A unique furanoid fatty acid from exocarpus seed oil

Morris, L. J.; Marshall, Michael O.; Kelly, William T.

doi:10.1016/s0040-4039(00)76045-x

Cited by 75 publications

(38 citation statements)

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“…Furan fatty acids have been detected at low levels in plants (33), animals, fungi (53), and bacteria (41,42). Fu18: 26 from native cherry plants (Exocarpus cupressiformis, Santalaceae) was the first furan fatty acid described (33). The furan fatty acids found in these Dehalococcoides strains differ from those previously reported in not having one or two methyl groups attached to the furan ring carbons.…”

Section: Resultsmentioning

confidence: 94%

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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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Section: Resultsmentioning

confidence: 94%

“…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). Fu18: 26 from native cherry plants (Exocarpus cupressiformis, Santalaceae) was the first furan fatty acid described (33).…”

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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“…This is the case (with restrictions), e.g. in simple acetylenic [155,156], allenic [157], saturated epoxy- [153], saturated hydroxy- [152], saturated keto- [158], saturated cyclopentene [159], and saturated furane fatty acids [24]. In contrast, the spectra of simple cyclopropane [160] and cyclopropene fatty acids [161] are not very helpful for structure elucidation of unknown derivatives.…”

Section: Gas Chromatography/mass Spectrometry Of Fatty Acidsmentioning

confidence: 99%

Screening analysis of unknown seed oils

Spitzer¹

1999

Fett/Lipid

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In the present paper, modern tools for the screening analysis of unknown seed oils have been reviewed. The known plant fatty acid structures have been divided into three groups (usual, unusual nonoxygenated, unusual oxygenated fatty acids) and examples for each class are presented. Moreover, the importance of chemotaxonomy for the screening analysis of some lipid components is discussed. The main part of the work is focussed on various aspects of preliminary seed oil analyses for the detection of unusual fatty acids and lipid classes and the analysis of fatty acid derivatives by gas chromatography and gas chromatography/mass spectrometry. Furthermore, some useful methods to obtain rapid information on the configuration of double bonds are cited. The paper concludes with a scheme for the detection of unusual fatty acids and lipid classes in seed oils.

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“…1 First identified in Exocarpus cupressiformis seed oil, 2 they occur in fish oils where they may be associated with reproductive cycles, 3 and are also found in marine sponges, 4 and in many plant species, which inevitably means they are present in many foods. 5 While their precise role remains unclear, urofuran acids [structure 1, but CO 2 H in place of the 3-methyl group], which occur in human urine are likely metabolites of these natural products.…”

Section: Introductionmentioning

confidence: 99%