Plocoralides A–C, polyhalogenated monoterpenes from the marine alga Plocamium corallorhiza

• Published in: Phytochemistry (Oxford) Vol. 66; no. 10; pp. 1108 - 1112
• Main Authors: Knott, Michael G., Mkwananzi, Henry, Arendse, Catherine E., Hendricks, Denver T., Bolton, John J., Beukes, Denzil R.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.05.2005; Elsevier
• Subjects: Algae; algae and seaweeds; anticarcinogenic activity; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Biochemistry & Molecular Biology; Biological and medical sciences; Cell Line, Tumor; Chemical constitution; chemical structure; cultured cells; cytotoxicity; Fundamental and applied biological sciences. Psychology; Halogenated monoterpenes; Humans; Hydrocarbons, Halogenated - isolation & purification; Life Sciences & Biomedicine; Marine; Molecular Structure; Monoterpenes - isolation & purification; Monoterpenes - pharmacology; monoterpenoids; octadiene; plant biochemistry; Plant cytology, morphology, systematics, chorology and evolution; Plant physiology and development; Plant Sciences; Plocamium; Plocamium - chemistry; Plocamium corallorhiza; Plocoralides; Science & Technology; spectral analysis; stereochemistry; Thallophyta; South Africa; Halogenated monoterpenes; Plocamium corallorhiza; Plocoralides; halogenated monoterpenes; PORTIERIA-HORNEMANNII; plocoralides; HERBIVORES; Plocamitan corallorhiza; NATURAL-PRODUCTS; CARTILAGINEUM; RED ALGA; CYTOTOXICITY; Molecular structure; Algae; Cytotoxicity; Isolation; Monoterpene; Biological activity; Thallophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2005.03.029

Organic extracts of Plocamium corallorhiza contain three new polyhalogenated monoterpenes, plocoralides A–C ( 1– 3). Compounds 1– 3 show moderate activity towards esophageal cancer cells. Three new polyhalogenated monoterpenes, plocoralides A–C ( 1– 3) along with three known compounds ( 4– 6) have been isolated from the organic extract of the red alga P. corallorhiza. Structures of the new compounds were characterized as 4,8-dibromo-1,1-dichloro-3,7-dimethyl-2 E,6 E-octadiene ( 1), 4,6-dibromo-1,1-dichloro-3,7-dimethyl-2 E,7-octadiene ( 2) and 4,8-dibromo-1,1,7-trichloro-3,7-dimethyl-2 E,5 Z-octadiene ( 3) on the basis of one- and two-dimensional NMR spectroscopic data and MS analyses. Compounds 2– 6 show moderate cytotoxicity toward esophageal cancer cells.