• 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).

• Archives of Pharmacal Research
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• v.26 no.3
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• pp.207-209
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• 2003

A new unsaturated hydroxy acid was isolated from the stem bark extract of Albizzia julibrissin through repeated silica gel and Sephadex LH-20 column chromatography. The chemical structure of the new acid was determined as (E)-4-hydroxy-dodec-2-enedioic acid on the basis of several spectral data including 2D-NMR. The stereochemical feature of the double bond was determined to be E on the basis of the coupling pattern of related proton signals in the $^1H-NMR$ and COSY 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.

• 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 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.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.369.3-369.3
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• 2002

Albizzia julibrissin Durazz (Leguminosae) is a small domed to flat-topped, spreading tree with smooth. gray-brown bark and doubly pinnate leaves. It grows abundantly in Korea. The dried stem bark of A. julibrissin is used as a tonic in China, Japan and Korea. From the stem bark of A. ju/ibrissin, a new unsaturated hydroxy fatty acid was isolated and characterized as 4-hydroxy-dodec-2E-enedioic acid on the basis of several data including 2D-NMR. (omitted)

• Journal of Microbiology and Biotechnology
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• v.14 no.6
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• pp.1217-1226
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• 2004

A psychrotrophic bacterial strain, Pseudomonas fluorescens BM07, synthesized unsaturated fatty acids (UFA) from fructose in response to lowering of growth temperature, and incorporated them into both polyhydroxyalkanoic acid (PHA) and membrane lipid. The blocking of PHA synthesis by adding 5 mM 2-bromooctanoic acid to the growth medium, containing 70 mM fructose, was found to be a useful means to profile the composition of membrane lipid by gas chromatography. As the growth temperature changed from 35 to $50^{\circ}C$, the total content of two UFA, 3-hydroxy-cis-5­dodecenoic acid ($C_{12:1}$) and 3-hydroxy-cis-7-tetradecenoic acid ($C_{14:1}$), in PHA increased from 31 to 44 $mol\%$. The growth at lower temperatures also led to an increase in the level of two major UFA, palmitoleic acid (C16:1 cis9) and cis-vaccenic acid (C18:1 cis11), in membrane lipid. A fraction of these membrane-lipid UFA was converted to their corresponding cyclopropane fatty acids (CFA). The CFA conversion was a function of culture time, exhibiting biphasic increase before and after entering the stationary phase. However, pH changes in growth media had no effect on the CFA conversion, which is contrary to the case of E. coli reported. The cells grown at $30^{\circ}C$ responded to a cold shock (lowering the medium temperature down to $10^{\circ}C$) by increasing the level of C16:1 cis9 and C 18: I cis II up to that of $10^{\circ}C$-grown control cells and concomitantly decreasing the relative level of cis-9,10­methylenehexadecanoic acid (the CFA converted from C16:1 cis9) from 14 to 8 $mol\%$, whereas the 10-grown cells exhibited little change in the lipid composition when exposed to a warmer environment of $30^{\circ}C$ for 12 h. Based on this one- way response, we suggest that this psychrotrophic strain responds more efficiently and sensitively to a cold shock than to a hot shock. It is also suggested that BM07 strain is a good producer of two unsaturated 3-hydroxyacids, $C_{12:1}\;and\;C_{141:1}$.

• KSBB Journal
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• v.24 no.1
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• pp.41-46
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• 2009

Vegetable oils are desirable inexpensive feedstocks for various bioproducts. The content of unsaturated fatty acids such as oleic and linoleic acids are 22% and 55% for soybean oil, 26% and 60% for corn oil, and 61% and 21% for canola oil, respectively. Keto and hydroxy fatty acids are useful industrial chemicals, used in plasticizer, surfactant, lubricant and detergent formulations because of their special chemical properties such as higher viscosity and reactivity compared with other fatty acids. In this study, a microbial isolate, Flavobacterium sp. strain DS5 (NRRL B-14859), was used to convert oleic acid to 10-ketostearic acid (10-KSA) via 10-hydroxystearic acid (10-HSA). Two bioconversion products, 10-KSA and 10-HSA, were quantitatively and qualitatively analyzed using gas chromatography, gas chromatography-mass spectrometry, and $^1H-$ and $^{13}C$-nuclear magnetic resonance. The maximum production of 10-KSA and 10-HSA in flask cultures were 3.4 g/L and 0.5 g/L, respectively. The optimum concentrations of glucose and yeast extract, addition time and volume of oleic acid for 10-KSA production were less than 20 g/L, more than 5 g/L, 18 hand 0.3 ml/50 ml, respectively.

• 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.

• Applied Biological Chemistry
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• v.34 no.2
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• pp.102-109
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• 1991

Quality of three kinds of honey from acacia, chestnut and polyflower sources, was evaluated by physicochemical and GC-MS analysis in respect to some chemical composition. The average contents of moisture, ash, HMF(hydroxy methyl furfurol) and free acidity were 19.7% , 0.028% , 18.28mg/kg and 8.85meq/kg , respectively, in acacia honey, 19.1% , 0.05% , 18.47mg/kg and 10.24 meq/kg , respectively, in polyflower honey, and 18.9% , 0.050% , 20.21mg/kg, 12.28meq/kg respectively, in chestnut honey. The average contents of glucose and fructose ranged from 31.0 to 32.0% and from 35.0 to 36.0% , respectively, in all three kinds of honey. The average ratio of fructose to glucose was 1.14 in all three kinds of honey. Fatty acid composition in honey identified by GC-MS analysis was dodecanoic acid, 10-hydroxy-2-decanoic acid, 6,9-undecadienoic acid, tetradecanoic acid, 12-(acetyl oxy) -9-octadecenoic acid and 14-octadecenoic acid. The content of 10-hydroxy-2-decenoic acid was about 10% in three kinds of honey.