CN111484403A - Preparation method of arylturmerone reference substance - Google Patents
Preparation method of arylturmerone reference substance Download PDFInfo
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Abstract
The invention provides a preparation method of an arylturmerone reference substance, which comprises the steps of uniformly puncturing the surface of clean fresh turmeric, performing intermittent microwave treatment at 300-500W, cutting into turmeric pieces with the thickness of 1-2 mm, performing steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment in sequence, crushing to obtain turmeric powder, and finally performing solvent extraction to obtain the arylturmerone reference substance. The method takes fresh turmeric as a raw material, promotes the generation of more arylturmerone through a specific drying procedure, and effectively improves the yield and the purity of the product; the raw material cost is low, and the further separation and purification by high performance liquid chromatography are not needed, so that the method is suitable for industrial production.
Description
Technical Field
The invention relates to the technical field of natural product extraction and separation, in particular to a preparation method of an aromatic turmerone reference substance.
Background
Turmeric is a perennial herb of the genus curcuma of the family zingiberaceae, the rhizome of which is mostly cylindrical or finger-shaped branched, is reddish yellow like ginger, has bright yellow cross section, and is suitable for growing in warm and humid environments with abundant sunlight and abundant rainfall. The turmeric is bitter in taste and warm in nature, and has the functions of breaking blood and promoting qi circulation, and relieving dysmenorrheal and pain in traditional Chinese medicine.
The chemical components contained in the turmeric are complex, the active components of the turmeric mainly comprise curcumin compounds, turmeric oil and the like, and in addition, resins, saccharides, sterols, fatty acids, polypeptides and the like are also included, and according to the reports of the literature, dozens of volatile oil components are found in the traditional Chinese medicine turmeric, including: borneol, camphor, terpineol, curcumene, arylturmerone, turmerone, phellandrene and the like.
Wherein, the arylturmerone belongs to terpene compounds, is one of important components of turmeric, and has wide prospects in aspects of clinical development and treatment of metabolic comprehensive diseases such as leukemia, malignant lymphoma, bacterial inflammation, fungal inflammation, diabetes, obesity and the like, birth control and the like.
In addition, the main components of the dry turmeric are about the same as those of the fresh turmeric, namely α -zingiberene, α -curcumene, curcumine, turmerone, ar-turmerone and the like, but the content difference is large, the three components with the highest content in the dry turmeric are respectively ar-turmerone (28.95%), α -curcumene (18.05%), unknown components (7.46%), and the three components with the highest content in the fresh turmeric are respectively turmerone (21.77%), ar-turmerone (11.91%) and α -zingiberene (11.33%), the reasons for different component contents of the dry turmeric and the fresh turmeric can be that some volatile chemical components are lost during the drying process of the fresh turmeric, and some active substances with more chemical properties are converted during the storage process to other stable substances in the dry turmeric.
The reference substance is a standard substance used for identifying, checking, measuring content and correcting performance of a checking instrument, is a reference for determining authenticity of a medicine in medicine inspection, and is an essential tool for controlling medicine quality, so that research and development of a preparation method of the ar-turmerone reference substance are very important.
Patent CN104478686B discloses a preparation method of a turmerone reference substance in turmeric volatile oil, which is characterized in that turmeric volatile oil is used as a raw material, and is subjected to pressure normal phase silica gel column rough separation, then pressure normal phase silica gel column fine separation and finally high performance liquid chromatography separation to obtain a turmerone reference substance with the purity of 99.95%. However, the preparation method has low yield of the arylturmerone, and in addition, the turmeric volatile oil is taken as the raw material, so that on one hand, the raw material cost is high, and on the other hand, a part of the arylturmerone is probably lost in the preparation process of the turmeric volatile oil, so that the preparation method of the patent is not suitable for industrial production as a whole.
Disclosure of Invention
The invention aims to provide a preparation method of an arylturmerone reference substance, which takes fresh turmeric as a raw material, has low cost, promotes the generation of more arylturmerone through a specific drying procedure, effectively improves the yield and the purity of a product, and is suitable for industrial production.
In order to achieve the purpose, the invention is realized by the following scheme:
a preparation method of an arylturmerone reference substance comprises the steps of uniformly puncturing the surfaces of cleaned fresh turmeric, performing intermittent microwave treatment at 300-500W, cutting into turmeric pieces with the thickness of 1-2 mm, performing steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment in sequence, crushing to obtain turmeric powder, and performing solvent extraction to obtain the arylturmerone reference substance; wherein, the specific method for solvent extraction comprises the following steps:
(A) firstly, utilizing the volume ratio of 1: 2-3: performing microwave extraction on 0.1-0.2 of a neopentane-diethyl ether-patchouli essential oil mixed solution to obtain an extract I;
(B) then adding the extract I into a mixture with a volume ratio of 1: 4-6: 5-8: and (3) fully and uniformly oscillating 8-10 of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution, extracting, taking an organic phase, concentrating under reduced pressure, and drying to obtain the artocarpin contrast product.
Preferably, a plurality of small holes are formed on the surface of the fresh turmeric by puncturing with a needle or puncturing equipment, the distance between every two adjacent small holes is 0.6-0.8 mm, the diameter of each small hole is 0.1-0.2 mm, and the depth of each small hole is 1-1.5 cm.
Preferably, the specific method of the batch microwave treatment is as follows: and pausing for 30s after the microwave treatment is carried out for 30s, and circulating in the same way until the cumulative microwave treatment time is 3-5 minutes.
Preferably, the process conditions of the steam explosion treatment are as follows: and (3) loading the turmeric slices into a blasting cavity of steam blasting equipment, keeping the turmeric slices under the condition of 2-3 MPa for 1-2 minutes, and then quickly releasing the pressure.
Preferably, the process conditions of the electron beam irradiation treatment are as follows: the dosage is 10-13 kGy, and the time is 8-12 minutes.
Preferably, the vacuum freeze-drying process conditions are as follows: freezing at the temperature of minus 40 ℃ to minus 50 ℃ for 8-10 hours, vacuumizing to 15-20 Pa, raising the temperature to 20-30 ℃, and continuously treating for 10-15 hours under the current vacuum degree condition.
Preferably, a jet mill is used for crushing, and the specific process conditions are as follows: the air flow pressure is 1200kPa, the feeding speed is 120r/min, the grading frequency is 30Hz, and the crushing time is 60-80 minutes.
Preferably, in the step (A), the mass volume ratio of the turmeric powder to the mixed solution of neopentane-diethyl ether-patchouli essential oil is 1 g: 6-9 m L.
Preferably, in the step (A), the neopentane-diethyl ether-patchouli essential oil mixed solution is prepared by ultrasonically oscillating neopentane, diethyl ether and patchouli essential oil in proportion for 5-10 minutes, and is ready to use.
Preferably, in the step (A), microwave extraction is realized by 300-500W intermittent microwave, and the specific process conditions are as follows: and pausing for 30s after treating the microwave for 30s, and circulating in such a way until the cumulative microwave treatment time is 8-10 minutes.
Further preferably, after microwave extraction is completed, the filtrate is filtered and the solvent is removed under reduced pressure to obtain extract I.
Preferably, in the step (B), the mass volume ratio of the extract I to the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is 1 g: 6-9 m L.
Preferably, in the step (B), the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is prepared by ultrasonically oscillating methyl tert-butyl ether, isopropyl acetate, methyl isobutyl ketone and water in proportion for 5 to 10 minutes, and the mixture is ready to use.
Preferably, in the step (B), the drying process conditions are as follows: drying the mixture for 15 to 24 hours at a temperature of between 60 and 80 ℃.
The invention has the beneficial effects that:
according to the method, firstly, fresh turmeric is cleaned, the surface of the fresh turmeric is uniformly punctured, then the fresh turmeric is subjected to intermittent microwave treatment at 300-500W, then the fresh turmeric is cut into turmeric pieces with the thickness of 1-2 mm, then steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment are sequentially carried out, turmeric powder is obtained through crushing, and finally solvent extraction is carried out, so that the arylturmerone reference substance is obtained. The method takes fresh turmeric as a raw material, promotes the generation of more arylturmerone through a specific drying procedure, and effectively improves the yield and the purity of the product; the raw material cost is low, and the further separation and purification by high performance liquid chromatography are not needed, so that the method is suitable for industrial production.
After the fresh turmeric surface is punctured uniformly, moisture is easier to escape during subsequent microwave treatment, and drying is facilitated, and on the other hand, air is facilitated to enter the interior, so that more arylturmerone is generated through chemical bond breakage rearrangement and the like under the action of microwaves. After the turmeric slices are cut into turmeric slices, steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment are sequentially carried out, and during the steam explosion treatment, the internal energy of steam is converted into mechanical energy and acts on the tissue cell layers of biomass, so that the internal structure is fully damaged, and the extraction of components is facilitated; the electron beam irradiation treatment is favorable for further degradation and transformation to generate more arylturmerone; during vacuum freeze drying, water is formed into ice crystals and the ice crystals are directly sublimated and dehydrated to form tiny pores, so that the subsequent extraction difficulty is reduced, and the extraction yield is improved.
Solvent extraction involves two groups of extraction solvents:
1. the mixed solution of neopentane-diethyl ether-patchouli essential oil is mainly used for extracting fat-soluble components, wherein the patchouli essential oil is sesquiterpene essential oil, and the extraction of the fat-soluble components is greatly promoted by adding a small amount of patchouli essential oil.
2. The methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution realizes the separation of the aromatic turmerone and ensures the purity of the product.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The patchouli essential oil is purchased from the company of hundred million hump chemical industries, Inc. of Guangzhou.
Example 1
A method for preparing aromatic turmerone reference substance comprises cleaning fresh Curcuma rhizome, pricking uniformly on the surface, processing with 300W intermittent microwave, cutting into Curcuma rhizome slices with thickness of 2mm, sequentially performing steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment, pulverizing to obtain Curcuma rhizome powder, and extracting with solvent to obtain aromatic turmerone reference substance; wherein, the specific method for solvent extraction comprises the following steps:
(A) firstly, carrying out microwave extraction on a neopentane-ether-patchouli essential oil mixed solution (neopentane 1L, ether 2L and patchouli essential oil 0.2L) to obtain an extract I;
(B) and then adding the extract I into a methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution (methyl tert-butyl ether 1L, isopropyl acetate 4L, methyl isobutyl ketone 8L and water 8L), fully and uniformly oscillating, extracting, taking an organic phase, concentrating under reduced pressure, and drying to obtain the arylturmerone reference substance.
Puncturing with a needle or a puncturing device to form multiple small holes on the surface of fresh Curcuma rhizome, wherein the distance between adjacent small holes is 0.8mm, the diameter of the small hole is 0.1mm, and the depth of the small hole is 1.5 cm.
The specific method of the batch microwave treatment comprises the following steps: the microwave treatment is suspended for 30s after 30s, and the process is circulated until the cumulative microwave treatment time is 3 minutes.
The technological conditions of the steam explosion treatment are as follows: loading the turmeric slices into a blasting cavity of steam blasting equipment, keeping the turmeric slices under the condition of 3MPa for 1 minute, and then quickly releasing the pressure.
The process conditions of the electron beam irradiation treatment are as follows: dose 13kGy, time 8 min.
The technological conditions of vacuum freeze drying are as follows: freezing at-50 deg.C for 8 hr, vacuumizing to 15Pa, raising the temperature to 30 deg.C, and treating under the current vacuum condition for 10 hr.
Crushing by using a jet mill, wherein the specific process conditions are as follows: the air pressure was 1200kPa, the feed rate was 120r/min, the classification frequency was 30Hz, and the pulverizing time was 80 minutes.
In the step (A), the mass volume ratio of the turmeric powder to the mixed solution of the neopentane-diethyl ether-patchouli essential oil is 1g to 6m L.
In the step (A), the neopentane-diethyl ether-patchouli essential oil mixed solution is prepared by ultrasonically oscillating neopentane, diethyl ether and patchouli essential oil in proportion for 10 minutes.
In the step (A), microwave extraction is realized by 300W intermittent microwave, and the specific process conditions are as follows: the microwave treatment is suspended for 30s after being treated for 30s, and the process is circulated until the cumulative microwave treatment time is 10 minutes. After microwave extraction, filtering to obtain filtrate, and removing solvent under reduced pressure to obtain extract I.
In the step (B), the mass-volume ratio of the extract I to the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is 1 g: 6m L.
In the step (B), the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is prepared by proportionally and ultrasonically oscillating methyl tert-butyl ether, isopropyl acetate, methyl isobutyl ketone and water for 10 minutes.
In the step (B), the drying process conditions are as follows: drying at 60 ℃ for 24 hours.
And (3) carrying out structure confirmation on the obtained arylturmerone reference substance:
EI-MS m/z：216(M+，6),201(M+-Me，7),132(11),119(44),91(25),83(100),77(14),55(70)。
example 2
A method for preparing aromatic turmerone reference substance comprises cleaning fresh Curcuma rhizome, pricking uniformly on the surface, performing intermittent microwave treatment at 500W, cutting into Curcuma rhizome slices with thickness of 1mm, performing steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment in sequence, pulverizing to obtain Curcuma rhizome powder, and extracting with solvent to obtain aromatic turmerone reference substance; wherein, the specific method for solvent extraction comprises the following steps:
(A) firstly, carrying out microwave extraction on a neopentane-ether-patchouli essential oil mixed solution (neopentane 1L, ether 3L and patchouli essential oil 0.2L) to obtain an extract I;
(B) and then adding the extract I into a methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution (methyl tert-butyl ether 1L, isopropyl acetate 6L, methyl isobutyl ketone 5L and water 10L), fully and uniformly oscillating, extracting, taking an organic phase, concentrating under reduced pressure, and drying to obtain the arylturmerone reference substance.
Puncturing with a needle or a puncturing device to form multiple small holes on the surface of fresh Curcuma rhizome, wherein the distance between adjacent small holes is 0.6mm, the diameter of the small hole is 0.2mm, and the depth of the small hole is 1 cm.
The specific method of the batch microwave treatment comprises the following steps: the microwave treatment is suspended for 30s after 30s, and the process is circulated until the cumulative microwave treatment time is 5 minutes.
The technological conditions of the steam explosion treatment are as follows: loading the turmeric slices into a blasting cavity of steam blasting equipment, keeping the turmeric slices under the condition of 2MPa for 2 minutes, and then quickly releasing pressure.
The process conditions of the electron beam irradiation treatment are as follows: dose 10kGy, time 12 min.
The technological conditions of vacuum freeze drying are as follows: freezing at-40 deg.C for 10 hr, vacuumizing to 20Pa, raising the temperature to 20 deg.C, and treating under the current vacuum condition for 15 hr.
Crushing by using a jet mill, wherein the specific process conditions are as follows: the air pressure was 1200kPa, the feed rate was 120r/min, the classification frequency was 30Hz, and the pulverizing time was 60 minutes.
In the step (A), the mass volume ratio of the turmeric powder to the mixed solution of the neopentane-diethyl ether-patchouli essential oil is 1g to 9m L.
In the step (A), the neopentane-diethyl ether-patchouli essential oil mixed solution is prepared by ultrasonically oscillating neopentane, diethyl ether and patchouli essential oil in proportion for 5 minutes.
In the step (A), microwave extraction is realized by 500W intermittent microwave, and the specific process conditions are as follows: the microwave treatment is suspended for 30s after being treated for 30s, and the process is circulated until the cumulative microwave treatment time is 8 minutes. After microwave extraction, filtering to obtain filtrate, and removing solvent under reduced pressure to obtain extract I.
In the step (B), the mass volume ratio of the extract I to the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is 1 g: 9m L.
In the step (B), the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is prepared by proportionally and ultrasonically oscillating methyl tert-butyl ether, isopropyl acetate, methyl isobutyl ketone and water for 5 minutes.
In the step (B), the drying process conditions are as follows: dried at 80 ℃ for 15 hours.
Example 3
A method for preparing aromatic curcumone reference substance comprises cleaning fresh Curcuma rhizome, pricking uniformly on the surface, processing with 450W intermittent microwave, cutting into Curcuma rhizome slices with thickness of 1.5mm, sequentially performing steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment, pulverizing to obtain Curcuma rhizome powder, and extracting with solvent to obtain aromatic curcumone reference substance; wherein, the specific method for solvent extraction comprises the following steps:
(A) firstly, carrying out microwave extraction on a neopentane-ether-patchouli essential oil mixed solution (neopentane 1L, ether 2.5L and patchouli essential oil 0.15L) to obtain an extract I;
(B) and then adding the extract I into a methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution (methyl tert-butyl ether 1L, isopropyl acetate 5L, methyl isobutyl ketone 7L and water 9L), fully and uniformly oscillating, extracting, taking an organic phase, concentrating under reduced pressure, and drying to obtain the arylturmerone reference substance.
Puncturing with a needle or a puncturing device to form multiple small holes on the surface of fresh Curcuma rhizome, wherein the distance between adjacent small holes is 0.7mm, the diameter of the small hole is 0.1mm, and the depth of the small hole is 1.2 cm.
The specific method of the batch microwave treatment comprises the following steps: the microwave treatment is suspended for 30s after 30s, and the process is circulated until the cumulative microwave treatment time is 4 minutes.
The technological conditions of the steam explosion treatment are as follows: loading the turmeric slices into a blasting cavity of steam blasting equipment, keeping the turmeric slices under the condition of 2.5MPa for 1.5 minutes, and then quickly releasing the pressure.
The process conditions of the electron beam irradiation treatment are as follows: dose 11kGy, time 10 min.
The technological conditions of vacuum freeze drying are as follows: freezing at-45 deg.C for 9 hr, vacuumizing to 18Pa, raising the temperature to 25 deg.C, and treating under the current vacuum condition for 12 hr.
Crushing by using a jet mill, wherein the specific process conditions are as follows: the air pressure was 1200kPa, the feed rate was 120r/min, the classification frequency was 30Hz, and the crushing time was 70 minutes.
In the step (A), the mass volume ratio of the turmeric powder to the mixed solution of the neopentane-ethyl ether-patchouli essential oil is 1g to 8m L.
In the step (A), the neopentane-diethyl ether-patchouli essential oil mixed solution is prepared by ultrasonically oscillating neopentane, diethyl ether and patchouli essential oil in proportion for 8 minutes.
In the step (A), microwave extraction is realized by 450W intermittent microwave, and the specific process conditions are as follows: the microwave treatment is suspended for 30s after being treated for 30s, and the process is circulated until the cumulative microwave treatment time is 9 minutes. After microwave extraction, filtering to obtain filtrate, and removing solvent under reduced pressure to obtain extract I.
In the step (B), the mass-volume ratio of the extract I to the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is 1 g: 8m L.
In the step (B), the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is prepared by proportionally and ultrasonically oscillating methyl tert-butyl ether, isopropyl acetate, methyl isobutyl ketone and water for 8 minutes.
In the step (B), the drying process conditions are as follows: drying at 70 deg.C for 20 hr.
Comparative example 1
A method for preparing aromatic turmerone reference substance comprises cleaning fresh Curcuma rhizome, pricking uniformly on the surface, cutting into Curcuma rhizome slices with thickness of 2mm, sequentially performing 300W intermittent microwave treatment, steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment, pulverizing to obtain Curcuma rhizome powder, and extracting with solvent to obtain aromatic turmerone reference substance; wherein, the specific method for solvent extraction comprises the following steps:
(A) firstly, carrying out microwave extraction on a neopentane-ether-patchouli essential oil mixed solution (neopentane 1L, ether 2L and patchouli essential oil 0.2L) to obtain an extract I;
(B) and then adding the extract I into a methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution (methyl tert-butyl ether 1L, isopropyl acetate 4L, methyl isobutyl ketone 8L and water 8L), fully and uniformly oscillating, extracting, taking an organic phase, concentrating under reduced pressure, and drying to obtain the arylturmerone reference substance.
Puncturing with a needle or a puncturing device to form multiple small holes on the surface of fresh Curcuma rhizome, wherein the distance between adjacent small holes is 0.8mm, the diameter of the small hole is 0.1mm, and the depth of the small hole is 1.5 cm.
The specific method of the batch microwave treatment comprises the following steps: the microwave treatment is suspended for 30s after 30s, and the process is circulated until the cumulative microwave treatment time is 3 minutes.
The technological conditions of the steam explosion treatment are as follows: loading the turmeric slices into a blasting cavity of steam blasting equipment, keeping the turmeric slices under the condition of 3MPa for 1 minute, and then quickly releasing the pressure.
The process conditions of the electron beam irradiation treatment are as follows: dose 13kGy, time 8 min.
The technological conditions of vacuum freeze drying are as follows: freezing at-50 deg.C for 8 hr, vacuumizing to 15Pa, raising the temperature to 30 deg.C, and treating under the current vacuum condition for 10 hr.
Crushing by using a jet mill, wherein the specific process conditions are as follows: the air pressure was 1200kPa, the feed rate was 120r/min, the classification frequency was 30Hz, and the pulverizing time was 80 minutes.
In the step (A), the mass volume ratio of the turmeric powder to the mixed solution of the neopentane-diethyl ether-patchouli essential oil is 1g to 6m L.
In the step (A), the neopentane-diethyl ether-patchouli essential oil mixed solution is prepared by ultrasonically oscillating neopentane, diethyl ether and patchouli essential oil in proportion for 10 minutes.
In the step (A), microwave extraction is realized by 300W intermittent microwave, and the specific process conditions are as follows: the microwave treatment is suspended for 30s after being treated for 30s, and the process is circulated until the cumulative microwave treatment time is 10 minutes. After microwave extraction, filtering to obtain filtrate, and removing solvent under reduced pressure to obtain extract I.
In the step (B), the mass-volume ratio of the extract I to the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is 1 g: 6m L.
In the step (B), the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is prepared by proportionally and ultrasonically oscillating methyl tert-butyl ether, isopropyl acetate, methyl isobutyl ketone and water for 10 minutes.
In the step (B), the drying process conditions are as follows: drying at 60 ℃ for 24 hours.
Comparative example 2
A method for preparing arylturmerone reference substance comprises cleaning fresh Curcuma rhizome, pricking uniformly on the surface, performing intermittent microwave treatment at 300W, cutting into Curcuma rhizome slices with thickness of 2mm, performing steam explosion treatment and vacuum freeze drying treatment in sequence, pulverizing to obtain Curcuma rhizome powder, and extracting with solvent to obtain arylturmerone reference substance; wherein, the specific method for solvent extraction comprises the following steps:
(A) firstly, carrying out microwave extraction on a neopentane-ether-patchouli essential oil mixed solution (neopentane 1L, ether 2L and patchouli essential oil 0.2L) to obtain an extract I;
(B) and then adding the extract I into a methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution (methyl tert-butyl ether 1L, isopropyl acetate 4L, methyl isobutyl ketone 8L and water 8L), fully and uniformly oscillating, extracting, taking an organic phase, concentrating under reduced pressure, and drying to obtain the arylturmerone reference substance.
Puncturing with a needle or a puncturing device to form multiple small holes on the surface of fresh Curcuma rhizome, wherein the distance between adjacent small holes is 0.8mm, the diameter of the small hole is 0.1mm, and the depth of the small hole is 1.5 cm.
The specific method of the batch microwave treatment comprises the following steps: the microwave treatment is suspended for 30s after 30s, and the process is circulated until the cumulative microwave treatment time is 3 minutes.
The technological conditions of the steam explosion treatment are as follows: loading the turmeric slices into a blasting cavity of steam blasting equipment, keeping the turmeric slices under the condition of 3MPa for 1 minute, and then quickly releasing the pressure.
The technological conditions of vacuum freeze drying are as follows: freezing at-50 deg.C for 8 hr, vacuumizing to 15Pa, raising the temperature to 30 deg.C, and treating under the current vacuum condition for 10 hr.
Crushing by using a jet mill, wherein the specific process conditions are as follows: the air pressure was 1200kPa, the feed rate was 120r/min, the classification frequency was 30Hz, and the pulverizing time was 80 minutes.
In the step (A), the mass volume ratio of the turmeric powder to the mixed solution of the neopentane-diethyl ether-patchouli essential oil is 1g to 6m L.
In the step (A), the neopentane-diethyl ether-patchouli essential oil mixed solution is prepared by ultrasonically oscillating neopentane, diethyl ether and patchouli essential oil in proportion for 10 minutes.
In the step (A), microwave extraction is realized by 300W intermittent microwave, and the specific process conditions are as follows: the microwave treatment is suspended for 30s after being treated for 30s, and the process is circulated until the cumulative microwave treatment time is 10 minutes. After microwave extraction, filtering to obtain filtrate, and removing solvent under reduced pressure to obtain extract I.
In the step (B), the mass-volume ratio of the extract I to the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is 1 g: 6m L.
In the step (B), the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is prepared by proportionally and ultrasonically oscillating methyl tert-butyl ether, isopropyl acetate, methyl isobutyl ketone and water for 10 minutes.
In the step (B), the drying process conditions are as follows: drying at 60 ℃ for 24 hours.
Comparative examples 3 to 6
The composition of the extraction solvent was adjusted, and the rest of the procedure was the same as in example 1, and is specifically shown in Table 1.
TABLE 1 adjustment of the ratio of extraction solvent in comparative examples 3 to 6
Comparative example 7
The patchouli essential oil was replaced with lemon essential oil as in example 1.
Comparative example 8
The same as in example 1 except that ethyl acetate was used instead of isopropyl acetate.
Test examples
The extraction yield of the arylturmerone reference substances (the quality of the obtained arylturmerone reference substance/the quality of turmeric) of the examples 1 to 3 and the comparative examples 1 to 8 was counted, and the purity was calculated by using a high performance liquid area normalization method, and the result is shown in table 2.
TABLE 2 extraction yield and purity results
| Extraction yield (mg/kg) | Purity (%) | |
| Example 1 | 3785 | ≥99.99 |
| Example 2 | 3786 | ≥99.99 |
| Example 3 | 3789 | ≥99.99 |
| Comparative example 1 | 2805 | 94.38 |
| Comparative example 2 | 2733 | 91.12 |
| Comparative example 3 | 3005 | 80.33 |
| Comparative example 4 | 3012 | 84.16 |
| Comparative example 5 | 3011 | 84.55 |
| Comparative example 6 | 3008 | 83.27 |
| Comparative example 7 | 3013 | 90.01 |
| Comparative example 8 | 3015 | 90.08 |
As shown in Table 2, the preparation methods of examples 1 to 3 have high extraction yield and high purity of the obtained product. Comparative example 1 placing the batch microwave treatment step after the slicing step affects the composition of the ingredients, reduces the extraction yield, and also affects the product purity; comparative example 2 omits electron beam irradiation treatment, reduces the generation of ar-turmerone, reduces the extraction yield, and also influences the product purity; in comparative examples 3-6, individual reagents were replaced, and the yield and purity of the obtained product were significantly reduced, indicating that the extraction solvent combination of the present invention can achieve a good extraction effect.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (10)
1. A preparation method of an arylturmerone reference substance is characterized by uniformly puncturing the surface of clean fresh turmeric, performing intermittent microwave treatment at 300-500W, cutting into turmeric pieces with the thickness of 1-2 mm, performing steam explosion treatment, electron beam irradiation treatment and vacuum freeze drying treatment in sequence, crushing to obtain turmeric powder, and finally performing solvent extraction to obtain the arylturmerone reference substance; wherein, the specific method for solvent extraction comprises the following steps:
(A) firstly, utilizing the volume ratio of 1: 2-3: performing microwave extraction on 0.1-0.2 of a neopentane-diethyl ether-patchouli essential oil mixed solution to obtain an extract I;
(B) then adding the extract I into a mixture with a volume ratio of 1: 4-6: 5-8: and (3) fully and uniformly oscillating 8-10 of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water mixed solution, extracting, taking an organic phase, concentrating under reduced pressure, and drying to obtain the artocarpin contrast product.
2. The method according to claim 1, wherein the fresh turmeric has a plurality of pores formed on the surface thereof by pricking with a needle or a pricking device, the distance between adjacent pores is 0.6 to 0.8mm, the diameter of the pores is 0.1 to 0.2mm, and the depth of the pores is 1 to 1.5 cm.
3. The preparation method according to claim 1, wherein the specific method of the batch microwave treatment is: and pausing for 30s after the microwave treatment is carried out for 30s, and circulating in the same way until the cumulative microwave treatment time is 3-5 minutes.
4. The preparation method according to claim 1, wherein the process conditions of the steam explosion treatment are as follows: and (3) loading the turmeric slices into a blasting cavity of steam blasting equipment, keeping the turmeric slices under the condition of 2-3 MPa for 1-2 minutes, and then quickly releasing the pressure.
5. The production method according to claim 1, wherein the process conditions of the electron beam irradiation treatment are: the dosage is 10-13 kGy, and the time is 8-12 minutes.
6. The preparation method according to claim 1, wherein the vacuum freeze-drying process conditions are as follows: freezing at the temperature of minus 40 ℃ to minus 50 ℃ for 8-10 hours, vacuumizing to 15-20 Pa, raising the temperature to 20-30 ℃, and continuously treating for 10-15 hours under the current vacuum degree condition.
7. The preparation method according to claim 1, wherein the jet mill is used for milling, and the specific process conditions are as follows: the air flow pressure is 1200kPa, the feeding speed is 120r/min, the grading frequency is 30Hz, and the crushing time is 60-80 minutes.
8. The preparation method according to claim 1, wherein in the step (A), the mass volume ratio of the turmeric powder to the mixed solution of neopentane-diethyl ether-patchouli essential oil is about 1 g: 6-9 m L.
9. The preparation method according to claim 1, wherein in the step (A), microwave extraction is realized by 300-500W batch microwave, and the specific process conditions are as follows: and pausing for 30s after treating the microwave for 30s, and circulating in such a way until the cumulative microwave treatment time is 8-10 minutes.
10. The preparation method according to claim 1, wherein in the step (B), the mass volume ratio of the extract I to the mixed solution of methyl tert-butyl ether-isopropyl acetate-methyl isobutyl ketone-water is 1 g: 6-9 m L.
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| CN104478686A (en) * | 2014-03-20 | 2015-04-01 | 贵州大学 | Preparation method of ar-turmerone reference substance in turmeric volatile oil |
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