CN109867653B - Preparation method of okra lactone - Google Patents
Preparation method of okra lactone Download PDFInfo
- Publication number
- CN109867653B CN109867653B CN201910179719.9A CN201910179719A CN109867653B CN 109867653 B CN109867653 B CN 109867653B CN 201910179719 A CN201910179719 A CN 201910179719A CN 109867653 B CN109867653 B CN 109867653B
- Authority
- CN
- China
- Prior art keywords
- lactone
- perennial
- okra
- extract
- sophora
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Images
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a preparation method of okra lactone. The method is to prepare the macrocyclic musk type famous and precious natural spice abelmoschus esculentus lactone from medicinal fungus sophora perennial polyporus (perniporia robiniophila (Murrill) Rvarden). Taking wild or artificially cultured or fermentation cultured sophora perennial fomes fomentarius as a raw material, and obtaining the okra lactone by the steps of organic solvent extraction, freezing dewaxing, alkali washing to remove free acid, column chromatography separation and purification and the like. The obtained okra lactone product has strong and elegant musk fragrance, and can be used as a fragrance fixative and a synergist to be applied to daily-use and edible essence.
Description
Technical Field
The invention relates to a preparation method of okra lactone. More specifically, the invention relates to a method for preparing natural spice abelmoschus esculentus lactone by artificially culturing a medicinal fungus, namely sophora japonica perennial polyporus (Murrill) Rvarden, and belongs to the technical field of flavors and fragrances.
Background
Abelmoscolide (ambrettolide), also called as muskmolide and muskiness of sunflower seed, is present in seed of Abelmoschus moschatus (L.) Mdeic of Malvaceae, and has chemical name of (Z) -1-oxacyclo heptadeca-8-ene-2-one and molecular formula of C16H28O2CAS registry number 123-69-3, structural formula:
wherein the numbers 1 to 17 are the ring atom system numbers.
The abelmoschus manihot lactone is a rare macrocyclic musk spice, has strong musk fragrance, is widely applied to daily-use and edible essences, and has the functions of a fragrance fixing agent and a synergist. Due to the limitation of resources, the large-scale production of pelargonide is difficult, and therefore, research on artificial synthesis of pelargonide has been conducted. Although a plurality of synthetic routes for synthesizing the okra lactone are researched and developed, the synthesis product cost is high due to long synthetic steps and strict synthetic condition requirements, and the synthesis method is difficult to popularize and apply to industrial production.
Disclosure of Invention
The invention aims to provide a method for preparing abelmoschus esculentus lactone from medicinal fungi sophora japonica (perennial polyporus robusta (Murrill) Rvarden) in the flavor and fragrance industry.
The invention also aims to provide a process for preparing the okra lactone by artificially culturing the perennial fomes sophorae.
Still another objective of the present invention is to provide a culture condition for the artificial culture of the perennial fomes sophorae.
The technical solution adopted by the invention to achieve the above purpose is as follows:
the invention relates to a preparation method of okra lactone, which is used for preparing the okra lactone from medicinal fungus sophora perennial fomes. Specifically, fruiting bodies or mycelia are obtained by artificially culturing a medicinal fungus, namely, sophora perennial polyporus fomentarius, and macrocyclic musk perfume okra lactone is further prepared by extraction, separation and purification, wherein the method comprises the following process steps:
(1) artificially culturing medicinal fungus, namely, sophora perennial polyporus, to obtain sporocarp or mycelium;
(2) extracting fruiting body or mycelium of perennial fomes sophorae with organic solvent;
(3) mixing the extractive solutions, cooling to about 0 deg.C, and filtering to remove residue after precipitation is completed;
(4) concentrating the filtrate at 50 deg.C under reduced pressure to recover solvent to obtain crude extract;
(5) dissolving the crude extract with petroleum ether, washing with sodium bicarbonate water solution or sodium carbonate water solution or sodium hydroxide water solution to remove free acid, washing with water to neutrality, and removing water layer to obtain petroleum ether extractive solution;
(6) dehydrating and drying the petroleum ether extract by using anhydrous sodium sulfate or anhydrous magnesium sulfate, and then concentrating under reduced pressure at the temperature of below 50 ℃ to recover petroleum ether to obtain an extract;
(7) dissolving the extract with anhydrous ethanol, freezing to-20 deg.C, filtering after precipitation, concentrating the filtrate at 50 deg.C under reduced pressure, and recovering ethanol to obtain absolute oil;
(8) purifying the purified oil by silica gel column chromatography to obtain the okra lactone.
Wherein the culture conditions of the sophora perennial pycnoporus in the step (1) are as follows: 200 g of potato, 20 g of cane sugar, 20 g of yeast extract, 15 g of agar, 2 g of magnesium sulfate, 3 g of monopotassium phosphate and 10.01 g of vitamin B are added with water to 1 liter, the pH value is 6.0, and the mixture is used as a culture medium and cultured in dark at the temperature of 25 ℃ for 8 days to 10 days.
Wherein the organic solvent in the step (2) is selected from one of petroleum ether, diethyl ether, ethyl acetate and ethanol, or a mixture of the petroleum ether, the diethyl ether, the ethyl acetate and the ethanol.
Compared with the prior art, the invention has the following outstanding advantages:
1. the medicinal fungus sophora japonica has abundant perennial chaetomium fortunei sources, can be produced by artificial cultivation and industrial fermentation, and has no worries about the raw materials compared with the preparation of the okra lactone from the seeds of the okra.
2. Compared with the artificial synthesis of the okra lactone, the invention has the advantages of cheap and easily obtained raw materials, simple and convenient preparation process, large-scale production and lower product cost.
3. Compared with the artificially synthesized okra lactone, the okra lactone prepared from the medicinal fungus sophora perennial fomes belongs to natural perfume and is more popular with consumers.
Drawings
FIG. 1 shows the chemical structural formula of abelmoschus manihot lactone.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof.
Example 1: cultivation of sophora japonica perennial pycnoporus
Strain: a medicinal fungus, i.e., a strain of perennial dormant sophora fungus (Perenniporia robiniophila (Murrill) Rvarden), is obtained by separating and purifying fruiting bodies of wild perennial dormant sophora fungus grown on living trees of Robinia pseudoacacia (Robinia pseudoacacia), and belongs to higher fungi of the genus Perenniporia of the family Polyporaceae of the order Polyporales in the fungal kingdom.
The culture conditions are as follows: on the basis of taking a comprehensive potato culture medium (CPDA culture medium) as a basic culture medium, the influence of factors such as carbon sources (glucose, sucrose, maltose, soluble starch and corn starch), nitrogen sources (yeast extract, peptone, beef extract, urea and ammonium sulfate), potassium dihydrogen phosphate, magnesium sulfate, vitamin B1, pH value, culture time and culture temperature on the growth condition of hyphae is researched by a single factor method, and the optimal culture condition of the sophora japonica perennial pycnopodioides is obtained by the following steps: 200 g of potato, 20 g of cane sugar, 20 g of yeast extract, 15 g of agar, 2 g of magnesium sulfate, 3 g of monopotassium phosphate and 10.01 g of vitamin B are added with water to 1 liter, the pH value is 6.0, and the mixture is used as a culture medium and cultured in dark at the temperature of 25 ℃ for 8 days to 10 days.
The culture method comprises the following steps: inoculating the strain of perennial fomes sophorae to a culture medium which is sterilized, cooled to room temperature, and performing static culture at 25 ℃ in a dark place for 8-10 days.
Example 2: preparation of sophora japonica perennial pycnoporus obliquus absolute
The culture total obtained in example 1 was extracted sufficiently 3 times with 5-fold ethanol at room temperature with stirring for 24 hours each time, and filtered. Mixing filtrates, cooling to about 0 deg.C, filtering to remove residue after precipitation is completed, and concentrating the filtrate at 50 deg.C under reduced pressure to recover ethanol to obtain crude extract.
Dissolving the crude extract with petroleum ether, washing with 5% sodium bicarbonate water solution or 5% sodium carbonate water solution or 1% sodium hydroxide water solution to remove free acid, washing with saturated salt water to neutrality, and removing water layer to obtain petroleum ether extract.
Dehydrating and drying the petroleum ether extract with anhydrous sodium sulfate or anhydrous magnesium sulfate, and concentrating under reduced pressure at below 50 deg.C to recover petroleum ether to obtain extract.
Dissolving the extract with 10-12 times of anhydrous ethanol, freezing to-20 deg.C, filtering after precipitation, and concentrating the filtrate at 50 deg.C under reduced pressure to recover ethanol to obtain pure oil.
Example 3: separation and purification of okra lactone
Purifying the clean oil by silica gel column chromatography, gradient eluting with petroleum ether-ethyl acetate (100: 0-90: 10, v/v), and tracking by thin layer chromatography to obtain colorless oily okra lactone. The spectral data are as follows:
1H NMR(400MHz，CDCl3)：δ5.32(t，2H，J＝4.6Hz，H-8，9)，4.13(t，2H，J＝5.4Hz，H-17)，2.32(t，2H，J＝6.4Hz，H-3)，2.05(m，4H，H-7，10)，1.63(m，4H，H-6，11)，1.33(m，14H，H-4，5，12，13，14，15，16)。
13C NMR(100MHz，CDCl3): delta 174.05(s, C-2), 130.31(d, C-8 or C-9), 130.15(d, C-9 orC-8), 63.82(t, C-17), 34.64(t, C-3), 29.52(t, C-7 or C-10), 28.90(t, C-10 or C-7), 28.81(t), 28.62(t), 28.56(t), 28.47(t), 27.76(t), 27.05(t), 26.91(t), 25.43(t), 25.37(t) (C-4, 5, 12, 13, 14, 15, 16).
EI-MS(m/z)：252[M]+。
The invention is creative and innovative in that the natural spice abelmoschus manihot lactone is prepared from medicinal fungus sophora perennial fomes for the first time. The invention also provides a culture condition for artificially culturing the sophora perennial fomes and a process for preparing the okra lactone from the sophora perennial fomes, which are creations and innovations of the invention.
Claims (1)
1. A method for preparing abelmoschus esculentus lactone by artificially culturing Perenniporia robiniophila (Murrill) Ryvarden of sophora perennial, which is characterized by comprising the following process steps:
(1) separating and purifying wild sophora japonica perennial chaetomium fruit bodies growing on the living trees of Robinia pseudoacacia to obtain sophora japonica perennial chaetomium seed strains;
(2) the strain is prepared by taking 200 g of potato, 20 g of cane sugar, 20 g of yeast extract, 15 g of agar, 2 g of magnesium sulfate, 3 g of monopotassium phosphate and 0.01 g of vitamin B1 as a culture medium, adding water to 1 liter, taking the pH value of 6.0 as the culture medium, and culturing for 8-10 days in a dark place at 25 ℃ to obtain the medicinal fungus sophora perennial polypore culture total;
(3) fully extracting the obtained culture total substance with 5 times of ethanol for 3 times, each time extracting for 24 hours, filtering, mixing filtrates, cooling to about 0 deg.C, filtering after precipitation is complete, concentrating the filtrate under reduced pressure below 50 deg.C, and recovering ethanol to obtain crude extract;
(4) dissolving the crude extract with petroleum ether, washing with 5% sodium bicarbonate water solution or 5% sodium carbonate water solution or 1% sodium hydroxide water solution to remove free acid, washing with saturated salt water to neutrality, and removing water layer to obtain petroleum ether extract;
(5) dehydrating and drying the petroleum ether extract by using anhydrous sodium sulfate or anhydrous magnesium sulfate, and then concentrating under reduced pressure at the temperature of below 50 ℃ to recover petroleum ether to obtain an extract;
(6) dissolving the extract with 10-12 times of anhydrous ethanol, freezing to-20 deg.C, filtering after precipitation, concentrating the filtrate at 50 deg.C under reduced pressure, and recovering ethanol to obtain absolute oil;
(7) purifying the clean oil by silica gel column chromatography, performing gradient elution by petroleum ether-ethyl acetate at volume ratio of 100: 0-90: 10, and tracking by thin layer chromatography to obtain colorless oily okra lactone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910179719.9A CN109867653B (en) | 2019-03-06 | 2019-03-06 | Preparation method of okra lactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910179719.9A CN109867653B (en) | 2019-03-06 | 2019-03-06 | Preparation method of okra lactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109867653A CN109867653A (en) | 2019-06-11 |
| CN109867653B true CN109867653B (en) | 2021-06-29 |
Family
ID=66920154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910179719.9A Expired - Fee Related CN109867653B (en) | 2019-03-06 | 2019-03-06 | Preparation method of okra lactone |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109867653B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011027906A1 (en) * | 2009-09-02 | 2011-03-10 | Takasago International Corporation | 7,10,13-cyclohexadecatrien-16-olide, and flavor or fragrance composition, fragrance or cosmetic product, food product or beverage or toiletry product comprising the same |
| CN108713015A (en) * | 2016-03-10 | 2018-10-26 | 奇华顿股份有限公司 | The preparation of macrolide |
-
2019
- 2019-03-06 CN CN201910179719.9A patent/CN109867653B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011027906A1 (en) * | 2009-09-02 | 2011-03-10 | Takasago International Corporation | 7,10,13-cyclohexadecatrien-16-olide, and flavor or fragrance composition, fragrance or cosmetic product, food product or beverage or toiletry product comprising the same |
| CN108713015A (en) * | 2016-03-10 | 2018-10-26 | 奇华顿股份有限公司 | The preparation of macrolide |
Non-Patent Citations (3)
| Title |
|---|
| "Chemoenzymatic preparation of musky macrolactones";Tancredi Fortunati et al.;《Tetrahedron》;20150307;第71卷;第2357-2362页 * |
| "微酸多年卧孔菌化学成分的研究";郭怀宇等;《中成药》;20180131;第40卷(第1期);第129-132页 * |
| "葱莲的化学成分研究";吴志平等;《中药材》;20081031;第31卷(第10期);第1508-1510页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109867653A (en) | 2019-06-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107746871A (en) | The method for preparing the rare saponin(e of ginseng using schizophyllum commune biologic converted ginseng saponin(e | |
| CN109867653B (en) | Preparation method of okra lactone | |
| CN107893033B (en) | Aspergillus fumigatus SQH4 and application thereof in preparation of taxifolin by biotransformation method | |
| CN103981104B (en) | Endophytic fungus and method for biologically converting glycyrrhizic acid into glycyrrhetinic glycoside by using same | |
| CN112646729B (en) | Sea squirt-derived fungus and application thereof | |
| CN1227243C (en) | Method of high effect preparing rhoxadunol | |
| CN116354917B (en) | Dendrobium aureosallowii endophytic fungus chromone compound DWT001 and preparation and application thereof | |
| CN101092611A (en) | Method for preparing purified Naringoside acid, and application of enzyme preparation | |
| CN108753626B (en) | Bacterial strain for biosynthesis of 16 β -hydroxy-19-nor-4-androstenedione and application thereof | |
| CN102329829B (en) | Method for converting daidzein into 8-hydroxydaidzein by utilizing penicillium | |
| CN102337308A (en) | Method for converting bergenin into special nitrogenous derivative by using penicillium | |
| CN109136111A (en) | A method of utilizing marine fungi large scale preparation tryptophan-alanine Cyclic dipeptides | |
| CN108841890B (en) | Method for producing citrinin by liquid and solid state fermentation of monascus with soybean isoflavone reduced | |
| CN114805276B (en) | Isochromene compound and preparation method and application thereof | |
| CN114605247B (en) | Diterpenoid derivative, preparation method thereof, analgesic, and ethyl acetate extract of fermentation product of Pleurotus cornucopiae | |
| CN110218750B (en) | Application of aspergillus versicolor strain in fermentation production of kojic acid | |
| CN101921815B (en) | Method for producing flavonoid compound by streptomyces | |
| CN116478121B (en) | New compound extracted from golden camellia endophyte metabolite and preparation method thereof | |
| KR101529709B1 (en) | Method for production of soybean isoflavone aglycone | |
| KR101424681B1 (en) | Preparation method of steviol and medium for koji mold culture | |
| CN108218884B (en) | Huperzine B derivative and preparation method thereof | |
| CN102276613B (en) | Sesquiterpene alkaloid compound as well as preparation method and application thereof | |
| CN106834133B (en) | Penicillium oxalicum and application thereof in preparation of linoleic acid triglyceride | |
| CN106636245A (en) | Method for preparing naringenin and apigenin by converting exocarpium citrus grandis leaf flavone by using microorganism | |
| CN103114042B (en) | Dothideomycete sp. mutant strain and method for catalytic production of betulin alcohol by using same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20210629 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |