CN111632057A - Application of rhamnose monosulfate trisaccharide and derivatives in skeletal muscle atrophy resistance - Google Patents

Application of rhamnose monosulfate trisaccharide and derivatives in skeletal muscle atrophy resistance Download PDF

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CN111632057A
CN111632057A CN202010529096.6A CN202010529096A CN111632057A CN 111632057 A CN111632057 A CN 111632057A CN 202010529096 A CN202010529096 A CN 202010529096A CN 111632057 A CN111632057 A CN 111632057A
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于明圣
于淼林
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Qingdao Central Hospital
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Abstract

The embodiment of the invention provides application of rhamnostriose monosulfate and derivatives thereof in skeletal muscle atrophy resistance, and the rhamnostriose monosulfate or the rhamnostriose monosulfate derivatives are applied to a medicament for resisting skeletal muscle atrophy, or the rhamnostriose monosulfate derivatives are applied to a functional food for resisting skeletal muscle atrophy. The rhamnostriose monosulfate is used for inhibiting the differentiation inhibition of TNF-alpha on skeletal muscle cells C2C12, promoting the generation of myosin MHC and myogenin of C2C12 and promoting the transformation of skeletal muscle myogenic cells into muscle fibers.

Description

Application of rhamnose monosulfate trisaccharide and derivatives in skeletal muscle atrophy resistance
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to an application of rhamnose monosulfate and a derivative thereof in skeletal muscle atrophy resistance.
Background
Skeletal muscle atrophy (abbreviated as muscular atrophy) mainly refers to the reduction of skeletal muscle mass and muscle function, the occurrence of muscular atrophy is the comprehensive expression of negative balance of degradation and synthesis of skeletal muscle protein, and influencing factors comprise related hormone change, active oxygen tissue level change, apoptosis and the like. Common causes of muscular atrophy include long-term malnutrition, loss or lack of movement of the systemic or local limbs, denervation, etc., and finding out and removing pathogenic causes is an important prerequisite for the treatment and prevention of diseases. Skeletal muscle atrophy caused by long-term malnutrition can be gradually improved under the conditions of removing causes and continuously supplementing comprehensive nutrition. The catabolism and synthesis of skeletal muscle proteins are influenced and regulated by a number of hormones, cytokines, proteasome inhibitors in the body. Aiming at the condition of reducing anabolic regulator substances, the method for preventing and treating muscular atrophy by supplementing a proper amount of growth factors is an effective method. In addition to insulin growth factor, recombinant human growth hormone (rhGH), adrenocorticotropic hormone releasing factor 2 receptor (CRF2R) agonist, nandrolone decanoate, creatine, losartan, vitamin D, leucine and the like, in recent years, research reports that vitamin E, resveratrol and mitochondrial nutrients have good antagonistic effect on animal muscle atrophy. The medicines respectively show different control effects on different forms of muscular atrophy, experimental animals of different months of age or people of different ages. However, no report is found at present on the research of rhamnose sulfate in resisting muscular atrophy.
Disclosure of Invention
The invention aims to provide application of rhamnose monosulfate and derivatives thereof in resisting skeletal muscle atrophy.
In order to achieve the purpose, the invention adopts the following technical scheme:
one aspect of the invention provides the use of rhamnotrise monosulfate in the treatment of skeletal muscle atrophy.
Another aspect of the present invention provides the use of a rhamnotrisaccharide monosulfate derivative for the treatment of skeletal muscle atrophy.
Optionally, the rhamnostriose monosulfate or the rhamnostriose monosulfate derivative is applied to a medicament for resisting skeletal muscle atrophy, or the rhamnostriose monosulfate derivative is applied to a functional food for resisting skeletal muscle atrophy.
Optionally, the rhamnotrise monosulfate is used for inhibiting the differentiation inhibition of TNF-alpha on skeletal muscle cell C2C12, promoting the generation of myosin MHC and myogenin of C2C12 and promoting the transformation of skeletal muscle myogenic cells into muscle fibers.
Optionally, the rhamnose monosulfate trisaccharide is prepared by taking green alga monostroma nitidum or enteromorpha as a raw material and performing chemical degradation, ultrafiltration and gel column separation; the molecular structure of the compound is alpha-L-Rhap- (2S04) - (1 → 3) -alpha-L-Rhap, the compound is formed by connecting a 1, 3 glycosidic bond with rhamnose (Rha) bond, and the molecular weight is 536.14 Da.
Optionally, the molecular structural formula of the rhamnostriose monosulfate is as follows:
Figure BDA0002533430360000021
optionally, the rhamnostriose monosulfate derivative includes: the method comprises the steps of using a sulfated derivative containing rhamnostriose monosulfate as a mother core, using a phosphorylated derivative containing rhamnostriose monosulfate as a mother core, and using an acetylated derivative containing rhamnostriose monosulfate as a mother core.
Optionally, the dosage of the rhamnose monosulfate is 10-300 mg/kg.
Optionally, the preparation method of the rhamnostriose monosulfate comprises the following steps:
1) preparing the green alga monostroma nitidum or the enteromorpha into an aqueous solution;
2) adding dilute hydrochloric acid into the aqueous solution obtained in the step 1), heating, stirring, degrading, and adjusting the pH value to be neutral by adopting NaOH;
3) concentrating and precipitating the solution obtained in the step 2) with ethanol, concentrating the supernatant by a rotary instrument, and desalting by a gel chromatographic column;
4) then separating and purifying by adopting a Bio-Gel P4 chromatographic column, detecting the sugar content of the eluent by a sulfuric acid phenol method, and drawing an elution curve;
5) and collecting the peak part, and freeze-drying to obtain the rhamnose monosulfate.
The invention has the beneficial effects that:
1. the invention provides application of rhamnose monosulfate and derivatives in skeletal muscle atrophy resistance.
2. In the embodiment of the invention, the rhamnostriose monosulfate or the rhamnostriose monosulfate derivative is applied to a medicament for resisting skeletal muscle atrophy, or the rhamnostriose monosulfate derivative is applied to a functional food for resisting skeletal muscle atrophy.
3. The embodiment of the invention adopts a cell model of TNF-alpha induced skeletal muscle atrophy, and finds the application of the rhamnostriose monosulfate in resisting the skeletal muscle atrophy. The experimental results show that: the rhamnose monosulfate can obviously inhibit the differentiation inhibition of TNF-alpha on skeletal muscle cell C2C 12; and effectively promotes the generation of myosin MHC and myogenin of C2C12, effectively promotes the transformation of skeletal muscle myogenic cells to muscle fibers, and has obvious effect of resisting skeletal muscle atrophy.
4. The raw materials of the embodiment of the invention are derived from marine natural green algae reef membranes or enteromorpha, have the advantages of rich resources, easy industrialization, safety, effectiveness and the like, and can be developed into medicines and functional foods (health care products) for resisting skeletal muscle atrophy, thereby having better market application prospect.
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FIG. 1 is a secondary mass spectrum of rhamnostriose monosulfate in the example of the present invention.
Detailed Description
The conception, the specific structure, and the technical effects produced by the present invention will be clearly and completely described in conjunction with the embodiments below, so that the objects, the features, and the effects of the present invention can be fully understood. It is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments, and those skilled in the art can obtain other embodiments without inventive effort based on the embodiments of the present invention, and all embodiments are within the protection scope of the present invention.
One embodiment of the invention provides the use of rhamnotrise monosulfate to combat skeletal muscle atrophy.
Specifically, the rhamnose monosulfate trisaccharide is applied to a medicament or functional food for resisting skeletal muscle atrophy.
The specific application mode is as follows: the rhamnose monosulfate trisaccharide can be directly taken as a medicine or a functional food.
The specific usage and dosage are as follows: the dosage of the rhamnose monosulfate is 20-750mg per time, 1-3 times per day. The dosage of the rhamnostriose monosulfate is 10-300 mg/kg.
In the embodiment of the invention, the rhamnostriose monosulfate can inhibit the differentiation inhibition of TNF-alpha on skeletal muscle cell C2C12, promote the generation of myosin MHC and myogenin of C2C12, promote the transformation of skeletal muscle myogenic cells to muscle fibers and have obvious effect of resisting skeletal muscle atrophy.
Another embodiment of the present invention provides the use of a rhamnotrise monosulfate derivative for the treatment of skeletal muscle atrophy.
Specifically, the rhamnose monosulfate trisaccharide derivative is applied to a medicament or functional food for resisting skeletal muscle atrophy.
The specific application mode is as follows: the rhamnose monosulfate trisaccharide derivative can be directly taken as a medicine or a functional food.
The specific usage and dosage are as follows: the dosage of the rhamnose monosulfate is 20-750mg per time, 1-3 times per day. The dosage of the rhamnostriose monosulfate is 10-300 mg/kg.
In the embodiment of the invention, the rhamnostriose monosulfate derivative can inhibit the differentiation inhibition of TNF-alpha on skeletal muscle cells C2C12, promote the generation of myosin MHC (major histocompatibility complex) and myogenin of C2C12, promote the transformation of skeletal muscle myogenic cells to muscle fibers and have obvious effect of resisting skeletal muscle atrophy.
In the embodiment of the invention, the rhamnostriose monosulfate derivative comprises the following components: the method comprises the steps of using a sulfated derivative containing rhamnostriose monosulfate as a mother core, using a phosphorylated derivative containing rhamnostriose monosulfate as a mother core, and using an acetylated derivative containing rhamnostriose monosulfate as a mother core.
Yet another embodiment of the invention provides rhamnotrise monosulfate and a preparation method thereof
The rhamnose monosulfate trisaccharide is prepared by taking green alga Monostroma nitidum or Enteromorpha as a raw material through chemical degradation, ultrafiltration and a gel column separation method; the molecular structure of the compound is alpha-L-Rhap- (2S04) - (1 → 3) -alpha-L-Rhap, the compound is formed by connecting a 1, 3 glycosidic bond with rhamnose (Rha) bond, and the molecular weight is 536.14 Da.
The preparation method of the rhamnostriose monosulfate comprises the following steps:
1) preparing the green alga monostroma nitidum or the enteromorpha into 0.5-1.5 wt% of water solution;
2) adding 0.2-1.0 wt% of dilute hydrochloric acid into the aqueous solution obtained in the step 1), heating to 80-100 ℃, stirring to degrade the aqueous solution for 4-6 hours, and adjusting the pH value to be neutral by adopting NaOH;
3) concentrating and precipitating the solution obtained in the step 2) with ethanol, concentrating the supernatant by a rotary instrument, and desalting by a gel chromatographic column Sephadex G10;
4) then separating and purifying by adopting a Bio-Gel P4 chromatographic column, detecting the sugar content of the eluent by a sulfuric acid phenol method, and drawing an elution curve;
5) and collecting the peak part, and freeze-drying to obtain the rhamnose monosulfate.
The following are specific examples.
Example 1
Preparing green alga enteromorpha algae powder into a 1 wt% aqueous solution, adding 0.5 wt% diluted hydrochloric acid into the enteromorpha aqueous solution, heating to 90 ℃, stirring and degrading for 5 hours, neutralizing with 0.1M NaOH to obtain pH7.0, concentrating, precipitating with ethanol, concentrating the supernatant by a rotary instrument, desalting by a Gel chromatographic column Sephadex G10, separating and purifying by a Bio-Gel P4 Gel chromatographic column, detecting the sugar content of the eluent by a phenol sulfate method, drawing an elution curve, collecting the peak part, and freeze-drying to obtain the rhamnose monosulfate.
The structural formula of the prepared rhamnostriose monosulfate is as follows:
Figure BDA0002533430360000061
an oligosaccharide sample (rhamnose monosulfate) was reacted with 0.05mol/l NaBH4 at 4 ℃ for 10 hours in a refrigerator, and the pH was adjusted to 7.0 with acetic acid water. The oligosaccharide sample was eluted with distilled water using AG50W-X8 column, then concentrated and lyophilized. In the mass spectrometry process, nitrogen is used as a blow-dry gas and a spray gas, the flow rate is 250L/h, and acetonitrile and water are used as a mobile phase at a ratio of 1: 1(V/V) for performing the analysis of the quality. In the secondary mass spectrum, the cone hole voltage is 80eV, argon is used as collision gas, and the flow rate is 15L/h. At the same time, the best sequence information is obtained while maintaining the collision energy exchanged at 20-50 eV. The ion source and solvent volatilization peak temperatures were 80 ℃ and 150 ℃, respectively.
According to a secondary mass spectrum of the monosulfated rhamnose, MS/MS fragment ions (m/z 225) (m/z243) (m/z371) (m/z 389) are generated by the breakage of glycosidic bonds, and the fragment ions (m/z 475) determine that a sulfate group is positioned at the C-2 position of rhamnose at the non-reducing end. According to the sequence analysis method of the rhamnose sulfate secondary mass spectrum, the structure of the rhamnose sulfate is deduced to be alpha-L-Rhap- (2S04) - (1 → 3) -alpha-L-Rhap.
Experimental test 1: effect of rhamnose monosulfate on TNF-alpha induced Release of LDH from skeletal muscle cells
The test was carried out using the rhamnostriose monosulfate prepared in example 1. The method comprises the following specific steps:
(1) cell culture: C2C12 cells were inoculated into DMEM complete medium (containing 100U/mL penicillin, 100U/mL streptomycin and 10% FBS) and cultured in a 5% CO2 incubator at 37 ℃.
(2) 8000 cells per hole are planted in a 96-hole plate, the 96-hole plate is placed in a constant-temperature cell culture box to be incubated for 12 hours, then, rhamnose monosulfate with different concentrations is added, and the 96-hole plate is placed in the constant-temperature cell culture box to be incubated for 12 hours continuously. After the incubation is finished, the culture medium is replaced, 100ng/ml of TNF-alpha is added into each hole, after the incubator is incubated for 48 hours, the supernatant is collected, and the LDH content in the supernatant is detected. Each time three replicates were performed and the experiment was repeated three times.
The experimental results are shown in Table 1, when the monostroma oligodisaccharide is administered at the concentrations of 50 mu mol/L, 100 mu mol/L and 200 mu mol/L, and 400 mu mol/L, the release level of LDH is significantly different from that of a control group, and the rhamnostriose monosulfate can significantly inhibit the release of TNF-alpha induced LDH in skeletal muscle cells and has obvious dose-dependent effect.
TABLE 1 Effect of rhamnostriose monosulfate on TNF- α induced LDH release from skeletal muscle cells
Group (mu mol/L) LDH release levels
Control group 1.0±0.02
Model set 2.1±0.02#
50 1.8±0.01*
100 1.6±0.03*
200 1.4±0.02
400 1.2±0.01*
Note: n is 9, x ± SD, P < 0.05, P < 0.001 compared to the model group
Experimental test 2: effect of rhamnostriose monosulfate on TNF- α -induced skeletal muscle differentiation protein the effect of rhamnostriose monosulfate on TNF- α -induced skeletal muscle differentiation protein was tested using the rhamnostriose monosulfate prepared in example 1.
(1) Cell culture: C2C12 cells were inoculated in DMEM complete medium (containing 1OOU/mL penicillin, 100U/mL streptomycin and 10% FBS) and cultured in a 5% CO2 incubator at 37 ℃.
(2) 8000 cells per hole are planted in a 96-hole plate, the 96-hole plate is placed in a constant-temperature cell culture box to be incubated for 12 hours, then, rhamnose monosulfate with different concentrations is added, and the 96-hole plate is placed in the constant-temperature cell culture box to be incubated for 12 hours continuously. And (3) after the incubation is finished, replacing the culture medium, adding 100ng/ml of TNF-alpha into each hole, continuously incubating in an incubator for 72 hours, extracting RNA, and performing fluorescent quantitative RT-PCR analysis on mRNA of MHC (major histocompatibility complex) and myogenin. The experiment was repeated three times.
The results are shown in table 2, and rhamnose monosulfate can significantly reverse the expression of TNF-alpha inhibited myofibrillar key proteins. The rhamnose monosulfate can obviously improve the expression of MHC (major histocompatibility complex) and increase the protein content of Myogenin. MHC and Myogenin are important indexes for measuring skeletal muscle function, and the expression level is obviously reduced in muscle atrophy diseases, so that the skeletal muscle function is degraded. The rhamnose monosulfate in the embodiment of the invention can effectively inhibit muscle damage and protect skeletal muscle from being interfered by diseases.
TABLE 2 Effect of rhamnostriose monosulfate on TNF- α induced skeletal muscle differentiation protein
Figure BDA0002533430360000081
Figure BDA0002533430360000091
It should be noted that, throughout the specification, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
The principles and embodiments of the present invention are explained herein using specific examples, which are presented only to assist in understanding the method and its core concepts of the present invention. It should be noted that there are no more than infinite trial-and-error modes objectively due to the limited character expressions, and it will be apparent to those skilled in the art that various modifications, decorations, or changes may be made without departing from the spirit of the invention or the technical features described above may be combined in a suitable manner; such modifications, variations, combinations, or adaptations of the invention using its spirit and scope, as defined by the claims, may be directed to other uses and embodiments.

Claims (9)

1. Application of rhamnose monosulfate trisaccharide in resisting skeletal muscle atrophy.
2. Application of the rhamnose monosulfate trisaccharide derivative in resisting skeletal muscle atrophy.
3. The use according to claim 1 or 2, characterized in that the rhamnostriose monosulfate or the rhamnostriose monosulfate derivative is applied in a medicament against skeletal muscle atrophy or in a functional food against skeletal muscle atrophy.
4. The use according to any of claims 1 to 3, wherein the rhamnotrisaccharide monosulfate is used to inhibit the inhibition of the differentiation of TNF- α on skeletal muscle cells C2C12, and to promote the production of C2C12 myosin MHC and myogenin, and the conversion of skeletal muscle myogenic cells into muscle fibers.
5. The application of claim 4, wherein the rhamnostriose monosulfate is prepared by taking green alga Monostroma nitidum or Enteromorpha as a raw material through chemical degradation, ultrafiltration and a gel column separation method; the molecular structure of the compound is alpha-L-Rhap- (2S04) - (1 → 3) -alpha-L-Rhap, the compound is formed by connecting a 1, 3 glycosidic bond with rhamnose (Rha) bond, and the molecular weight is 536.14 Da.
6. The use according to claim 4 or 5, wherein the rhamnose monosulfate has the following molecular formula:
Figure FDA0002533430350000011
7. the use according to claim 2, characterized in that said rhamnose monosulfate derivative comprises: the method comprises the steps of using a sulfated derivative containing rhamnostriose monosulfate as a mother core, using a phosphorylated derivative containing rhamnostriose monosulfate as a mother core, and using an acetylated derivative containing rhamnostriose monosulfate as a mother core.
8. The use according to claim 1 or 2, characterized in that the rhamnose monosulfate is used in an amount of 10-300 mg/kg.
9. The use according to claim 1 or 2, characterized in that the preparation process of the rhamnostriose monosulfate comprises the following steps:
1) preparing the green alga monostroma nitidum or the enteromorpha into an aqueous solution;
2) adding dilute hydrochloric acid into the aqueous solution obtained in the step 1), heating, stirring, degrading, and adjusting the pH value to be neutral by adopting Na 0H;
3) concentrating and precipitating the solution obtained in the step 2) with ethanol, concentrating the supernatant by a rotary instrument, and desalting by a gel chromatographic column;
4) then separating and purifying by adopting a Bio-Gel P4 chromatographic column, detecting the sugar content of the eluent by a sulfuric acid phenol method, and drawing an elution curve;
5) and collecting the peak part, and freeze-drying to obtain the rhamnose monosulfate.
CN202010529096.6A 2020-06-10 2020-06-10 Application of rhamnose monosulfate trisaccharide and derivatives in skeletal muscle atrophy resistance Pending CN111632057A (en)

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CN102993244A (en) * 2012-11-26 2013-03-27 中国海洋大学 Oligorhamnose monomer and preparation method thereof
CN104586878A (en) * 2015-01-14 2015-05-06 青岛海洋生物医药研究院股份有限公司 Fucoidan sulfate and application of low-molecular-weight fucoidan sulfate in preparation of metabolic syndrome resistant medicines and health products
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