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什么是α-单脂肪酸甘油酯?

工夫:2019-05-10 10:37泉源:未知 作者:admin 点击:

什么是α-单脂肪酸甘油酯?


One

α-单脂肪酸甘油酯是一类甘油酯,其由经由过程甘油的sn1-位取脂肪酸衔接的构成酯键,而且果其强抗微生物感化而著名。 图1给出了酯化回响反映的示意图,以得到这类α-单脂肪酸甘油酯。 脂肪酸的氢原子(H)取甘油份子的羟基(OH)回响反映,致使水分子(H2O)的构成,并在脂肪酸的氧原子取碳原子之间发生共价键。 

Alpha-monoglycerides are a class of glycerides that are composed of a fatty acid linked to the sn1-position of glycerol via an ester bond and are known for their strong antimicrobial effects. Figure 1 gives a schematic overview of the esterification reaction to obtain such an α-monoglyceride. The hydrogen atom (H) of the fatty acid reacts with the  hydroxyl  group  (OH) of the glycerol molecule resulting in the formation of a water  molecule  (H2O)  and  creating  a  covalent  bond  between the oxygen atom of the fatty acid and the carbon atom of the glycerol molecule.

图一(Figure 1)

 

(A)脂肪酸和甘油的酯化回响反映构成α-单脂肪酸甘油酯

(A)   Esterification reaction of a fatty acids and glycerol to form an α-monoglyceride.

 

(B)丁酸和甘油酯化后构成α-单丁酸甘油酯。

(B)   Formation of α-monobutyrin after esterification of butyric acid and glycerol.


Two

α-单脂肪酸甘油酯、α-甘油二酯和α-甘油三酯的分子结构的差别如图2所示。当一种脂肪酸取甘油的第一个碳原子(sn1-位置)联合时,该份子称为α-单脂肪酸甘油酯。当一种脂肪酸取甘油份子的第二个碳原子联合时,构成β-单脂肪酸甘油酯。主要的是要晓得只要α-单脂肪酸甘油酯有抗菌感化。甘油三酯是一种脂肪,在一般的消化历程中剖析,是能量的泉源。

The difference between the molecular structure of α-monoglyceride, α-diglyceride and α- triglyceride is shown in Figure 2.When one fatty acid is bound to the first carbon atom (sn1- position) of glycerol, the molecule is termed an α-monoglyceride. A β-monoglyceride is formed when one fatty acid is bound to the second carbon atom of the glycerol molecule. It is important to know that only the α-monoglycerides have antimicrobial effects. A triglyceride is a fat, which is broken down during normal digestion processes and is a source of energy.

图二(Figure 2.)

α-单脂肪酸甘油酯、甘油二酯和甘油三酯的示意图概述

Schematic overview of α-monoglyceride, diglyceride and triglyceride

 

Three

凭据脂肪酸的链少,能够发生差别的α-单脂肪酸甘油酯(图3)。短链α-单脂肪酸甘油酯(SCFA)和中链α-单脂肪酸甘油酯(MCFA)具有差别的特性,短链的Alpha-单脂肪酸甘油酯像α-单丙酸甘油酯和单丁酸甘油酯,丙酸和丁酸的α-单甘油酯离别对革兰氏阴性菌有抑止感化。

Depending on the chain length of the fatty acid, different α-monoglycerides can be produced (Figure 3). A distinction can be made between α-monoglycerides of short chain fatty acids (SCFA) and α-monoglycerides of medium chain fatty acids (MCFA), which have  different  characteristics. Alpha-monoglycerides of SCFA such as α-monopropionin and α-monobutyrin, the α-monoglycerides of propionic acid and butyric acid respectively, are mainly active against gram negative bacteria.

图三(Figure 3.)

FRAmelco的五种常用的α-单脂肪酸甘油酯

Overview of the five commonly produced α-monoglycerides by FRAmelco.


多重上风

取游离脂肪酸比拟,α-单脂肪酸甘油酯的强共价键具有多重上风(表1)。α-单甘油酯不依赖于酸碱度,因而不会离解。在饲料加工历程中不挥发、不侵蚀、热稳固。另外,单脂肪酸苦酯具有中性的味道和气息,但更主要的是,研讨注解,α-单脂肪酸苦酯与其相对应的游离脂肪酸比拟,具有更强的抗菌感化。

The strong covalent bond of α-monoglycerides results in multiple benefits compared to free fatty acids (Table 1). Alpha-monoglycerides are pH independent and consequently do not dissociate. They are non-volatile, non-corrosive and heat stable during feed processing. Furthermore, monoglycerides have a neutral taste and odor, but more important, research has shown that α-monoglycerides have a much stronger antimicrobial effect compared to their corresponding free fatty acids.

另外,α-单脂肪酸甘油酯是两亲性化合物,具有亲脂性,由于它们的脂肪酸尾部和亲水性性,因为其亲水性骨干(甘油)。那使得α-单脂肪酸甘油酯在水中自乳化。因而,它们在四种差别的情况中运动:火、饲料、胃和肠道。Framelco的α-单脂肪酸甘油酯基产物有枯燥和液体两种情势,有些借经由过程饮用水运用的。

Moreover, α-monoglycerides are amphiphilic compounds possessing both lipophilic (fat-loving) properties, due to their fatty acid tail and hydrophilic (water-loving) properties, due to their hydrophilic backbone (glycerol). This makes α-monoglycerides self emulsifying in water. Consequently they are active in four different environments: water, feed, stomach, and the intestinal tract. FRAmelco’s α-monoglycerides based products are available in dry and liquid form and some are applied also via drinking water.

表1(Table 1)

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对照游离脂肪酸和α-单脂肪酸甘油酯之间的差别

Comparison between free fatty acids and α-monoglycerides.
 

抗菌感化

取游离脂肪酸比拟,α-单脂肪酸甘油酯的强共价键具有多重上风(表1)。α-单甘油酯不依赖于酸碱度,因而不会离解。在饲料加工历程中不挥发、不侵蚀、热稳固。另外,单脂肪酸苦酯具有中性的味道和气息,但更主要的是,研讨注解,α-单脂肪酸苦酯与其相对应的游离脂肪酸比拟,具有更强的抗菌感化。

The strong covalent bond of α-monoglycerides results in multiple benefits compared to free fatty acids (Table 1). Alpha-monoglycerides are pH independent and consequently do not dissociate. They are non-volatile, non-corrosive and heat stable during feed processing. Furthermore, monoglycerides have a neutral taste and odor, but more important, research has shown that α-monoglycerides have a much stronger antimicrobial effect compared to their corresponding free fatty acids.

另外,α-单脂肪酸甘油酯是两亲性化合物,具有亲脂性,由于它们的脂肪酸尾部和亲水性性,因为其亲水性骨干(甘油)。那使得α-单脂肪酸甘油酯在水中自乳化。因而,它们在四种差别的情况中运动:火、饲料、胃和肠道。Framelco的α-单脂肪酸甘油酯基产物有枯燥和液体两种情势,有些借经由过程饮用水运用的。

Moreover, α-monoglycerides are amphiphilic compounds possessing both lipophilic (fat-loving) properties, due to their fatty acid tail and hydrophilic (water-loving) properties, due to their hydrophilic backbone (glycerol). This makes α-monoglycerides self emulsifying in water. Consequently they are active in four different environments: water, feed, stomach, and the intestinal tract. FRAmelco’s α-monoglycerides based products are available in dry and liquid form and some are applied also via drinking water.

表1(Table 1)

对照游离脂肪酸和α-单脂肪酸甘油酯之间的差别

Comparison between free fatty acids and α-monoglycerides.


感化部位

有机酸只在酸性情况中有活性,那意味着消化系统的第一部分。那能够用它们的pka值去注释。pka值是50%的有机酸离解后落空杀菌机能的pH值(图4A)。然则,为了得到最好的肠道康健和机能,这些添加剂在肠道情况中也具有活性是很重要的(图4B)。因为单脂肪酸甘油酯是稳固且不依赖于酸碱度的份子,因而它们在全部胃肠道中都很活泼。

Organic acids are only active in an acidic environment, meaning the first part of the digestive system. This can be explained by their pKa value. The pKa-value is the pH at which 50% of the organic acid is dissociated, losing the bactericidal properties (Figure 4A).However, for optimal gut health and performance, it is important that these additives are also active in the intestinal environment (Figure 4B). As α-monoglycerides are stable and pH independent molecules, they are active in the entire gastro-intestinal tract.

图四(Figure 4)

(A)五种有机酸的pka值。

(A)pKa value of five organic acids.

(B)家禽胃肠道有机酸和单脂肪酸甘油酯感化部位的对照

(B)Comparison between the site of action of organic acids and α-monoglycerides in the gastrointestinal tract of poultry

 


感化体式格局
中链α-单脂肪酸甘油酯

中链的α-单脂肪酸甘油酯重要对革兰氏阳性细菌有感化,但好像也具有抗病毒的特性。因为这些α-单脂肪酸甘油酯的两亲性,它们构成胶束,使它们可以或许融入这些微生物的脂质膜,从而改动渗透性。中链的α-单脂肪酸甘油酯以至能够损坏这些细菌的细胞膜和使病原体病毒的囊膜走漏(图6)。另外,革兰氏阳性菌和囊膜病毒没有完好的膜,不克不及有用的粘附侵入宿主细胞,从而不克不及熏染和滋生。

Alpha-monoglycerides of MCFA have mainly effects against gram positive bacteria, but also seem to have antiviral properties. Due to the amphiphilic nature of these α-monoglycerides they form micelles, which may provide them with the ability to get incorporated into the lipid membrane of these microorganisms, thereby altering the permeability. Alpha-monoglycerides of MCFA may even disrupt the cell membrane of these bacteria and the fat envelop of viruses which makes  the  pathogen leaky (Figure 6). Furthermore, gram positive bacteria and fat enveloped viruses can not properly adhere to, and invade, a host cell without an intact membrane. In this way infection and multiplication will not be possible.

另外,借以为α-单脂肪酸甘油酯对膜的滋扰会改动跨膜旌旗灯号转导,从而抑止有害的中隐卵白。并且,更多的亲脂性份子,如中链的α-单脂肪酸甘油酯,更倾向于从肠细胞背淋巴体系转运,而不是经由过程门静脉到肝脏。这样一来,除肠道中的间接抗菌感化中,这些α-单脂肪酸甘油酯借具有系统性感化,由于它们被完好天运输到身材的其他器官,在那里它们能够资助抵抗熏染

Furthermore, it is thought that interference of α-monoglycerides with the membrane modifies the transmembrane signal transduction which results in inhibition of harmful exoproteins. Moreover, it is suggested that more lipophilic molecules like α-monoglycerides of MCFA have more tendency to be transported from the enterocytes to the lymphatic system instead of going via the portal vein to the liver. In this way, besides the immediate antimicrobial effect in the intestine, these α-monoglycerides have a systemic effect as they are transported intact to other organs of the body where they can help fighting infections.

 

总之中链α-单脂肪酸甘油酯如:α-单酸楚甘油酯、α-单葵酸甘油酯、α-单月桂酸甘油酯对革兰氏阳性军更有用。停止了多项研讨,曾经证实了α-单脂肪酸甘油酯在体外和体内的均有抗菌感化,许多科学文献注解,中链的α-单脂肪酸甘油酯,尤其是α-单月桂酸甘油酯,具有抗病毒的特性。

In contrast,α-monoglycerides of MCFA like α-monocaprylin, α-monocaprin and α-monolaurin are more efficient against gram positive bacteria. Multiple studies have been conducted which prove the antibacterial effect of α-monoglycerides in vitro and in vivo. In addition, scientific literature  is  suggesting  α-monoglycerides of MCFA, and more particularly α-monolaurin, have antiviral properties.

图五(Figure 5).

中链α-单脂肪酸甘油酯甘油酯对细菌的感化体式格局。

The mode of action of α-monoglycerides of MCFA’s on bacteria

短链α-单脂肪酸甘油酯

短链的α-单脂肪酸甘油酯和中链的单甘油酯的感化体式格局略有差别。

The mode of action of α-monoglycerides of SCFA and-monoglycerides of MCFA are slightly different.

短链的α-单脂肪酸甘油酯重要对革兰氏阴性菌有感化。人们以为没有一种感化体式格局,然则这些α-单脂肪酸甘油酯有几种感化体式格局能够影响细菌。细菌需求甘油去保持其主要功用和膜的构成。甘油是由细菌经由过程专门的蛋白质通道(火甘油三酯)从情况中吸取的。短链的α-单脂肪酸甘油酯可被以为是甘油,并经由过程这些通道被动转运。在细菌内部,酶剖析单脂肪酸甘油酯,开释脂肪酸,低落细菌内部的酸碱度。大概,这些卵白通道也能够被α-单脂肪酸甘油酯阻断,由于它们的分子结构比甘油大。效果,细菌不再可以或许吸取甘油,并将殒命。另外,脂肪酸借能够经由过程在转录程度下调基因去改动DNA,并抑止到场宿主细胞入侵的蛋白质天生(TTSS复合物)。

Alpha-monoglycerides of SCFA have mainly an effect against gram negative bacteria. It is thought that there is not one mode of action, but that there are several ways these α-monoglycerides can affect bacteria. Bacteria need glycerol for vital functions and to build up their membrane. Glycerol is taken up from the environment by the bacteria through specialized protein channels (aquaglyceroporin). The α-monoglycerides of SCFA may be recognized as glycerol and passively be transported through these channels. Inside the bacteria enzymes break down the _-monoglycerides and the fatty acid is released which lowers the internal pH of the bacteria. Alternatively, these protein channels may also be blocked by α-monoglycerides, since their molecular structure is larger compared to glycerol. As a result bacteria are no longer able to take up glycerol and will die. In addition, the fatty acid can alter DNA by down regulation of the genes at transcription level and inhibit the protein production involved in invasion of host cells (TTSS Complex).

图六(Figure 6).

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短链α-单脂肪酸甘油酯对细菌的感化形式

The mode of action of α-monoglycerides of SCFAs on bacteria

 

 

泉源:荷兰FRAmelco/佰高威衰公司

声明:本文为“华康植物康健服务平台”所有,未经允许,制止转载!谢谢合作

 


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