CN108143836A - With the method for eutectic solvent extraction tea seed oil different shape phenolic compound - Google Patents

With the method for eutectic solvent extraction tea seed oil different shape phenolic compound Download PDF

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CN108143836A
CN108143836A CN201810048533.5A CN201810048533A CN108143836A CN 108143836 A CN108143836 A CN 108143836A CN 201810048533 A CN201810048533 A CN 201810048533A CN 108143836 A CN108143836 A CN 108143836A
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des
phenolic compound
seed oil
tea seed
water
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CN108143836B (en
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王晓琴
王俐娟
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Huaqiao University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/82—Theaceae (Tea family), e.g. camellia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/35—Extraction with lipophilic solvents, e.g. Hexane or petrol ether
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/50—Methods involving additional extraction steps
    • A61K2236/55—Liquid-liquid separation; Phase separation

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  • Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

The invention discloses a kind of methods with eutectic solvent extraction tea seed oil different shape phenolic compound, DES solvents are added in after tea seed oil is mixed with normal hexane to be uniformly mixed, and sequestered phenolic compound DES extracting solutions are obtained after vortex oscillation and centrifugation under 20~70 DEG C of water-baths；Resultant product alkaline hydrolysis centrifuges out water phase, adds in DES solvents in remaining oil phase, merge to obtain mating type phenolic compound extracting solution with water phase for DES layers after centrifugation.The present invention realizes the extraction to the sequestered phenolic compound and mating type phenolic compound of tea seed oil using eutectic solvent, and extraction yield is high, and reaction condition is mild, and suitable for practical application, research and utilization to follow-up tea seed oil provide guidance.

Description

With the method for eutectic solvent extraction tea seed oil different shape phenolic compound
Technical field
The present invention relates to the extracting methods of phenolic compound, and tea seed oil is extracted with eutectic solvent more particularly to a kind of The method of different shape phenolic compound.
Background technology
Phenolic compound is a kind of polyphenols being widely present in plant, is a kind of important time in plant Metabolite is given birth to, contains several phenolic hydroxyl group groups in molecular structure, phenolic acid class, flavones is broadly divided into according to structure feature Class, tannins, flavanol compound and glycoside etc..Research shows that vegetable phenol ingredient is a kind of natural, people can be removed Internal NO and ROS free radicals, and the large biological molecule damage that can be induced free radical plays a protective role；In addition, it is also It can inhibit oxidase active, activate antioxidase system, there is apparent antioxidant effect.
Tea seeds are the seeds of Theaceae Camellia tea tree, and fat content is up to 30% or so, rich in natural phenolic chemical combination Object.The improvement and active constituent exploitation that phenolic compound can be for tea seed oil refinery practice in research tea seed oil provide science Directive function.Phenolic compound is closely tied with diffluent sequestered phenolic compound in tea seed oil and with other matrix The form of the mating type phenolic compound of conjunction exists, and research application at present focuses mostly in sequestered phenolic compound, mating type by In not readily dissolving and extracting, research application is limited.Potential a large amount of mating type phenolic compounds in plant, if not considering mating type phenol Class compound is unable to objective evaluation oil quality and the mechanism of action.Thus, seek in a kind of practical, efficient tea seed oil to dissociate The extracting method of type and mating type phenolic compound has great importance.
Invention content
It is an object of the invention to overcome the shortcomings of present in the prior art, a kind of eutectic solvent extraction tealeaves is provided The method of seed oil different shape phenolic compound.
The technical scheme is that：
A kind of method with eutectic solvent extraction tea seed oil different shape phenolic compound includes the following steps：
1) by choline chloride and Hydrogen Proton compound donator according to volume ratio 1：0.5~2 ratio Hybrid Heating congruent melting is extremely Clarification forms DES solvents；
2) DES extracts tea seed oil sequestered phenolic compound：DES solvents are added in after tea seed oil is mixed with normal hexane It is uniformly mixed, stirring and discontinuous vortex oscillation under 20~70 DEG C of water-baths are taken out, be collected after centrifugation DES layers and obtain the first DES Extracting solution, normal hexane is added in into the first DES extracting solutions, is centrifuged off normal hexane layer after mixing, obtains sequestered phenols Compound DES extracting solutions；
3) DES extracts tea seed oil mating type phenolic compound：After resultant product merges after twice being centrifuged in step 2) Sodium hydroxide solution is added in, stirs and is protected from light alkaline hydrolysis, hydrolyzate is adjusted to pH and is in neutrality, and centrifuges out water phase, toward residue oil phase Middle addition DES solvents, stirring and discontinuous vortex oscillation, are collected after centrifugation DES layers and obtain the 2nd DES under 20~70 DEG C of water-baths Extracting solution, normal hexane is added in into the 2nd DES extracting solutions, is centrifuged off normal hexane layer after mixing, is merged with the water phase Obtain mating type phenolic compound extracting solution；
4) sequestered phenolic compound DES extracting solutions and mating type phenolic compound extracting solution are crossed into XAD-16 macropores respectively Resin chromatography column, so as to recycle phenolic compound.
Optionally, the Hydrogen Proton compound donator be glycerine, xylitol, ethylene glycol, malonic acid, in propylene glycol extremely Few one kind.
Optionally, in step 2), the bath temperature is 40~60 DEG C.
Optionally, in step 3), the bath temperature is 40~60 DEG C.
Optionally, in step 2), according to following proportionate relationship, 6g tea seed oils is taken to add in 3~7mL hexane solutions and are shaken It swings after shaking up, adds 4~8g DES solvents and mixing, under 20~70 DEG C of water-baths, stir 0.5~2h, during which every 10~ 20min 0.5~2min of vortex oscillation take out, and 10~20min is centrifuged under 3000~4000rmp rotating speeds, collect DES layers.
Optionally, in step 3), according to following proportionate relationship, resultant product adds after merging after twice being centrifuged in step 2) Enter 0.1~0.3mol/L, 10~15mL of sodium hydroxide solution, stirring avoids being layered, and is protected from light 8~15h of alkaline hydrolysis, the dense salt of hydrolyzate Acid is adjusted to PH and is in neutrality, under 2500~3500rmp rotating speeds centrifuge 5~15min, isolate water phase, toward residue oil phase in addition 4~ 8g DES solvents, vortex mixing stir 0.5~2h, during which every 10~20min vortex oscillations 0.5 after under 20~70 DEG C of water-baths ~2min takes out, and 10~20min is centrifuged under 3000~4000rmp rotating speeds, collects DES layers.
Optionally, step 2) and 3) in, it is described to collect DES layers of process and be repeated at least once more respectively, and set DES respectively Layer obtains the first DES extracting solutions and the 2nd DES extracting solutions.
Optionally, step 2) and 3) in, respectively into the first DES extracting solutions and the 2nd DES extracting solutions add in 3~7mL just Hexane is uniformly mixed after centrifuging 3~10min under 2500~3500rmp rotating speeds, isolates normal hexane layer to remove remaining oil Fat.
Optionally, in step 4), the sequestered phenolic compound DES extracting solutions and mating type phenolic compound are extracted Liquid respectively with 1~2BV/h flow velocity loadings after, then eluted successively with deionized water, methanol solution, keep flow velocity in 2~3BV/h, Meoh eluate is collected, by the meoh eluate concentrated by rotary evaporation being collected into doing, with molten, the mistake of methanol-water weight that volume ratio is 50% 0.22 μm of organic filter membrane.
Beneficial effects of the present invention are：
It is realized using eutectic solvent to the sequestered phenolic compound of tea seed oil and carrying for mating type phenolic compound It takes, extraction yield is high, and reaction condition is mild, and suitable for practical application, the research and utilization of follow-up tea seed oil are provided Guidance.
Specific embodiment
The present invention is described in further detail in following embodiment.
Embodiment 1
1. prepared by eutectic solvent (DES)
Choline chloride and the congruent melting of Hydrogen Proton compound donator Hybrid Heating are extremely clarified.The Hydrogen Proton acceptor compound of use It is and its as shown in table 1 with choline chloride molal weight proportioning.Precise choline chloride and a series of Hydrogen Proton compound donators In beaker, sealing is placed on water bath with thermostatic control at 80 DEG C, stirs, until obtaining the liquid of clear, takes out, is stood under room temperature It is spare.
Table 1DES
2.DES extracts tea seed oil sequestered phenolic compound
Accurately weigh 6g tea seed oils in 50mL centrifuge tubes, add in 5mL hexane solutions and shake shake up after, add 6g DES solvents and the mixing under turbula shaker, test tube are placed under 25 DEG C of water-baths, stir 1h, during which per 15min vortex oscillations 1min.It takes out, 15min is centrifuged under 3500rmp rotating speeds, collect DES layers, repeat above-mentioned step and play extraction twice, gather DES twice Extracting solution obtains the first DES extracting solutions.5mL n-hexane reagents are added in into the first DES extracting solutions, be fully vortexed mixing, then 5min is centrifuged under 3000rmp rotating speeds, isolates hexane layer to wash away remaining grease to get to sequestered phenolic compound DES extracting solutions.
3.DES solvent extraction tea seed oil mating type phenolic compounds
To it is above-mentioned centrifuge twice after resultant product (tea seed oil and normal hexane after extraction sequestered phenolic compound it is mixed Close solution) merge after add in 0.2mol/L sodium hydroxide solution 12mL, stirring avoids being layered, and is protected from light alkaline hydrolysis 12h, and hydrolyzate is with dense Hydrochloric acid is adjusted to PH and is in neutrality, and centrifuges 10min under 3000rmp rotating speeds, isolates water phase.It is molten that 6g DES are added in into remaining oil phase Agent, 25 DEG C of stirring in water bath 1h after vortex mixing, during which per 15min vortex oscillations 1min.Sample centrifuges under 3500rmp rotating speeds 15min collects DES layers, is repeated twice, DES layers of set obtains the 2nd DES extracting solutions, and 5mL is added in into the 2nd DES extracting solutions Then n-hexane reagent, abundant mixing centrifuge 5min under 3000rmp rotating speeds, isolate hexane layer, merge after alkaline hydrolysis water layer and DES layers, obtain mating type phenolic compound extracting solution.
4. recycle phenolic compound
Above-mentioned sequestered phenolic compound DES extracting solutions, mating type phenolic compound extracting solution, were intended to XAD-16 macropores Resin chromatography column, so as to recycle phenolic compound.After 1.5BV/h flow velocity loadings, then successively with 200mL deionized waters, 200mL Methanol solution elutes, and keeps flow velocity in 2.5BV/h, collection meoh eluate.By the meoh eluate being collected into 36 DEG C of backspins Steaming is concentrated to dryness, molten with 250 μ L methanol-waters (50%, v/v) weight, is crossed 0.22 μm of organic filter membrane, is protected from light refrigeration.
Above-mentioned phenolic compound is analyzed, using HPLC-QqQ-MS multiple-reaction monitorings (MRM) pattern, is drawn simultaneously 25 kinds of standard items phenolic compound linearity curves, quantified by external standard method analysis tea seed oil different shape phenolic compound.
Chromatographic condition is shown in Table shown in 2,3.
2 chromatography primary condition of table
3 gradient elution program of table
Mass spectrometry parameters are shown in as shown in table 4.
4 Mass Spectrometry Conditions of table
Each ion pair parameter that multiple-reaction monitoring pattern (MRM) measures optimization is shown in Table 5.
5 ion parameters of table
6 phenolic compound regression equation of table, the range of linearity, detection limit and quantitative limit
Testing result is shown in Table 7 and table 8：
7 difference DES solvent extraction tea seed oil sequestereds phenolic compound of table forms (μ g/g)
As seen from Table 7,31 kinds of phenolic compounds are detected altogether, wherein including 14 kinds of phenolic acid compounds, 11 kinds of flavones Class compound, 6 kinds of flavonoid glycoside compounds.Different eutectic solvents can extract free state phenolic compound, and obtain total Phenol content is generally higher than conventional methanol/aqueous solvent, and it is choline chloride/glycerine that wherein total phenol content is highest, hence it is evident that is higher by often The methanol/water extracting solution of rule.
8 difference DES solvent extraction tea seed oil mating types phenolic compound of table forms (μ g/g)
As can be seen from Table 8, different eutectic solvents can extract reference state phenolic compound, and obtained total phenol content Generally higher than conventional methanol/aqueous solvent.Reference state phenolic compound may be with fatty glyceride in grease or micro free fat Fat acid, which combines, to be existed, it is made to be not easy to extract, wherein phenolic acid class accounting is up to 90% or so.Hydroxyl, the carboxyl of phenolic acid compound can As Hydrogen Proton donor groups, the existing interaction between DESs may increase its dissolubility and extraction efficiency, compare simultaneously In flavone compound, steric hindrance is obviously reduced.
Embodiment 2
DES (choline chloride-glycerine 1:2) respectively in 30 DEG C, 40 DEG C, 50 DEG C, 60 DEG C, 70 DEG C of extraction tea seed oils differences Form phenolic compound, extracting mode is with reference to embodiment 1, and the result is shown in tables 9.
9 different temperatures of table extracts tea seed oil sequestered phenolic compound and mating type phenolic compound (μ g/g)
Temperature has influence to different content of phenolic compounds, but to its distribution proportion and does not make significant difference.For free State and reference state phenolic compound, most of phenolic compound extraction content reach peak value, but also have a small number of phenols at 50 DEG C Compound such as vanillic acid extracted amount highest at 70 DEG C, and cinnamic acid, ferulic acid the extracted amount highest at 60 DEG C.
Above-described embodiment is only used for further illustrating the present invention a kind of with eutectic solvent extraction tea seed oil not similar shape The method of state phenolic compound, but the invention is not limited in embodiments, and every technical spirit according to the present invention is to above real Any simple modification, equivalent change and modification that example is made is applied, is each fallen in the protection domain of technical solution of the present invention.

Claims (9)

  1. A kind of 1. method with eutectic solvent extraction tea seed oil different shape phenolic compound, it is characterised in that including following Step：
    1) by choline chloride and Hydrogen Proton compound donator according to volume ratio 1：0.5~2 ratio Hybrid Heating congruent melting is extremely clarified Form DES solvents；
    2) DES extracts tea seed oil sequestered phenolic compound：The mixing of DES solvents is added in after tea seed oil is mixed with normal hexane Uniformly, stirring and discontinuous vortex oscillation under 20~70 DEG C of water-baths, take out, and are collected after centrifugation DES layers and obtain the first DES extractions Liquid, normal hexane is added in into the first DES extracting solutions, is centrifuged off normal hexane layer after mixing, obtains sequestered phenols chemical combination Object DES extracting solutions；
    3) DES extracts tea seed oil mating type phenolic compound：Resultant product adds in after merging after twice being centrifuged in step 2) Sodium hydroxide solution stirs and is protected from light alkaline hydrolysis, and hydrolyzate is adjusted to pH and is in neutrality, and centrifuges out water phase, adds into remaining oil phase Enter DES solvents, stirring and discontinuous vortex oscillation under 20~70 DEG C of water-baths are collected after centrifugation DES layers and obtain the 2nd DES extractions Liquid, normal hexane is added in into the 2nd DES extracting solutions, is centrifuged off normal hexane layer after mixing, and knot is merged to obtain with the water phase Mould assembly phenolic compound extracting solution；
    4) sequestered phenolic compound DES extracting solutions and mating type phenolic compound extracting solution are crossed into XAD-16 macroreticular resins respectively Chromatographic column, so as to recycle phenolic compound.
  2. 2. according to the method described in claim 1, it is characterized in that：The Hydrogen Proton compound donator for glycerine, xylitol, At least one of ethylene glycol, malonic acid, propylene glycol.
  3. 3. according to the method described in claim 1, it is characterized in that：In step 2), the bath temperature is 40~60 DEG C.
  4. 4. according to the method described in claim 1, it is characterized in that：In step 3), the bath temperature is 40~60 DEG C.
  5. 5. according to the method described in claim 1, it is characterized in that：In step 2), according to following proportionate relationship, 6g tea seeds are taken After oil addition 3~7mL hexane solutions and concussion shake up, 4~8g DES solvents and mixing are added, in 20~70 DEG C of water-baths Under, stir 0.5~2h, during which 0.5~2min of every 10~20min vortex oscillations, take out, under 3000~4000rmp rotating speeds from 10~20min of the heart collects DES layers.
  6. 6. according to the method described in claim 5, it is characterized in that：It, will be in step 2) according to following proportionate relationship in step 3) 0.1~0.3mol/L, 10~15mL of sodium hydroxide solution are added in after resultant product merges after centrifuging twice, stirring is avoided being layered, be kept away Light 8~15h of alkaline hydrolysis, hydrolyzate are adjusted to PH with concentrated hydrochloric acid and are in neutrality, and 5~15min, separation are centrifuged under 2500~3500rmp rotating speeds Going out water phase, 4~8g DES solvents are added in into remaining oil phase, vortex mixing stirs 0.5~2h after under 20~70 DEG C of water-baths, Period 0.5~2min of every 10~20min vortex oscillations takes out, and 10~20min is centrifuged under 3000~4000rmp rotating speeds, collects DES layers.
  7. 7. according to the method described in claim 6, it is characterized in that：Step 2) and 3) in, it is described collect DES layer process distinguish Be repeated at least once more, and respectively set DES layers obtain the first DES extracting solutions and the 2nd DES extracting solutions.
  8. 8. according to the method described in claim 6, it is characterized in that：Step 2) and 3) in, respectively to the first DES extracting solutions and the 3~7mL n-hexanes are added in two DES extracting solutions, is uniformly mixed after centrifuging 3~10min under 2500~3500rmp rotating speeds, divides Normal hexane layer is separated out to remove remaining grease.
  9. 9. according to the method described in claim 1, it is characterized in that：In step 4), the sequestered phenolic compound DES is carried After taking liquid and mating type phenolic compound extracting solution respectively with 1~2BV/h flow velocity loadings, then it is molten with deionized water, methanol successively Liquid elutes, and keeps flow velocity in 2~3BV/h, collection meoh eluate, by the meoh eluate concentrated by rotary evaporation being collected into dry, use The methanol-water weight that volume ratio is 50% is molten, crosses 0.22 μm of organic filter membrane.
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CN108640966A (en) * 2018-07-23 2018-10-12 广西壮族自治区农业科学院农产品加工研究所 A kind of eutectic solvent and extraction process for extracting Tea Saponin in leached tea oil slag
CN108913195A (en) * 2018-07-12 2018-11-30 太原理工大学 A kind of method of phenolic compound during direct conversion solution of Selective Separation coal is oily
CN109706113A (en) * 2019-02-28 2019-05-03 华侨大学 A method of soybean mitochondria is extracted using eutectic solvent

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