Volatile halogenated metabolites from marine red algae

Abstract

A significant number of halogenated low molecular weight metabolites have exhibited an impressive array of biological properties ranging from antimicrobial to insecticidal activities. Studies on the natural products chemistry of the red seaweeds were recently stimulated by the discovery of the acyclic monoterpene halomon, which exhibits selective antitumor activity in the National Cancer Institute's human tumor and disease oriented in vitro screen.The present review is a taxonomy based compilation of the available literature on the halogenated volatile metabolites (C 1 -C 10 ) produced by red seaweeds, with a short description of the reported ecological and pharmaceutical activities. The review begins with a presentation of simple halogenated hydrocarbons and phenols, showing their wide occurrence in rhodophyta, along with a description of simple halogenated lipids in some of the most frequently investigated red algae species and finally focuses on the chemical composition of individual red algae species.

Toward a List of Molecules as Potential Biosignature Gases for the Search for Life on Exoplanets and Applications to Terrestrial Biochemistry

“…The anthropogenically produced gas concentrations are noted ''1'' for similar reasons. Other references are as follows: (2) Hallenbeck and Benemann (2002); (3) Anderson and Levine (1986); (4) Ryter and Otterbein (2004); (5) Wentworth et al (2003); (6) Paul and Pohnert (2011); (7) Monson et al (2012); (8) Belay and Daniels (1987); (9) Pyysalo (1976); (10) Vitousek et al (2013); (11) Belser (1979); (12) Gribble (2003); (13) Kuhn et al (2000); (14) Nightingale et al (1995); (15) Kladi et al (2004); (16) Watts (2000); (17) Ballschmiter (2003); (18) Finster (2008); (19) Geng and Mu (2006). Columns are IUPAC name, molecular formula, SMILES description, molecular weight, boiling point (e = experimentally measured, p = predicted), production by life (Y/N), and references for molecules produced by life.…”

Exploring the Chemistry and Biology of Vanadium-dependent Haloperoxidases

“…Some of the most frequently reported halometabolites are produced by marine red algae (Rhodophyceae) and include halogenated indoles, terpenes, acetylenes, phenols, and volatile hydrocarbons (9,10,15,18,19). Among the red, brown, and green algae, Rhydophyta are * This work was supported, in whole or in part, by National Institutes of Health Grant AI52445 (to B. S. M.) and by Ruth L. Kirschstein National Research Service Award GM067550 from the National Institutes of Health Training Program in Marine Biotechnology at the Scripps Institution of Oceanography (to J. M. W.).…”

Characterization of polysaccharides from Hypnea spinella (Gigartinales) and Halopithys incurva (Ceramiales) and their effect on RAW 264.7 macrophage activity

“…Specifically, the culturing of Hypnea spinella (Rhodophyta, Hypneaceae) and Halopithys incurva (Rhodophyta, Rhodomelaceae) have recently gained interest due to their production of metabolites with antimicrobial and antifungal activities. H. incurva synthesizes 2,3-dibromo-4,5-dihydroxybenzyl alcohol (lanosol), which has been shown to have high toxic effects on bacteria and other algae (Kladi et al 2004). Furthermore, it has been reported that extracts from H. incurva exert antimicrobial activity against Staphylococcus aureus MB5393 (González del Val et al 2001).…”