Unique fatty acid transformation catalyzed by anaerobic bacteria
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1 1 1,
2 Unique fatty acid transformation catalyzed by anaerobic bacteria Isomerization Dehydrating isomerization Desaturation Saturation Hydration
3 Isomerization of non-conjugated diene to conjugated diene Linoleic acid transformation to LA by lactic acid bacteria
4 Linoleic acid onjugated linoleic acid trans-vaccenic acid Stearic acid Analytical level (less than 0.5 mg/ml) Bifidobacterium breve Bifidobacterium bifidum Bifidobacterium dentium Bifidobacterium lactis cis-9,trans-11 cis-9,trans-11 Megasphaera elsdenii trans-10,cis-12 Propionibacterium freudenreichii cis-9,trans-11 (>80%) cis-9,trans-11(78%), trans-9,trans-11(21%), trans-10,cis-12(1%) cis-9,trans-11(90%), trans-9,trans-11(8%), trans-10,cis-12(2%) Butyrivibrio fibrisolvens A38 cis-9,trans-11 (95%) Lactobacillus reuteri cis-9,trans-11(59%), trans-10,cis-12(41%) Lactobacillus acidophilus cis-9,trans-11(86%), trans-9,trans-11(6%), trans-10,cis-12(8%) Lactobacillus acidophilus cis-9,trans-11(85%), trans-9,trans-11(3%), trans-10,cis-12(12%)
5 GL chromatogram of methyl esters of fatty acids produced from LA by Lactobacillus acidophilus AKU1137 ellular fatty acids A, 14:0 B, 16:0, 16:1( 9) D, 18:1( 9) E, 18:1( 11) F, 19:0 (cyclopropane) Linoleic acid a b olumn : HR-SS-10, 0.25 mm I.D. x 50m Initial temp. : 200 Program rate : 2 /min Final temp. : 220 Injection temp. : 250 Detector temp. : 250 arrier gas : He (225 kpa) Make up gas : N 2 (55 ml/min) FID H 2 : 60 kpa Air : 60 kpa Split ratio : 1/50 B d A E D F c a 9 11 LA Retention time (min) b 9 11 LA2 c 12 HY1 d 12 HY2
6 LA production from linoleic acid by washed cells of lactic acid bacteria Linoleic acid 9 12 HY2 12 HY1 12 LA LA2 9 11
7 LA production from linoleic acid by washed cells of L. plantarum AKU 1009a Linoleic acid : 12% (w/v) Washed cells : 33% (w/v) Aerobic (A) Linoleic acid : 2.6% (w/v) Washed cells : 23% (w/v) Aerobic () Fatty acid (mg/ml reaction mixture) LA: 40 mg/ml Yield: 33% Linoleic acid LA Fatty acid (mg/ml rection mixture) LA: 20 mg/ml Yield: 80% Linoleic acid LA (B) Reaction time (h) Fatty acid composition (wt.%) (D) Reaction time (h) Fatty acid composition (wt.%) ellular FA LA LA1 LA2 HY1 HY2 ellular FA LA2 HY1 LA LA1
8 LA production by Lactobacillus plantarum AKU 1009a Linoleic acid LA1 LA2 LA production: 40 mg/ml LA1 selective condition LA1 purity: 75% LA2 selective condition LA2 purity: 97% LA was obtained as free fatty acid form almost associated with the cells
9 onjugated fatty acids production by lactic acid bacteria Linoleic acid LA1 LA2 LA production: 40 mg/ml LA1 selective condition LA1 purity: 75% LA2 selective condition LA2 purity: 97% α-linolenic acid ALA1 ALA2 ALA production: 25 mg/ml ALA1 selective condition ALA1 purity: 85% ALA2 selective condition ALA2 purity: 85% GLA production: 9 mg/ml γ-linolenic acid GLA1 GLA2 GLA1 selective condition GLA1 purity: 80% GLA2 selective condition GLA2 purity: 87%
10 Dehydration of hydroxy fatty acid to conjugated fatty acid Ricinoleic acid transformation to LA by lactic acid bacteria
11 LA production from ricinoleic acid by washed cells of lactic acid bacteria Linoleic acid (cis-9, cis-12-octadecadienoic acid) Ricinoleic acid (12-hydroxy-cis-9-octadecaenoic acid) HY1 (10-hydroxy-trans-12-octadecaenoic acid) 12 HY2 (10-hydroxy-cis-12-octadecaenoic acid) LA 1 (cis-9,trans-11-octadecadienoic acid) LA 2 (trans-9, trans-11-octadecadienoic acid)
12 LA production from castor oil by washed cells of lactic acid bacteria H 2 H H Triric inole in in c astor oil Linoleic acid (cis-9,cis-12-octadecadienoic acid) :0 18:0 18:1 18:2 Dihydroxy acid RA 0 18: Fatty acid composition (wt.%) HY1 (10-hydroxy-trans-12-octadecaen oic acid ) 12 Lipase (Lipase M"Amano"10) Detergent (Lubrol PX) HY2 (10-hydroxy-cis-12-octadecaenoic acid) 12 9 Ricinoleic acid (12-hydroxy-cis-9-octadecaenoic acid) LA 1 (cis-9,trans-11-octadecadienoic acid) LA 2 (trans-9, trans-11-octadecadienoic acid)
13 LA production by microorganisms astor oil Lipase Ricinoleic acid (12-hydroxy-cis-9-octadecaenoic acid) 9 Linoleic acid (cis-9,cis-12-octadecadienoic acid) 9 12 LA production : 2.5 ~ 7.5 mg/ml LA1 : ~ 50% LA2 : ~ 82% Free fatty acid Lactic acid bacteria LA production : 20 ~ 40 mg/ml LA1 : ~ 75% LA2 : ~ 97% Free fatty acid 9 11 cis-9,trans-11-octadecadienoic acid 9 11 trans-9,trans-11-octadecadienoic acid
14 trans-vaccenic acid desaturation to LA by filamentous fungi
15 LA production from trans-vaccenic acid through 9 desaturation 11 trans-vaccenic acid (trans-11-octadecaenoic acid) 9-Desaturation 9 11 LA1 (cis-9,trans-11-octadecadienoic acid) 9 11 LA2 (trans-9,trans-11-octadecadienoic acid)
16 ulture conditions Strain : Delacroiaxia coronata IF 8586 Substrate conc. : 33.3 mg/ml Substrate addition: Inoculation Medium : Dextrin 5.0%, Tryptone 2.0% Thiourea 0.83 mmol/ml ph : 9.0 ulture temp. : 28 Time courses of LA production from t-vame LA1 8.0 LA (mg/ml) LA Time (days)
17 LA production by microorganisms astor oil Lipase Ricinoleic acid (12-hyd ro xy-cis-9-octad ecaenoic acid) Linoleic acid (cis-9,cis-12-octadecadienoic acid) LA production : 2.5 ~ 7.5 mg/ml LA1 : ~ 50% LA2 : ~ 82% Free fatty acid Lactic acid bacteria LA production : 20 ~ 40 mg/ml LA1 : ~ 75% LA2 : ~ 97% Free fatty acid 9 11 cis-9,tran s-11-octadecadienoic acid 9 11 trans-9,trans-11-octadecadienoic acid Molds 11 LA production : ~ 13 mg/ml LA1 : ~ 98% LA2 : ~ 10% Triacylglycerol trans-11-octadecaenoic acid trans-vaccenic acid
18 Saturation of polyunsaturated fatty acid by anaerobic microorganisms
19 Saturation of arachidonic acid and EPA by lostridium bifermentans JM 1386 Arachidonic acid (cis-5,cis-8,cis-11,cis-14-eicosatetraenoic acid) EPA (cis-5,cis-8,cis-11,cis-14,cis-17-eicosapentaenoic acid) cis-5,cis-8,trans-13-eicosatrienoic acid cis-5,cis-8,trans-13,cis-17-eicosatetraenoic acid (UK1) (UK2)
20 Putative pathway of unsaturated fatty acids by. bifermentans JM1386 ω9 ω6 ω9 ω6 ω9 ω6 Linoleic acid (18:2) Eicosapentaenoic acid (20:5) Arachidonic acid (20:4) ω9 ω7 c9,t11-la ω9 ω7 c5,c8,c11,t13,c17-20:5 ω9 ω7 c5,c8,c11,t13-20:4 ω9 ω7 t9e,t11-la ω9 ω7 c5,c8,t11,t13,c17-20:5 ω9 ω7 c5,c8,t11,t13-20:4 t11-va ω7 ω7 c5,c8,t13,c17-20:4 ω7 c5,c8,t13-20:3
21 Transformation of polyunsaturated fatty acids by cell-free extracts of. Bifermentans JM 1386 Substrate Structure Transformation Linoleicacid(LA; 18:2n-6) g-linolenicacid(gla; 18:3n-6) a-linolenicacid(ala; 18:3n-3) Dihomo-g-linolenicacid(DGLA; 20:3n-6) Arachidonicacid(AA; 20:4n-6) Eicosapentaenoicacid(EPA; 20:5n-3) Docosahexaenoicacid(DHA; 22:6n-3) - ω9 ω6 ω9 ω7 ω9 ω7 ω7
22 Hydration of unsaturated fatty acid to hydroxyl fatty acid
23 Putative pathway of LA transformation by Pediococcus sp. LBK Hydration LA Hydration 10 HYA :1 12 Hydration 9 Hydration LA ,13--18:0
24 Transformation of unsaturated fatty acid Substrate α-linolenic acid γ-linolenic acid Stearidonic acid leic acid :1 Ricinolecic acid HYA Dihomo-γ-linolenic acid Arachidonic acid cis-9,cis-12,cis-15-18:3 cis-6,cis-9,cis-12-18:3 cis-6,cis-9,cis-12,cis-15-18:4 cis-9-18:1 13-hydroxy-cis-9-18:1 12-hydroxy-cis-9-18:1 10-hydroxy-cis-12-18:1 cis-8,cis-11,cis-14-20:3 cis-5,cis-8,cis-11,cis-14-20:4 Transformation - -
25 Lactic acid bacteria 9 H 10 Pediococcus sp. LBK 454 H H 13 H H Hydroxy fatty acids Stereoselective for R-configuration Resins, waxes, nylons, plastics, corrosion inhibitors, cosmetics, coatings, lubricants, etc..
26 Unique fatty acid transformation catalyzed by anaerobic bacteria Isomerization Dehydrating isomerization Desaturation Saturation Hydration
27 ex) L. plantarum
28 A 9 12 dehydration dehydration HY2 12 HY1 12 LA LA B trans - 9 desaturation 11 γ α D GLA ALA GLA ALA
29
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