Oxylipins in fungi

Abstract

In nearly every living organism, metabolites derived from lipid peroxidation, the so‐called oxylipins, are involved in regulating developmental processes as well as environmental responses. Among these bioactive lipids, the mammalian and plant oxylipins are the best characterized, and much information about their physiological role and biosynthetic pathways has accumulated during recent years. Although the occurrence of oxylipins and enzymes involved in their biosynthesis has been studied for nearly three decades, knowledge about fungal oxylipins is still scarce as compared with the situation in plants and mammals. However, the research performed so far has shown that the structural diversity of oxylipins produced by fungi is high and, furthermore, that the enzymes involved in oxylipin metabolism are diverse and often exhibit unusual catalytic activities. The aim of this review is to present a synopsis of the oxylipins identified so far in fungi and the enzymes involved in their biosynthesis.

Gene expression and metabolite changes during Tuber magnatum fruiting body storage

“…Fungal oxylipins can be involved in regulating morphogenetic and growth processes, in secondary metabolite production as well as in environmental responses. However, knowledge on the effect of these compounds on fungal differentiation is still limited (Brodhun and Feussner 2011). In the T. magnatum fruiting bodies studied in this investigation, extensive changes took place in the linoleate-derived metabolites during cold storage, a result that is in line with the induction of genes involved in the fatty acid metabolism observed by Zampieri et al (2011) in the mycelium of T. melanosporum during a cold treatment.…”

“…Among the putatively identified metabolites, one oxidized derivative of linoleic acid (oxylipins) was detected, and this metabolite positively characterized the T 3 samples, indicating that it increased during 4 °C storage. Oxylipins, which comprise a large family of fatty acid-derived molecules, originating from eicosanoic and octadecanoic acids, have been described in many fungi (Brodhun and Feussner 2011). Although a role in life cycle control has been proposed for these compounds, mostly during the sexual and asexual development, knowledge on their physiological functions and biosynthetic pathways in fungi is still scarce (Brodhun and Feussner 2011).…”

“…Oxylipins, which comprise a large family of fatty acid-derived molecules, originating from eicosanoic and octadecanoic acids, have been described in many fungi (Brodhun and Feussner 2011). Although a role in life cycle control has been proposed for these compounds, mostly during the sexual and asexual development, knowledge on their physiological functions and biosynthetic pathways in fungi is still scarce (Brodhun and Feussner 2011). Octadecanoid based oxylipins have been found in various Ascomycetes, including Aspergillus species (Mazur et al 1990(Mazur et al , 1991Jernerén and Oliw 2012), Gaeumannomyces graminis (Brodowsky et al 1992) and T. indicum (Gao et al 2001).…”

Catalytic Convergence of Manganese and Iron Lipoxygenases by Replacement of a Single Amino Acid

“…Plant LOX pathways oxygenate C 18 fatty acids to volatile jasmonates, aldehydes, and a series of other metabolites (9). These oxylipins participate in the chemical warfare between plants and microorganisms or herbivores and act as signals in plant development (2,5,9,10).…”

“…polyunsaturated fatty acids with 1Z,4Z-pentadiene units to hydroperoxides, which are precursors to biological mediators in mammals, plants, and fungi (2,4,5). In humans, LOX products are formed from oxidation of arachidonic acid, and these eicosanoids interact with G-protein-coupled receptors; modulate asthma and allergic inflammation, atherosclerosis, and skin water permeability; and contribute to oxidative stress and cancer development (4, 6 -8).…”