In-vitro cytotoxic activities of the major bromophenols of the red alga Polysiphonia lanosa and some novel synthetic isomers

• Published in: Journal of natural products (Washington, D.C.) Vol. 67; no. 9; pp. 1445 - 1449
• Main Authors: Shoeib, N.A, Bibby, M.C, Blunden, G, Linley, P.A, Swaine, D.J, Wheelhouse, R.T, Wright, C.W
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.09.2004; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Biological and medical sciences; Chemistry, Medicinal; Drug Screening Assays, Antitumor; England; General pharmacology; Hydrocarbons, Brominated - chemistry; Hydrocarbons, Brominated - isolation & purification; Hydrocarbons, Brominated - pharmacology; Inhibitory Concentration 50; Isomerism; Life Sciences & Biomedicine; Marine; Medical sciences; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; Plant Sciences; Polysiphonia lanosa; Rhodomelaceae; Rhodophyta; Science & Technology; Tumor Cells, Cultured; England; CELLS; PHENOLS; CARCINOMA; GROWTH; Human; Rhodophyta; Halophenols; Pharmacognosy; Algae; Cytotoxicity; Organic bromine compounds; In vitro; Biological activity; Isomer; Medicinal plant; Marine environment; Cytometry; Polyphenol; Cell line; Cell cycle; Phenols; Isolation; Colon; Tumor cell; Thallophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0305268

Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa, The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 < 20 mumol were also tested against HCT-116 cells. Compound 3c (2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether) was the most active compound against both cell lines (IC50 = 1.72 and 0.80 mumol, respectively), and its effect on the cell cycle was studied using flow cytometry.