• Journal of Plant Biotechnology
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• v.36 no.2
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• pp.97-105
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• 2009

Seed storage lipids of plants, essential for seed germination as energy supplier, have been used for humankind and animal as nutrition sources. Fatty acids of vegetable oils have the characters appropriate for industry based on their chain length, the position and the number of double bonds. So they are used as raw materials for lubricants, cosmetics, soaps, paints and plastics or as energy source such as bio-diesel. However, there is a limit that applies vegetable oils from typical oil crops for industrial uses, mainly because of the mixture of five common fatty acids. Therefore, identification of unusual fatty acids for industrial uses from diverse plant resources and metabolic engineering to produce unusual fatty acids have been carried out in Arabidopsis as a model for the study of oilseed biology. Here, we discuss the unusual fatty acids for industrial uses, the genes synthesizing them in lipid metabolism, and the current limits in production of transgenic plants accumulating unusual fatty acid in their seeds. In addition, we describe our work on metabolic engineering of Brassica napus for the production of the unusual fatty acid ricinoleic acid in the seed, because of its industrial uses.

• Natural Product Sciences
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• v.1 no.1
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• pp.5-9
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• 1995

The metabolites of marine mollusk Mytilus edulis were isolated and characterized, revealing the presence of the rare free fatty acids and proteinogenic amino acids together with a non-proteinogenic free amino acid, taurine. The free fatty acids in this organism were particularly interesting for the presence of both unusual n-6 acid [20:4 (n-6)] and triple bond containing acid (2,5-octadecadiynoic acid). In addition to the proteinogenic amino acids commonly found in proteins, non-proteinogenic free amino acid taurine was isolated and the structure was determined by its physicochemical properties. Recently taurine has been given much interest in the molecular level because of diverse biological activities and the medicinal properties. Furthermore, the result of the analyses of analyses of free amino acids showed that glycine, glutamic acid, serine and alanine, which were considered to be related to the taste of this organism, are predominantly present.

• Applied Biological Chemistry
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• v.44 no.1
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• pp.20-23
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• 2001

Several unusual fatty acids including myristic acid (14 : 0) and lauric acid (12 : 0) were investigated in the Iris family and other related plants. Especially the roots of Iris tecorum contained 75.9% myristic acid in total fatty acid contents and that of Iris germanica contained 57% myristic and 15.5% lauric acid (12 : 0) whereas 10.7% lauric acid and 9.5% capric acid (10 : 0) were detected in the roots of iris ensata as compared to the total fatty acid contents. The total fatty acid contents in the seeds of Foeniculi fructus and Torilis japonica was relatively higher 193.3 mg/g dry wt and 128.2 mg/g dry wt, respectively. 64.5% linoleic acid (18 : 2) and 48.9% ${\alpha}-linolenic$ acid (18 : 3) were observed in the seeds and leaves of iris tectorum whereas its lateral roots contained 9.5% caprylic acid (8 : 0) and 8.6% capric acid. The percentage of myristic acid of the total fatty acid in the immature seeds of iris tectorum and Iris germanica was 10.8% and 15.6%, respectively.

• Food Science and Biotechnology
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• v.15 no.1
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• pp.107-111
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• 2006

Kernel oils of Lindera erythrocarpa seeds had high level of unusual fatty acid. Picolinyl ester of this unknown fatty acid showed molecular ion at m/z = 317 with other diagnostic ions such as m/z = 151, 191 (40 amu between two peaks), 204, and 218 on GC-MS. Characteristic peak at $720\;cm^{-1}$ appeared in IR spectrum. In $^1H-NMR$ spectrum both methylene protons at C-3 and C-6 resonated at ${\delta}2.309$ and ${\delta}2.012$, and methine protons of double bond resonated in lower magnetic field centered at ${\delta}5.296$ (C-4) and ${\delta}5.387$ (C-5) as multiplet (J = 9.7Hz). In $^{13}C-NMR$, signals at ${\delta}22.669$ and ${\delta}27.048$ were due to C-3 and C-6 of ${\delta}^4$-monoenoic acid. Results obtained from spectroscopic measurements confirmed unknown fatty acid as cis-4-tetradecenoic acid (cis-4-$C_{14:1}$). Main fatty acid components of oils were cis-4-$C_{14:1}$ (44.5-45.1%), oleic acid ($C_{18:1}$), 20.4-21.3%), and lauric acid ($C_{12:0}$, 11.6-12.4%), along with trace amounts of cis-4-$C_{12:1}$ and cis-4-$C_{16:1}$.

• Journal of the Korean Wood Science and Technology
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• v.34 no.5
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• pp.104-110
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• 2006

We investigated why aspen extractives are more resistant in kraft pulping than pine extractives. Residual extractives content in aspen kraft pulps were 0.5~1.1% compared with 0.1~0.2% in pine pulps. This different response arises from the different composition of extractives in wood chips. Resin acids in pine were almost completely removed in kraft pulping but those are not existence in aspen. Slower saponification of aspen steryl esters resulted from different chemical structure of aspen steryl esters. Main sterols in aspen steryl esters were 24-methyl cyclolanostenol which was highly resistant to alkaline hydrolysis with its characteristic steric hindrance. Sterols in aspen were not well removed in kraft pulping. The relative composition of sterol in aspen kraft pulps was increased with increasing pulping time. The presence of fatty acids in aspen kraft pulps is considered to unusual. Fatty acids in alkaline are supposed to be well ionized and removed well in the washing stage. Nevertheless, there were significant amount of fatty acids remaining in aspen kraft pulps.

• Journal of Plant Biotechnology
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• v.37 no.2
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• pp.220-227
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• 2010

Fatty acids in seed oil from plants are essential for human nutrients and have been used for industrial purpose. The growing demands of seed oil as food resources and feedstocks for industrial uses have attempted to modify fatty acid composition and to increase oil content in transgenic plants. However, production of unusual fatty acids in transgenic plants are limited, which is not synthesized the level same as original plants. This bottleneck was common for production of several unusual fatty acids in transgenic plants and suggests that there is different for substrate preference in oil metabolic pathway enzymes between host oil plants and original wild plants. Review of acyltransferases involved in acyl-editing and seed oil accumulation of oil plant and wild-plant producing unusual fatty acids will design strategies to maximize the production of unusual fatty acids in transgenic plants. In here, we identified eleven acyltransferase genes in castor based on sequence homology, which will be useful to increase hydroxy unusual fatty acids in transgenic plants.

• Journal of the Korean Applied Science and Technology
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• v.18 no.1
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• pp.67-77
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• 2001

In search for several fatty acid with unusual structure in vegetable oils, we have found that unknown peaks were shown on GLC in the analysis of fatty acids of the lipids from the pulp of ripened jujube (Zizypus jujuba var. inermis) fruits. These fatty acids were identified as a series of cis-monoenoic acids with ${\omega}-5$ double bond system such as $C_{14:1{\omega}5}$, $C_{16:1{\omega}5}$ and $C_{18:1{\omega}5}$, including ${\omega}-7$ fatty acid as $C_{16:1{\omega}7}$ and $C_{18:1{\omega}7}$, by GLC, solid-phase extraction silver ion-column chromatographic, GLC-mass spectrometric and IR techniques. First of all, total fatty acid methyl esters were resolved into saturated and branched fatty acid, monoenoic acid, dienoic acid, and trienoic acid fraction, respectively, with 100% dichloromethane (DCM), DCM/acetone (9:1, v/v) 100% acetone, and acetone/ acetonitrile (97:3, v/v) solvent system. Unknown fatty acids were included in the monoenoic fraction and were confirmed to have cis-configuration by IR. Picolinyl esters of monoenoic fatty acids gave distinct molecular ion peak and dominant diagnostic peaks, for example, m/z 317, 220 and 260 fragment for $cis-C_{14:1{\omega}5}$, m/z 345, m/z 248 and 288 fragment for $cis-C_{16:1{\omega}5}$ and m/z 373, m/z 276 and 316 fragment for $cis-C_{18:1{\omega}5}$. In this way the occurrence of $cis-C_{16:1{\omega}7}$ and $cis-C_{18:1{\omega}7}$ could be deduced from the appearance of prominent fragments as m/z 345, 220 and 260, and m/z 373, 248 and 280. Level of total ${\omega}-5$ fatty acids amounted to about 30% in the fatty acid composition with the predominance of $C_{16:1{\omega}5}$ $ (18.7{\sim}25.0%)$, in the semi-ripened and/or ripened samples collected in September 14 ($C_{16:1{\omega}5}$ ; 18.7%, $C_{14:1{\omega}5}$ ; 3.6% and $C_{18:1{\omega}5}$ ; 3.0%), September 22 ($C_{16:1{\omega}5}$ ; 25.0%, $C_{14:1{\omega}5}$ ; 1.4% and $C_{18:1{\omega}5}$ ; 2.6%), and October $7 (C_{16:1{\omega}5}$ ; 24.7%, $C_{14:1{\omega}5}$ ; 7.7% and $C_{18:1{\omega}5}$ ; 2.5%). However, the lipids extracted from unripened jujube in July and August contain these unusual fatty acids as low as negligible. It could be observed that the level of ${\omega}-5$ fatty acids in the pulps increased sharply with an elapse of ripening time of jujube fruits. Other monoenoic fatty acids with ${\omega}-7$ series, $C_{16:1{\omega}7}$ (palmitoleic acid) and $C_{18:1{\omega}7}$ (cis-vaccenic acid) could be detected. And in the lipids of the kernel and leaf of jujube, none of ${\omega}-5$ fatty acids could be detected.

• Bulletin of the Korean Chemical Society
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• v.23 no.12
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• pp.1778-1784
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• 2002

Novel membrane lipids containing the unusual very long chain fatty $acid{\alpha}{\omega}-1316-dimethyloctacosanedioate$, dimethyl. Ester (DME C30) was isolated and purified from thermophilic anaerobic eubacterium, Thermoanaerobacter ethanolicus. Structures of the lipids containing the bifunctional fatty acyl components were proposed by various analyses such as $^1H,\;^{13}C,\;^{31}P$ nuclear magnetic resonance (NMR), Fourier transform infrared(FTIR) spectroscopy, gas chromatography/mass spectrometry (GC/MS) and fast atom bombardment mass spectrometry (FAB/MS). Combined with the GC/MS, $^1H,\;and\;^{13}C$NMR data, we confirmed that the head groups of the lipids contained the glycerol and/or glucosamine molecules. $^{31}P$ NMR spectrum also showed that the lipids contained phosphate in a phosphodiester linkage. The proposed structures of these novel lipid components were the ones in which two head groups were linked by the membrane spanning fatty acyl component(DME C30)and regular chain fatty acids on glycerol moiety of each head group.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.38 no.2
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• pp.139-145
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• 2012

There is a unique type of fatty acid in the hair surface. 18-methyleicosanoic acid (18-MEA) is an unusual anteiso fatty acid covalently linked to the outermost surface of hair cuticle. A layer of 18-MEA is located in the upper ${\beta}$-layer of the CMC that is responsible for the low surface energy and low friction resistance of the hair's outer surface. The high mobility of 18-MEA molecule facilitates spreading of extraneous lipid by decreasing interfacial shear strength. In this study, we introduced N-hydroxyl succinimidyl ester functional group to the one end of C10 - 40 isoalkyl acid for regenerating hair surface with covalently bound fatty acid layer. The re-hydrophobicization of hair surface has been investigated by contact angle measurement. The inner moisture content of hair at different levels of humidity (40, 55, 70 %RH) was measured by electric moisture analyzer. Treatment with Hydroxysuccinimidyl C10 - 40 Isoalkyl Acidate (HCIA) was supposed to make hair surface smoother by filling the cracks between cuticles with covalently bound fatty acid monomolecular layer like cuticle glue. This glue effect was also confirmed with line profile of AFM images. Therefore, the moisture and structural components of inner hair were not easily flown out and the optimum moisture content could be kept constantly though the outside humidity level was changed. The lateral force microscopy (LFM) by using atomic force microscope showed that the friction force of hair surface treated with HCIA was decreased. It also showed the constantly sustained friction value even after shampooing repeated 15 times.

• Korean Journal of Pharmacognosy
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• v.6 no.1
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• pp.15-21
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• 1975

The free fatty acids were prepared from the ethereal fraction of Panax ginseng. The prepared acids were methylated with diazomethzne. The methyl esters of saturated and unsaturated fatty acids were separated by the means of mercuric acetate method and column chromatography. The separated methyl esters were gaschromatographed and analyzed. The obtained conclusions were as follows. 1. The root of six-year old Korean Panax ginseng contains 0.28% of free fatty acids. 2. It was found that 24 kinds of free fatty acids existed in Panax ginseng. Among them, 22 kinds of free fatty acids were indentified by the gas chromatogram and the graphical method but the rest, 2 kinds of them were not identified by the only gas chromatographical data. The amount of each free fatty acid which was not identified was predominant and they were supposed to be unusual free fatty acids which would not commonly exist in nature. These results were shown in Table III. 3. $L_{EE}$ and $L_{EE}$ reported that n18:3 existed in Panax ginseng. However, in this experiment, n18:3 did not exist in Panax ginseng, and instead, peak XVI appeared between n18:2 and n18:3 as shown in Fig. 9.