• Journal of the Korean Applied Science and Technology
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• v.27 no.2
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• pp.114-122
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• 2010

Hydroxy fatty acids have gained important attentions because of their special properties such as higher viscosity and reactivity compared to non-hydroxy fatty acids. The new bacterial isolate Pseudomonas aeruginosa (PR3) had been well studied to produce mono-, di-, and tri-hydroxy fatty acids from different unsaturated fatty acids. Of those hydroxy fatty acids, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) was produced with high yield from oleic acid by P. aeruginosa PR3. Mostly, the substrates used for the production of hydroxy fatty acid by microorganisms were free fatty acids or synthetic lipids. However, it is highly plausible to use vegetable oils containing oleic acid such as olive oil for DOD production by P. aeruginosa PR3. As a first step to address the utilization of olive oil as a substrate for DOD production, we tried to determine the effect of vessel type on DOD production from olive oil by P. aeruginosa PR3. Of two different flask types of normal flask and baffled-flask, baffled-flask was highly effective for DOD production with all the media tested. Maximum increase of productivity by baffled-flask represented 221% with the medium supplemented with whey powder instead of lactose. Results from this study demonstrated that vessel type and medium composition could be both significant factors for DOD production from olive oil by P. aeruginosa PR3.

• Archives of Pharmacal Research
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• v.25 no.4
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• pp.438-440
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• 2002

A new unsaturated hydroxy fatty acid was isolated from the leaves of Cucurbita moschata through repeated silica gel column chromatography and chemical methods. The structure of the new fatty acid was determined as 13-hydroxy-9, 11, 15-octadecatrienoic acid on the basis of several spectral data including 2D-NMR. The stererostructures of double bonds were determined to be 9Z, 11 E and 15E by coupling patterns of related proton signals in the $^1H-NMR$ and NOESY experiments.

• Journal of Microbiology and Biotechnology
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• v.13 no.3
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• pp.360-365
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• 2003

The ability of 19 lactic acid bacteria to produce hydroxy fatty acids (HFAs) from unsaturated food fatty acids (USFAs) was tested. HFAs are related to human ailments, including steatorrhea. All the cultures produced HFAs from USFAs, unless their growth was inhibited by free USFAs. Lactococcus lactis subsp. lactis KFRI 131 converted oleic, linoleic, and linolenic acid into 10-hydroxyoctadecanoic acid (10-HODA), 10-hydroxyoctadecaenoic acid (10-HODEA), and 10-hydroxyoctadecadienoic acid (10-HODDEA), respectively. Both a USFA and a surfactant were needed for the bacterium to convert the fatty acid into the corresponding HFA. It was apparent that the production of 10-HODA was growth-related, while that of 10-HODDEA was not. It was unclear whether the production of 10-HODEA was growth-related.

• Korean Journal of Microbiology
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• v.43 no.2
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• pp.130-136
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• 2007

Natural 6-dodecen-4-olide (Butte lactone) was produced from plant oils containing high unsaturated fatty acids via two-stage microbial hiotransformation. After unsaturated fatty acids were liberated from plant oil by microbial lipase, these were converted to optically active hydroxyl fatty acid (HFA) by hydroxylation reaction of Pseudomonas sp. NRRLB-2994. When safflower oil containing >75% unsaturated fatty acid, linoleoic acid wasused, Pseudomonas sp. produced 8g/L of 10-hydroxy-12(z)-octadecanoicacid with average of 39.2% bioconversion efficiency during 48 hr biotransformation period. The recovered 10-hydroxy-12-octadecanoic acid was further bioconverted to 4-hydroxy-6-dodecenoic acid via partial ${\beta}-oxidation$ by Yarriowia lipolytica ATCC34088. 4-hydroxy-6-dodecenoic acid in culture was lactonized by lowering pH to 4.0 using $4N\;H_{2}SO_{4}$ and heating for 5 min to 6-dodecen-4-olide (Butter lactone). Natural 6-dodecen-4-olide had characteristic aroma properties when compared to 6-dodecan-4-oilde (dodecalactone) and 4-decen-4-olide (decalactone).

• BMB Reports
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• v.57 no.2
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• pp.86-91
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• 2024

The fatty acids content of castor (Ricinus communis L.) seed oil is 80-90% ricinoleic acid, which is a hydroxy fatty acid (HFA). The structures and functional groups of HFAs are different from those of common fatty acids and are useful for various industrial applications. However, castor seeds contain the toxin ricin and an allergenic protein, which limit their cultivation. Accordingly, many researchers are conducting studies to enhance the production of HFAs in Arabidopsis thaliana, a model plant for oil crops. Oleate 12-hydroxylase from castor (RcFAH12), which synthesizes HFA (18:1-OH), was transformed into an Arabidopsis fae1 mutant, resulting in the CL37 line producing a maximum of 17% HFA content. In addition, castor phospholipid:diacylglycerol acyltransferase 1-2 (RcPDAT1-2), which catalyzes the production of triacylglycerol by transferring HFA from phosphatidylcholine to diacylglycerol, was transformed into the CL37 line to develop a P327 line that produces 25% HFA. In this study, we investigated changes in HFA content when endogenous Arabidopsis PDAT1 (AtPDAT1) of the P327 line was edited using the CRISPR/Cas9 technique. The successful mutation resulted in three independent lines with different mutation patterns, which were transmitted until the T4 generation. Fatty acid analysis of the seeds showed that HFA content decreased in all three mutant lines. These findings indicate that AtPDAT1 as well as RcPDAT1-2 in the P327 line are involved in transferring and increasing HFAs to triacylglycerol.

• Journal of the Korean Chemical Society
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• v.51 no.1
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• pp.51-55
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• 2007

The fatty acid composition of thiocyanate utilizing Bacillus brevis isolated from carbonization wastewater was determined by Gas Chromatography and the results were analyzed. In addition to the saturated and unsaturated straight chain fatty acids this B. brevis strain contained a hydroxy fatty acid. The hydroxy fatty acids in general are shown to be interesting chemotaxonomic markers of bacteria. Cyclopropane fatty acids are totally absent in this strain. A comparison of the fatty acid composition of this strain with B-33 and B-34 strains of Bacillus brevis shows that there are deviations among these strains. The deviation in Bacillus brevis could be due to the stress effect of thiocyanate. This result supports that fatty acid synthesis depends highly on the environment.

• Analytical Science and Technology
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• v.8 no.4
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• pp.901-906
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• 1995

Studies on the chemical constituents from a Korean wild mushroom, Phellinus ribis, were carried out. A triterpenoid, two peroxysterols, and a chlorobenzene compound were isolated from the hexane soluble fraction of the methanol extract of dried fruiting bodies of the basidomycetes. Those compounds identifed were 3-hydroxy-20(29)-lupen-28-oic acid (betulinic acid), 5,8-epidioxyergosta-6,22-dien-3-ol(ergosterol peroxide), 5,8-epidioxyergosta-6,9(11),22-trien-3-ol (dehydroperoxyergosterol), and 1,2,4,5-tetrachloro-3,6-dimethoxybenzene. Structural studies were carried out on molecular species of a ceramide and cerebroside isolated from the chloroform soluble fraction of the methanol extract. For ceramide, the major component fatty acids were a-hydroxy fatty acid isomers of $C_{22:00}{\sim}C_{25:00};$ the predominant long-chain bases were trihydroxy sphinganine of $C_{17}{\sim}C_{18}$. The structure of a cerebroside containing mono-sugar was assumed that the long-chain base was $C_{19:2}$ sphingadienine; the major fatty acids were $C_{16}{\sim}C_{15}$ ${\alpha}$-hydroxy fatty acid isomers.

• Korean Journal of Microbiology
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• v.25 no.1
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• pp.67-72
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• 1987

Cellular fatty acid composition of eight strains, indluding six strains of Comamonas terrigena, and two type strains of Pseudomonas acidovorans, and P. testosteroni was determined by gas-liquid chromatography. Almost the same composition was found in all the strains tested, and hexadecanoic acid, hexadecenoic acid, and octadecenoic acid were accounted more than 70% of total fatty acid. However, P. testosteroni differed from C. terrigena and P. acidovorans by the presence of comparatively large amonuts of 2-hydroxy-hexadecanoic acid, and C. terrigena contained three to eight times as much tetradecanoic acid in P. acidovorans and P. testosteroni. According to the similarity values calculated on the basis of fatty acid composition, C. terrigena strains were divided into three groups differentiated in the requirement of growth factors, and C. terrigena, P. acidovorans, and P. testosteroni strains occupied separate position each other in the dendrogram.

• Journal of the Korean Society of Food Science and Nutrition
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• v.31 no.2
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• pp.177-183
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• 2002

Cerebroside fatty acids, sugars and long-chain sphingoid bases in raw soybean and soybean fermented foods (chongkukjang and deunjang) were analyzed using gas chromatography-mass spectrometry (GC-MS) and high-pH anion exchange chromatography with pulsed amerometric detection (HPAEC-PAD). Fatty acids of acid-hydrolyzed cerebrosides were derivatized to O-TMS methylester and analysed. The major fatty acids in raw soybean and chongkukjang cerebrosides were identified as 2-hydroxyhexadecanoic acid (16 : 0h), 2-hydroxydocosanoic acid (22 : 0h) and 2-hydroxytetracosanoic acid (24 : 0h). In the case of deunjang cerebroside, 24 : 0h (40.9%) and 22 : 0h (23.4%) were major fatty acids, but 16 : 0h, 23 : 0h, 25 : 0h and 26 : 0h were also detected. Long-chain sphingoid bases of acid-hydrolyzed cerebrosides from raw soybean, chongkukjang and deunjang consisted primarily of 4-tracts, 8-tracts-sphingadienine (dihydroxy base, d18 : 2$\Delta$$^{4trans, 8trans}$) and sis-tracts isomers of 4-hydroxy-sphingenine (trihydroxy base, tl8:1$\Delta$$^{4trans or cis}$) with much less amounts of phytosphingosine (tl8: 0) and isomers of sphingenine (d18 : 1). Although deunjang is a soybean food fermented by fungi and microorganisms for a long period, 2-hydroxyoctadec-3-enoic acid (18 : 1h) and branched 9-methyl-4,8-sphingadienine known as compositional cerebroside fatty acids in Aspergillus species were not detected. Mass spectrum for sugar derivatives in cerebrosides of soybean foods including raw soybean and fermented soybean showed that C-1 of glucose moiety was linked to ceramide backbone as like a monoglucosylceramide.

• Environmental Mutagens and Carcinogens
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• v.15 no.2
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• pp.140-147
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• 1995

For studying the effect of different dietary fats on carcinogenesis, fatty acid composition of membrane and lipid peroxidation were measured. Male Sprague-Dawley rats were fed on diet containing 15%(w/w) beef tallow or soybean oil. A single dose of 50 mg 2-AAF/kg B.W. was injected i.p. in each diet group 10 times. Rats were sacrifled after 1, 5, 10, and 15 weeks from the first injection. By 2-AAF injection, !ipid peroxidation increased slightly compared to control group. The rats fed on different fats had similar MDA production and those fed on soybean oil had slightly higher free radical concentration measured by ESR. In young rats, iipid peroxidation level was high and hydroxy radical production was higher in soybean oil group than in beef tallow group. With age, the lipid peroxidation values were decreased initially then increased. The fatty acid composition in microsomal membrane was reflected by dietary fatty acid composition. In soybean oil group, monoenoic acid was lower and polyunsaturated fatty acid was higher than beef tallow group. Linoleic acid contents showed the most discrepancy among groups. By 2-AAF treatment, iinoleic acid content and unsaturation index increased in soybean oil group. But in beef tallow group, there was no difference in fatty acid contents.