新型水产诱食剂溴化DMPT的合成及应用研究
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摘要
DMPT(Dimethyl-β-Propiothetin)，化学名称为S，S-二甲基-β-内酸噻亭，存在于海洋浮游植物体内，是一种硫代谢产物。DMPT对多种海、淡水鱼类及长臂虾的生长、摄食均有不同程度的促进作用，并且能提高饲料利用率，增强鱼对不良环境的抵抗力。本文以市售二甲硫醚与3-溴丙酸按1.5：1的摩尔比，在40℃回流反应24h，得到溴化DMPT，经无水乙醚洗涤、甲醇溶液重结晶提纯后，得到溴化DMPT晶体，纯度达到96％以上。建立了测定溴化DMPT纯度的分光光度法，以及测定鱼肉、饲料中DMPT含量的气相色谱法，从而对DMPT的稳定性，尤其是添加到饲料中以后的稳定性进行了试验，并以鲫鱼为例，对DMPT在鱼体内的积累和消除做了初步探讨。本文的重点是DMPT的应用效果，分别以鲫鱼、慈鲷科热带观赏鱼非洲王子、黑鲷、大菱鲆为例，研究了DMPT对淡水及海水幼鱼摄食和生长的影响。实验证明，饲料中添加0.1g／kg溴化DMPT对鲫鱼、慈鲷均有诱食作用；添加0.2g／kg溴化DMPT，可使鲫鱼、慈鲷、黑鲷、大菱鲆的增重率分别达到对照组的1.3、1.8、1.6、1.2倍，黑鲷、大菱鲆的体长增长率分别达到对照组的1.6、1.1倍，饵料系数分别下降了14.3％、26.4％、16.8％、6.9％，这种差别与鱼的代谢有关。
DMPT (Dimethyl-β-Propiothetin) is a kind of tertiarly sulfonium compounds. It widely exists in sea alga cells and is a metabolite from sulfur. DMPT can promote feeding motion and improve the growth of many species of sea fish and freshwater fish. Meanwhile, it can improve the physique and enhance the resistance of fish to the harmful circumstances.
DMPT is synthesized by the reaction of dimethylsulfide to 3-bromopropionic acid at around 40℃ during the reflux period for 24 hours, and purified by washing it with cold dry ether and crystallizing it from its methanol solution. The purity of the DMPT crystal obtained is above 96%, and the production rate is about 73%.
The head-space gas chromatogram method to determine the purity of DMPT crystal, as well as the content of DMPT in feed and fish muscles has been established in the paper. The stability of DMPT crystal, especially the stability of DMPT after put into the feed, is also reported in the paper. Furthermore, with carassius auratus as an example, the accumulation and elimination of DMPT in fish muscle was primarily testes.
The emphasis of this study was put on the effects of DMPT on the ingestion and growth of juvenile fishes, for example carassius auratus, Labidochromis caeruleus, Sparus macrocephalus and Scophthalmus maximus. It's proved that 0.1g/kg DMPT bromide in formulated feed promotes feeding motion, while 0.2g/kg DMPT bromide in feed makes the body weight increase of the above fishes reach 1.3, 1.8, 1.6, 1.2-fold of the contrast groups, respectively. With 0.2g/kg DMPT bromide in feed, the body length increase of Sparus macrocephalus and Scophthalmus maximus reach 1.6 and 1. 1-fold of the contrast groups respectively. On the other hand, the feed conversion rate drops 14. 3%, 26.4% and 6.9% accordingly. The difference between the effects is due to the difference between the metabolism of fishes.
DMPT (Dimethyl-β-Propiothetin) is a kind of tertiarly sulfonium compounds. It widely exists in sea alga cells and is a metabolite from sulfur. DMPT can promote feeding motion and improve the growth of many species of sea fish and freshwater fish. Meanwhile, it can improve the physique and enhance the resistance of fish to the harmful circumstances.
DMPT is synthesized by the reaction of dimethylsulfide to 3-bromopropionic acid at around 40℃ during the reflux period for 24 hours, and purified by washing it with cold dry ether and crystallizing it from its methanol solution. The purity of the DMPT crystal obtained is above 96%, and the production rate is about 73%.
The head-space gas chromatogram method to determine the purity of DMPT crystal, as well as the content of DMPT in feed and fish muscles has been established in the paper. The stability of DMPT crystal, especially the stability of DMPT after put into the feed, is also reported in the paper. Furthermore, with carassius auratus as an example, the accumulation and elimination of DMPT in fish muscle was primarily testes.
The emphasis of this study was put on the effects of DMPT on the ingestion and growth of juvenile fishes, for example carassius auratus, Labidochromis caeruleus, Sparus macrocephalus and Scophthalmus maximus. It's proved that 0.1g/kg DMPT bromide in formulated feed promotes feeding motion, while 0.2g/kg DMPT bromide in feed makes the body weight increase of the above fishes reach 1.3, 1.8, 1.6, 1.2-fold of the contrast groups, respectively. With 0.2g/kg DMPT bromide in feed, the body length increase of Sparus macrocephalus and Scophthalmus maximus reach 1.6 and 1. 1-fold of the contrast groups respectively. On the other hand, the feed conversion rate drops 14. 3%, 26.4% and 6.9% accordingly. The difference between the effects is due to the difference between the metabolism of fishes.
引文
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[8] 李炜，焦念志．环境因子对三种常见微藻细胞中二甲基硫丙酸含量影响的初步研究．海洋与湖沼，1999，30(6)：635—639．
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[10] 焦念志，柳承璋，陈念红．东海二甲基硫丙酸的分布及其制约因素的初步研究．海洋与湖沼，1999，30(5)：525—531．
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[15] 丛玉艳，张建勋．甜菜碱在水产养殖中的应用．中国饲料，1998，(17)：22—23．
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[21] 占秀安．甜菜碱促进肉鸡生长的作用机理研究．浙江农业学报，2000。12(4)：209—212．
[22] 崔贞，张曼平．海水中二甲基硫(DMS)的测定方法及其来源的研究．黄渤海海洋，1999，17(J)：71—74．
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[25] Kenji Nakajima, Aritsune Uchida, Yuzaburo Ishida. Effect of a feeding attractant, dimethyl-β-propiothetin, on growth of marine fish. Bulletin of the Japanese Society of Scientific Fisheries, 1990,56(7): 1151--1154.
[26] Kenji nakajima, Aritsune Uchida, Yuzaburo Ishida. Effect of supplemental dietary feeding attractant, dimethyl-β-propiothetin, on growth of goldfish. Bulletin of the Japanese Society of Scientific Fisheries, 1989,55(7): 1291.
[27] Kenji Nakajima. Effects of diet-supplemented dimethyl-β-propiothetin on growth and thrust power of goldfish, carp, and red sea bream. Bulletin of the Japanese Society of Scientific Fisheries, 1991, 57(4): 673--679.
[28] Kenji Nakajima. Effects of dimethyl-β-propiothetin on growth and thrust power of rainbow Trout. Bulletin of the Japanese Society of Scientific Fisheries, 1991, 57(8): 1603.
[29] Kenji Nakajima. Dimethyl-β-propiothetin, a potent growth and molt stimulant for striped prawn. Bulletin of the Japanese Society of Scientific Fisheries, 1991, 57(9): 1717--1722.
[30] Kenji Nakajima. Activation effect of a short term of dimethyl-β-propiothetin supplememtation on growth and rainbow trout. Bulletin of the Japanese Society of Scientific Fisheries, 1992, 58(8): 1453--1458.
[31] Aritsune Uchida, Tomoaki Ooguri, Takehiro Ishida, Yuzaburo Ishida. Incorporation of Methylthiopropanoic acid in the dinoflagellate Crypthecodinium cohnii. Bulletin of the Japanese Society of Scientific Fisheries, 1993,59(5): 851--855.
[32] Kenji Nakajima. Dimethylthetin- and betaine-homocysteine methyltransferase activities from livers of fish, chicken, and Mammals. Bulletin of the Japanese Society of Scientific Fisheries, 1993, 59(8): 1389--1393.
[33] A. Vairavamurthy, M. O. Andreae, R. L. Iverson. Biosynthesis of dimethylsulfide and dimethyl propiothetin by Hymenomonas carterae in relation to sulfur source. Limnal. Oceanogr.,1985,30(1): 59--70.
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dimethylsulfoniopropionate concentrations in nearshore waters. Limnal. Oceanogr., 1988, 33(3): 364--375.
[35] Iverson R. L., Nearhoff F. L., Andreae M. 0.. Production of dimethylsulfonium propionate and dimethylsulfide by phytoplankton in estuarine and coastal waters. Limnal. Oceanogr., 1989, 34(1):53--67.
[36] Dickson D. M. J., Kirst G. O.. The effect of nitrogen dieficiency, methiionine and inhibitors of methioinine metabolism on the DMSP contents of Tetraselmis subcordiformis (Stein). Mar. Biol.,1992,112:497--503.
[37] G. A. Maw. Thetin-homocysteine transmethylase a preliminary manomeyric study of the enzyme from rat liver. Biochem. J., 1956, 63:116--124.
[38] 饭田 遥，中添纯一，齐藤洋昭，德永俊夫．鱼类-β-．日本水产学会志，1986，52(12)：2155—2161．
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[43] 兰州大学复旦大学化学系有机化学教研组．有机化学实验．人民教育出版社，1978．26—28，55—61。
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[2] 张阳军．水产饲料复合诱食素的开发利用．粮食与饲料工业，2001，(6)：25—26，30．
[3] 钟国清．甜菜碱及其应用．中国饲料，1997，(3)：27—28．
[4] 薛永瑞，金兆峰．甜菜碱及其复合剂在鲤鱼饲料中的添加效果．中国饲料，1995，(10)：17—18．
[5] 唐建勋．鱼虾的非营养性饲料添加剂．中国饲料，1997，(22)：29—30．
[6] 贾卫斌，胡波等．碘化改性大蒜素的应用研究．中国饲料，1997，(19)：15—16．
[7] 范晓，周永航．海藻中的甜菜碱及其类似物．海洋科学，1999，23(3)：24—26．
[8] 李炜，焦念志．环境因子对三种常见微藻细胞中二甲基硫丙酸含量影响的初步研究．海洋与湖沼，1999，30(6)：635—639．
[9] 杨桂朋，戚佳琳．影响海水中二甲基硫分布的生物因素．海洋科学，2000，24(3)：37—40．
[10] 焦念志，柳承璋，陈念红．东海二甲基硫丙酸的分布及其制约因素的初步研究．海洋与湖沼，1999，30(5)：525—531．
[11] 侯彩霞，汤章城．细胞相容性物质的生理功能及其作用机制．植物生理学通讯，1999，35(1)：1—7．
[12] 梁峥，骆爱玲．甜菜碱和甜菜碱合成酶．植物生理学通讯，1995，31(1)：1—8．
[13] 王娟，李德全．逆境条件下植物体内渗透调节物质的积累与活性氧代谢．植物学通报，2001，18(4)：459—465．
[14] 马玉龙，张文斌，周学．甜菜碱营养机理研究．中国饲料，1999，(18)：11—13．
[15] 丛玉艳，张建勋．甜菜碱在水产养殖中的应用．中国饲料，1998，(17)：22—23．
[16] 梁冬生，苏晓鸥，陈益众．甜菜碱．饲料工业，1997，18(3)：34—37．
[17] 王俊卿，刘瑞林．甜菜碱、蛋氨酸和胆碱在动物新陈代谢中的作用及相互关系。山西大学学报(自然科学版)，2001，24(4)：348—351．
[18] 崔玉民．甜菜碱合成工艺的研究．化学试剂，2001，23(5)：313—314．
[19] 曾端．肉碱和甜菜碱营养生理作用比较．中国饲料，2001，(12)：18—19．
[20] 刘瑞生．甜菜碱在水产养殖中的应用．中国饲料，2001，(10)29—30．
[21] 占秀安．甜菜碱促进肉鸡生长的作用机理研究．浙江农业学报，2000。12(4)：209—212．
[22] 崔贞，张曼平．海水中二甲基硫(DMS)的测定方法及其来源的研究．黄渤海海洋，1999，17(J)：71—74．
[23] 王永华，焦念志．顶空气相色谱法测定海水二甲基硫和浮游植物细胞二甲基硫丙酸的研究．海洋与湖沼，1996，27(1)：46—50．
[24] Kenji Nakajima, Aritsune Uchida, Yuzaburo Ishida. A new feeding attractant, dimethyl-β-propiothetin, for freshwater fish. Bulletin of the Japanese Society of Scientific Fisheries, 1989,55(4): 689--695.
[25] Kenji Nakajima, Aritsune Uchida, Yuzaburo Ishida. Effect of a feeding attractant, dimethyl-β-propiothetin, on growth of marine fish. Bulletin of the Japanese Society of Scientific Fisheries, 1990,56(7): 1151--1154.
[26] Kenji nakajima, Aritsune Uchida, Yuzaburo Ishida. Effect of supplemental dietary feeding attractant, dimethyl-β-propiothetin, on growth of goldfish. Bulletin of the Japanese Society of Scientific Fisheries, 1989,55(7): 1291.
[27] Kenji Nakajima. Effects of diet-supplemented dimethyl-β-propiothetin on growth and thrust power of goldfish, carp, and red sea bream. Bulletin of the Japanese Society of Scientific Fisheries, 1991, 57(4): 673--679.
[28] Kenji Nakajima. Effects of dimethyl-β-propiothetin on growth and thrust power of rainbow Trout. Bulletin of the Japanese Society of Scientific Fisheries, 1991, 57(8): 1603.
[29] Kenji Nakajima. Dimethyl-β-propiothetin, a potent growth and molt stimulant for striped prawn. Bulletin of the Japanese Society of Scientific Fisheries, 1991, 57(9): 1717--1722.
[30] Kenji Nakajima. Activation effect of a short term of dimethyl-β-propiothetin supplememtation on growth and rainbow trout. Bulletin of the Japanese Society of Scientific Fisheries, 1992, 58(8): 1453--1458.
[31] Aritsune Uchida, Tomoaki Ooguri, Takehiro Ishida, Yuzaburo Ishida. Incorporation of Methylthiopropanoic acid in the dinoflagellate Crypthecodinium cohnii. Bulletin of the Japanese Society of Scientific Fisheries, 1993,59(5): 851--855.
[32] Kenji Nakajima. Dimethylthetin- and betaine-homocysteine methyltransferase activities from livers of fish, chicken, and Mammals. Bulletin of the Japanese Society of Scientific Fisheries, 1993, 59(8): 1389--1393.
[33] A. Vairavamurthy, M. O. Andreae, R. L. Iverson. Biosynthesis of dimethylsulfide and dimethyl propiothetin by Hymenomonas carterae in relation to sulfur source. Limnal. Oceanogr.,1985,30(1): 59--70.
[34] Suzanne M. Turner, Gillian Malin Peter S. Liss, Derek S. Harbour, Patrick M. Holligan. The seasonal variation of dimethyl sulfide and
dimethylsulfoniopropionate concentrations in nearshore waters. Limnal. Oceanogr., 1988, 33(3): 364--375.
[35] Iverson R. L., Nearhoff F. L., Andreae M. 0.. Production of dimethylsulfonium propionate and dimethylsulfide by phytoplankton in estuarine and coastal waters. Limnal. Oceanogr., 1989, 34(1):53--67.
[36] Dickson D. M. J., Kirst G. O.. The effect of nitrogen dieficiency, methiionine and inhibitors of methioinine metabolism on the DMSP contents of Tetraselmis subcordiformis (Stein). Mar. Biol.,1992,112:497--503.
[37] G. A. Maw. Thetin-homocysteine transmethylase a preliminary manomeyric study of the enzyme from rat liver. Biochem. J., 1956, 63:116--124.
[38] 饭田 遥，中添纯一，齐藤洋昭，德永俊夫．鱼类-β-．日本水产学会志，1986，52(12)：2155—2161．
[39] 德永俊夫，饭田 遥，中村弘二．日本水产学会志，1977，43(10)：1209—1217．
[40] 饭田 遥，德永俊夫．贝类．日本水产学会志，1986，52(3)：557—563．
[41] 饭田 遥，中村弘二，德永俊夫．干挥发性含硫化合物量变化．日本水产学会志，1986，52(6)：1077—1080．
[42] 饭田 遥，中村弘二，德永俊夫．海藻中-β-．日本水产学会志，1985，51(7)：1145—1150．
[43] 兰州大学复旦大学化学系有机化学教研组．有机化学实验．人民教育出版社，1978．26—28，55—61。
[44] 林海．鱼虾饲料手册．北京：中国农业大学出版社，1999．138。
[45] 李爱杰．水产动物营养与饲料学．北京：中国农业出版社，1996．151—152。
[46] 熊家林，张珩．饲料添加剂．北京：化学工业出版社精细化工出版中心，2001．27，19—22，78—79，300—301。
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