• Title/Summary/Keyword: Octadecenoic Acid

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Identification of Petroselinic Acid (Cis-6-octadecenoic Acid) in the Seed Oils of Some of the Family Umbelliferae (Panax schinseng, Aralia continentalis and Acanthopanax sessiliflorus) by GC-MS, IR, $^1H-and$ $^13C-NMR$ Spectroscopic Techniques

  • Kim, Seong-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.4
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    • pp.323-331
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    • 2005
  • Fatty acid compositions of the seed oils of P. schinseng, A. continentalis and A. sessiliflorus, were analyzed by gas chromatography (GC) equipped with a capillary column. A large unusual peak was observed just before the peak corresponding to oleic acid $(cis-9-C_{18:1})$. This unknown fatty acid was isolated by silver ion chromatography and then derivatized into the picolinyl ester. The mass spectrum of the picolinyl ester showed molecular ion at m/z=373 with other diagnostic ions such as m/z=178, 218, 232, 246, 274, 288, 302 and 344. Characteristic absorption peaks at $720\;cm^{-1}$, $1640\;cm^{-1}$ and $3010\;cm^{-1}$ in IR spectrum indicated the presence of cis-configurational double bond in the molecule. The $^1H-NMR$ spectrum of this acid gave two quintets centered at ${\delta}1.638$ (2H, C-3) and ${\delta}1.377$ (2H, C-4), and two multiplets centered at ${\delta}2.022{\sim}2.047$ (2H, C-5) and ${\delta}2.000{\sim}2.022$ (2H, C-8), and multiplet signals of olefinic protons centered at ${\delta}5.3015{\sim}5.3426$ (C-6, J=9.5 Hz) and ${\delta}\;5.3465{\sim}5.3877$ (C-7, J=9.5 Hz). The $^13C-NMR$ spectrum showed 18 carbon resonance signals including an overlapped signal at ${\delta}29.7002$ for C-12 and ${\delta}29.6520$ for C-13 (or they can be reversed), and other highly resolved signals at ${\delta}33.950$, ${\delta}24.558$, ${\delta}26.773$ and ${\delta}27.205$ due to C-2, C-3, C-5 and C-8 of a ${\Delta}^6-octadecenoic$ acid, respectively. From analysis results this unknown fatty acid could be identified as cis-6-octadecenoic acid. The seed oils of P. schinseng and A. sessiliflorus contained petroselinic acid (59.7%, 56.0%), oleic acid (18.3%, 6.1%) and linoleic acid (16.2%, 30.4%) with small amount of palmitic acid (3.0%, 3.1%) while the seed oil of A. continentalis comprised mainly oleic acid (30.2%), petroselinic acid (29.0%), linoleic acid (24.1%) and palmitic acid (13.1%).

Effects of Treatment with the Extract from the Root Bark of Morus alba on the Cell Composition and the Shape Change of Microorganisms (상백피 추출물이 미생물의 균체성분 및 형태 변화에 미치는 영향)

  • 박욱연;성희경;목종수;장동석
    • Journal of Food Hygiene and Safety
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    • v.10 no.3
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    • pp.147-153
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    • 1995
  • The ethanol extract from the root bark of Morus alba showed the strongest antimicrobial activity on the growth of almost all the tested microorganisms which were food-borne pathogens and food-related microorganisms. Therefore, fatty acid composition, amino acid composition and shape change of microorganisms treated with the ethanol extract from the root bark of Morus alba were examined. In effects of treatment with the ethanol extract on the fatty acid compositions of B. subtilis, S. aureus and E. coli, fatty aicd compositions such as hexadecanoic acid (16:0) and octadecanoic acid (18:2) of the tested strains were increased but pentadecanoic acid (15:0) heptadecanoic acid (17:0) and acid (16:1) and octadecenoic acid (18:1) of E. coli were decreased. The ethanol extract did not significantly affect the aminn acid composition of the tested strains. Transmission electron micrographs of microorgani는 treated with the ethanol extract exhibited morphological changes that irregularly contracted cell surface in S. aureus and destructed cell walls in B. subtilis and E. coli.

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Microbial bioconversion of natural Philippine nut oils into a value-added hydroxy fatty acid, 7,10-dihydroxy-8(E)-octadecenoic acid (미생물 생변환을 통한 필리핀 너트유로부터 기능성 지방산 7,10-dihydroxy-8(E)-octadecenoic acid 생산)

  • Dasangrandhi, Chakradhar;Ellamar, Joel B.;Kim, Young Soon;Kim, In Hwan;Kim, Hak-Ryul
    • Korean Journal of Food Science and Technology
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    • v.49 no.1
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    • pp.28-34
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    • 2017
  • Biocatalytic modification of natural resources can be used to generate novel compounds with specific properties, such as higher viscosity and reactivity. The production of hydroxy fatty acids (HFAs), originally found in low quantities in plants, is a good example of the biocatalytic modification of natural vegetable oils. HFAs show high potential for application in a wide range of industrial products, including resins, waxes, nylons, plastics, lubricants, cosmetics, and additives in coatings and paintings. In a recent study, Pseudomonas aeruginosa strain PR3 was used to produce 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) from oleic acid. This present study focused primarily on the utilization of three natural nut oils obtained from the Philippines -pili nut oil (PNO), palm oil (PO), and virgin coconut oil (VCO)- to produce DOD by P. aeruginosa strain PR3. Strain PR3 produced DOD from PNO and PO only, with PNO being the more efficient substrate. An optimization study to achieve the maximum DOD yield from PNO revealed the optimal incubation time and medium pH to be 48 h and 8.0, respectively. Among the carbon sources tested, fructose was the most efficiently used, with a maximum DOD production of 130 mg/50 mL culture. Urea was the optimal nitrogen source, with a maximum product yield of 165 mg/50 mL culture. The results from this study demonstrated that PNO could be used as an efficient substrate for DOD production by microbial bioconversion.

Cellular fatty acid composition in comamonas terrigena (Comamonas terrigena의 균체지방산 조성)

  • 하덕모;안병학
    • 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.

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Constituents of Antimutagenic Factor from Brown Rice (현미의 항돌연변이 활성물질의 구성성분)

  • Chun, Hyang-Sook;Moon, Tae-Wha;Kim, In-Ho
    • Applied Biological Chemistry
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    • v.38 no.5
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    • pp.478-483
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    • 1995
  • To investigate the constituents of antimutagenic factor from brown rice, methanol extracts were fractionated into ether, ethylacetate, buthanol and aqueous fractions. The ether fractions showed distinct antimutagenic effect and active spot were selected by silica gel chromatography. The specific activity of active spot decreased with isolation of the active components from the methanol extract. Qualitative analyses of the active spot by using various spraying reagents revealed that ninhydrin and orcinol did not develop colored reactions. But, ferric chloride, 2,7-dichlorofluorescein, antimony pentachloride, phosphomolybdic acid, bromothymol blue and rhodamine 6G led to colored reactions. These results suggested that the consitituents of active material were neither polar nor nitrogen-containing compounds and that they may contain phenolic compounds and fatty acid derivatives. Main compounds of the active spot were analyzed to be o-hydroxy benzyl alcohol(saligenin), octanoic acid(caprylic acid), 9,12-cis-octadecadienoic acid(linoleic acid), 11-cis-octadecenoic acid(oleic acid), hexadecanoic acid(palmitic acid), 1H-indole-2-carboxylic acid and 1,2-benzenedicarboxylic acid(phthalate) in GC/Mass spectrum, and antimutagenicity of these active compounds using standard regeant was reconfirmed in S. typhimurium reversion assay.

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Fragrance and Metabolite Components of Flowers from Korean Native Apocynum lancifolium Russanov

  • Kim, JoHoon;Lee, JaeMyun;Park, YeGun;Ann, SeoungWon;Baik, JungAe
    • Journal of Environmental Science International
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    • v.30 no.10
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    • pp.879-889
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    • 2021
  • This study characterizes the volatile aromatic and metabolite components of domestic native Apocynum lancifolium blossom. The accurate characterization of fragrances collected from the blossom was carried out using gas chromatography-mass. A total of 70 chemical components were identified, including ketones of acetophenone (29.22%), phenylethyl alcohol (10.54%), methyl-benzenemethanol (8.43%), benzyl alcohol (7.97%), natural bicyclic sesquiterpene types of caryophyllene (6.08%), gurjunene (6.20%), humulene (1.90%), and ocimene (1.04%). Overall, the content of ketones, alcohols, and terpenes was higher than that of others. The major metabolite components were pentanoic acid, malic acid, fructofuranoside, quinic acid, tagatose, sorbose, galactose, inositol, galactaric acid, glucopyranoside, and octadecenoic acid.

Bacteriological Characteristics of Plesiomonas shigelloides Isolated from the Aquatic Environments and Diarrheal Patients in Pusan Area (부산 근교의 수계환경과 설사환자로 부터 분리된 Plesiomonas shigelloides 의 세균학적 특성)

  • 성희경;장동석;이원재;김용호;이정화
    • Korean Journal of Microbiology
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    • v.31 no.2
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    • pp.105-112
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    • 1993
  • Plesiomonas shigelloides distributed in the aquatic systems was isolated and identified in this study and compared with the c1inica] isolates in view of their physiological characteristics, Biochemica] charactristics of the isolates of P. shigelloides one sample taken from Gupo and two samples taken from Mu]gum, were studied. However, none was isolated in Haeundae, Dadaepo, Kangdong and Nakdong estuary. The isolated bacteria had an optimum growth condition in peptone water of $25~35^{\circ}C$, pH 7.5-8.0 and 1% NaCI concentration. The cell grew most properly on the selective enrichment media which were made from adding inositol to peptone water. DNase was s]owly produced and the results were different from those of other studies. The components of the fatty acid were 3% of 3-hydroxy]ated fatty acid containing $C_{12}~C_{18}$. 0-10% cyclopropane ($C_{17:0}$), 25~30% hexadecanoic acid ($C_{16:0}$), 32~43% hexadecenoic acid ($C_{16:1}$), 1~2% octadecanoic acid ($C_{16:0}$), and 9~14% octadecenoic acid ($C_{18:1}$). Bacterio]ogica] characteristics, susceptibility of antibiotics, and the components of fatty acid of the c1inica] isolates were similar to those of the strains isolated from the aquatic systems. The strains isolated from c1inica] sources degraded lactose more fast than those isolated from the aquatic systems. There existed resistant bacteria to chlorampenicol in the strains from patients, but there were no resistant bacteria in the strains from the aquatic systems. The components of fatty acid of the clinical isolates were 0~2% $C_{17:0 cyclo}$ and 2~3% $C_{18:0}$, but those of the strains from the aquatic systems were 2~10% and 1~2%, respectvely, which showed the quantitative difference between both components.

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Two-Stage Microbial Biotransformation for the Production of 6-Dodecen-4-olide (Butter Lactone) from Plant Oils Containing Unsaturated Fatty Acids (불포화 지방산 함유 식물유를 이용한 천연 6-Dodecen-4-oilde (Butter Lactone) 생산을 위한 2-Stage Microbial Biotransformation)

  • Kwon, Soon-Hyang;Kim, Kyoung-Ju;Kim, Yang-Hwi Augustine
    • 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).

Nutritional Analysis of Wild Conyza canadensis L. Extract (야생 망초(Conyza canadensis L) 추출물의 영양성분 분석)

  • Kim, Hong Yul;Song, Hyun Sook;Lee, Geo Lyong
    • Journal of Naturopathy
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    • v.11 no.2
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    • pp.100-108
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    • 2022
  • Background: It has been reported that various substances exist in wild Conyza canadensis, but I think that the overall compositional analysis is still insufficient. Purposes: This study was to set extraction conditions and search for various nutritional components in the wild C. canadensis. Methods: Various extracts were extracted and analyzed using different analytical instruments to suggest and study the conditions for component analysis. Results: As for the general nutritional components of C. canadensis leaf extract, carbohydrates were 46.4%, crude protein 26.5%, moisture 16.3%, raw meal 9.5%, and natural fat 1.2%. The dietary fiber content was 30.76%. Free fructose, glucose, sucrose, and maltose were separated, and the amount of fructose was as high as 4,144.2 mg/100 g. In addition, we found 64.87 mg/g of K, 4.09 mg/g of P, 1.77 mg/g of Mg, and 0.16 mg/g of disodium in the extracts. A total of 20 fatty acids have appeared. In addition, unsaturated fatty acids (octadecenoic acid, octadecadienoic acid, and linolenic acid) were detected. Linolenic acid was high at 54.1%. The saturated fatty acid content was 0.39 g/100 g, and the trans fatty acid content was 0.01 g/100 g. No cholesterol was found in the plant. Riboflavin was at 0.4 mg/100 g, with six essential amino acids and 24 amino acids. Conclusions: As a result of the primary research on the plant, various nutritional and functional ingredients exist in the extract, and natural healing uses are available.

Whole Cell Bioconversion of Ricinoleic Acid to 12-Ketooleic Acid by Recombinant Corynebacterium glutamicum-Based Biocatalyst

  • Lee, Byeonghun;Lee, Saebom;Kim, Hyeonsoo;Jeong, Kijun;Park, Jinbyung;Park, Kyungmoon;Lee, Jinwon
    • Journal of Microbiology and Biotechnology
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    • v.25 no.4
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    • pp.452-458
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    • 2015
  • The biocatalytic efficiency of recombinant Corynebacterium glutamicum ATCC 13032 expressing the secondary alcohol dehydrogenase of Micrococcus luteus NCTC2665 was studied. Recombinant C. glutamicum converts ricinoleic acid to a product, identified by gas chromatography/mass spectrometry as 12-ketooleic acid (12-oxo-cis-9-octadecenoic acid). The effects of pH, reaction temperature, and non-ionic detergent on recombinant C. glutamiucm whole cell bioconversion were examined. The determined optimal conditions for production of 12-ketooleic acid are pH 8.0, 35℃, and 0.05 g/l Tween80. Under these conditions, recombinant C. glutamicum produces 3.3 mM 12-ketooleic acid, with a 72% (mol/mol) maximum conversion yield, and 1.1 g/l/h volumetric productivity in 2 h; and 3.9 mM 12-ketooleic acid, with a 74% (mol/mol) maximum conversion yield, and 0.69 g/l/h maximum volumetric productivity in 4 h of fermentation. This study constitutes the first report of significant production of 12-ketooleic acid using a recombinant Corynebacterium glutamicum-based biocatalyst.