CN115010604A - Diterpene component in hyssop officinalis and preparation method and application thereof - Google Patents
Diterpene component in hyssop officinalis and preparation method and application thereof Download PDFInfo
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- CN115010604A CN115010604A CN202210635164.6A CN202210635164A CN115010604A CN 115010604 A CN115010604 A CN 115010604A CN 202210635164 A CN202210635164 A CN 202210635164A CN 115010604 A CN115010604 A CN 115010604A
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention relates to the technical field of separation and purification of aerial parts of schizonepeta bracteata, and discloses a diterpene component in hyssop officinalis and a preparation method and application thereof. The invention discloses Nepetabate I for the first time and animal experiments show that the Nepetabate I has obvious effects of resisting inflammation and inhibiting inflammation, can play a role of synergistic inflammation resistance, has definite curative effect, high safety and easily obtained raw materials, and can be applied to preparation of medicaments with anti-inflammatory effect.
Description
Technical Field
The invention relates to the technical field of separation and purification of aerial parts of schizonepeta bracteata, and discloses a diterpene component in hyssop officinalis, a preparation method and application thereof, wherein the diterpene component in the hyssop officinalis is short for Nepetabrate I.
Background
Inflammation is a defensive response of the animal body to various inflammatory factors and their resulting damage, a protective response involving immune cells, blood vessels and molecular mediators. Inflammatory tissue swelling, often accompanied by pain, fever, bacterial and viral infections. Nepeta brachiata Benth, a Nepeta plant of Nepeta of Labiatae (Labiatae), has Uygur name of ancestor, has pharmacological effects of generating heat, warming lung, relieving asthma, dispelling cold, relieving cough, eliminating dampness, eliminating phlegm, removing sweat, removing toxic substances, diminishing inflammation, and relieving swelling, and is mainly used for treating wet-cold and mucous respiratory diseases. Modern pharmacological studies have shown that extracts have significant anti-inflammatory activity, but there are fewer related studies to characterize their chemical composition. Therefore, the development and utilization of the monomeric compound of the schizonepeta cataria are carried out, the potential medicinal value of the monomeric compound is further excavated, the structure and the physicochemical properties of the monomeric compound are determined and characterized, and the systematic evaluation of the abietane diterpene anti-inflammatory capability of the schizonepeta cataria is of great significance for the development and utilization of the plants of the schizonepeta cataria.
The medicinal effect of the schizonepeta bracteata mainly comes from terpenoids in the schizonepeta bracteata, including monoterpenes and diterpenoids, wherein diterpenoids as main ingredients have better anti-inflammatory and bacteriostatic activities. Therefore, the method develops and utilizes the abietane diterpenoid monomeric compounds of the schizonepeta bracteata, further excavates the potential medicinal value of the monomeric compounds, determines and characterizes the structure and the physicochemical properties of the monomeric compounds of the schizonepeta bracteata, and has important significance for developing and utilizing the schizonepeta bracteata.
Disclosure of Invention
The invention provides a diterpene component in hyssop, a preparation method and application thereof, overcomes the defects of the prior art, discloses Nepetate I for the first time, and the Nepetate I has obvious effects of resisting inflammation and inhibiting inflammation, can play a synergistic anti-inflammatory role, has exact curative effect and high safety, is easy to obtain raw materials, and can be applied to preparation of medicaments with anti-inflammatory effects.
One of the technical schemes of the invention is realized by the following measures: a Nepetabnate I, the chemical structural formula is as follows:
the following is a further optimization or/and improvement of one of the above-mentioned technical solutions of the invention:
the Nepetabnate I is obtained according to the following method: firstly, smashing and sieving overground parts of schizonepeta bracteata, adding ethanol, soaking for 3 to 4 hours at room temperature, heating and refluxing the ground schizonepeta bracteata with 50% methanol for 3 times, wherein each time lasts for about 3 hours, combining extracting solutions, and concentrating under reduced pressure to obtain a total extract; secondly, dispersing the schizonepeta tenuifolia total extract into suspension with water, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butyl alcohol, and concentrating the extract to obtain extracts of all parts; step three, performing silica gel column chromatography on the n-butanol part, and performing dichloromethane-methanol gradient elution at a ratio of 50:1 to 1:1, wherein 6 parts are obtained in the order of 50:1, 20:1, 10:1, 5:1, 2:1 and 1: 1; and fourthly, purifying and separating the 3 rd fraction after gradient elution of high performance liquid chromatography, and collecting eluate to obtain Nepetabrate I at 17.8 minutes.
In the first step, 8mL to 12mL of ethanol is added per 1g of aerial part of Nepeta cataria.
In the fourth step, the eluent for gradient elution of the high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
the second technical scheme of the invention is realized by the following measures: a preparation method of Nepetabnate I is characterized by comprising the following steps: firstly, smashing and sieving overground parts of schizonepeta bracteata, adding ethanol, soaking for 3 to 4 hours at room temperature, heating and refluxing the ground schizonepeta bracteata with 50% methanol for 3 times, wherein each time lasts for about 3 hours, combining extracting solutions, and concentrating under reduced pressure to obtain a total extract; secondly, dispersing the schizonepeta tenuifolia total extract into suspension with water, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butyl alcohol, and concentrating the extract to obtain extracts of all parts; step three, performing silica gel column chromatography on the n-butanol part, and performing dichloromethane-methanol gradient elution at a ratio of 50:1 to 1:1, wherein 6 parts are obtained in the order of 50:1, 20:1, 10:1, 5:1, 2:1 and 1: 1; and fourthly, purifying and separating the 3 rd fraction after gradient elution of high performance liquid chromatography, and collecting eluate to obtain Nepetabrate I at 17.8 minutes.
The following is further optimization or/and improvement of the second technical scheme of the invention:
in the first step, 8mL to 12mL of ethanol is added per 1g of aerial part of Nepeta cataria.
In the fourth step, the eluent for gradient elution by the high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
the third technical scheme of the invention is realized by the following measures: an application of Nepetabnate I in preparing the medicines for preventing inflammation.
The fourth technical scheme of the invention is realized by the following measures: an application of Nepetabnate I in preparing the anti-inflammatory medicines.
The fifth technical scheme of the invention is realized by the following measures: an application of Nepetabnate I in preparing health-care products for preventing and treating inflammation.
The invention discloses Nepetabrate I for the first time, and animal experiments show that the Nepetabrate I has obvious effects of resisting inflammation and inhibiting inflammation, can play a role of synergistic inflammation resistance, has definite curative effect, high safety and easily obtained raw materials, and can be applied to preparation of medicaments with anti-inflammatory effect.
Drawings
FIG. 1 is a chemical structural diagram of Nepetabnate I of the present invention.
FIG. 2 is a HR-MS spectrum of Nepetabnate I of the present invention.
FIG. 3 is a 1H-NMR spectrum of Nepetabnate I of the invention.
FIG. 4 is a 13C-APT spectrum of Nepetabnate I of the present invention.
FIG. 5 is a spectrum of the Nepetabate I H1-H1 COSY.
FIG. 6 shows the HSQC spectrum of Nepetabnate I of the present invention.
FIG. 7 is an HMBC spectrum of Nepetabnate I of the present invention.
FIG. 8 is a NOESY spectrum of Nepetabnate I of the present invention.
FIG. 9 is a graph of experimental swelling inhibition in animals for Nepetabrate I of the present invention.
Detailed Description
The present invention is not limited by the following examples, and specific embodiments may be determined according to the technical solutions and practical situations of the present invention. The various chemical reagents and chemical articles mentioned in the invention are all the chemical reagents and chemical articles which are well known and commonly used in the prior art, unless otherwise specified; the percentages in the invention are mass weight percentages unless otherwise specified; the solution in the present invention is an aqueous solution in which the solvent is water, for example, a hydrochloric acid solution is an aqueous hydrochloric acid solution, unless otherwise specified; the normal temperature and room temperature in the present invention generally mean a temperature of 15 ℃ to 25 ℃, and are generally defined as 25 ℃.
The invention is further described below with reference to the following examples:
example 1: the Nepetabnate I has a chemical structural formula as follows:
example 2: as an optimization of the above embodiment, it was obtained as follows: firstly, smashing and sieving overground parts of schizonepeta bracteata, adding ethanol, soaking for 3 to 4 hours at room temperature, heating and refluxing the ground schizonepeta bracteata with 50% methanol for 3 times, wherein each time lasts for about 3 hours, combining extracting solutions, and concentrating under reduced pressure to obtain a total extract; secondly, dispersing the schizonepeta tenuifolia total extract into suspension with water, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butyl alcohol, and concentrating the extract to obtain extracts of all parts; step three, performing silica gel column chromatography on the n-butanol part, and performing dichloromethane-methanol gradient elution at a ratio of 50:1 to 1:1, wherein 6 parts are obtained in the order of 50:1, 20:1, 10:1, 5:1, 2:1 and 1: 1; and fourthly, purifying and separating the 3 rd fraction after gradient elution of high performance liquid chromatography, and collecting eluate to obtain Nepetabrate I at 17.8 minutes.
Example 3: as an optimization of the above example, in the first step, 8mL to 12mL of ethanol was added per 1g of aerial part of Nepeta cataria.
Example 4: as an optimization of the above embodiment, in the fourth step, the eluent for gradient elution by high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
example 5: the preparation method of the Nepetabnate I is carried out according to the following steps: firstly, smashing and sieving overground parts of schizonepeta bracteata, adding ethanol, soaking for 3 to 4 hours at room temperature, heating and refluxing the ground schizonepeta bracteata with 50% methanol for 3 times, wherein each time lasts for about 3 hours, combining extracting solutions, and concentrating under reduced pressure to obtain a total extract; secondly, dispersing the schizonepeta cataria total extract into suspension with water, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butyl alcohol, and concentrating the extract to obtain extracts of all parts; step three, performing silica gel column chromatography on the n-butanol part, and performing dichloromethane-methanol gradient elution at a ratio of 50:1 to 1:1, wherein 6 parts are obtained in the order of 50:1, 20:1, 10:1, 5:1, 2:1 and 1: 1; and fourthly, purifying and separating the 3 rd fraction after gradient elution of high performance liquid chromatography, and collecting eluate to obtain Nepetabrate I at 17.8 minutes.
Example 6: the Nepetabnate I is applied to preparing the medicine for preventing inflammation.
Example 7: the Nepetabnate I is applied to preparing anti-inflammatory drugs.
Example 8: the Nepetabnate I is applied to preparing health-care products for preventing and treating inflammation.
Example 9: the Nepetabnate I is obtained according to the following method: firstly, smashing and sieving overground parts of schizonepeta bracteata, adding ethanol, soaking for 3 to 4 hours at room temperature, heating and refluxing the ground schizonepeta bracteata with 50% methanol for 3 times, wherein each time lasts for about 3 hours, combining extracting solutions, and concentrating under reduced pressure to obtain a total extract; secondly, dispersing the schizonepeta tenuifolia total extract into suspension with water, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butyl alcohol, and concentrating the extract to obtain extracts of all parts; thirdly, performing silica gel column chromatography on the n-butanol part, and performing dichloromethane-methanol gradient elution with the ratio of 50:1 to 1:1, wherein the elution sequence is 50:1, 20:1, 10:1, 5:1, 2:1 and 1:1 in sequence to obtain 6 parts; and fourthly, purifying and separating the 3 rd fraction after gradient elution of high performance liquid chromatography, and collecting eluate to obtain Nepetabrate I at 17.8 minutes.
The Nepetabrate I obtained in the example 9 of the invention is subjected to nuclear magnetic resonance hydrogen spectrum (C) 1 H-NMR) and nuclear magnetic resonance carbon Spectroscopy (C 13 C-APT), HR-MS spectrum, 1H-NMR spectrum, 13 C-APT spectrum, H 1 -H 1 The COSY spectrum, HSQC spectrum, HMBC spectrum and NOESY spectrum are shown in FIGS. 2 to 8.
The maps of fig. 3 and 4 were analyzed with reference to fig. 2, 5, 6, 7, and 8, and the peaks of fig. 3 and 4 were assigned, and the peak assignment of fig. 3 and 4 is shown in table 1. As can be seen from the data in fig. 3, fig. 4 and table 1, the chemical structural formula of the nepetanate I of the present invention is shown in fig. 1, and the nepetanate I of the present invention is amorphous powder and is easily soluble in chloroform and methanol.
The Nepetabnate I is subjected to animal anti-inflammatory pharmacodynamic experiments, and xylene is utilized in the animal anti-inflammatory experiments to cause mouse ear swelling.
The method comprises the following steps of randomly dividing 40 male mice of Kunming species into groups according to weight, wherein each group comprises 10 mice, namely a blank group, a model group, a low-dose group and a high-dose group, so that no significant difference in weight among experimental groups is guaranteed, marking is carried out by adopting 5% picric acid, and weighing is carried out so as to carry out subsequent experiments. The experiment period is 10 days, each group of the test objects are administrated by the intragastric mode according to the group, and the experiment period is free diet. The mice are fasted for more than 12 hours one day before killing the mice, drinking water is not controlled during the fasting period, the mice are weighed and recorded after the last gastric lavage, 0.03mL of dimethylbenzene is uniformly coated on the upper and lower surfaces of the left ear of each mouse to cause inflammation after one hour, each mouse is placed in a cage to avoid mutual licking, and the mice are killed by taking off the neck after one hour. Cutting off double ears along the base line of auricle, punching round ear plates on the symmetrical parts of the left ear and the right ear of the mouse by using a puncher with the diameter of 6mm, precisely weighing the mass by using a one-ten-thousandth analytical balance, and calculating the swelling degree and swelling inhibition rate of ears. (swelling degree of ear ═ right round ear mass-left round ear mass, swelling inhibition rate ═ model group ear average swelling degree-administration group ear average swelling degree)/model group ear average swelling degree ] × 100%).
The animal experiment swelling degree inhibition graph of Nepetabrate I of the invention is shown in FIG. 9, and FIG. 9 shows that the swelling degree of Nepetabrate I of the invention is obviously reduced in each administration group compared with the normal group and the model group.
In conclusion, the invention discloses Nepetabrate I for the first time and animal experiments show that the Nepetabrate I has obvious effects of resisting inflammation and inhibiting inflammation, can play a role in synergistic inflammation resistance, has definite curative effect, high safety and easily obtained raw materials, and can be applied to preparation of medicaments with anti-inflammatory effect.
The technical characteristics form an embodiment of the invention, which has strong adaptability and implementation effect, and unnecessary technical characteristics can be increased or decreased according to actual needs to meet the requirements of different situations.
TABLE 1
Claims (10)
1. A Nepetabnate I, characterized by the chemical structural formula:
2. nepetabnate I according to claim 1, characterised in that it is obtained according to the following process: firstly, smashing and sieving overground parts of schizonepeta bracteata, adding ethanol, soaking for 3 to 4 hours at room temperature, heating and refluxing the ground schizonepeta bracteata with 50% methanol for 3 times, wherein each time lasts for about 3 hours, combining extracting solutions, and concentrating under reduced pressure to obtain a total extract; secondly, dispersing the schizonepeta tenuifolia total extract into suspension with water, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butyl alcohol, and concentrating the extract to obtain extracts of all parts; thirdly, performing silica gel column chromatography on the n-butanol part, and performing dichloromethane-methanol gradient elution with the ratio of 50:1 to 1:1, wherein the elution sequence is 50:1, 20:1, 10:1, 5:1, 2:1 and 1:1 in sequence to obtain 6 parts; and fourthly, purifying and separating the 3 rd fraction after gradient elution of high performance liquid chromatography, and collecting eluate to obtain Nepetabrate I at 17.8 minutes.
3. The method of claim 2, wherein in the first step 8mL to 12mL of ethanol is added per 1g of aerial parts of nepeta cataria.
4. Nepetabnate I according to claim 2 or 3, wherein in the sixth step, the eluent for gradient elution by high performance liquid chromatography is a mixture of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
5. A process for the preparation of nepetanate I according to claim 1, characterised in that it is carried out according to the following steps: firstly, smashing and sieving overground parts of schizonepeta bracteata, adding ethanol, soaking for 3 to 4 hours at room temperature, heating and refluxing the ground schizonepeta bracteata with 50% methanol for 3 times, wherein each time lasts for about 3 hours, combining extracting solutions, and concentrating under reduced pressure to obtain a total extract; secondly, dispersing the schizonepeta tenuifolia total extract into suspension with water, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butyl alcohol, and concentrating the extract to obtain extracts of all parts; step three, performing silica gel column chromatography on the n-butanol part, and performing dichloromethane-methanol gradient elution at a ratio of 50:1 to 1:1, wherein 6 parts are obtained in the order of 50:1, 20:1, 10:1, 5:1, 2:1 and 1: 1; and fourthly, purifying and separating the 3 rd fraction after gradient elution of high performance liquid chromatography, and collecting eluate to obtain Nepetabrate I at 17.8 minutes.
6. The method of preparing Nepetabnate I according to claim 5, wherein in the first step, 8mL to 12mL of ethanol is added per 1g of aerial part of Nepeta cataria.
7. The method for preparing Nepetabnate I according to claim 5 or 6, wherein in the fourth step, the eluent for gradient elution of high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
8. use of nepetafibrate I as defined in claim 1, 2, 3 or 4, for the preparation of a medicament for the prevention of inflammation.
9. Use of nepetafibrate I as defined in claim 1 or 2 or 3 or 4, for the preparation of an anti-inflammatory medicament.
10. Use of nepetanate I according to claim 1, 2, 3 or 4 for the preparation of a health product for the prevention and treatment of inflammation.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116098934A (en) * | 2023-01-18 | 2023-05-12 | 浙江树人学院 | Functional herba Schizonepetae extract and its application in relieving colitis and regulating intestinal flora |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114853610A (en) * | 2022-06-07 | 2022-08-05 | 新疆维吾尔自治区中药民族药研究所 | Preparation method and application of abietane diterpene in schizonepeta bracteata |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114853610A (en) * | 2022-06-07 | 2022-08-05 | 新疆维吾尔自治区中药民族药研究所 | Preparation method and application of abietane diterpene in schizonepeta bracteata |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116098934A (en) * | 2023-01-18 | 2023-05-12 | 浙江树人学院 | Functional herba Schizonepetae extract and its application in relieving colitis and regulating intestinal flora |
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