CN111675740A - Potholin glucoside, application of pinosylin glucoside and preparation method of pinosylin glucoside - Google Patents
Potholin glucoside, application of pinosylin glucoside and preparation method of pinosylin glucoside Download PDFInfo
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- CN111675740A CN111675740A CN202010421556.3A CN202010421556A CN111675740A CN 111675740 A CN111675740 A CN 111675740A CN 202010421556 A CN202010421556 A CN 202010421556A CN 111675740 A CN111675740 A CN 111675740A
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- pinosylvin
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- 229930182478 glucoside Natural products 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 150000008131 glucosides Chemical class 0.000 title description 7
- YCVPRTHEGLPYPB-VOTSOKGWSA-N Pinosylvin Natural products OC1=CC(O)=CC(\C=C\C=2C=CC=CC=2)=C1 YCVPRTHEGLPYPB-VOTSOKGWSA-N 0.000 claims abstract description 74
- YCVPRTHEGLPYPB-UHFFFAOYSA-N pinosylvine Natural products OC1=CC(O)=CC(C=CC=2C=CC=CC=2)=C1 YCVPRTHEGLPYPB-UHFFFAOYSA-N 0.000 claims abstract description 63
- -1 pinosylvin glucoside Chemical class 0.000 claims abstract description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 25
- 230000008569 process Effects 0.000 claims abstract description 18
- 230000006378 damage Effects 0.000 claims abstract description 14
- 230000036542 oxidative stress Effects 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940126062 Compound A Drugs 0.000 claims abstract description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 239000000047 product Substances 0.000 claims abstract description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 4
- 238000004440 column chromatography Methods 0.000 claims abstract description 4
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- 238000010790 dilution Methods 0.000 claims abstract description 4
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- 239000011259 mixed solution Substances 0.000 claims abstract description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 3
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTIXKCRFFJGDFG-UHFFFAOYSA-N Chrysin Natural products C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
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- FGUBFGWYEYFGRK-HNNXBMFYSA-N Pinocembrin Natural products Cc1cc(C)c2C(=O)C[C@H](Oc2c1)c3ccccc3 FGUBFGWYEYFGRK-HNNXBMFYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
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- PYIXHKGTJKCVBJ-UHFFFAOYSA-N Astraciceran Natural products C1OC2=CC(O)=CC=C2CC1C1=CC(OCO2)=C2C=C1OC PYIXHKGTJKCVBJ-UHFFFAOYSA-N 0.000 description 1
- NDVRQFZUJRMKKP-UHFFFAOYSA-N Betavulgarin Natural products O=C1C=2C(OC)=C3OCOC3=CC=2OC=C1C1=CC=CC=C1O NDVRQFZUJRMKKP-UHFFFAOYSA-N 0.000 description 1
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- 208000026350 Inborn Genetic disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IHPVFYLOGNNZLA-UHFFFAOYSA-N Phytoalexin Natural products COC1=CC=CC=C1C1OC(C=C2C(OCO2)=C2OC)=C2C(=O)C1 IHPVFYLOGNNZLA-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
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- 125000003147 glycosyl group Chemical group 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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Abstract
The invention provides pinosylvin glucoside, which is used for protecting oxidative stress injury in a weak sperm optimization process. The preparation method of the pinosylvin glucoside comprises the following steps: (1) adding 0.2mmol of compound A and 0.22mmol of compound B into a 25mL round-bottom flask under the protection of nitrogen, adding 5mL of MeOH, stirring the reaction solution at 40 ℃ for 2 h; (2) after the reaction is finished, cooling to room temperature, and adding 10ml of ethyl acetate for dilution; (3) washing the reaction mixed solution with saturated saline solution for 3 times, extracting the organic phase with ethyl acetate, drying the organic phase with anhydrous sodium sulfate, and concentrating the crude product under reduced pressure to purify the crude product by column chromatography to obtain a yellow product C, namely 40 percent pinosylvin glucoside. The invention aims to prepare pinosylvin-3-O-b-D-glucoside, which is added in the process of centrifuging the weak and weak semen, and is subjected to biochemical detection and analysis to analyze the concentration change of active oxygen (ROS) and Malondialdehyde (MDA) of the semen of a control group, so as to discuss the function of the pinosylvin glucoside in the process of centrifuging the weak and weak semen outside.
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to pinosylvin glucoside, application of pinosylvin glucoside and a preparation method of pinosylvin glucoside.
Background
Pinosylvin (pinosylvin) is a derivative of natural trans-1, 2-stilbene, appears in wood pulp of pine and eucalyptus, tea oil and herbal medicine, is stilbene, is low in water solubility, so that glycosyl and other polar genes are often introduced to increase the water solubility of the stilbene, and the structure of the pinosylvin-3-O-b-D-glucoside is as follows.
As pinosylvin naturally exists in nature, but the solubility of pinosylvin is low, at present, no report on the existence of a natural glucoside compound exists in pinosylvin, but a pinosylvin-3-O-b-D-glucoside compound can be prepared by chemical synthesis, has good antioxidation and is supported by a large amount of researches.
Other stilbene derivatives such as pinosylvin and the like have been subjected to relatively extensive pharmacological research, and are hot spots for research and development of various antioxidant products. The pinosylvin has very effective antibacterial activity on a plurality of fungi, and when trees are infected by fungi, the trees can secrete the pinosylvin to be used as phytoalexin. Therefore, the pinosylvin has wide research and development prospects on the antioxidant and antibacterial effects of animals.
Oligoasthenospermia is one of the indications of assisted reproductive therapy, preferably, the in vitro semen treatment of sperms is a conventional step in the assisted reproductive technology treatment, and aims to obtain a sperm suspension without seminal plasma, cell debris and pathogenic microorganism pollution, recover enough sperms with normal morphology and functions, the centrifugation process in the in vitro optimized treatment of the sperms is a key point for inducing the excessive generation of active oxygen, and a plurality of important antioxidant substances in the seminal plasma are removed in the treatment process, so that the sperms are more easily subjected to peroxidation damage.
Disclosure of Invention
Experiments prove that the pinosylvin glucoside crystal can resist oxidation, and has the effects of reducing oxidative stress damage of excessive active oxygen generated in the optimization process to sperms and improving the quality of the sperms.
In order to solve the above technical problem, an embodiment of the present invention provides a pinosylvin glycoside, wherein the chemical formula of the pinosylvin glycoside is shown as formula (I):
the pinosylvin glycoside is a yellow solid with a melting point of 163-165 ℃ and a molecular weight of 388.
The invention also provides application of the pinosylvin glucoside in protecting oxidative stress injury in the optimization process of weak sperm.
Wherein the effective dose range of the pinosylvin glucoside for protecting oxidative stress injury in the weak sperm optimization process is 1umol/L-30 umol/L.
The pinosylvin glucoside can also be prepared into oral preparations, injections, granules, pills, capsules, powders, sustained-release preparations, controlled-release preparations, targeted preparations and other preparations for patients with weak sperm in medical treatment.
The invention also provides a preparation method of the pinosylvin glucoside, wherein the preparation equation of the pinosylvin glucoside is as shown in formula (II):
the preparation method comprises the following steps:
(1) adding 0.2mmol of compound A and 0.22mmol of compound B into a 25mL round-bottom flask under the protection of nitrogen, adding 5mL of MeOH, stirring the reaction solution at 40 ℃ for 2 h;
(2) after the reaction is finished, cooling to room temperature, and adding 10ml of ethyl acetate for dilution;
(3) washing the reaction mixed solution with saturated saline solution for 3 times, extracting the organic phase with ethyl acetate, drying the organic phase with anhydrous sodium sulfate, concentrating the crude product under reduced pressure, and purifying the crude product by column chromatography to obtain a yellow product C which is the pinosylvin glucoside, wherein the reaction yield is 40%.
Preferably, the compound A is ((3, 5-dimethoxyphenyl) ethynyl) benzene, and the chemical formula is shown as the formula (III):
the chemical formula of the compound B is shown as the formula (IV):
the compound C is pinosylvin glucoside, and the chemical formula is shown as a formula (V):
wherein the volume ratio of ethyl acetate to petroleum ether in the purification in the step (3) is 1: 4.
the technical scheme of the invention has the following beneficial effects:
1. the invention aims to prepare pinosylvin-3-O-b-D-glucoside, which is added in the process of centrifuging the weak and weak semen, and is subjected to biochemical detection and analysis to analyze the concentration change of active oxygen (ROS) and Malondialdehyde (MDA) of the semen of a control group, so as to discuss the function of the pinosylvin glucoside in the process of centrifuging the weak and weak semen outside.
2. Experiments prove that the pinosylvin glucoside crystal can resist oxidation, reduce oxidative stress damage of excessive active oxygen generated in the optimization process to sperms and improve the quality of the sperms.
Drawings
FIG. 1 is a hydrogen spectrum of pinosylvin glycoside prepared by the present invention;
FIG. 2 is a carbon spectrum of the pinosylvin glycoside prepared by the present invention.
Detailed Description
In order to make the technical problems, technical solutions and advantages of the present invention more apparent, the following detailed description is given with reference to the accompanying drawings and specific embodiments.
The inventor finds that the pinosylvin and the glucoside thereof have obvious protective effect on oligoasthenospermia sperms through long-term research. Through further research, the pinosylvin and the glucoside compounds thereof can reduce oxidative stress damage and reduce the generation of active oxygen (ROS) and Malondialdehyde (MDA) through antioxidation, thereby further protecting weak and weak sperms.
The invention aims to prepare pinosylvin-3-O-b-D-glucoside, which is added in the process of centrifuging the weak and weak semen, and is subjected to biochemical detection and analysis to analyze the concentration change of active oxygen (ROS) and Malondialdehyde (MDA) of the semen of a control group, so as to discuss the function of the pinosylvin glucoside in the process of centrifuging the weak and weak semen outside.
Based on the theory, the invention provides the pinosylvin glucoside, and the chemical formula of the pinosylvin glucoside is shown as the formula (I):
the pinosylvin glycoside is a yellow solid with a melting point of 163-165 ℃ and a molecular weight of 388.
The invention also provides application of the pinosylvin glucoside, which is used for protecting oxidative stress injury of oligospermia in the optimization process, and can be prepared into oral preparations, injections, granules, pills, capsules, powder, sustained-release preparations, controlled-release preparations, targeted preparations and preparations of other administration routes for patients with oligospermia in medical treatment.
Wherein the effective dose range of the pinosylvin glucoside for protecting oxidative stress injury in the weak sperm optimization process is 1umol/L-30 umol/L.
The invention also provides a preparation method of the pinosylvin glucoside, wherein the preparation equation of the pinosylvin glucoside is as shown in formula (II):
the preparation method comprises the following steps:
(1) adding 0.2mmol of compound A and 0.22mmol of compound B into a 25mL round-bottom flask under the protection of nitrogen, adding 5mL of MeOH, stirring the reaction solution at 40 ℃ for 2 h;
(2) after the reaction is finished, cooling to room temperature, and adding 10ml of ethyl acetate for dilution;
(3) the reaction mixture was washed with saturated brine for 3 times, the organic phase was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the crude product was concentrated under reduced pressure and purified by column chromatography (ethyl acetate/petroleum ether: 1/4) to obtain pinosylvin glycoside as a yellow product C (yield 40%).
(E)-Pinosylvin-3-O-β-D-glucuronide:Yellowish solid；m.p.163–165℃；1HNMR(400MHz,DMSO):d＝3.39–3.21(m,3H；H-2”,H-3”,H-4”),3.87(d,J＝9.6Hz,1H；H-5”),4.98(d,J＝7.6Hz,1H；H-1”),5.24(d,J＝4.8Hz,1H；-OH),5.41(d,J＝5.2Hz,1H；-OH),6.32(br s,1H；H-4),6.58(s,1H；H-6),6.66(s,1H；H-2),6.87(d,J＝8.4Hz,2H；H-3’,H-5’),6.93(d,J＝16.4Hz,1H；H-8),7.01(d,J＝16.4Hz,1H；H-7),7.40(d,J＝8.4Hz,2H；H-2’,H-6’),9.50ppm(br s,1H；phenolic-OH)；13CNMR(100MHz,DMSO):d＝71.8(C-2”,C-3”orC-4”),73.4(C-2”,C-3”or C-4”),75.9(C-2”,C-3”or C-4”),76.2(C-5”),100.5(C-1”),103.0(C-4),105.2(C-2),107.6(C-6),116.0(C-3’,5’),125.5(C-7),128.3(C-2’,6’),128.4(C-8),129.0(C-1’),139.8(C-1),157.8(C-4’),158.8(C-3),158.9(C-5),170.6ppm(C-6”)；MS:m/z 388[M+].
Preferably, the compound A is ((3, 5-dimethoxyphenyl) ethynyl) benzene, and the chemical formula is shown as the formula (III):
the chemical formula of the compound B is shown as the formula (IV):
the compound C is pinosylvin glucoside, and the chemical formula is shown as a formula (V):
FIG. 1 shows the hydrogen spectrum of the pinosylvin glycoside prepared by the present invention. FIG. 2 shows a carbon spectrum of the pinosylvin glycoside prepared by the present invention.
The reduction of oxidative stress damage to sperm by excess reactive oxygen species generated during the preferred process is further demonstrated below in conjunction with the specific examples.
The method comprises the following steps:
the method comprises the following steps: general sample: 9-2019-10-2018, 30 oligospermia specimens in a andrology laboratory of procreation medicine, the age is 25-40 years, the male is healthy, the history of smoking, alcoholism and long-term exposure to harmful substances, the history of genital tract infection and varicocele, the history of trauma and genetic diseases, the history of asexual dysfunction and the like are avoided. The routine examination of the semen before the operation is carried out according to WHO manual of human semen examination and treatment laboratories.
Step two, grouping and processing: each sperm sample is liquefied in an incubator at 37 ℃ for 20 minutes and then mixed evenly, 1500ml of semen is taken from each sample and divided into 3 equal parts, namely 500m1, which are respectively encoded into 1 group, 2 group and 3 group, wherein 1 group is a control group, only 100ml of EBSS liquid is added into the control group without centrifugation, 2 group is a centrifugation control group, 100ml of EBSS liquid is added into the control group for centrifugation, 3 group is a silver pinocembrin glucoside centrifugation group, and silver pinocembrin glucoside EBSS solution (15-mmol/L) is added into the control group for centrifugation. The concentration of active oxygen and malonaldehyde in each semen after being treated by the above 3 methods was measured.
Step three, reagents and instruments: pinosylvin glycosides (purity 98%) were provided by charcot biotechnology limited, shanxi; the Malondialdehyde (MDA) detection kit is provided by the bioengineering research institute of Jiangsu Nanjing; the active oxygen (ROS) determination adopts a luminol chemiluminescence determination method, adopts a sperm cell active oxygen chemiluminescence detection kit produced by Shanghai Jimei biological agents, and is strictly operated according to the kit specification, and the instrument is a LuminMax-C chemiluminescence detector.
Step four, a statistical method: all data were reported as mean. + -. standard deviation (. + -. s) of stress function. Indicated, SPSS17.0 statistical software was used for analysis, and comparisons between groups were performed using the t-test.
Step five, experimental results: compared with blank control, the ROS and MDA levels of the centrifugation control group are obviously increased, and the statistical significance is achieved (P is less than 0.05, and P is less than 0.05); the ROS and MDA levels of the pinosylvin glucoside centrifugation group are obviously reduced compared with those of the centrifugation control group, and the results are shown in a table 1, wherein the results have statistical significance (P is less than 0.05 and P is less than 0.05).
TABLE 1
And (4) conclusion: the preferential centrifugation of weak sperm outside the sperm body of the assisted reproduction technology can stimulate the sperm to generate excessive active oxygen, and the oxidative stress is caused. The addition of pinosylvin glucoside before centrifugation can reduce the level of active oxygen, protect oxidative stress damage to a certain extent, and improve the overall function of sperms. Before semen is optimized, a certain concentration of pinosylvin glucoside is added to reduce the oxidative stress damage of the excessive active oxygen generated in the optimization process to the sperms, thereby improving the quality of the sperms.
While the foregoing is directed to the preferred embodiment of the present invention, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (8)
1. The pinosylvin glycoside is characterized in that the chemical formula of the pinosylvin glycoside is shown as a formula (I):
the pinosylvin glycoside is a yellow solid with a melting point of 163-165 ℃ and a molecular weight of 388.
2. Use of pinosylvin glycoside for the protection of oxidative stress damage during the process of oligozoospermia.
3. The use of pinosylvin glycoside according to claim 2, wherein the effective dose of pinosylvin glycoside for protecting against oxidative stress injury during the oligozoospermia-preferred process is in the range of 1 to 30 umol/L.
4. The use of the pinosylvin glycoside according to claim 2, wherein the composition can be prepared into oral preparations, injections, granules, pills, capsules, powders, sustained-release preparations, controlled-release preparations, targeted preparations and other administration routes for patients with oligospermia.
5. A preparation method of pinosylvin glucoside is characterized in that the preparation equation of the pinosylvin glucoside is as formula (II):
the preparation method comprises the following steps:
(1) adding 0.2mmol of compound A and 0.22mmol of compound B into a 25mL round-bottom flask under the protection of nitrogen, adding 5mL of MeOH, stirring the reaction solution at 40 ℃ for 2 h;
(2) after the reaction is finished, cooling to room temperature, and adding 10ml of ethyl acetate for dilution;
(3) washing the reaction mixed solution with saturated saline solution for 3 times, extracting the organic phase with ethyl acetate, drying the organic phase with anhydrous sodium sulfate, concentrating the crude product under reduced pressure, and purifying the crude product by column chromatography to obtain a yellow product C which is the pinosylvin glucoside, wherein the reaction yield is 40%.
6. The method for preparing pinosylvin glycoside according to claim 5, wherein the compound A is ((3, 5-dimethoxyphenyl) ethynyl) benzene, and the chemical formula is shown as formula (III):
the chemical formula of the compound B is shown as the formula (IV):
7. the method for preparing pinosylvin glycoside according to claim 5, wherein the compound C is pinosylvin glycoside having a chemical formula shown in formula (V):
8. the method for preparing pinosylvin glycoside according to claim 5, wherein the volume ratio of ethyl acetate to petroleum ether in the purification in step (3) is 1: 4.
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