T-Lymphocytes / Q000187:drug effects; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D004224:Diterpenes; D012503:Saponins; C470333:euniolide; C470334:succinolide