• Title/Summary/Keyword: Furan fatty acid

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Optimal Production of a Novel Furan Fatty Acid from 7,10-dihydroxy-8(E)-octadecenoic Acid by Heat Treatment

  • Ellamar, Joel B.;Sohn, Hye-Ran;Kim, Hak-Ryul
    • Current Research on Agriculture and Life Sciences
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    • v.31 no.1
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    • pp.25-29
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    • 2013
  • As a specialty oil, furan fatty acids have gained special attentions since they are known to play important roles in biological systems including human. Although several studies reported chemical synthesis of furan fatty acids, their synthesis consisted of complicated chemical multistep with chemical catalysts. Recently, a simple one-step heat treatment method was developed to produce a novel furan fatty acid, 7,10-epoxy-octadeca-7,9-dienoic acid (7,10-EODA) from a dihydroxyl fatty acid 7,10-dihydroxy-8(E)-octadecenoic acid (DOD). In this report we studied about optimization of environmental conditions for the maximum production of 7,10-EODA from DOD by heat treatment. Production of 7,10-EODA was maximized at over $85^{\circ}C$ for at least over 48 hour in hexane. Solvent volume for maximum production should be over 300 mL per 10 mg DOD.

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Furan in Thermally Processed Foods - A Review

  • Seok, Yun-Jeong;Her, Jae-Young;Kim, Yong-Gun;Kim, Min Yeop;Jeong, Soo Young;Kim, Mina K.;Lee, Jee-yeon;Kim, Cho-il;Yoon, Hae-Jung;Lee, Kwang-Geun
    • Toxicological Research
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    • v.31 no.3
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    • pp.241-253
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    • 2015
  • Furan ($C_4H_4O$) is a volatile compound formed mostly during the thermal processing of foods. The toxicity of furan has been well documented previously, and it was classified as "possible human carcinogen (Group 2B)" by the International Agency for Research on Cancer. Various pathways have been reported for the formation of furan, that is, thermal degradation and/or thermal rearrangement of carbohydrates in the presence of amino acids, thermal degradation of certain amino acids, including aspartic acid, threonine, ${\alpha}$-alanine, serine, and cysteine, oxidation of ascorbic acid at higher temperatures, and oxidation of polyunsaturated fatty acids and carotenoids. Owing to the complexity of the formation mechanism, a vast number of studies have been published on monitoring furan in commercial food products and on the potential strategies for reducing furan. Thus, we present a comprehensive review on the current status of commercial food monitoring databases and the possible furan reduction methods. Additionally, we review analytical methods for furan detection and the toxicity of furan.

Effect of Roasting Condition and Cold-pressed Flaxseed (Linum usitatissimum L.) oil on Fatty Acid Composition and Volatile Compound (볶음조건과 저온압착이 아마씨유(Linum usitatissimum L.)의 지방산 조성 및 휘발성 성분에 미치는 영향)

  • Won, Sae Bom
    • Journal of Convergence for Information Technology
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    • v.10 no.11
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    • pp.177-184
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    • 2020
  • The objective of this study was to investigate the effect of cold-pressed flaxseed oil through the roasting temperature (unroasted and roasted at 150℃ and 200℃) and time (10 and 20 min) on the chemical changes. Cold-pressed flaxseed oil extraction yield was calculated with respect to the roasted process and total phenolic content, fatty acid composition, and volatile compound were analyzed. The extraction yield was increased in the roasted oil compared to the unroasted oil. Total phenolic content was significantly higher in oil from the roasted at 150℃ for 20 min compared to other roasting condition. Fatty acid composition was not affected by the extraction process. The content of aldehyde, ketone, furan, and pyrazine was higher than in the roasted at 200℃ compared to the unroasted and roasted at 150℃. These findings suggest that cold-pressed flaxseed oil extracted from the roasted at 150℃ for 20 min may be considered acceptable for safe extraction process.

Components in Commercial Douchi-a Chinese Fermented Black Bean Product by Supercritical Fluid Extraction

  • Kim, Joo-Shin;Chung, Hau-Yin
    • Preventive Nutrition and Food Science
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    • v.13 no.1
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    • pp.12-17
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    • 2008
  • Douchi, a popular seasoning agent in Chinese dishes prepared by the Aspergillus oryzae fermentation of black beans, was subjected to supercritical fluid extraction (SFE) and gas chromatography-mass spectrometry analysis for its volatile components. A total of 73 components were identified in two commercial brands, which were positively confirmed and quantified. Among the common components in the two brands were 18 acids, 12 alcohols, 11 aldehydes, 9 esters, 1 furan, 11 other oxygen-containing compounds, 4 pyrazines, 2 pyridines and 5 miscellaneous compounds. The most abundant components found were acetic acid, benzoic acid, 2,6-dimethylpyrazine, 2-piperidinone, 3-methylbutanoic acid, maltol, 4-ethylphenol, 2-methylpropanoic acid, butanoic acid, 2-pyrrolidinone, all fatty acids and some esters.

Sensitive and Mild Fluorogenic Reagents for Biogenic Carboxylic Acids in HPLC

  • Ushijima, Tamano;Saito, Mikihiko;Sasamoto, Kazumi;Ohkura, Yosuke;Ueno, Keiyu
    • Analytical Science and Technology
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    • v.8 no.4
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    • pp.545-551
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    • 1995
  • Five acid hydrazides as precolumn fluorescence derivatization reagents for carboxylic acids in HPLC, which have the benzofuran or benzothiazole moiety conjugated to a furan, thiophene or oxazoline ring, were synthesized and examined in view of reactivity, separability and sensitivity. Of these hydrazides, 2-(5-hydrazinocarbonyl-2-oxazolyl)-5,6-dimethoxybenzothiazole (BTOH) was most favorable. The detection limit of lauric acid as a model acid was 0.1 pmol per $10-{\mu}l$ injection volume at S/N=3, which was roughly equal to that of an analogous compound, 2-(5-hydrazinocarbonyl-2-furyl)-5,6-dimethoxybenzothiazole. The reagent allowed rapid assays of carboxylic acids ($C_{12:0}-C_{20:4}$) within 20 min with satisfactory scparability. The method was applied to the determination of fatty acids in human sera from healthy volunteers as well as from patients with diabetes or thyroid dysfunction.

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Control of Aflatoxin and Characteristics of the Quality in Doenjang(soybean paste) Prepared with Antifungal Bacteria (길항미생물에 의한 된장 중 아플라톡신 제어 및 그 품질특성)

  • Kang, Kil-Jin;Park, Jong-Hoon;Cho, Jung-Il
    • Korean Journal of Food Science and Technology
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    • v.32 no.6
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    • pp.1258-1265
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    • 2000
  • In oder to acquire microbial agents that can be utilized for control of aflatoxin produced by Aspergillus. flavus and Asp. parasiticus, antifungal bacteria were isolated. Antifungal bacteria was identified as Bacillus spp. based on morphology and physico-biochemical characteristics. Amount of aflatoxin $B_1$ from Doenjang(soybean paste) prepared with Asp. flavus, Asp. parasiticus, antifungal bacteria(Bacillus sp.), or mixture of Asp. flavus and Asp. parasiticus was 27.2 ppb, 30.3 ppb, 3.4 ppb, and 3.7 ppb, respectively. Aflatoxin $B_1$ was not detected from Doenjang(control) and Doenjang prepared with antifungal bacteria. Content and compositions of free sugars, fatty acid, organic acid and free amino acid in Doenjang prepared with Asp. flavus and Asp. parasiticus, antifungal bacteria and mixture of Asp. flavus and Asp. parasiticus were not significantly different. For volatile flavor compounds of Doenjang prepared with antifungal bacteria, 2-pentyl furan and butanoic acid were disappeared or reduced, while octadecene compounds were produced. However, those of Doenjang prepared with Asp. flavus or Asp. parasiticus and Doenjang(control) were not significantly different. These results suggested that the antifungal bacteria(Bacillus sp.) inhibited production of aflatoxin and that antifungal bacteria did not effect the quality of Doenjang.

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Flavor Constituents in Enzyme Hydrolysates from Shore Swimming Crab and Spotted Shrimp (민꽃게 및 꽃새우 효소가수분해물의 풍미발현성분)

  • ;;Chi-Tang Ho
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.30 no.5
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    • pp.787-795
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    • 2001
  • For the developing natural fisheries flavoring substances using crustacea, the flavor constituents of enzyme hydrolysates from shore swimming crab (crab) and spotted shrimp (shrimp) were investigated. In taste-active compounds of both enzyme hydrolysates, total free amino acid contents of crab and shrimp enzyme hydrolysates were 5,226.7 mg% and 8,757.3 mg%, respectively. The major amino acids were taurine, glutamic acid, proline, asparagine, glycine, alanine, valine, leucine, lysine anserine and arginine. As for ATP related compounds, AMP was the principal component and small amounts of IMP was detected in both enzyme hydrolysates. In the quarternary ammonium bases, betaine was the principal component (593.8mg%), and contents of TMAO and betaine in both samples were 60.7 mg% and 850.0 mg%, 124.1 mg% and 755.9 mg%, respectively. The major components were Na, K, P and Cl in inorganic ions. The major fatty acids of both sample were 14 : 0, 16 : 0, 16 : 1n7, 18 : 1n9, 20 : 5n3 and 22 : 6n3, and composition ration of n3 polyunsaturated fatty acids of were 27.8% and 28.5%, respectively. Total 99~109 volatile compounds were detected as a cooked odor of crab and shrimp enzyme hydrolysates by SDE apparatus/gas chromatography/mass spectrometry. The volatile flavor compounds identified from cooked crab enzyme hydrolysate were composed of 6 acids, 10 alcohols, 7 aldehydes, 11 ketones, 1 ester, 5 phenols, 4 benzenes, 22 hydrocarbons, 1 furan, 21 nitrogen containing compounds and 11 micellaneous compounds. And the volatile flavor compounds indentified from cooked shrimp enzyme hydrolysate were composed of 13 acids, 10 alcohols, 6 aldehydes, 10 ketones, 3 esters, 2 phenols, 5 benzenes, 36 hydrocarbons, 1 furan, 14 nitrogen containing compounds and 8 micellaneous compounds.

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Antimicrobial activity of 7,10-epoxy-octadeca-7,9-dienoic acid crude extract against methicillin-resistant Staphylococcus aureus (메티실린 저항성 황색포도상구균에 대한 7,10-epoxy-octadeca-7,9-dienoic acid 조추출물의 항균 활성 연구)

  • Su-Hyeon Son;Ye-Ji Park;Su-Hyeon Lee;Ju-Hyeon Choi;Hak-Ryul Kim
    • Journal of Applied Biological Chemistry
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    • v.66
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    • pp.98-104
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    • 2023
  • Effective and alternative strategies to control methicillin-resistant Staphylococcus aureus (MRSA) are consistently needed. Previous study presented that 7,10-epoxy-octadeca-7,9-dienoic acid (EODA) was produced from 7,10-dihydroxy-8(E)-octadecenoic acid through one-step heat treatment. Further studies confirmed that EODA was highly active against broad range of pathogenic bacteria including MRSA, promising development of a novel antibacterial agent to control MRSA. However, there are some practical huddles for industrialization of EODA, especially high cost for fine purification. To address this problem, this study was focused on determination of any changes in the antibacterial activities of EODA when used as a crude extract. As a result, any significant changes in the antibacterial activities of EODA was not detected and additional synergistic effect for commercial antibiotics on antibacterial activity was sustained as it was.

Foliage Contact Herbicidal Activity of Dehydrocostus lactone Derived from Saussurea lappa (목향(Saussurea lappa) 유래 Dehydrocostus lactone의 경엽 접촉 살초 활성)

  • Cho, Kwang-Min;An, Xue-Hua;Chon, Jae-Kwan;Kim, Hyo-Sun;Chun, Jae-Chul
    • Korean Journal of Weed Science
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    • v.30 no.4
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    • pp.421-428
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    • 2010
  • A foliage contact herbicidal substance was separated from ethyl ether fraction in n-hexane extract of Saussurea lappa roots and identified as dehydrocostus lactone [(3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[5,4-d]furan-2-one](DHCL). When DHCL at 4,000 ppm was foliage-applied to two grasses and two broadleaf plants, greater than 85% necrotic injury was obtained from large crabgrass, maize and soybean, whereas only about 40% necrotic injury appeared in black nightshade, indicating that DHCL has no gross morphological selectivity, but shows difference in contact response among the plant species tested. Conductivity in incubation medium of the leaf disks treated with DHCL increased as the incubation time continued. Relatively low contact injury in black nightshade as compared with the other three plant species tested was attributed to decrease in absorption of DHCL due to relatively high amount of cuticle. DHCL did not require light in the herbicidal action and there were no inhibitory effects on seed germination and cell elongation. Acetyl-CoA carboxylase activity was inhibited by 30% and 58% at $100\;{\mu}M$ and $1000\;{\mu}M$ DHCL, respectively. These results suggested that the herbicidal action of DHCL was related with inhibition of fatty acid synthesis which in turn caused to weaken cell membrane integrity.

Germination-Induced Changes in Flavoring Compound Profiles and Phytonutrient Contents in Scented Rice (향미벼의 발아 전 후 향기 성분 및 기능성 지질성분 함량의 변화)

  • Mahmud, MM Chayan;Das, Animesh Chandra;Lee, Seul-Ki;Kim, Tae-Hyeong;Oh, Yejin;Cho, Yoo-Hyun;Lee, Young-Sang
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.61 no.4
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    • pp.242-250
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    • 2016
  • Although rice has been cultivated as a major food crop for approximately 5,000 years, the interest of customers in 'scented rice' is a recent trend in the Korean market. As a part of developing a germinated scented rice variety, the newly bred scented rice variety 'Cheonjihyang-1 se' was germinated for 24 h, and changes in profiles of flavor-related volatiles, lipophilic phytonutrients, and fatty acids were investigated. The profiling of volatile compounds by using a headspace-gas chromatography-mass spectrometry (HS-GC-MS) revealed a total of 56 odor-active flavoring compounds; 52 at the pre-germination stage, 51 at the post-germination stage, and 47 common at both stages. The major flavoring compounds were nonanol and benzene, which constituted 11.5% and 6.6%, respectively, of the total peak area in pre-germinated rice, and 19.4% and 6.5%, respectively, in post-germinated rice. Germination induced an increase in 13 flavoring compounds, including 3,3,5-trimethylheptane and 1-pentadecene, which increased by 763 and 513%, respectively by germination. However, we observed a germination-induced decrease in most of the other flavoring compounds. Especially, the most important scented rice-specific popcorn-flavoring compound, 2-acetyl-1-pyrroline, showed 89% decrease due to germination. Furthermore, the germination of scented rice induced a decrease in the content of various phytonutrients. For example, the total contents of phytosterols, squalene, and tocols decreased from 207.97, 31.74, and $25.32{\mu}g\;g^{-1}$ at pre-germination stage down to 136.66, 25.12, and $17.76{\mu}g\;g^{-1}$, respectively at post-germination stage. The fatty acid compositions were also affected by germination. The composition of three major fatty acids, linoleic, oleic, and palmitic acids, increased from 36.6, 34.2, and 24.4%, respectively, at the pre-germination stage to 37.9, 36.9, and 20.7%, respectively, at the post-germination stage. All these results suggested significant changes in the flavor-related compounds and phytonutrients of the scented rice variety 'Cheonjihyang-1 se' during the process of germination, and subsequently the need for developing a more precise process of germination to enhance the flavor and nutritional quality of the germinated scented rice products.