CN116693589A - Ergosterol compound and preparation method and application thereof - Google Patents

Ergosterol compound and preparation method and application thereof Download PDF

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Publication number
CN116693589A
CN116693589A CN202310678396.4A CN202310678396A CN116693589A CN 116693589 A CN116693589 A CN 116693589A CN 202310678396 A CN202310678396 A CN 202310678396A CN 116693589 A CN116693589 A CN 116693589A
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methanol
ethyl acetate
ergosterol
eluent
column chromatography
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郑永标
陈清华
林衍佺
马璐
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Fujian Gutian Kangyida Biotechnology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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
    • A23L31/00—Edible extracts or preparations of fungi; Preparation or treatment thereof
    • A23L31/10—Yeasts or derivatives thereof
    • A23L31/15—Extracts
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • 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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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Microbiology (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention discloses an ergosterol compound, a preparation method and application thereof, wherein the ergosterol compound is 5 alpha-ergosterol-7, 22-diene-3 beta, 5,6 beta-triol, and the molecular formula is C 28 H 46 O 3； The molecule is derived from tremella, and has good application in the development of tremella functional health food.

Description

Ergosterol compound and preparation method and application thereof
Technical Field
The invention relates to ergosterol compounds, a preparation method and application thereof, which can be used for developing tremella functional food.
Background
Sterols are cyclopentanol-phenanthrenes which contain 4 rings and side chains, are widely found in oils and fats of animals or plants, are present in the animal body in the form of esters of higher fatty acids, or are present in the tissues of plants in the form of glycosides. The sterol compound has various structure types and special physiological effects, and can be used as hormone, vitamin, toxin, medicine and the like.
Ergosterol is an important component of fungal cell membrane, has unique physiological function, can enhance the disease resistance of human body, is an important fat-soluble vitamin D2 source, has obvious antibacterial and antitumor effects, and is widely applied to the development of medicines. Can also be used as feed additive to increase the laying rate and hatching rate of livestock and poultry. Ergosterol is an important pharmaceutical raw material for producing sterols such as cortisone, hormone progesterone and the like. Ergosterol derivatives are of a wide variety and have a wide variety of biological activities.
The tremella is a traditional rare edible fungus in China, has higher nutritive value, has fruit bodies which are the same as other edible mushrooms, contains rich carbohydrates, proteins, vitamins and minerals, is delicious and tasty, and is a very popular nourishing food. Currently, in order to improve the value of tremella products, various deep-processing products of tremella are also developed, such as tremella beverage, tremella soup, tremella wine, tremella cosmetics, tremella yogurt, instant tremella and the like. However, the development of the products is mainly based on the nutritional value of tremella, the value of the products is low, and the support force for improving the development of the whole tremella industry is limited. Tremella has higher medicinal value, and the tremella has the efficacy recorded in Chinese medicinal books. Tremella has flat nature, sweet taste, and good effects of invigorating lung, stomach and kidney meridian, is beneficial to five viscera, has the effects of invigorating qi and blood, is suitable for weakness of five viscera, deficiency of qi and blood, lusterless complexion and lusterless hair, has the effects of strengthening essence, tonifying kidney, moistening lung, promoting fluid production, relieving cough, clearing heat, nourishing stomach, invigorating qi and blood, strengthening heart, strengthening body, nourishing brain and refreshing, and is recorded in Shennong's herbal meridian, ming's miscellaneous records, ben Cao Jing Ji Zhi, xin Xiu Ben Cao and Ben Cao Hui Jing Ji and China Ben Cao.
However, the material basis of the tremella efficacy effect is not clearly analyzed at present, the content measurement of crude polysaccharide or total polysaccharide is mainly focused, small molecular chemical components of tremella are less concerned, the deep processing direction and form of tremella products lack targets, and development of tremella efficacy products with high added value is restricted. Based on the above background, the study of the present invention was conducted.
Disclosure of Invention
In order to solve the problems, the invention provides a method for extracting ergosterol compounds from tremella and application thereof in developing functional foods.
The technical scheme of the invention is as follows:
the invention provides an ergosterol compound, which is 5 alpha-ergosterol-7, 22-diene-3 beta, 5,6 beta-triol, and has a molecular formula of C 28 H 46 O 3 The structural formula is as follows:
the invention also provides a preparation method of the ergosterol compound, which comprises the following steps:
(1) Extracting tremella sample with organic solvent to remove organic phase and obtain organic extract; extracting the obtained organic extract with ethyl acetate and water, and concentrating to obtain ethyl acetate extract;
(2) Primary separation of products: subjecting the ethyl acetate extract obtained in the step (1) to reverse phase column chromatography, respectively eluting with methanol water or acetone water with different concentrations, collecting, centrifuging, concentrating to remove eluent, adding methanol for dissolving, performing thin layer chromatography, and combining according to the color development result of the thin layer chromatography to obtain initial components containing target compounds;
(3) Secondary separation of products: then, further separating and purifying the initial component containing the target compound by adopting gel column chromatography, taking methanol or acetone as an eluent, collecting in a fractional manner, and combining according to thin layer chromatography to obtain the final component containing the target compound;
(4) Finally, carrying out normal phase silica gel column chromatography on the final component containing the target compound obtained in the step (3), and eluting with an eluent composition to obtain the target compound;
the eluent composition consists of a component A and a component B, wherein the component A is any one of petroleum ether, dichloromethane or chloroform; the component B is any one of ethyl acetate, acetone or methanol.
Further, the reversed-phase silica gel column chromatography in the step (2) is performed by gradient elution with methanol water or acetone water with different gradients, wherein the volume ratio of the methanol or the acetone is respectively as follows: 0-100%.
Further, the concentration of the acetone or methanol eluent in the gel column chromatography in the step (3) is 50-100%.
Further, the normal phase silica gel column chromatography in the step (4) adopts dichloromethane or chloroform for column packing.
Further, the eluent composition in the step (4) is in a volume ratio of 100: 1-20 petroleum ether or dichloromethane to ethyl acetate or acetone, or the volume ratio is 100: the volume ratio of chloroform to methanol is 1-20.
Further, the specific steps of the step (1) are as follows: drying and crushing tremella, leaching with methanol for three times to obtain a methanol extract, extracting the methanol extract with ethyl acetate and water for 3 times according to the same volume, and removing an ethyl acetate phase to obtain an ethyl acetate extract.
Further, the specific steps of the step (2) are as follows: separating and purifying ethyl acetate extract by reversed phase column chromatography, sequentially eluting with ultrapure water, 30% methanol water solution, 50% methanol water solution, 70% methanol water solution and 100% methanol as eluent, separating, collecting, centrifuging, concentrating, removing eluent, adding methanol, dissolving, performing thin layer chromatography, and combining to obtain initial components containing target compound according to thin layer chromatography result.
The invention also protects the development and application of the ergosterol compound in tremella functional health food.
The invention has the following beneficial effects:
1. the ergosterol compound prepared by the invention is 5 alpha-ergosterol-7, 22-diene-3 beta, 5,6 beta-triol, and the molecular formula is C 28 H 46 O 3 The method comprises the steps of carrying out a first treatment on the surface of the . The molecule is derived from Tremella, and has functions in TremellaThe health food has good application in development.
2. The invention provides a novel method for extracting ergosterol compounds from tremella, which is used for obtaining the ergosterol compounds according to the invention through repeated chromatography and matching of eluent compositions.
Drawings
FIG. 1 is a hydrogen spectrum of the compound prepared in example 1;
FIG. 2 is a carbon spectrum of the compound prepared in example 1;
FIG. 3 shows the chemical structure of the compound prepared in example 1.
Detailed Description
The following examples are illustrative of the present invention and are not intended to limit the scope of the invention. Unless otherwise indicated, the technical means used in the examples are conventional means well known to those skilled in the art, and all raw materials used are commercially available. But are not intended to limit the scope of the invention. Unless otherwise indicated, the technical means used in the examples are conventional means well known to those skilled in the art, and all raw materials used are commercially available.
Example 1
Drying Jin Yaner fresh product in a 60 ℃ oven, weighing, drying to 1150g, crushing, leaching with 4L of methanol, carrying out ultrasonic treatment for 30min, standing at room temperature overnight, and leaching for three times to obtain methanol leaching substances. The methanol extract was then purified according to ethyl acetate: water = 300:300 extraction 3 times. The ethyl acetate phase was removed to give 7.12g of ethyl acetate extract.
The ethyl acetate extract (7.12 g) was further separated and purified by reverse phase column chromatography using pure water and 4 aqueous methanol solutions (30% methanol, 50% methanol, 70% methanol and 100% methanol) of different volume concentrations as eluents, eluting 1.5L each of the gradients, collecting in separate bottles, collecting 150mL each bottle, taking 5mL each bottle, centrifuging, concentrating to remove the eluent, adding 0.5mL of methanol for dissolution, performing thin layer chromatography analysis, and combining the initial components 959.2mg of the target compound according to the thin layer chromatography result.
The fractions obtained in the previous step were subjected to gel column chromatography, collected by separating tubes with methanol as an eluent, 1 tube (about 5 mL) was collected every 1 hour, and 272.7mg of the final fraction containing the objective compound was obtained by combining according to thin layer chromatography analysis.
Separating and purifying the component obtained in the last step by adopting normal phase column chromatography, and taking chloroform and methanol with different volume ratios as eluent, wherein the volume ratio of the chloroform to the methanol of the eluent is 40:1 to obtain 1.7mg of the compound.
Example 2:
drying Jin Yaner fresh product in a 60 ℃ oven, weighing, drying to 1150g, crushing, leaching with 4L of methanol, carrying out ultrasonic treatment for 30min, standing at room temperature overnight, and leaching for three times to obtain methanol leaching substances. The methanol extract was then purified according to ethyl acetate: water = 300:300 extraction 3 times. The ethyl acetate phase was removed to give 7.12g of ethyl acetate extract.
The ethyl acetate extract (7.12 g) was further separated and purified by reverse phase column chromatography using pure water and 4 aqueous methanol solutions (30% methanol, 50% methanol, 70% methanol and 100% methanol) of different volume concentrations as eluents, eluting 1.5L each of the gradients, collecting in separate bottles, collecting 150mL each bottle, taking 5mL each bottle, centrifuging, concentrating to remove the eluent, adding 0.5mL of methanol for dissolution, performing thin layer chromatography analysis, and combining the initial components 959.2mg of the target compound according to the thin layer chromatography result.
The fractions obtained in the previous step were subjected to gel column chromatography, collected by separating tubes with methanol as an eluent, 1 tube (about 5 mL) was collected every 1 hour, and 272.5mg of the final fraction containing the objective compound was obtained by combining according to thin layer chromatography analysis.
Separating and purifying the component obtained in the last step by adopting normal phase column chromatography, and taking chloroform and methanol with different volume ratios as eluent, wherein the volume ratio of the chloroform to the methanol of the eluent is 100:1, so as to obtain 1.65mg of the compound.
Example 3:
drying Jin Yaner fresh product in a 60 ℃ oven, weighing, drying to 1150g, crushing, leaching with 4L of methanol, carrying out ultrasonic treatment for 30min, standing at room temperature overnight, and leaching for three times to obtain methanol leaching substances. The methanol extract was then purified according to ethyl acetate: water = 300:300 extraction 3 times. The ethyl acetate phase was removed to give 7.11g of an ethyl acetate extract.
The ethyl acetate extract (7.11 g) was further separated and purified by reverse phase column chromatography using pure water and 4 aqueous methanol solutions (30% methanol, 50% methanol, 70% methanol and 100% methanol) of different volume concentrations as eluents, eluting 1.5L each of the gradients, collecting in separate bottles, collecting 150mL each bottle, taking 5mL each bottle, centrifuging, concentrating to remove the eluent, adding 0.5mL of methanol for dissolution, performing thin layer chromatography analysis, and combining the initial components 959.2mg of the target compound according to the thin layer chromatography result.
The fractions obtained in the previous step were subjected to gel column chromatography, collected by separating tubes with methanol as an eluent, 1 tube (about 5 mL) was collected every 1 hour, and 273.2mg of the final fraction containing the objective compound was obtained by combining according to thin layer chromatography analysis.
Separating and purifying the component obtained in the last step by adopting normal phase column chromatography, and taking chloroform and methanol with different volume ratios as eluent, wherein the volume ratio of the chloroform to the methanol of the eluent is 10:1 to obtain 1.54mg of the compound.
Example 4
Drying Jin Yaner fresh product in a 60 ℃ oven, weighing, drying to 1150g, crushing, leaching with 4L of methanol, carrying out ultrasonic treatment for 30min, standing at room temperature overnight, and leaching for three times to obtain methanol leaching substances. The methanol extract was then purified according to ethyl acetate: water = 300:300 extraction 3 times. The ethyl acetate phase was removed to give 7.12g of ethyl acetate extract.
The ethyl acetate extract (7.12 g) was further separated and purified by reverse phase column chromatography using pure water and 4 aqueous methanol solutions (30% methanol, 50% methanol, 70% methanol and 100% methanol) of different volume concentrations as eluents, eluting 1.5L each of the gradients, collecting in separate bottles, collecting 150mL each bottle, taking 5mL each bottle, centrifuging, concentrating to remove the eluent, adding 0.5mL of methanol for dissolution, performing thin layer chromatography analysis, and combining the initial components 959.2mg of the target compound according to the thin layer chromatography result.
The fractions obtained in the previous step were subjected to gel column chromatography, collected by separating tubes with methanol as an eluent, 1 tube (about 5 mL) was collected every 1 hour, and 273.2mg of the final fraction containing the objective compound was obtained by combining according to thin layer chromatography analysis.
Separating and purifying the component obtained in the last step by adopting normal phase column chromatography, and obtaining 1.61mg of the compound when the volume ratio of petroleum ether to ethyl acetate serving as an eluent is 40:1 by taking chloroform and methanol with different volume ratios as the eluent.
Example 5
Drying Jin Yaner fresh product in a 60 ℃ oven, weighing, drying to 1150g, crushing, leaching with 4L of methanol, carrying out ultrasonic treatment for 30min, standing at room temperature overnight, and leaching for three times to obtain methanol leaching substances. The methanol extract was then purified according to ethyl acetate: water = 300:300 extraction 3 times. The ethyl acetate phase was removed to give 7.13g of an ethyl acetate extract.
The ethyl acetate extract (7.13 g) was further separated and purified by reverse phase column chromatography using pure water and 4 aqueous methanol solutions (30% methanol, 50% methanol, 70% methanol and 100% methanol) of different volume concentrations as eluents, eluting 1.5L each of the gradients, collecting in separate bottles, collecting 150mL each bottle, taking 5mL each bottle, centrifuging, concentrating to remove the eluent, adding 0.5mL of methanol for dissolution, performing thin layer chromatography analysis, and combining the initial components 959.25mg of the target compound according to the thin layer chromatography result.
The fractions obtained in the previous step were subjected to gel column chromatography, collected by separating tubes with methanol as an eluent, 1 tube (about 5 mL) was collected every 1 hour, and 273.24mg of the final fraction containing the objective compound was obtained by combining according to thin layer chromatography analysis.
Separating and purifying the component obtained in the last step by adopting normal phase column chromatography, and obtaining 1.65mg of the compound when the volume ratio of the eluent dichloromethane to the acetone is 40:1 by taking chloroform and methanol with different volume ratios as the eluent.
FIG. 3 shows the chemical structure of ergosterol prepared in example 1, which was resolved into 5α -ergosta-7, 22-diene-3β,5,6β -triol based on hydrogen and carbon spectral data. The compound is white substance, nailAlcohol-soluble, vanillin-concentrated sulfuric acid solution developed a mauve color. 1 H NMR(600MHz,Methanol-d 4 )δ5.31–5.25(m,1H),5.22(dd,J＝7.7,6.7Hz,1H),3.98(tt,J＝11.4,4.9Hz,1H),3.55(dt,J＝5.3,2.1Hz,1H),2.27(t,J＝7.4Hz,1H),2.13–2.07(m,2H),1.86(td,J＝6.9,5.9Hz,1H),1.81–1.71(m,2H),1.72–1.66(m,1H),1.66–1.39(m,6H),1.38–1.28(m,7H),1.00(d,J＝6.7Hz,1H),1.06(s,3H),1.04(d,J＝6.6Hz,3H),0.94(d,J＝6.8Hz,3H),0.87(d,J＝6.8Hz,3H),0.85(d,J＝6.8Hz,3H),0.65(s,3H)。 13 C NMR(151MHz,Methanol-d 4 )δ12.81,18.21,18.89,20.08,20.46,21.66,23.04,24.02,29.15,31.77,33.92,34.38,38.16,40.52,40.73,41.79,44.36,44.38,44.71,55.92,57.42,68.40,74.25,76.95,119.08,133.26,137.03,143.77。
The foregoing description is only illustrative of the present invention and is not intended to limit the scope of the invention, and all equivalent structures or equivalent processes or direct or indirect application in other related arts are included in the scope of the present invention.

Claims (9)

1. An ergosterol compound, characterized in that: the ergosterol compound is 5α -ergosterol-7, 22-diene-3β,5,6β -triol, and the molecular formula is C 28 H 46 O 3 The structural formula is as follows:
2. a preparation method of ergosterol compounds is characterized in that: the method comprises the following steps:
(1) Extracting tremella sample with organic solvent to remove organic phase and obtain organic extract; extracting the obtained organic extract with ethyl acetate and water, and concentrating to obtain ethyl acetate extract;
(2) Primary separation of products: subjecting the ethyl acetate extract obtained in the step (1) to reverse phase column chromatography, respectively eluting with methanol water or acetone water with different concentrations, collecting, centrifuging, concentrating to remove eluent, adding methanol for dissolving, performing thin layer chromatography, and combining according to the color development result of the thin layer chromatography to obtain initial components containing target compounds;
(3) Secondary separation of products: then, further separating and purifying the initial component containing the target compound by adopting gel column chromatography, taking methanol or acetone as an eluent, collecting in a fractional manner, and combining according to thin layer chromatography to obtain the final component containing the target compound;
(4) Finally, carrying out normal phase silica gel column chromatography on the final component containing the target compound obtained in the step (3), and eluting with an eluent composition to obtain the target compound;
the eluent composition consists of a component A and a component B, wherein the component A is any one of petroleum ether, dichloromethane or chloroform; the component B is any one of ethyl acetate, acetone or methanol.
3. The process for the preparation of ergosterol compounds according to claim 2, characterized in that: the reversed-phase silica gel column chromatography in the step (2) is carried out by gradient elution with methanol water or acetone water with different gradients, wherein the volume ratio of the methanol or the acetone is respectively as follows: 0-100%.
4. The process for the preparation of ergosterol compounds according to claim 2, characterized in that: the concentration of the acetone or methanol eluent in the gel column chromatography in the step (3) is 50-100%.
5. The process for the preparation of ergosterol compounds according to claim 2, characterized in that: and (3) loading the normal phase silica gel column chromatography in the step (4) by using dichloromethane or chloroform.
6. The process for the preparation of ergosterol compounds according to claim 2, characterized in that: the eluent composition in the step (4) is 100 in volume ratio: 1-20 petroleum ether or dichloromethane to ethyl acetate or acetone, or the volume ratio is 100: the volume ratio of chloroform to methanol is 1-20.
7. The process for the preparation of ergosterol compounds according to claim 2, characterized in that: the specific steps of the step (1) are as follows: drying and crushing tremella, leaching with methanol for three times to obtain a methanol extract, extracting the methanol extract with ethyl acetate and water for 3 times according to the same volume, and removing an ethyl acetate phase to obtain an ethyl acetate extract.
8. The process for the preparation of ergosterol compounds according to claim 2, characterized in that: the specific steps of the step (2) are as follows: separating and purifying ethyl acetate extract by reversed phase column chromatography, sequentially eluting with ultrapure water, 30% methanol water solution, 50% methanol water solution, 70% methanol water solution and 100% methanol as eluent, separating, collecting, centrifuging, concentrating, removing eluent, adding methanol, dissolving, performing thin layer chromatography, and combining to obtain initial components containing target compound according to thin layer chromatography result.
9. The use of ergosterol compounds according to claim 1 in the development of functional health food for tremella.
CN202310678396.4A 2023-06-08 2023-06-08 Ergosterol compound and preparation method and application thereof Pending CN116693589A (en)

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