• Title/Summary/Keyword: double bond

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Screening of Anti-Biofilm Compounds from Marine-Derived Fungi and the Effects of Secalonic Acid D on Staphylococcus aureus Biofilm

  • Wang, Jie;Nong, Xu-Hua;Zhang, Xiao-Yong;Xu, Xin-Ya;Amin, Muhammad;Qi, Shu-Hua
    • Journal of Microbiology and Biotechnology
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    • v.27 no.6
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    • pp.1078-1089
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    • 2017
  • Biofilm formation of Staphylococcus aureus is one of its mechanisms of drug resistance. Anti-biofilm screening of 106 compounds from marine-derived fungi displayed that 12 compounds inhibited S. aureus biofilm formation by >50% at the concentration of $100{\mu}g/ml$, and only secalonic acid D (SAD) and B inhibited by >90% at $6.25{\mu}g/ml$ without inhibiting cell growth after 24-h incubation. Meanwhile, it was found that the double bond between C-1 and C-10 of citrinin derivatives and the C-C connection position of two chromone monomers may be important for their anti-biofilm activities. Moreover, SAD slightly facilitated biofilm eradication and influenced its architecture. Furthermore, SAD slowed the cell growth rate in the preceding 18-h incubation and differentially regulated transcriptional expression of several genes, such as agr, isaA, icaA, and icaD, associated with biofilm formation in planktonic and biofilm cells, which may be the reason for the anti-biofilm activity of SAD. Finally, SAD acted synergistically against S. aureus growth and biofilm formation with other antibiotics. These findings indicated that various natural products from marine-derived fungi, such as SAD, could be used as a potential biofilm inhibitor against S. aureus.

Fatty Acid Compositions of Some Seed Oils from the Pinaceae Family (솔과 식물 종실유의 지방산 조성)

  • Kim, Seong-Jin;Kim, Gee-Su;Yi, Min-Ok;Joh, Yong-Goe
    • Journal of the Korean Applied Science and Technology
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    • v.9 no.2
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    • pp.149-156
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    • 1992
  • Levels of total lipids in the seeds of three species of the Pinaceae family were determined and their fatty acid compositions were also analyzed by a gas-chromatograph equipped with a capillary column coated with Carbowax 20M. The results are summarized as follows: Lipid contents of the seeds amounted to 56.9% in P. koraiensis, 29.9% in P. thunbergii, and 21.2% in P. rigida. In all lipids 19${\sim}$20 fatty acid were detected and, surprisingly, fatty acids having ${\Delta}^5$-non-methylene interrupted conjugate double bond such as ${\Delta}^{5, 9}-C_{18:2},{\Delta}^{5, 9, 12}-C_{18:3}\;and\;{\Delta}^{5, 11, 14}-C_{20:3}$ occurred in appreciable amounts. In the lipids of P. koraiensis, the main component was $C_{18:2}{\omega}_6(45.0%)$, followed by $C_18:1{\omega} _9(26.9%)$ and ${\Delta}^{5, 9, 12}-C_{18:3}(14.6%)$, and then ${\Delta}^{5, 9}-C_{18:2}(2.2%)$ and ${\Delta}^{5, 11, 14}-C_{20:3}$ were also present. Levels of saturated fatty acid such as $C_{16:0}\;and\;C_{18:0}$ were as low as 7.5%. The seed oil of P. thunbergii predominantly comprised $C_{18:2}{\omega}_6(45.2%)$, and was then occupied by equal amounts ${\Delta}^{5, 9, 12}-C_{18:3}(18.1%)$ and $C_{18:1}{\omega}_9(18.1%)$. Its ${\Delta}^5, 11, 14}-C_{20:3}(5.8%)$ level was the highest in the samples tested. ${\Delta}^{5, 9}-C_{18:2}(2.8%)$ was also detected with other minor components. In the oils from the seeds of P. rigida, $C_{18:2}{\omega}_6$ was present as a main component, accompanied by $C_{18:1}{\omega}_9(21.6%)$ and ${\Delta}^{5, 9, 12}-C_{18:3}(20.3%)$. The latter showed higher level than in any other samples. A minor component corresponding to ${\Delta}^{5, 9, 12, 15}-C_{18:4}$(not confirmed by GC-Mass) occurred in P. thunbergii and P. rigida.

Difference of the Chemical Compositions Between Petroleum Ether Extract and its Tall Oil in Pitch Pine, Pinus Rigida Mill (리기다소나무재(材)의 유기용매(有機溶媒) 추출물(抽出物)과 그 tall oil 간의 조성(組成)의 차이(差異))

  • Ko, Sang-Woon;Ahn, Won-Yung
    • Journal of the Korean Wood Science and Technology
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    • v.16 no.2
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    • pp.79-89
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    • 1988
  • This experiment was carried out to investigate the difference of compositions between petroleum ether extract and its tall oil in Pinus rigida Mill. xylem and to obtain the basic data on effective extraction and its utilization of by-product, resin and fatty acid, when pulp making. After both petroleum ether extract from wood meal and its tall oil in pitch pine were separated to the resin and fatty acid by using DEAE-Sephadex and aluminum oxide column, these were analyzed with gas chromatograph. The results obtained were as follows: 1. Fatty acids contained as ester form in living trees were varied by peroxide of organic solvent in petroleum ehter extraction and cooking chemicals in cooking. 2. Pimaric-type acid was eluted earlier than abietic-type acid in resin acids and the fewer the carbons, the earlier the elution in fatty acids. 3. The retention time of SE-30 column was even smaller than that of OV-101 column but the relative retention time obtained by using methyl pimarate and methyl stearate as internal standard was nearly identical. 4. Both petroleum ether extract and tall oil mainly consisted of resin acids, expecially abietic-type acid. 5. Tall oil had more fatty acid but less resin acid than petroleum ether extract. Also, the content of unidentified materials was increased owing to the isomerization and the shift of double bond position in unsaturated fatty acids by high temperature and cooking chemicals when cooking.

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Mating Disruption of Grapholita molesta by RNA Interference of a Fatty Acid Desaturase Expressed in Adult Abdomen (복숭아순나방 성충 복부에서 발현하는 불포화효소의 RNA 간섭과 교미교란)

  • Kim, Kyusoon;Jung, Chung Ryul;Yang, Chang Yeol;Kwon, Gimyeon;Kim, Yonggyun
    • Korean journal of applied entomology
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    • v.56 no.1
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    • pp.61-67
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    • 2017
  • Two major sex pheromone components (Z-8-dodecenyl acetate and E-8-dodecenyl acetate) are known in the peach fruit moth, Grapholita molesta. From a putative biosynthetic pathway of these sex pheromone components, delta 10 desaturase ($10{\Delta}$ DES) has been proposed to play a crucial role in synthesizing a species-specific stereoisomer of the double bond. However, its molecular identity was not known. This study determined a putative desaturase (Gm-comp1575) as a $10{\Delta}$ DES candidate from G. molesta transcriptome constructed from the sex pheromone gland. Its open reading frame encodes 370 amino acid sequence with a predicted molecular weight at 43.2 kDa and isoelectric point at 8.77. It was predicted to have four transmembrane domains and six glycosylation sites at N-terminal or cytosolic domains. A phylogenetic analysis with its predicted amino acid sequence indicated that Gm-comp1575 is closely related with known $10{\Delta}$ DES genes of other insects. Gm-comp1575 transcript was detected in female adults at sex pheromone gland and other abdominal tissues. RNA interference of Gm-comp1575 significantly reduced attractiveness of virgin females in apple orchard compared to control females. These results suggest that Gm-comp1575 is associated with sex pheromone biosynthesis of G. molesta.

Analysis of Free Fatty Acid Formation and Oxidative Rancidity for Deep Flying Oil Produced by Traditional and Modified Fryers (전통식과 개량식 튀김기에 대한 튀김기름의 유리지방산 생성 및 산패도 측정 비교)

  • Choi, Il-Sook;Choi, Soo-Keun;Lee, Young-Soon
    • Culinary science and hospitality research
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    • v.17 no.4
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    • pp.316-325
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    • 2011
  • The property of deep frying oil is one of die important factors in fried food quality. The purpose of this study is to identify die quality of deep frying oil in continuous usages for 4 days by two types of fryers: traditional and modified fryers. After frying polk cutlets, die flying oil was kept not only for several physical analyses such as color, viscosity, and water content but also for quality analyses of flying oil such as free fatty acid, double bond changes and oxidative rancidity formation. The fried oil by a traditional flyer was significantly increased in die physical values of color and viscosity than that by a modified fryer. In die acid value, the fried oil by a traditional fryer was significantly increased in free fatty acid than that by a modified fryer while die iodine value was significantly decreased in die fried oil by a traditional fryer when compared to control oil and fried oil by a modified fryer. In die peroxide value as an indicator of primary oxidation products, die fried oil by both fryers was significantly increased till die second day but decreased in die value after die third day because of unstable hydroperoxides' decomposition. In die p-anicidine value as an indicator of secondary oxidation products, die fried oil in a traditional fryer was significantly increased in die value than that in a modified fry.

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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%).

Antibacterial activity of isothiocyanates from cruciferous vegetables against pathogenic bacteria in olive flounder (십자화과 채소 유래 isothiocyanates의 넙치 어병세균에 대한 항균활성)

  • Ko, Mi-Ok;Ko, Jeong-Yeon;Kim, Mi-Bo;Lim, Sang-Bin
    • Food Science and Preservation
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    • v.22 no.6
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    • pp.886-892
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    • 2015
  • The antimicrobial effects of ten isothiocyanates (ITCs) present in cruciferous vegetables and radish root hydrolysate were investigated against pathogenic bacteria from olive flounder. Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were measured against two gram-positive bacterial strains (Streptococcus parauberis, S. iniae) and four gram-negative bacterial strains (Edwardsiella tarda, Vibrio ichthyoenteri, V. harveyi, Photobacterium damselae) by using a broth microdilution technique. The antibacterial activity of ITCs was in the order sulforaphane > sulforaphene > phenylethyl ITC > erucin > benzyl ITC > iberin > I3C > allyl ITC > phenyl ITC > hexyl ITC. The susceptibility of fish pathogens to ITCs was in the order of V. harveyi > E. tarda > P. damselae > S. parauberis > S. iniae > V. ichthyoenteri. Antimicrobial activity (MIC) of radish root hydrolysate was 0.250 mg/mL against S. iniae, 0.438 mg/mL against S. parauberis, and 0.500 mg/mL against both E. tarda and V. harveyi. The aliphatic ITCs were potent inhibitors of the growth of fish pathogens, followed by aromatic ITCs and indolyl ITC. The presence of a double bond in the chemical structure of ITCs decreased antibacterial activity, while ITCs with a thiol (-S-) group and a longer carbon chain increased antibacterial activity. These results suggest that ITCs have strong antibacterial activities and may be useful in the prevention of fish pathogens.

Pharmacological Activities of Flavonoids (V): Spasmolytic Activities of Flavones and Flavonols on Rat Ileal Smooth Muscle Contraction Induced by Electrical Stimulation and Anaphylactic Reaction (Flavonoids의 약리작용(V) - 전기자극 및 과민반응으로 유발된 흰쥐 회장의 평활근수축에서 Flavones 및 Flavonols의 진경효과 -)

  • Ahn, Hong-Zick;Lee, Ji-Yun;Kim, Soo-Jeong;Kim, Jung-Min;Park, Ju-Hyun;Park, Sung-Hun;Sim, Sang-Soo;Kim, Chang-Jong
    • YAKHAK HOEJI
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    • v.51 no.2
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    • pp.150-156
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    • 2007
  • Some flavonoids have spasmolytic activities in various smooth muscles, but structure-activity relationships on their spasmolytic activity and its mechanism are unclear. In this study, effects of flavones (flavone and apigenin) and flavonols (quercetin and rutin) on the rat ileal smooth muscle contraction were studied in vitro and in vitro. In the electric stimulation-induced contraction, all of four flavonoids inhibited concentration-dependently the rat ileal smooth muscle contraction induced by electric stimulation (10 mV, 0.1 cps, 0.1 msec duration), IC$_{50}$ of quercetin, apigenin, flavone and rutin were 0.98${\times}$10$^{-5}$, 1.20${\times}$10$^{-5}$, 1.55${\times}$10$^{-5}$ and 1.85${\times}$10$^{-5}$ M, respectively. Flavonoids at a concentration of 2${\times}$10$^{-5}$ M also significantly inhibited the anaphylactic contraction and decreased concentration-dependently the mast cell degranulation by anaphylactic reaction, IC$_{50}$ of quercetin, apigenin, flavone and rutin were 4.0${\times}$10$^{-5}$, 7.5${\times}$10$^{-5}$, 8.0${\times}$10$^{-5}$ and 9.5${\times}$10$^{-5}$ M, respectively. These results indicated that flavones and flavonols inhibited the rat ileal smooth muscle contraction induced by electric stimulation because of their antagonism against acetylcholine and have spasmolytic activities on anaphylactic contraction which may be due to their mast cell-stabilizing activities. Furthermore, double bond of C$_{2,3}$ in benzene ring of flavonoids may be important in the their antispasmodic activities on the rat ileal smooth muscle contraction induced by electric stimulation and anaphylactic reaction.

Formation of Cyclodextrin Adsorbent Using Fatty Acid as a Ligand and Fractionation of $\alpha$-, $\beta$- and ${\gamma}$-cyclodextrins (Fatty Acid를 Ligand로한 Cyclodextrin Adsorbent의 제조와 $\alpha$-, $\beta$-, ${\gamma}$-Cyclodextrin의 분획)

  • 정승환;박동찬이용현
    • KSBB Journal
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    • v.10 no.5
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    • pp.491-498
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    • 1995
  • In order to fraclionate ${\alpha}$-, ${\beta}$- and ${\gamma}$-cyclodextrins(CDs) from CD reaction mixture, various CD adsorbents were manufactured using fatty acids as the ligand molecules and anion exchange resins as matrix. Among several anion exchange resins, DEAE Cellulose was found to be the most suitable matrix for binding fatty acid. The binding stability between DEAE Cellulose and capric acid was tested under the various operation conditions, such as temperature, ethanol concentration, and ionic strength. Specific CD adsorbents manufactured with different chain-length fatty acids, saturated and unsaturated, were compared in terms of the recovery yield and selectivity of ${\alpha}$-, ${\beta}$- and ${\gamma}$-CDs. Stearic acid (C18, saturated) was identified as the most effective ligand for fractionation of ${\alpha}$-CD, and linoleic acid ((C18, unsaturated ) for ${\beta}$-CD. The spacer length between the matrix and ligand was required for effective adsorption of CDs, and the double bond in fatty acid molecules was also acted as an important factor determining recovery yield and selectivity. The elusion patterns of ${\alpha}$- and ${\alpha}$-, ${\beta}$-CD from column packed with stearic acid and linoleic acid CD adsorbents were also investigated at the various elusion conditions for fractionation of ${\alpha}$- and ${\beta}$-CD.

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Effect of CQ-amine ratio on the degree of conversion in resin monomers with binary and ternary photoinitiation systems

  • Moon, Ho-Jin;Shin, Dong-Hoon
    • Restorative Dentistry and Endodontics
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    • v.37 no.2
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    • pp.96-103
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    • 2012
  • Objectives: This study evaluated the effect of camphorquinone (CQ)-amine ratio on the C=C double bond conversion of resins with binary and ternary photoinitiation systems. Materials and Methods: Two monomer mixtures (37.5 Bis-GMA/37.5 Bis- EMA/25 TEGDMA) with binary systems (CQ/DMAEMA in weight ratio, group A [0.5/1.0] and B [1.0/0.5]) and four mixtures with ternary system (CQ/OPPI/DMAEMA, group C [0.1/1.0/0.1], D [0.1/1.0/ 0.2], E [0.2/1.0/0.1] and F [0.2/1.0/0.2]) were tested: 1 : 2 or 2 : 1 CQ-amine ratio in binary system, while 1 : 1 ratio was added in ternary system. The monomer mixture was cured for 5, 20, 40, and 300 sec with a Demetron 400 curing unit (Demetron). After each exposure time, degree of conversion (DC) was estimated using Fourier transform infrared (FTIR) spectrophotometer (Nicolet 520, Nicolet Instrument Corp.). The results were analyzed by ANOVA followed by Scheffe test, with p = 0.05 as the level of significance. Results: DC (%) was expressed in the order of curing time (5, 20, 40, and 300 sec). Group A ($14.63{\pm}10.42$, $25.23{\pm}6.32$, $51.62{\pm}2.69$, $68.52{\pm}2.77$); Group B ($4.04{\pm}6.23$, $16.56{\pm}3.38$, $37.95{\pm}2.79$, $64.48{\pm}1.21$); Group C ($16.87{\pm}5.72$, $55.47{\pm}2.75$, $60.83{\pm}2.07$, $68.32{\pm}3.31$); Group D ($23.77{\pm}1.64$, $61.05{\pm}1.82$, $65.13{\pm}2.09$, $71.87{\pm}1.17$); Group E ($28.66{\pm}2.92$, $56.68{\pm}1.33$, $60.66{\pm}1.17$, $68.78{\pm}1.30$); Group F ($39.74{\pm}6.31$, $61.07{\pm}2.58$, $64.22{\pm}2.29$, $69.94{\pm}2.15$). Conclusion: All the monomers with ternary photoinitiation system showed higher DC than the ones with binary system, until 40 sec. Concerning about the effect of CQ-amine ratio on the DC, group A converted into polymer more than group B in binary system. However, there was no significant difference among groups with ternary system, except group C when cured for 5 sec only.