Oxidation Decomposition of Unsaturated Fatty Acids by Singlet Oxygen in Phospholipid Bilayer Membranes

Watabe, Naoki; Ishida, Yu; Ochiai, Akira; Tokuoka, Yoshikazu; Kawashima, Norimichi

doi:10.5650/jos.56.73

Cited by 41 publications

(40 citation statements)

References 20 publications

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“…Fatty acids are targets for direct or indirect damage by ROS (1,(5)(6)(7)(8)16), particularly when ROS are produced by integral membrane enzymes in the respiratory chain or the photosynthetic apparatus (1,7,8,16,18). The R. sphaeroides σ E protein activates a transcriptional stress response to 1 O 2 , a ROS that is generated by integral membrane proteins of the photosynthetic apparatus (16,17,19).…”

Section: Resultsmentioning

confidence: 99%

“…In cells and organelles, fatty acids maintain bilayer stability, provide a permeability barrier, act as secondary messengers in signaling pathways, and aid the function of integral membrane proteins (1)(2)(3). Fatty acids also help maintain viability in response to temperature and environmental changes and can be targets for modification by reactive oxygen species or membrane-active agents (2)(3)(4)(5)(6)(7)(8). Fatty acids, or the products derived from them, are valuable as food additives, specialty chemicals, and petroleum substitutes (9)(10)(11)(12).…”

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confidence: 99%

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Synthesis and scavenging role of furan fatty acids

Lemke¹,

Peterson²,

Ziegelhoffer³

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

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Fatty acids play important functional and protective roles in living systems. This paper reports on the synthesis of a previously unidentified 19 carbon furan-containing fatty acid, 10,13-epoxy-11-methyl-octadecadienoate (9-(3-methyl-5-pentylfuran-2-yl)nonanoic acid) (19Fu-FA), in phospholipids from Rhodobacter sphaeroides. We show that 19Fu-FA accumulation is increased in cells containing mutations that increase the transcriptional response of this bacterium to singlet oxygen ( 1 O 2 ), a reactive oxygen species generated by energy transfer from one or more light-excited donors to molecular oxygen. We identify a previously undescribed class of S-adenosylmethionine-dependent methylases that convert a phospholipid 18 carbon cis unsaturated fatty acyl chain to a 19 carbon methylated trans unsaturated fatty acyl chain (19M-UFA). We also identify genes required for the O 2 -dependent conversion of this 19M-UFA to 19Fu-FA. Finally, we show that the presence of 1 O 2 leads to turnover of 19Fu-Fa in vivo. We propose that furan-containing fatty acids like 19Fu-FA can act as a membrane-bound scavenger of 1 O 2 , which is naturally produced by integral membrane enzymes of the R. sphaeroides photosynthetic apparatus.radical scavenger | oxygenated fatty acid | fatty acyl methylase

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis and scavenging role of furan fatty acids

Lemke¹,

Peterson²,

Ziegelhoffer³

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

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show abstract

“…All three ROS may interact directly with various molecules and in this way irreversibly destroy or alter the function of the target and cause visible damage (Sies and Menck 1992; Halliwell and Gutteridge 1989; Girotti 2001 ; Davies 2004; Watabe et al 2007). As the accumulation of these ROS in chloroplasts correlates with changes in nuclear gene expression, they have been also perceived as signaling molecules that may initiate stress responses (Forman and Cadenas 1997; Klotz 2002; Finkel 2003; Apel and Hirt 2004).…”

Section: O2-mediated Signaling In the Conditional Flu Mutant Of Arabmentioning

confidence: 99%

Singlet oxygen-mediated signaling in plants: moving from flu to wild type reveals an increasing complexity

Kim

Apel

2013

Photosynth Res

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Singlet oxygen (1O2)-mediated signaling has been established in the conditional fluorescent (flu) mutant of Arabidopsis. In the dark, the flu mutant accumulates free protochlorophyllide (Pchlide), a photosensitizer that in the light generates 1O2. The release of 1O2 leads to growth inhibition of mature plants and bleaching of seedlings. These 1O2-mediated responses depend on two plastid proteins, EXECUTER (EX) 1 and 2. An ex1/ex2/flu mutant accumulates in the dark Pchlide and upon illumination generates similar amounts of 1O2 as flu, but 1O2-mediated responses are abrogated in the triple mutant. The 1O2- and EX-dependent signaling pathway operates also in wild type placed under light stress. However, it does not act alone as in flu, but interacts with other signaling pathways that modulate 1O2-mediated responses. Depending on how severe the light stress is, 1O2- and EX-dependent signaling may be superimposed by 1O2-mediated signaling that does not depend on EX and is associated with photo-oxidative damage. Because of its high reactivity and short half-life, 1O2 is unlikely to be a signal that is translocated across the chloroplast envelope, but is likely to interact with other plastid components close to its site of production and to generate more stable signaling molecules during this interaction. Depending on the site of 1O2 production and the severity of stress, different signaling molecules may be expected that give rise to different 1O2-mediated responses.

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“…They generate singlet oxygen ( 1 O 2 ) in the membrane, changing its biophysical properties and leading to the inhibition of the viral-cell membrane fusion necessary for target cell infection 4, 5 . 1 O 2 -mediated lipid oxidation targets the C=C double bonds of unsaturated phospholipid acyl chains, introducing polar hydroperoxide groups in the hydrophobic region of the lipid bilayer 6 . The presence of these oxidized phospholipids results in several membrane properties changes, which negatively impact on its ability to undergo the extreme membrane curvature transitions necessary for virus-cell fusion.…”

Section: Introductionmentioning

confidence: 99%

Effects of singlet oxygen generated by a broad-spectrum viral fusion inhibitor on membrane nanoarchitecture

Hollmann

Gonçalves

Augusto

et al. 2015

Nanomedicine: Nanotechnology, Biology and Medicine

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Targeting membranes of enveloped viruses represents an exciting new paradigm to explore on the development of broad-spectrum antivirals. Recently, broad-spectrum small-molecule antiviral drug were described, preventing enveloped virus entry at an intermediate step, after virus binding but before virus–cell fusion. Those compounds, including an oxazolidine-2,4-dithione named JL103 that presented the most promissing results, act deleteriously on the virus envelope but not at the cell membrane level. In this work, by using atomic force microscopy (AFM), we aimed at unraveling the effects that JL103 is able to induce in the lipid membrane architecture at the nanoscale. Our results indicate that singlet oxygen produced by JL103 decreases membrane thickness, with and expansion of the area per phospholipid, by attacking the double bonds of unsaturated phospholipids. This membrane reorganization prevents the fusion between enveloped virus and target cell membranes, resulting in viral entry inhibition.

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Oxidation Decomposition of Unsaturated Fatty Acids by Singlet Oxygen in Phospholipid Bilayer Membranes

Cited by 41 publications

References 20 publications

Synthesis and scavenging role of furan fatty acids

Synthesis and scavenging role of furan fatty acids

Singlet oxygen-mediated signaling in plants: moving from flu to wild type reveals an increasing complexity

Effects of singlet oxygen generated by a broad-spectrum viral fusion inhibitor on membrane nanoarchitecture

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