Biosynthesis of furan fatty acids (F-acids) by a marine bacterium, Shewanella putrefaciens

Shirasaka, Norifumi; Nishi, Kiyohiko; Shimizu, Sakayu

doi:10.1016/s0005-2760(97)00042-8

Cited by 38 publications

(32 citation statements)

References 25 publications

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“…Because fish and filter feeders, such as shellfish, would lack any enzymes to generate F-acids, the contents of F-acids are probably dependent on either the consumption of the real producer, such as algae (53), or the production by intestinal bacteria (54,55). The New Zealand green-lipped mussel is specially regarded among the other bivalves by the New Zealand coastline, suggesting that the habitat of the mussel might be crucial for the higher concentration of F-acids exerting anti-inflammatory activity.…”

Section: Resultsmentioning

confidence: 99%

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Wakimoto

Kondo

Nii

et al. 2011

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

102

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A lipid extract of Perna canaliculus (New Zealand green-lipped mussel) has reportedly displayed anti-inflammatory effects in animal models and in human controlled studies. However, the anti-inflammatory lipid components have not been investigated in detail due to the instability of the lipid extract, which has made the identification of the distinct active components a formidable task. Considering the instability of the active component, we carefully fractionated a lipid extract of Perna canaliculus (Lyprinol) and detected furan fatty acids (F-acids). These naturally but rarely detected fatty acids show potent radical-scavenging ability and are essential constituents of plants and algae. Based on these data, it has been proposed that F-acids could be potential antioxidants, which may contribute to the protective properties of fish and fish oil diets against chronic inflammatory diseases. However, to date, in vivo data to support the hypothesis have not been obtained, presumably due to the limited availability of F-acids. To confirm the in vivo anti-inflammatory effect of F-acids in comparison with that of eicosapentaenoic acid (EPA), we developed a semisynthetic preparation and examined its anti-inflammatory activity in a rat model of adjuvant-induced arthritis. Indeed, the F-acid ethyl ester exhibited more potent anti-inflammatory activity than that of the EPA ethyl ester. We report on the in vivo activity of F-acids, confirming that the lipid extract of the green-lipped mussel includes an unstable fatty acid that is more effective than EPA.

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Section: Resultsmentioning

confidence: 99%

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Wakimoto

Kondo

Nii

et al. 2011

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

102

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“…More remarkable than the lack of monounsaturated PLFA is the presence of furan PLFA derivatives in Dehalococcoides. Mid-chain-branched and furan fatty acids are synthesized from monounsaturated PLFA in other bacteria (1,41,42). Furan fatty acids have been detected at low levels in plants (33), animals, fungi (53), and bacteria (41,42).…”

Section: Resultsmentioning

confidence: 99%

Phospholipid Furan Fatty Acids and Ubiquinone-8: Lipid Biomarkers That May Protect Dehalococcoides Strains from Free Radicals

White

Geyer

Peacock

et al. 2005

Appl Environ Microbiol

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Dehalococcoides species have a highly restricted lifestyle and are only known to derive energy from reductive dehalogenation reactions. The lipid fraction of two Dehalococcoides isolates, strains BAV1 and FL2, and a tetrachloroethene-to-ethene-dechlorinating Dehalococcoides-containing consortium were analyzed for neutral lipids and phospholipid fatty acids. Unusual phospholipid modifications, including the replacement of unsaturated fatty acids with furan fatty acids, were detected in both Dehalococcoides isolates and the mixed culture. The following three furan fatty acids are reported as present in bacterial phospholipids for the first time: 9-(5-pentyl-2-furyl)-nonanoate (Fu18:26), 9-(5-butyl-2-furyl)-nonanoate (Fu17:25), and 8-(5-pentyl-2-furyl)-octanoate (Fu17:26). The neutral lipids of the Dehalococcoides cultures contained unusually large amounts of benzoquinones (i.e., ubiquinones [UQ]), which is unusual for anaerobes. In particular, the UQ-8 content of Dehalococcoides was 5-to 20-fold greater than that generated in aerobically grown Escherichia coli cultures relative to the phospholipid fatty acid content. Naphthoquinone isoprenologues (MK), which are often found in anaerobically grown bacteria and archaea, were also detected. Dehalococcoides shows a difference in isoprenologue pattern between UQ-8 and MK-5 that is atypical of other bacteria capable of producing both quinone types. The difference in UQ-8 and MK-5 isoprenologue patterns strongly suggests a special function for UQ in Dehalococcoides, and Dehalococcoides may utilize structural modifications in its lipid armamentarium to protect against free radicals that are generated in the process of reductive dechlorination.Tetrachloroethene (PCE) and trichloroethene (TCE) are ideal solvents for degreasing and dry cleaning, and their widespread use has led to massive groundwater pollution. Many impacted subsurface environments are cocontaminated with more readily degradable petroleum hydrocarbons at many military sites or with starch at dry-cleaning sites. Microbes readily utilize aerobically degradable substrates, thus depleting oxygen in the groundwater and inducing anaerobiosis. Biotic and abiotic processes acting on these chlorinated solvents facilitate the formation and accumulation of toxic intermediates such as the dichloroethenes (DCEs) and the human carcinogen vinyl chloride (VC). Of the 1,430 contaminated sites listed on the U.S. EPA National Priorities List, 64% contain TCE, 54% contain PCE, and 35% contain VC (51).A variety of subsurface bacteria are capable of anaerobic reductive dehalogenation, which represents the initial attack on these chlorinated solvents (43). Sulfate-reducing and acetogenic bacteria as well as methanogenic archaea can fortuitously catalyze reductive dehalogenation by free or enzymebound, metal ion-containing, heat-stable tetrapyrroles (9). Calculations of redox potentials for corresponding Cl-alkyl/ alkyl couples range from ϩ250 to ϩ487 mV, suggesting that chloroorganic compounds are favorable electron acceptors (7)....

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“…In sum, we identified conditions and enzymes needed for bacterial synthesis of 19Fu-FA. Compounds predicted to be 19Fu-FA and 19M-UFA have been provisionally identified in bacteria before (43,44), but information on their cellular abundance, the enzymes needed for their synthesis, and their cellular role have not yet been reported. We also identified conditions to increase production of 19Fu-FA in both native and foreign hosts, such as E. coli.…”

Section: Discussionmentioning

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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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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Biosynthesis of furan fatty acids (F-acids) by a marine bacterium, Shewanella putrefaciens

Cited by 38 publications

References 25 publications

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Phospholipid Furan Fatty Acids and Ubiquinone-8: Lipid Biomarkers That May Protect Dehalococcoides Strains from Free Radicals

Synthesis and scavenging role of furan fatty acids

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