Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity and analysis

Biosynthesis and function of polyacetylenes and allied natural products

“…With rare exceptions, all other families of plants and the Basidiomycete fungi produce linear polyacetylenes. Chemotaxonomic analysis has been used as confirmation of phylogenetic relationships and to construct models for the chemical genesis of metabolites; a series of papers by Christensen and coworkers cover the most recent systematic efforts in this regard [13][14][15][16][17]136]. For example, most of the screened Asteraceae in Heliantheae, Cynareae, Astereae and Anthemideae produce acetylenic natural products (9200 species and 524 genera are known; 15% and 41% of the species and assigned genera, respectively, have been investigated).…”

“…Epidemiological studies often tout the cancer-protective attributes of foods and vegetables; in this regard, many studies support the cytotoxic effects of 4B and related polyacetylenes from carrot and ginseng [136,470,471]. The source-dependent chemoprotective behavior of carotene (i.e., whether it was ingested in carrots or as a pure compound used as food additive) has been a paradox that may be resolved by the recognition of potentially chemoprotective polyacetylenes in the root crop.…”

“…Falcarinol (4B) is a noted allergen [136,476]. One hypothesis for the sensitization by 4B is that it undergoes an S N 1-like substitution reaction via a resonance-stabilized carbocation allowing the formation of protein-4B antigenic conjugates through cysteine and amine-containing biomolecules.…”

Handbook of Plant Food Phytochemicals

“…Numerous peer reviewed publications support a protective role for plant phenolic compounds (especially flavonoids); isothiocyanates from Brassica species; polyacetylenes from carrot (Daucus carota) and flavonols and cysteine sulfoxides from onion (A llium cepa) in human health (reviewed in [29,39,89,190]) , and these crops will form the basis for this review. Onion (Allium cepa) is believed to be the major source of human flavonol intake.…”

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

“…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.…”