TWI548348B - 具天竺葵酸之抗微生物調配物 - Google Patents
具天竺葵酸之抗微生物調配物 Download PDFInfo
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- TWI548348B TWI548348B TW101138206A TW101138206A TWI548348B TW I548348 B TWI548348 B TW I548348B TW 101138206 A TW101138206 A TW 101138206A TW 101138206 A TW101138206 A TW 101138206A TW I548348 B TWI548348 B TW I548348B
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- Prior art keywords
- acid
- hexenal
- trans
- feed
- geranium
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Description
本申請案主張2011年10月20日申請之美國臨時申請案61/549,661之優先權,其以引用的方式併入本文中。
一種由有機酸與醛之混合物組成的抗微生物調配物,其中該組合當與添加高含量之另一組分相比時產生協同效應。
疾病控制及預防中心(Centers for Disease Control and Prevention,CDC)估計每年有大約六分之一的美國人或48,000,000人罹患食因性疾病。另外,每年有128,000人住院治療且約3,000人死於食因性疾病。在2011年報告中,CDC估計有20,000例沙門氏菌(Salmonella)導致住院治療,且此等病例中有378例導致死亡。亦估計在美國,大腸桿菌(E.coli)O157:H7造成約62,000例食因性疾病及約1,800例食因性疾病相關的住院治療。
喬治城大學皮尤慈善信託基金會(Pew Charitable Trusts of Georgetown University)之研究表明每年食因性疾病使美國在健康相關費用上之花費達1520億美元。
隨著世界傾向於更天然的及/或有機抗微生物劑,為滿足獲得此等抗微生物劑之需求已進行了大量的研究,以及由於此等新型天然/有機產品不易商購,故新原材料之成本
提高。
甲醛作為防腐劑已使用多年。兩項專利(US 5,547,987及US 5,591,467)教示使用甲醛來控制動物飼料中之沙門氏菌。此等專利未提出甲醛與有機酸之組合將提供如本發明中所述之協同效應。
已在許多植物中發現新的抗微生物劑。此等抗微生物劑保護植物免受細菌、真菌、病毒及昆蟲侵襲。此等抗微生物劑(其為植物精油之組分)可為酸性、醇類或醛類化學物質。
本發明所用之揮發性化合物中之一者為反式-2-己烯醛,其為具有共軛雙鍵的六碳醛C6H10O,且MW=98.14。醛由通式RCHO表示,其中R可為氫、或芳族、脂族或雜環基團。其中度溶於水且溶解度隨分子量增加而降低。不飽和脂族醛包括丙烯醛、反式-2-丁烯醛、2-甲基-2-丁烯醛、2-甲基-(E)-2-丁烯醛、2-戊烯醛、反式-2-己烯醛、反式-2-己烯-1-醇、2-甲基-2-戊醛、2-異丙基丙烯醛、2-乙基-2-丁烯醛、2-乙基-2-己烯醛、(Z)-3-己烯醛、3,7-二甲基-6-辛烯醛、3,7-二甲基-2,6-辛二烯醛、(2E)-3,7-二甲基-2,6-辛二烯醛、(2Z)-3,7-二甲基-2,6-辛二烯醛、反式-2-壬烯醛、(2E,6Z)-壬二烯醛、10-十一醛、2-十二烯醛、2,4-己二烯醛及其他醛。
反式-2-己烯醛存在於許多可食用植物中,諸如蘋果、梨、葡萄、草莓、奇異果、蕃茄、橄欖等。植物及植物提取物已成功用於尋找新型抗微生物劑的研究中。舉例而言,腰果蘋果(cashew apple)針對幽門螺旋桿菌
(Helicobacter pylori)及豬霍亂沙門氏菌(S.cholerasuis)(50-100 μg/ml)有效。發現兩種主要組分為漆樹酸(anacardic acid)及反式-2-己烯醛。測定反式-2-己烯醛的最小抑制活性及最小殺生物活性分別為400及800 μg/ml(Kubo,J.;Lee,J.R.;Kubo,I.Anti-Helicobacter pylori Agents from the Cashew Apple.J.Agric.Food Chem.1999,第47卷,533-537;Kubo,I.及K.Fujita,Naturally Occurring Anti-Salmonella Agents.J.Agric.Food Chem.2001,第49卷,5750-5754)。Kim及Shin發現反式-2-己烯醛(247 mg/L)針對蠟狀芽孢桿菌(B.cereus)、鼠傷寒沙門氏菌(S.typhimurium)、腸炎弧菌(V.parahaemolyticus)、單核球增多性李氏菌(L.monocytogenes)、金黃色葡萄球菌(S.aureus)及大腸桿菌O157:H7有效(Kim,Y.S.;Shin,D.H.Volatile Constituents from the Leaves of Callicarpa japonica Thunb.and Their Antibacterial Activities.J.Agric.Food Chem.2004,第52卷,781-787)。Nakamura及Hatanaka(Green-leaf-derived C6-aroma compounds with potent antibacrerial action that act on both gram-negative and gram-positive bacteria.J.Agric.Food Chem.2002,第50卷,第26期,7639-7644)表明(3E)-己烯醛以3-30 μg/ml之含量有效控制金黃色葡萄球菌、大腸桿菌及鼠傷寒沙門氏菌。反式-2-己烯醛完全抑制丁香假單胞致病菌(P.syringaepathovars)(570 μg/L空氣)及大腸桿菌(930微克/公升空氣)的增殖(Deng,W.;Hamilton-Kemp,T.;Nielsen,M.;Anderson,R.;Collins,G.;
Hilderbrand,D.Effects of Six-Carbon Aldehydes and Alcohols on Bacterial Proliferation.J.Agric.Food Chem.1993,第41卷,506-510)。據觀測250 μg/ml的反式-2-己烯醛有效抑制莖點黴屬菌絲體(Phoma mycelium)的生長(Saniewska,S.及M.Saniewski,2007.The effect of trans-2-hexenal and trans-2-nonenal on the mycelium growth of Phoma narcissi in vitro,Rocz.AR.Pozn.CCCLXXXIII,Ogrodn.第41卷,189-193)。在控制水果黴菌的研究中發現反式-2-己烯醛在40 μL/L下對杏不具植物毒性,但對桃及油桃具植物毒性(Neri,F.,M.Mari,S.Brigati及P.Bertolini,2007,Fungicidal activity of plant volatile compounds for controlling Monolinia laxa in stone fruit,Plant Disease第91卷,第1期,30-35)。反式-2-己烯醛(12.5 μL/L)有效控制引起藍色黴菌的擴展青黴(Penicillium expansum)(Neri,F.;Mari,M.;Menniti,A.;Brigati,S.;Bertolini,P.Control of Penicillium expansum in pears and apples by trans-2-hexenal vapours.Postharvest Biol.and Tech.2006,第41卷,101-108.Neri,F.;Mari,M.;Menniti,A.M.;Brigati,S.Activity of trans-2-hexenal against Penicillium expansum in 'Conference' pears.J.Appl.Micrbiol.2006,第100卷,1186-1193)。Fallik,E.等人(Trans-2-hexenal can stimulate Botrytis cinerea growth in vitro and on strawberries in vivo during storage,J.ASHS.1998,第123卷,第5期,875-881)及Hamilton-Kemp等人(J.Agric.Food Chem.1991,第39
卷,第5期,952-956)表明反式-2-己烯醛蒸氣抑制葡萄孢屬孢子及蘋果花粉萌發。
美國公開申請案第2007/0087094號提出至少兩種殺微生物活性GRAS化合物與少於50%的醇(異丙醇或異丙醇/乙醇)組合使用作為殺微生物劑。反式-2-己烯醛可視為GRAS化合物中之一種(Schuer.Process for Improving the Durability of,and/or Stabilizing,Microbially Perishable Products.美國公開申請案第2007/0087094號)。又,Archbold等人觀測到以0.86或1.71 mmol(分別為每1.1 L容器100或200微升純淨的化合物)使用2-己烯醛於採收後薰蒸無籽鮮食葡萄2週顯示控制黴菌的前景(Archbold,D.;Hamilton-Kemp,T.;Clements,A.;Collins,R.Fumigating 'Crimson Seedless' Table Grapes with (E)-2-Hexenal Reduces Mold during Long-term Postharvest Storage.HortScience.1999,第34卷,第4期,705-707)。
美國專利5,698,599提出一種藉由用反式-2-己烯醛處理食物來抑制黴菌毒素在食物中產生的方法。在8 ng/L空氣之濃度下,反式-2-己烯醛完全抑制黃麴菌(A.flavus)、點青黴(P.notatum)、鏈格孢菌(A.alternate)、枯萎病菌(F.oxysporum)、枝孢黴菌屬(Cladosporium species)、枯草桿菌(B.subtilis)及農桿腫瘤菌(A.tumerfaciens)之生長。當在控制飲料中之酵母(105 CFU/瓶)方面比較反式-2-己烯醛與檸檬醛時,發現25 ppm之反式-2-己烯醛及熱處理(56℃持續20分鐘)等效於100-120 ppm檸檬醛。在未經熱
處理之飲料中,需要35 ppm之反式-2-己烯醛以使其穩定(Belletti,N.;Kamdem,S.;Patrignani,F.;Lanciotti,R.;Covelli,A.;Gardini,F.Antimicrobial Activity of Aroma Compounds against Saccharomyces cerevisiae and Improvement of Microbiological Stability of Soft Drinks as Assessed by Logistic Regression.AEM.2007,第73卷,第17期,5580-5586)。反式-2-己烯醛不僅已用作抗微生物劑而且已觀測到有效控制昆蟲。揮發物(亦即反式-2-己烯醛)針對甲蟲有效,諸如赤擬穀盜(Tibolium castaneum)、穀蠹(Rhyzopertha dominka)、穀象(Sitophilus granaries)、米象(Sitophilus orazyzae)及鏽赤扁穀盜(Cryptolestes perrugineus)(Hubert,J.;Munzbergova,Z.;Santino,A.Plant volatile aldehydes as natural insecticides against stored-product beetles.Pest Manag.Sci.2008,第64卷,57-64)。美國專利6,201,026(Hammond等人,Volatile Aldehydes as Pest Control Agents)提出具有3個或3個以上碳之有機醛用於控制蚜蟲。
若干專利提出使用反式-2-己烯醛作為芳香劑或香料。美國專利6,596,681提出反式-2-己烯醛作為表面清潔用抹布中之芳香劑的用途。美國專利6,387,866、美國專利6,960,350及美國專利7,638,114提出使用精油或萜類(例如反式-2-己烯醛)作為香料用於抗微生物產品。美國專利6,479,044展示一種包含陰離子界面活性劑、聚陽離子抗微生物劑及水的抗微生物溶液,其中添加精油作為香料。此香料可為諸如反式-2-己烯醛之萜類或其他類型之萜類。美
國專利6,323,171、美國專利6,121,224及美國專利5,911,915展示一種含有陽離子界面活性劑之抗微生物目的微乳液,其中添加精油作為香料。此香料可含有包括反式-2-己烯醛之各種萜類。美國專利6,960,350展示一種抗真菌芳香劑,其中當不同萜類組合使用(例如反式-2-己烯醛與苯甲醛)時,存在協同效應。
反式-2-己烯醛之作用模式據認為是細胞膜由於不飽和醛與巰基或半胱胺酸殘基反應或與肽及蛋白質中之胺基形成希夫鹼(Schiff base)而變化(Deng,W.;Hamilton-Kemp,T.;Nielsen,M.;Anderson,R.;Collins,G.;Hilderbrand,D.Effects of Six-Carbon Aldehydes and Alcohols on Bacterial Proliferation.J.Agric.Food Chem.1993,第41卷,506-510)。反式-2-己烯醛據報導充當界面活性劑但其可能藉由被動擴散而滲透穿過質膜。一旦進入細胞內部,其α,β-不飽和醛部分即與生物學上重要的親核基團反應。此醛部分已知在生理條件下主要經1,4-加成與巰基反應(Patrignani,F.;Lucci,L;Belletti,N.;Gardini,F.;Guerzoni,M.E.;Lanciotti,R.Effects of sub-lethal concentratiors of hexanal and 2-(E)-hexenal on membrane fatty acid composition and volatile compounds of Listeria monocytogenes,Staphylococcus aureus,Salmonella enteritidis and Escherichia coli.International J.Food Micro.2008,第123卷,1-8)。
據表明反式-2己烯醛抑制鼠傷寒沙門氏菌及金黃色葡萄球菌係由於其分配在脂質雙層中之疏水性及氫鍵。亦已
表明破壞電子傳遞系統及擾動膜滲透性為作用模式(Gardini,F.;Lanciotti,R.;Guerzoni,M.E.Effect of trans-2-hexenal on the growth of Aspergillus flavus in relation to its concentration,temperature and water activity.Letters in App.Microbiology.2001,第33卷,50-55)。擴展青黴腐敗之抑制可能係由於對萌發分生孢子之真菌膜的破壞。(Neri,F.;Mari,M.;Menniti,A.;Brigati,S.;Bertolini,P.Control of Penicillium expansum in pears and apples by trans-2-hexenal vapours.Postharvest Biol.and Tech.2006,第41卷,101-108;Neri,F.;Mari,M.;Menniti,A.M.;Brigati,S.Activity of trans-2-hexenal against Penicillium expansum in 'Conference' pears.J.Appl.Micrbiol.2006,第100卷,1186-1193)。
已進行研究來比較反式-2-己烯醛與類似化合物。Deng等人展示不飽和揮發物反式-2-己烯醛及反式-2-己烯-1-醇展現比飽和揮發物己醛及1-己醇更大的抑制作用(Deng,W.;Hamilton-Kemp,T.;Nielsen,M.;Anderson,R.;Collins,G.;Hilderbrand,D.Effects of Six-Carbon Aldehydes and Alcohols on Bacterial Proliferation.J.Agric.Food Chem.1993,第41卷,506-510)。反式-2-己烯醛比己醛、壬醛及反式-2-辛烯醛更具抗所有ATCC細菌菌株活性(Bisignano,G.;Lagana,M.G.;Trombetta,D.;Arena,S.;Nostro,A.;Uccella,N.;Mazzanti,G.;Saija,A.In vitro antibacterial activity of some aliphatic aldehydes from Olea europaea L FEMS Microbiology Letters.2001,第198卷,9-13)。其他人已發現(E)-2-己烯醛具有比
己醛、1-己醇、(E)-2-己烯-1-醇及(Z)-3-己烯-1-醇更低的最小抑制真菌生長濃度,如對於若干黴菌物種所測定,基本上醛>酮>醇(Andersen,R.A.;Hamilton-Kemp,T.;Hilderbrand,D.F.;McCraken Jr.,C.T.;Collins,R.W.;Fleming,P.D.Structure-Antifungal Activity Relationships among Volatile C6 and C9 Aliphatic Aldehydes,Ketones,and Alcohols.J.Agric.Food Chem.1994,第42卷,1563-1568)。己烯醛及己酸比己醇更有效抑制沙門氏菌(Kubo,I.及K.Fujita,Naturally Occurring Anti-Salmonella Agents.J.Agric.Food Chem.2001,第49卷,5750-5754)。
Muroi等人表明反式-2-己烯醛展現廣泛的抗微生物活性但其生物活性(50至400 μg/mL)通常不夠有效以致於不被考慮用於實際應用(Muroi,H.;Kubo,A.;Kubo,I.Antimicrobial Activity of Cashew Apple Flavor Compounds..J.Agric.Food Chem.1993,第41卷,1106-1109)。研究已顯示反式-2-己烯醛可增強某些類型抗微生物劑之有效性。若干專利提出對胺基糖苷類抗生素使用增強劑(美國專利5,663,152),且對多黏菌素抗生素使用增強劑(美國專利5,776,919及美國專利5,587,358)。此等增強劑可包括吲哚、大茴香腦(anethole)、3-甲基吲哚、2-羥基-6-R-苯甲酸或2-己烯醛。當針對ATCC及臨床分離之微生物菌株一起測試反式-2-庚烯醛、反式-2-壬烯醛、反式-2-癸烯醛及(E,E)-2,4-癸二烯醛(比率為1:1:1:1)時觀測到強烈的協同效應(Bisignano,G.;Lagana,M.G.;Trombetta,D.;Arena,S.;
Nostro,A.;Uccella,N.;Mazzanti,G.;Saija,A.In vitro antibacterial activity of some aliphatic aldehydes from Olea europaea L.FEMS Microbiology Letters.2001,第198卷,9-13)。
經由食用食物及飲料,人類每日暴露至反式-2-己烯醛中。人類對於反式-2-己烯醛之暴露量為約350微克/公斤/天,98%來源於天然來源且2%來自人工調味劑。反式-2-己烯醛不太可能對人類有毒,因為大鼠中之毒性含量為人類正常攝入量之30倍(Stout,M.D.;Bodes,E.;Schoonhoven,R.;Upton,P.B.;Travlos,G.S.;Swenberg,J.A.Toxicity,DNA Binding,and Cell Proliferation in Male F344 Rats following Short-term Gavage Exposures to Trans-2-hexenal.Soc.Toxicologic.Pathology 2008年3月24日,1533-1601在線)。在另一大鼠研究中,以0(對照組)、260、640、1600或4000 ppm飼料之膳食含量饋入反式-2-己烯醛持續13週未誘發血液學參數或器官重量的任何變化。在4000 ppm下,體重及攝入量降低,但不顯著(Gaunt,I.F.;Colley,J.Acute and Short-term Toxicity Studies on trans-2-Hexenal.Fd Cosmet.Toxicol.1971,第9卷,775-786)。
即使在水果中,梨及蘋果在反式-2-己烯醛(12.5 μL/L)中暴露24小時至7天亦不影響水果外觀、色澤、堅實度、可溶性固體含量或可滴定酸度。在經訓練之品味小組中,在未經處理及經反式-2-己烯醛處理之「金冠(Golden Delicious)」蘋果的感官品質方面未觀測到顯著差異,而在
「巴特利特(Bartlett)」、「阿巴特(Abate Fetel)」及「皇家嘎拉(Royal Gala)」水果中察覺到保持異味(Neri,F.;Mari,M.;Menniti,A.;Brigati,S.;Bertolini,P.Control of Penicillium expansum in pears and apples by trans-2-hexenal vapours.Postharvest Biol.and Tech.2006,41,101-108;Neri,F.;Mari,M.;Menniti,A.M.;Brigati,S.Activity of trans-2-hexenal against Penicillium expansum in 'Conference' pears.J.Appl.Micrbiol.2006,第100卷,1186-1193)。
已發現檸檬醛及肉桂醛抗真菌。此等醛之作用模式為藉由與來自真菌之硫基(-SH)反應(Ceylan E及D Fung.Antimicrobial Activity of Spices.J.Rapid Methods in Microbiology.2004,第12卷,1-55)。
美國專利6,750,256及美國專利RE 39543提出使用如α-己基肉桂醛之芳族醛來控制螞蟻群體但未提出醛與有機酸組合以改良活性成分有效性或減少活性成分或改良其對細菌控制之有效性的任何協同效應。
胡荽(Coriandrum sativum)之精油含有55.5%之醛,該醛對防止革蘭氏陽性(gram positive)及革蘭氏陰性(gram negative)細菌之生長有效。此等醛包括:正辛醛、壬醛、2E-己烯醛、癸醛、2E-癸烯醛、十一烯醛、十二醛、2E-十二烯醛、十三醛、2E-十三烯-1-醛及3-十二烯-1-醛(Matasyoh,J.C.,Z.C.Maiyo,R.R.Ngure及R.Chepkorir.Chemical Composition and Antimicrobial Activity of the Essential Oil of Coriandrum sativum.Food Chemistry.2009第113卷,
526-529)。
目前使用糠醛(一種環狀醛)作為殺真菌劑及殺線蟲劑,但尚無如本發明中所說明之糠醛與有機酸(亦即壬酸)組合使用之報導。
兩種醛(正癸醛及壬醛)對控制真菌生長有效(Dilantha Fernando,W.G.,R.Ramaranthnam,A.Krihnamoorthy及S.Savchuck.Identification and use of potential organic antifungal volatiles in biocontrol.Soil Biology and Biochemistry.2005第37卷,955-964)。
先前技術尚未表明或觀測到使用醛與有機酸組合本身改良組分中之任一者的抗微生物活性。已表明與精油之組合具協同性且作為抗生素之增強劑。
市售黴菌抑制劑及殺細菌劑由單一有機酸或有機酸與甲醛之混合物構成。此等酸主要為丙酸、苯甲酸、丁酸、乙酸及甲酸。有機酸已為降低食因性感染之發病率的主要添加劑。短鏈脂肪酸發揮其抗微生物活性之機制為未解離(RCOOH=非離子化)酸具脂質可滲透性,且以此方式其可穿過微生物細胞壁且在微生物中鹼性更大的內部解離(RCOOH→RCOO-+H+),從而使得細胞質存活不穩定。(Van Immerseel,F.,J.B.Russell,M.D.Flythe,I.Gantois,L.Timbermont,F.Pasmans,F.Haesebrouck及R.Ducatelle.2006.The use of organic acids to combat Salmonella in poultry:a mechanistic explanation of the efficacy,Avian Pathology,第35卷,第3期,182-188;Paster,N.1979,A
commercial study of the efficiency of propionic acid and acid and calcium propionate as fungistats in poultry feed, Poult.Sci.第58卷,572-576)。
天竺葵酸(壬酸)為天然存在之脂肪酸。其為油狀無色流體,在低溫下變為固體。相比於丁酸,其具有微弱的氣味且幾乎不溶於水。天竺葵酸已用作非選擇性除草劑。Scythe(57%天竺葵酸、3%相關脂肪酸及40%惰性物質)為由Mycogen/Dow Chemicals製造的廣效萌芽後或枯萎死亡(burn-down)除草劑。天竺葵酸之除草作用模式首先係由於在黑暗與日光期間的膜洩漏,其次為由在日光期間由自類囊體膜移出之敏化葉綠素所產生之自由基驅動的過氧化反應(B.Lederer,T.Fujimori.,Y.Tsujino,K.Wakabayashi及P Boger,2004.Phytotoxic activity of middle-chain fatty acids II:peroxidation and membrane effects.Pesticide Biochemistry and Physiology 80:151-156)。
Chadeganipour及Haims(2001)展示中鏈脂肪酸防止石膏樣小芽胞菌(M.gypseum)生長之最小抑制濃度(MIC)為:在固體介質上,0.02 mg/ml癸酸及0.04 mg/ml天竺葵酸;及在液體介質中,0.075 mg/ml癸酸及0.05 mg/ml天竺葵酸。獨立地且不以混合物形式測試此等酸(Antifungal activities of pelargonic and capric acid on Microsporum gypseum" Mycoses第44卷,第3-4期,109-112)。N.Hirazawa等人(Antiparasitic effect of medium-chain fatty acids against ciliated Crptocaryon irritans infestation in the
red sea bream Pagrus major,2001,Aquaculture第198卷,219-228)發現壬酸以及C6至C10脂肪酸有效控制寄生蟲海水白點蟲(C.irritans)的生長且C8、C9及C19更有效。發現哈茨木黴(Trichoderma harzianum)(一種用於可可植物的生物控制)產生天竺葵酸作為許多化學品之一,其有效控制可可病原體萌發及生長。(M Aneja,T.Gianfagna及P.Hebbar,2005)。
若干美國專利揭示使用天竺葵酸作為殺真菌劑及殺細菌劑:美國公開申請案2004/026685揭示用於農業用途之殺真菌劑,其由一或多種脂肪酸及一或多種不同於脂肪酸之有機酸構成。在有機酸與脂肪酸之混合物中,有機酸充當有效的脂肪酸增效劑以起殺真菌劑的作用。美國專利5,366,995揭示經由使用脂肪酸及其衍生物來根除植物中之真菌及細菌感染且增強植物中之殺真菌劑及殺細菌劑之活性的方法。此調配物含有80%天竺葵酸或其鹽用於控制植物真菌。所用脂肪酸主要為C9至C18。美國專利5,342,630揭示含有增強C8至C22脂肪酸之功效的無機鹽之植物用新穎殺蟲劑。一個實施例展示具有2%天竺葵酸、2%癸酸、80%滑石、10%碳酸鈉及5%碳酸鉀之粉末產品。美國專利5,093,124揭示包含α單羧酸及其鹽之植物用殺真菌劑及殺節肢動物劑。殺真菌劑較佳由經活性鹼金屬(諸如鉀)部分中和之C9至C10脂肪酸組成。所述混合物由溶解於水中之40%活性成分組成且包括10%天竺葵酸、10%癸酸及20%椰子脂肪酸,所有成分皆經氫氧化鉀中和。美國專利
6,596,763揭示控制皮膚感染之方法,其包含C6至C18脂肪酸或其衍生物。美國專利6,103,768及美國專利6,136,856揭示脂肪酸及衍生物根除植物中存在之真菌及細菌感染的獨特效用。此方法為非預防性的,但在已確定之感染中展示有效性。具有80%天竺葵酸、2%乳化劑及18%界面活性劑之Sharpshooter(一種市售產品)展示針對青黴菌及葡萄孢屬的有效性。美國專利6,638,978揭示由甘油脂肪酸酯、脂肪酸(C6至C18)與第二脂肪酸(C6至C18)之二元混合物構成的用於保存食物之抗微生物防腐劑,其中第二脂肪酸不同於第一脂肪酸。WO 01/97799揭示使用中鏈脂肪酸作為抗微生物劑。其顯示pH值自6.5升高至7.5提高了含有具6-8個碳之鏈之短鏈脂肪酸的MIC。
天竺葵酸係用作食物處理設施中之食物接觸表面消毒溶液的組分。來自EcoLab之產品由作為活性成分之6.49%天竺葵酸組成,用於作為所有食物接觸表面之消毒劑(12CFR178.1010 b)。FDA已明確天竺葵酸作為合成的食物調味劑(21 CFR 172.515),作為用於接觸食物中(12 CFR 178.1010 b)及洗滌中或輔助水果及蔬菜之鹼液剝離(12 CFR 173.315)的佐劑、製造助劑及消毒劑。天竺葵酸被USDA列舉在USDA特許物質清單(USDA list of Authorized Substances),1990,第5.14章,Fruit and Vegetable Washing Compounds下。
本發明僅關於使用一些自植物提取或化學合成之醛,其藉由添加有機酸、尤其壬酸來協同改良此等化合物之抗
微生物能力。
本發明之一個目的為提供一種協同改良有機酸及醛之殺微生物作用的組成物。
該組成物可為包含有機酸或若干有機酸與醛組合之混合物的溶液。
該組成物可進一步包含由脂肪加氧酶途徑產生之揮發性醛。
組成物之醛包含丁醛、十一烯醛、檸檬醛、癸醛、癸烯醛、2,4-癸二烯醛及其他來自C1至C24碳長度或形狀之醛。
組成物之有機酸包含具1至24個碳之鏈長度的飽和、不飽和、環狀有機酸或其他有機酸。
本發明之有效混合物包含1至70體積%有機酸。
本發明之有效混合物包含0至70體積%天竺葵酸。
本發明之有效混合物包含5至50%醛。
本發明之有效混合物包含0至70體積%水。
組成物針對存在於飼料及主要飼料成分中之各種真菌有效。
組成物針對存在於飼料及主要飼料成分中之各種細菌有效。
組成物針對存在於水中之各種細菌及真菌有效。
組成物針對關於自纖維素、澱粉或糖醱酵製造醇有害的微生物有效。
在本說明書及隨後申請專利範圍中,將提及多個術語,其應被限定具有以下含義。
組分之「體積百分比(volume percent)」係以包括該組分之調配物或組成物之總體積計。
組成物之有機酸可包含甲酸、乙酸、丙酸、丁酸、天竺葵酸、乳酸及其他C2至C24脂肪酸或含有C1至C24脂肪酸之單甘油酯、二甘油酯或三甘油酯。此等脂肪酸包含短鏈、中鏈、長鏈脂肪酸或短鏈、中鏈、長鏈三酸甘油酯。
術語化合物之「有效量(effective amount)」意謂能夠執行化合物之功能或表示有效量之特性的量,諸如化合物提供所需抗微生物效益之無毒但充足的量。因此所屬技術領域的一般技術者可僅使用常規實驗來確定適當有效量。
調配物不僅可在主要組分(亦即有機酸)之濃度方面,而且可在所用醛之類型及水濃度方面變化。本發明可藉由自調配物添加或刪除有機酸及醛之類型而以若干方式修改。
術語組成物之「協同效應或協同性(synergistic effect or synergy)」意謂當成分以混合物形式而非以個別組分之形式添加時改良防腐作用。
本發明之組成物包含有效量之具1至24個碳之鏈的有機酸及醛。
該組成物可包含1至100體積%有機酸、0至99體積%乙酸、0至99體積%丙酸、0至99%乳酸、0至99%天竺葵酸。該組成物可包含0至99%水。該組成物可包含0至99%其他醛。
本發明針對細菌及真菌有效。
將本發明應用於水。
將本發明應用於進入混合器之前的原材料。
將本發明應用於混合器中未混合之原材料。
在原始成分混合期間應用本發明。
以液體形式或以與載體混合之乾燥產品形式應用本發明。
以提供混合物在整個飼料中之均一及均質分佈的形式應用本發明。
本發明之一個目的在於控制飼料及飼料原料中之微生物的含量。有機酸及醛之若干混合物產生在緩衝液及飼料中展示抗細菌有效性的若干調配物。本發明之其他目的為調配具有天然存在之化合物或使用安全之化合物的抗微生物劑。本發明中所用之所有化學品目前皆已批准供人類用作抗微生物劑、風味增強劑及香料。
當使用有機酸及醛時,存在出人意料的結果,亦即協同效應及累加效應。
在整個本申請案中,提及多個公開案。為了更充分地描述本發明所屬領域之目前先進技術,此等公開案之揭示內容以全文引用的方式併入本申請案中。
以表1中所示濃度將甲醛及/或天竺葵酸添加至試管中。使溶液渦旋10秒以確保混合。每次處理為一式三份的管。添加鼠傷寒沙門氏菌懸浮液(103 cfu/ml,ATCC #14028)至三個含有各調配物之試管中。使溶液渦旋,在室溫下培育24小時,塗在SMA(標準方法瓊脂(Standard Methods Agar))上24小時,隨後計數沙門氏菌群落。呈相比於對照組值減少之百分比形式的各調配物之有效性示於下表中。
觀測關於甲醛及甲醛:天竺葵酸處理之劑量反應曲線。所測試之最高劑量之天竺葵酸不具殺細菌性。0.00125%及0.0025%之天竺葵酸似乎提高甲醛之有效性。
以表2中所示濃度將甲醛及/或天竺葵酸添加至試管中。使溶液渦旋10秒以確保混合。每次處理為一式三份的管。添加鼠傷寒沙門氏菌懸浮液(103 cfu/ml,ATCC #14028)至三個含有各調配物之試管中。使溶液渦旋,在室溫下培育24小時,且塗在SMA(標準方法瓊脂)上24小時,隨後計數沙門氏菌群落。呈相比於對照組值減少之百分比形式的各調配物之有效性示於下表中。
觀測關於甲醛、天竺葵酸及甲醛:天竺葵酸處理之劑量反應曲線。0.00125%及0.0025%之天竺葵酸對減少沙門氏菌不具有顯著影響。然而,當此等含量之天竺葵酸與甲醛混合時,甲醛之殺細菌功效得到改良。
如表3中所呈現,製備5份調配物用於試管內研究。以0.01%及0.05%之濃度將調配物添加至試管中。使溶液渦旋10秒以確保混合。每次處理為一式三份的管。
將鼠傷寒沙門氏菌懸浮液(104 cfu/ml)添加至三個含有各調配物之不同稀釋液的試管中。使管渦旋,在室溫下培育24小時,接著將溶液塗在SMA(標準方法瓊脂)上持續48小時,隨後計數沙門氏菌群落。如下表中所示,以相比於對照組值減少之百分比形式報導各調配物之有效性。
10%之天竺葵酸增加反式-2-己烯醛之功效。
選擇來自研究3之三個調配物來測試其針對飼料中之鼠傷寒沙門氏菌(ATCC # 14028)之有效性。用含量為每公克飼料103 cfu之鼠傷寒沙門氏菌之肉及骨粉接種物修改家禽糊狀飼料。隨後用下文列出之0、1.5或2 kg/MT之調配物中之任一者處理經污染的飼料。24小時後,將未經處理及經處理之飼料的10 g子樣品懸浮於90 ml巴特菲爾德緩衝液(Butterfield buffer)中。將稀釋液塗在XLT-4瓊脂上且在37℃下培育48小時,隨後計數沙門氏菌群落。在處理後第7天再次取樣以進行沙門氏菌計數。所用配方示於下表中。
結果:下表顯示所有調配物針對沙門氏菌有效。提高天竺葵酸之含量產生與高含量之己烯醛類似的功效。
選擇實施例3中所用之5個調配物來測試其針對鼠傷寒沙門氏菌之有效性。用鼠傷寒沙門氏菌之肉及骨粉接種物修改家禽糊狀飼料。隨後用0或2 kg/MT之調配物中之任一者處理經污染的飼料。24小時後,將經處理之飼料的10 g子樣品懸浮於90 ml巴特菲爾德緩衝液中。將稀釋液塗在XLT-4瓊脂上且在37℃下培育48小時,隨後計數沙門氏菌群落。在處理後第7天再次取樣以進行沙門氏菌計數。
下表顯示所有調配物針對沙門氏菌有效。
相同濃度之天竺葵酸及反式-2-己烯醛產生與高含量(25%)反式-2-己烯醛類似的有效性。
關於飼料中之殘餘活性來比較由25%反式-2-己烯醛、5%天竺葵酸及70%水性有機酸構成之來自實施例3之配方1與反式-2-己烯醛。相比於1公斤/噸之己烯醛:天竺葵酸組合產品(0.25公斤/噸之己烯醛),用0.1、0.25、0.5或1.0公斤/噸之己烯醛處理家禽糊狀飼料。在處理後第1天、第6天及第13天,以含量為每公克飼料103 cfu之鼠傷寒沙門
氏菌之肉及骨粉接種物污染飼料。24小時後,將未經處理及經處理之飼料的10 g子樣品懸浮於90 ml巴特菲爾德緩衝液中。將稀釋液塗在XLT-4瓊脂上且在37℃下培育48小時,隨後計數沙門氏菌群落。
下表比較天竺葵酸對己烯醛針對沙門氏菌之殘餘活性的影響。
添加天竺葵酸(5%)至反式-2-己烯醛中產生比反式-2-己烯醛自身更佳的抗沙門氏菌有效性。
7種醛(丁醛、檸檬醛、十一烯醛、癸二烯醛、肉桂醛、癸醛及糠醛)與反式-2-己烯醛、天竺葵酸、丙酸及乙酸摻合,如表9中所呈現。包括20%(X-1)及25%(F18)己醛:有機酸產品作為陽性對照組。以0.1%、0.05%、0.01%及0.005%之濃度添加調配物至試管中。使溶液渦旋10秒以使溶液均勻混合。每次處理為一式三份的管。將鼠傷寒沙門氏菌懸浮液(104 cfu/ml)添加至三個含有各調配物之不同稀釋液的試管中。使溶液渦旋,在室溫下培育24小時,接著塗在XLT-4瓊脂上持續48小時,隨後計數沙門氏菌群落。
呈相比於對照組值減少之百分比形式的各調配物之有效性示於下表中。
1.在5%天竺葵酸下,丁醛本身不如反式-2-己烯醛有效。
2.在10%天竺葵酸下,20%丁醛與20%反式-2-己烯醛一樣有效。
3.在5%及10%天竺葵酸下,丁醛可部分替代反式-2-己烯醛。
4.在5%天竺葵酸下,檸檬醛本身不如反式-2-己烯醛有效。
5.在10%天竺葵酸下,20%檸檬醛與20%反式-2-己烯醛一樣有效。
6.在5%及10%天竺葵酸下,檸檬醛可部分替代反式-2-己烯醛。
7.在5%及10%天竺葵酸下,十一烯醛可替代反式-2-己烯醛。
8.在5%及10%天竺葵酸下,癸二烯醛可替代反式-2-己烯醛。
9.在5%及10%天竺葵酸下,肉桂醛可替代反式-2-己烯醛。
10.在5%及10%天竺葵酸下,癸醛可替代反式-2-己烯醛。
11.在5%及10%天竺葵酸下,糠醛可替代反式-2-己烯醛。
12.所有所測試調配物與具有25%或20%反式-2-己烯醛之陽性配方或甲酸/丙酸調配物一樣有效且在一些情況中比此等調配物更佳。
天竺葵酸增強各個醛及醛組合之功效。熟習此項技術者將顯而易知,可在不悖離以上教示之精神及範疇的情況下進行本發明之變化及修改。希望本說明書及實施例僅視為例示性而非限制性的。
Claims (5)
- 一種用於延長水、飼料或飼料成分之貯藏期限的抗微生物組成物,其包含:水、5-10wt.%之天竺葵酸、15-25wt.%之乙酸、40-50wt.%之丙酸、5-25wt.%反式-2-己烯醛、及5-20wt.%之C1-C24醛,其選自由丁醛、十一烯醛、2,4癸二烯醛、肉桂醛、癸醛和糠醛組成之群。
- 一種用於延長水、飼料或飼料成分之貯藏期限的抗微生物組成物,其包含:5-10wt.%之天竺葵酸、15-25wt.%之乙酸、40-50wt.%之丙酸、及5-20wt.%之C1-C24醛,其選自由十一烯醛、2,4癸二烯醛、肉桂醛、癸醛和糠醛組成之群。
- 一種用於延長水、飼料或飼料成分之貯藏期限的方法,其包含:將有效量之組成物噴霧處理或混合至水、飼料或飼料成分,該組成物包含:水、5-10wt.%之天竺葵酸、15-25wt.%之乙酸、 40-50wt.%之丙酸、5-25wt.%反式-2-己烯醛、及5-20wt.%之C1-C24醛,其選自由丁醛、十一烯醛、2,4癸二烯醛、肉桂醛、癸醛和糠醛組成之群。
- 一種用於延長水、飼料或飼料成分之貯藏期限的方法,其包含:將有效量之組成物噴霧處理或混合至水、飼料或飼料成分,該組成物包含:水、5-10wt.%之天竺葵酸、15-25wt.%之乙酸、40-50wt.%之丙酸、5-25wt.%反式-2-己烯醛、及5-20wt.%之C1-C24醛,其選自由十一烯醛、2,4癸二烯醛、肉桂醛、癸醛和糠醛組成之群。
- 如申請專利範圍第3項或第4項之方法,其中該組成物針對存在於飲用水、飼料及飼料成分中之細菌、病毒、黴漿菌或真菌有效。
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AU2012326529A1 (en) | 2014-04-03 |
JP2014534967A (ja) | 2014-12-25 |
US20150031762A1 (en) | 2015-01-29 |
PT2768539T (pt) | 2017-03-13 |
IL231976A0 (en) | 2014-05-28 |
BR112014009503A2 (pt) | 2017-04-18 |
US10736343B2 (en) | 2020-08-11 |
ES2618638T3 (es) | 2017-06-21 |
CN103889464A (zh) | 2014-06-25 |
WO2013059012A1 (en) | 2013-04-25 |
PL2768539T3 (pl) | 2017-07-31 |
AR088347A1 (es) | 2014-05-28 |
CN103889464B (zh) | 2018-10-26 |
LT2768539T (lt) | 2017-04-10 |
ZA201402849B (en) | 2015-04-29 |
EP2768539B1 (en) | 2016-12-07 |
MX2014004618A (es) | 2014-05-27 |
CA2848777A1 (en) | 2013-04-25 |
EP2768539A1 (en) | 2014-08-27 |
KR20140078680A (ko) | 2014-06-25 |
EP2768539A4 (en) | 2015-11-18 |
TW201316907A (zh) | 2013-05-01 |
HUE033375T2 (en) | 2017-11-28 |
CL2014000855A1 (es) | 2014-09-05 |
RU2014115606A (ru) | 2015-11-27 |
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