title: Cytotoxic halogenated monoterpenes from Plocamium cartilagineum.
abstract: As a result of our efforts to identify bioactive agents from marine algae, we have isolated and identified one new halogenated monoterpene 1 [(-)-(5E,7Z)-348-trichloro-7-dichloromethyl-3-methyl-157-octatriene] in addition to three known compounds (2, 3 and 4) from the red alga Plocamium cartilagineum collected by hand from the eastern coast of South Africa. Compound 1 was found to be active as a cytotoxic agent in human lung cancer (NCI-H460) and mouse neuro-2a cell lines (IC504 μg/mL). Two of these compounds (3 and 4) were found to have cytotoxic activity in other cell line assays, especially against human leukaemia and human colon cancers (IC501.3 μg/mL). None of these metabolites were active as sodium channel blockers or activators. All structures were determined by spectroscopic methods (UV, IR, LRMS, HRMS, 1D NMR and 2D NMR). 1D and 2D NOE experiments were carried out on these compounds to confirm the geometry of the double bonds.
authors.affiliation: a College of Pharmacy , Oregon State University , Corvallis , OR , USA.|b Faculty of Pharmacy , Cairo University , Cairo , Egypt.
authors.forename: Omar M M
authors.initials: OM
authors.lastname: Sabry
authors.affiliation: a College of Pharmacy , Oregon State University , Corvallis , OR , USA.
authors.forename: Douglas E
authors.initials: DE
authors.lastname: Goeger
authors.affiliation: c Division of Hematology and Oncology Department of Internal Medicine , Henry Ford Hospital , Detroit , MI , USA.
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Valeriote
authors.affiliation: a College of Pharmacy , Oregon State University , Corvallis , OR , USA.|d Center for Marine Biotechnology and Biomedicine , Scripps Institution of Oceanography, University of California , San Diego , CA , USA.
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003110:Colonic Neoplasms / Q000188:drug therapy; D054879:Halogenation; D006801:Humans; D007938:Leukemia / Q000188:drug therapy; D008175:Lung Neoplasms / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D044725:Plocamium / Q000737:chemistry*; D013057:Spectrum Analysis
chemical_list: D000970:Antineoplastic Agents; D039821:Monoterpenes
keywords: Halogenated monoterpenes; Plocamium cartilagineum; human colon cancers; human leukaemia; human lung cancers