Anticancer activity of natural and synthetic acetylenic lipids

Abstract

This review is a comprehensive survey of acetylenic lipids and their derivatives, obtained from living organisms, that have anticancer activity. Acetylenic metabolites belong to a class of molecules containing triple bond(s). They are found in plants, fungi, microorganisms, and marine invertebrates. Although acetylenes are common as components of terrestrial plants, fungi, and bacteria, it is only within the last 30 years that biologically active polyacetylenes having unusual structural features have been reported from plants, cyanobacteria, algae, invertebrates, and other sources. Naturally occurring aquatic acetylenes are of particular interest since many of them display important biological activities and possess antitumor, antibacterial, antimicrobial, antifouling, antifungal, pesticidal, phototoxic, HIV-inhibitory, and immunosuppressive properties. There is no doubt that they are of great interest, especially for the medicinal and/or pharmaceutical industries. This review presents structures and describes cytotoxic and anticancer activities only for more than 300 acetylenic lipids and their derivatives isolated from living organisms.

Biosynthesis and function of polyacetylenes and allied natural products

“…Acetylenic carotenoids are broadly distributed among Bacillariophyceae, Cryptophyceae, Dinophyceae, Euglenophyceae, Haptophyceae, and Xanthophyceae species [459] and those with biological activity have been reviewed separately by Dembitsky [22].…”

The convergent evolution of defensive polyacetylenic fatty acid biosynthesis genes in soldier beetles

“…Many polyacetylenics have highly potent biological activities, which are used in defence against pathogens and predators 3,12,15 , and some have been investigated as human anti-cancer and anti-microbial treatments 13,16,18,20 . Conjugated polyacetylenic compounds are also very difficult to synthesize chemically; however, we have described a biosynthetic route using soldier beetle genes for heterologous production of these chemicals in yeast using mild conditions.…”

“…The challenging chemistry and variety of potent biological activities of polyacetylenic fatty acids, which includes activities against cancer cells, infecting microbes and plant alleopathy [12][13][14][15][16][17][18][19][20] , have excited interest among natural-product prospectors and bioactive discovery programmes, and have propelled our interest in new molecular structures and biosynthetic origins. In this report, we describe a three-gene pathway isolated from the Australian soldier beetle C. lugubris, leading to an 18-carbon precursor of DHMA, and the first eukaryote biosynthesis of conjugated polyacetylenic compounds.…”

Acides gras inhabituels des organismes marins : une illustration de la biodiversité moléculaire marine

“…Des AG acétyléniques ont été identifiés surtout chez les éponges. De tels AG, de masses moléculaires élevées et à activité biologique potentielle, ont été ainsi trouvés dans de nombreuses espèces d'éponges des genres Petrosia et Xestospongia (Quinn et Tucker, 1985 ;Hirsch et al, 1987 ;Dembitsky, 2006) (figure 10). De tels AG, isolés de l'éponge Oceanapia sp., ont une activité significative contre des bacté-ries et des champignons, en particulier ceux à systèmes conjugués (Matsunaga et al, 2000).…”