CN102690208A - Method for extracting hydroxyl sanshool from zanthoxylum oil - Google Patents
Method for extracting hydroxyl sanshool from zanthoxylum oil Download PDFInfo
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Abstract
本发明公开的一种从花椒油中提取羟基山椒素的方法，其工艺步骤是：1）将花椒油用甲醇依次进行室温浸提、离心分离、层析除多酚、冷冻、旋转蒸发得浓缩物；2）先将浓缩物用甲醇溶解后，用硅胶柱进行梯度洗脱并等份收集洗脱液，再将薄层层析法初步确定的目标物所在的洗脱液进行浓缩干燥；3）将所得浓缩物用制备型液相色谱进行细分纯化，并分别收集两个最大吸收峰的洗脱液进行旋转蒸发即得羟基山椒素Ⅰ和Ⅱ。本发明提供的方法不仅填补了现有技术的空白，为该领域提供了一种可作为花椒麻味定量的标准品，且前处理简单、操作方便，分离提纯的分离物纯度高。The invention discloses a method for extracting hydroxy sanshool from Zanthoxylum bungeanum oil. The process steps are: 1) The Zanthoxylum bungeanum oil is subjected to room temperature leaching with methanol, centrifugation, chromatography to remove polyphenols, freezing, and rotary evaporation to obtain concentration. 2) Dissolve the concentrate in methanol first, then use a silica gel column for gradient elution and collect the eluate in equal portions, and then concentrate and dry the eluate where the target object initially determined by thin-layer chromatography is located; 3 ) Subdivided and purified the obtained concentrate by preparative liquid chromatography, and collected the eluents of the two maximum absorption peaks respectively and carried out rotary evaporation to obtain hydroxy sanshool I and II. The method provided by the invention not only fills in the gaps in the prior art, but also provides a standard product that can be used as a quantitative standard for the numbing taste of prickly ash, and has simple pretreatment, convenient operation, and high purity of the separated and purified isolate.
Description
Technical field
The invention belongs to the technical field of from xanthoxylum, extracting bioactive ingredients, be specifically related to a kind of method of from Fructus Zanthoxyli oil, extracting the hydroxyl sanshool.
Background technology
Fructus Zanthoxyli oil is meant directly and soaks Chinese prickly ash or adopt organic solvent lixiviate, supercritical CO with edible oil
2The xanthoxylum oleoresin that methods such as extraction make mixes the made flavor oil with spicy hot flavor with appropriate amount of edible oil.In links such as storage and sale, cause loss of active ingredients and microbial contamination because the processing of Fructus Zanthoxyli oil has significantly reduced Chinese prickly ash, solved pepper grain and Chinese prickly ash pulvis and given culinary art and the edible inconvenience that brings, therefore favored by the human consumer.But Fructus Zanthoxyli oil market is also lack of standardization at present, and Product labelling is only indicated raw material mostly, and does not appear on the label as the fiber crops flavor substances content of Fructus Zanthoxyli oil important indicator.How isolating high purity Chinese prickly ash fiber crops flavor material, to be the focus of domestic research as Chinese prickly ash and products thereof fiber crops flavor quantitative standards article always, also is the focus that each Chinese prickly ash manufacturing enterprise pays close attention to.
At present; Report about from Chinese prickly ash, extracting fiber crops flavor material has: 00112633.4 discloses a kind of method through preparing Chinese Prickly ash flavouring by high-temp and high-pressure boiling in water; But the numb monosodium glutamate that extracts through this method is except containing sanshool, sanshool, green pepper alcohol; Also contain vegeto-alkalis such as green pepper alkali, Yin Yujian, composition is complicated, at all can not be as product fiber crops flavor quantitative standards article.03132341.3 disclosed is a kind of technology of utilizing supercritical fluid technology to separate the Chinese prickly ash spicy component; This process equipment manipulation technical requirements is higher; And prepared spicy component is preliminary extract; Can only be used for suitability for industrialized production, as the raw material of food and medicine, unsuitable as fiber crops flavor quantitative standards article.
The inventor finds that in early-stage Study sanshool is the staple of Chinese prickly ash fiber crops flavor material, has strong impulse property, is one type of chain unsaturated fatty acids acid amides, is soluble in organic solvents such as chloroform, methyl alcohol, ethanol, anhydrous diethyl ether at normal temperatures.Sanshool can be divided into α-sanshool, β-sanshool, γ-sanshool, hydroxyl-α-sanshool, hydroxy-beta-sanshool, hydroxyl-γ-sanshool, hydroxyl-ε-sanshool etc. again, and the relative content of hydroxyl-α wherein-sanshool and hydroxyl-γ-sanshool is obviously greater than other sanshool.These sanshools all have the uv-absorbing phenomenon at 200 nm to 300 nm, and maximum absorption band occurred at 270 nm places.Therefore, the inventor thinks that from Fructus Zanthoxyli oil separation of pure dissolves these two kinds of sanshools and can be used as Chinese prickly ash fiber crops flavor quantitative standards article.But regrettably existing also do not have bibliographical information separation of pure from Fructus Zanthoxyli oil to dissolve the method for these two kinds of sanshools.
Summary of the invention
The objective of the invention is to defective, a kind of method of from Fructus Zanthoxyli oil, extracting the hydroxyl sanshool is provided to prior art.
The method of from Fructus Zanthoxyli oil, extracting the hydroxyl sanshool provided by the invention is characterized in that its process step and condition are following:
(1) in the Fructus Zanthoxyli oil of 20～40 ml, 1:20 ~ 30 add methyl alcohol by volume, first room temperature mechanical vibration 20 ~ 30min; Sonic oscillation 5 ~ 10min under ultrasonic frequency 35 ~ 55Hz then, again with vat liquor under the speed of 2500 ~ 3000r/min, centrifugal 10 ~ 15 min; Get supernatant, cross Al
2O
3Chromatography column is removed polyphenol, and freezing 12～18 hours of-20 ℃ of following lucifuges are rotated evaporation with extracting solution under≤40 ℃, promptly get enriched material;
(2) be 50 ~ 80% dissolve with methanol with enriched material with 3 ~ 4ml concentration of volume percent earlier; And press on sample and silicagel column mass ratio 1:40 ~ 50 appearance, using concentration of volume percent then is 70 ~ 80% methyl alcohol, carries out the constant gradient wash-out with elution flow rate 0.5 ~ 1.5ml/min; And by every part of collecting amount is that 80 ~ 120 ml equal portions are collected elutriant; And the combination thin layer chromatography, the elutriant that the target compound of tentatively confirming is belonged to is rotated evaporation under≤40 ℃, promptly get enriched material;
(3) the gained enriched material is diluted to 5 ~ 10 mg/ml earlier with hplc grade methanol, is further purified with preparative liquid chromatography then, and the elutriant of collecting two maximum absorption bands respectively is rotated evaporation under≤40 ℃, promptly get hydroxyl sanshool I and II.
Thin layer chromatography described in the above method is: with the methyl alcohol of volume ratio 1:9 and chloroform mixed solution as developping agent; Above-mentioned elutriant is carried out point sample on thin layer plate; Launch, and place under the uv lamp of 254 nm, second component that obvious purple dot occurs is confirmed as target compound place component.
The chromatographic column model of the preparative liquid chromatography described in the above method is ODS-4251K, and specification is 10 * 250 mm, 5 μ m, and preparation condition is: the use concentration of volume percent is 70 ~ 80% methanol aqueous solution wash-out earlier, 20 ~ 40 min; Using concentration of volume percent again is 80 ~ 100% methanol aqueous solution wash-out, and collects the elutriant of two maximum absorption bands respectively; Flow velocity is 1.5 ~ 2 ml/min, 25 ℃ of column temperatures, ultraviolet detection wavelength 270 nm; Sample size 100 ~ 200 μ l.
Gained hydroxyl sanshool I of the present invention is mainly hydroxyl-ε-sanshool, hydroxyl-α-sanshool and hydroxy-beta-sanshool, is isomers between them; Gained hydroxyl sanshool II is mainly hydroxyl-γ-sanshool and hydroxyl-γ-different sanshool, also is isomers between them, and its structural formula is distinguished as follows:
The present invention has following advantage:
1, since disclosed by the invention be the method for from Fructus Zanthoxyli oil, extracting the hydroxyl sanshool, thereby filled up the blank of prior art on the one hand, also a kind of Chinese prickly ash fiber crops quantitative standards article of distinguishing the flavor of that can be used as are provided on the other hand for this field.
2, because the extraction raw material that the present invention adopts is a Fructus Zanthoxyli oil, thereby pre-treatment is simple, easy to operate.
3, because the present invention adopts methyl alcohol to extract the hydroxyl sanshool in the Fructus Zanthoxyli oil, it separates the isolate purity height of purifying.Through detecting, separating obtained hydroxyl sanshool I relative content can reach 94.92%, and hydroxyl sanshool II relative content can reach 84.98%.
Description of drawings
Accompanying drawing is the high-efficient liquid phase chromatogram of Fructus Zanthoxyli oil methanol extract of the present invention.The analysis condition of this color atlas: MN Nucleodur 1100-5 C18 post (4 * 125 mm, 5 μ m); Flow velocity, 0.5 ml/min; Column temperature, 25 ℃; Detect wavelength, 270 nm; Gradient eluent: 35 ~ 75% (v/v) acetonitrile solution gradient elution, 40 min; 75 ~ 100% (v/v) acetonitrile solution gradient elution, 10 min; 100% (v/v) acetonitrile wash-out, 5 min; Sample size: 20 μ l.Visible from figure: 1) relative content of hydroxyl-α-sanshool and hydroxyl-γ-sanshool is obviously greater than other sanshool; 2) sanshool all has the uv-absorbing phenomenon at 200 nm to 300 nm, but maximum absorption band occurs at 270 nm places.
Embodiment
Through embodiment the present invention is carried out concrete description below, be necessary to be pointed out that at this present embodiment only is used for the present invention is further specified, can not be interpreted as restriction protection domain of the present invention.The person skilled in the art in this field can make some nonessential improvement and adjustment to the present invention according to the content of the invention described above.
Embodiment 1
20 ml Fructus Zanthoxyli oil are added in the methyl alcohol of 1:20 by volume, first room temperature mechanical 20 min that vibrate are sonic oscillation 5 min under the 35Hz in ultrasonic frequency then, again with vat liquor under the speed of 2500r/min, centrifugal 10min; Get supernatant, cross Al
2O
3Chromatography column is removed behind the polyphenol in freezing 12 hours of-20 ℃ of following lucifuges; Extracting solution is rotated evaporation under≤40 ℃, gets enriched material 0.95g.
First with the dissolve with methanol of enriched material with 3 ml 70% (v/v), and press sample and the last appearance of silicagel column mass ratio 1:40, using 70% (v/v) meoh eluate then is that 0.5ml/min carries out the constant gradient wash-out with the elution flow rate; And by every part of collecting amount is that 120 ml equal portions are collected elutriant; And the combination thin layer chromatography, under the uv lamp with 254 nm, second component that obvious purple dot occurs is confirmed as target compound place component; With its concentrate drying, get enriched material 82.3 mg.
Enriched material is diluted to 5 mg/ml earlier with hplc grade methanol, is further purified by following condition with preparative liquid chromatography then:
The chromatographic column model is ODS-4251K, and specification is 10 * 250 mm, 5 μ m, and preparation condition is: elder generation is with methanol aqueous solution wash-out 40 min of 70% (v/v); Use the methanol aqueous solution wash-out of 80% (v/v) again, when wash-out 28 min and 41 min, collect the elutriant of two maximum absorption bands respectively; Flow velocity is 1.5ml/min, 25 ℃ of column temperatures, ultraviolet detection wavelength 270 nm; Sample size 100 μ l.
Two parts of elutriant rotary evaporations are got hydroxyl sanshool I 6 mg, hydroxyl sanshool II 5 mg.
Embodiment 2
30 ml Fructus Zanthoxyli oil are added in the methyl alcohol of 1:25 by volume, first room temperature mechanical vibration 25min is sonic oscillation 8 min under the 45Hz in ultrasonic frequency then, again with vat liquor under the speed of 2800r/min, centrifugal 12min; Get supernatant, cross Al
2O
3Chromatography column is removed behind the polyphenol in freezing 15 hours of-20 ℃ of following lucifuges; Extracting solution is rotated evaporation under≤40 ℃, gets enriched material 1.275g.
First with the dissolve with methanol of enriched material with 3.5 ml 75% (v/v), and press sample and the last appearance of silicagel column mass ratio 1:45, using 75% (v/v) meoh eluate then is that 1ml/min carries out the constant gradient wash-out with the elution flow rate; And collect elutriant for the 100ml equal portions by every part of collecting amount; And the combination thin layer chromatography, under the uv lamp with 254nm, second component that obvious purple dot occurs is confirmed as target compound place component; With its concentrate drying, get enriched material 102mg.
Enriched material is diluted to 8mg/ml earlier with hplc grade methanol, is further purified by following condition with preparative liquid chromatography then:
The chromatographic column model is ODS-4251K, and specification is 10 * 250 mm, 5 μ m, and preparation condition is: elder generation is with methanol aqueous solution wash-out 30 min of 75% (v/v); Use the methanol aqueous solution wash-out of 90% (v/v) again, when wash-out 26 min and 40min, collect the elutriant of two maximum absorption bands respectively; Flow velocity is 1.8ml/min, 25 ℃ of column temperatures, ultraviolet detection wavelength 270 nm; Sample size 150 μ l.
Two parts of elutriant rotary evaporations are got hydroxyl sanshool I 7mg, hydroxyl sanshool II 6mg.
Embodiment 3
40 ml Fructus Zanthoxyli oil are added in the methyl alcohol of 1:30 by volume, first room temperature mechanical vibration 30min is sonic oscillation 10min under the 55Hz in ultrasonic frequency then, again with vat liquor under the speed of 3000r/min, centrifugal 15min; Get supernatant, cross Al
2O
3Chromatography column is removed behind the polyphenol in freezing 18 hours of-20 ℃ of following lucifuges; Extracting solution is rotated evaporation under≤40 ℃, gets enriched material 1.901g.
First with the dissolve with methanol of enriched material with 4 ml80% (v/v), and press sample and the last appearance of silicagel column mass ratio 1:50, using 80% (v/v) meoh eluate then is that 1.5ml/min carries out the constant gradient wash-out with the elution flow rate; And collect elutriant for the 80ml equal portions by every part of collecting amount; And the combination thin layer chromatography, under the uv lamp with 254nm, second component that obvious purple dot occurs is confirmed as target compound place component; With its concentrate drying, get enriched material 120mg.
Enriched material is diluted to 10mg/ml earlier with hplc grade methanol, is further purified by following condition with preparative liquid chromatography then:
The chromatographic column model is ODS-4251K, and specification is 10 * 250 mm, 5 μ m, and preparation condition is: elder generation is with the methanol aqueous solution wash-out 20min of 80% (v/v); Use the methanol aqueous solution wash-out of 100% (v/v) again, when wash-out 25min and 38min, collect the elutriant of two maximum absorption bands respectively; Flow velocity is 2ml/min, 25 ℃ of column temperatures, ultraviolet detection wavelength 270nm; Sample size 200 μ l.
Two parts of elutriant rotary evaporations are got hydroxyl sanshool I 8mg, hydroxyl sanshool II 7mg.
For hydroxyl sanshool I and the hydroxyl sanshool II of investigating extraction, the present invention detects with liquid chromatographmass spectrometer embodiment 1 is extract obtained, and testing conditions is following:
1) chromatographic condition: MN Nucleodur 1100-5 C18 post (4 * 125 mm, 5 μ m); Flow velocity, 0.5 ml/min; Column temperature, 25 ℃; Detect wavelength, 270 nm; Gradient eluent: 35 ~ 75% (v/v) acetonitrile solution gradient elution, 40 min; 75 ~ 100% (v/v) acetonitrile solution gradient elution, 10 min; 100% (v/v) acetonitrile wash-out, 5 min; Sample size: 20 μ l.
2) mass spectrum condition: electric spray ion source (ESI), positive ion electrospray leaves; Spray voltage 4500V; End voltage 350 V; Dry gas flow velocity 10 L/min, 350 ℃ of drying temperatures; Atomization gas pressure 2. 07 * 10
2KPa; Sweep limit: m/ z 150 ~ 400.
Detected result is: hydroxyl sanshool I molecular weight is 263; Relative content is 94.92%, wherein hydroxyl-ε-sanshool (relative content is 4.06%), hydroxyl-α-sanshool (relative content is 82.82%) and hydroxy-beta-sanshool (relative content is 8.04%); Hydroxyl sanshool II molecular weight is 289, and relative content is 84.98%, wherein hydroxyl-γ-sanshool (relative content is 81.55%) and hydroxyl-γ-different sanshool (relative content is 3.43%).
Claims (3)
1. method of from Fructus Zanthoxyli oil, extracting the hydroxyl sanshool is characterized in that its process step and condition are following:
(1) in the Fructus Zanthoxyli oil of 20～40 ml, 1:20 ~ 30 add methyl alcohol by volume, first room temperature mechanical vibration 20 ~ 30min; Sonic oscillation 5 ~ 10min under ultrasonic frequency 35 ~ 55Hz then, again with vat liquor under the speed of 2500 ~ 3000r/min, centrifugal 10 ~ 15 min; Get supernatant, cross Al
2O
3Chromatography column is removed polyphenol, and freezing 12～18 hours of-20 ℃ of following lucifuges are rotated evaporation with extracting solution under≤40 ℃, promptly get enriched material;
(2) be 50 ~ 80% dissolve with methanol with enriched material with 3 ~ 4ml concentration of volume percent earlier; And press on sample and silicagel column mass ratio 1:40 ~ 50 appearance, using concentration of volume percent then is 70 ~ 80% methyl alcohol, carries out the constant gradient wash-out with elution flow rate 0.5 ~ 1.5ml/min; And by every part of collecting amount is that 80 ~ 120 ml equal portions are collected elutriant; And the combination thin layer chromatography, the elutriant that the target compound of tentatively confirming is belonged to is rotated evaporation under≤40 ℃, promptly get enriched material;
(3) the gained enriched material is diluted to 5 ~ 10 mg/ml earlier with hplc grade methanol, is further purified with preparative liquid chromatography then, and the elutriant of collecting two maximum absorption bands respectively is rotated evaporation and promptly gets hydroxyl sanshool I and II under≤40 ℃.
2. the method for from Fructus Zanthoxyli oil, extracting the hydroxyl sanshool according to claim 1; It is characterized in that described thin layer chromatography is: with the methyl alcohol of volume ratio 1:9 and chloroform mixed solution as developping agent; Above-mentioned elutriant is carried out point sample on thin layer plate; Launch, and place under the uv lamp of 254 nm, second component that obvious purple dot occurs is confirmed as target compound place component.
3. the method for from Fructus Zanthoxyli oil, extracting the hydroxyl sanshool according to claim 1 and 2; The model that it is characterized in that the chromatographic column of described preparative liquid chromatography is ODS-4251K; Specification is 10 * 250 mm; 5 μ m, preparation condition is: the use concentration of volume percent is 70 ~ 80% methanol aqueous solution wash-out earlier, 20 ~ 40 min; Using concentration of volume percent again is 80 ~ 100% methanol aqueous solution wash-out, and collects the elutriant of two maximum absorption bands respectively; Flow velocity is 1.5 ~ 2 ml/min, 25 ℃ of column temperatures, ultraviolet detection wavelength 270 nm; Sample size: 100 ~ 200 μ l.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106866455A (en) * | 2015-12-11 | 2017-06-20 | 西南大学 | A kind of preparation method of high-purity numb-taste components |
| CN106977416A (en) * | 2017-04-25 | 2017-07-25 | 四川大学 | A kind of method of quick preparation high-purity hydroxyl α sanshools |
| CN107033017A (en) * | 2017-04-25 | 2017-08-11 | 四川大学 | A kind of method of quick preparation high-purity hydroxyl γ sanshools |
| CN107966514A (en) * | 2017-11-28 | 2018-04-27 | 晨光生物科技集团股份有限公司 | The detection method of numb-taste component of zanthoxylum content in a kind of pepper extract |
| CN109444284A (en) * | 2018-12-14 | 2019-03-08 | 成都中医药大学 | Method that is a kind of while measuring flavor substance in Chinese prickly ash and/or rattan green pepper and its oil product |
| CN109674012A (en) * | 2018-12-20 | 2019-04-26 | 四川大学 | Method that is a kind of while extracting fragrance matter and spicy components in Chinese prickly ash |
| CN109856346A (en) * | 2019-01-25 | 2019-06-07 | 峨眉山万佛绿色食品有限公司 | A kind of Tengjiao oil method of quality control |
| CN112881561A (en) * | 2021-01-22 | 2021-06-01 | 四川省食品药品检验检测院(四川省药品质量研究所、四川省医疗器械检测中心) | System and method for determining sanshool in rattan pepper |
| CN113040230A (en) * | 2019-12-27 | 2021-06-29 | 丰益(上海)生物技术研发中心有限公司 | Zanthoxylum oil capable of rapidly entering hemp |
| CN113816870A (en) * | 2021-08-25 | 2021-12-21 | 沈阳药科大学 | A method for rapidly extracting different sanshool monomers |
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| CN106866455A (en) * | 2015-12-11 | 2017-06-20 | 西南大学 | A kind of preparation method of high-purity numb-taste components |
| CN106866455B (en) * | 2015-12-11 | 2019-11-19 | 西南大学 | A kind of preparation method of high-purity Zanthoxylum bungeanum flavor substance |
| CN106977416A (en) * | 2017-04-25 | 2017-07-25 | 四川大学 | A kind of method of quick preparation high-purity hydroxyl α sanshools |
| CN107033017A (en) * | 2017-04-25 | 2017-08-11 | 四川大学 | A kind of method of quick preparation high-purity hydroxyl γ sanshools |
| CN107966514A (en) * | 2017-11-28 | 2018-04-27 | 晨光生物科技集团股份有限公司 | The detection method of numb-taste component of zanthoxylum content in a kind of pepper extract |
| CN107966514B (en) * | 2017-11-28 | 2020-12-18 | 晨光生物科技集团股份有限公司 | Method for detecting content of sanshoamides in pepper extract |
| CN109444284B (en) * | 2018-12-14 | 2021-09-24 | 成都中医药大学 | A method for simultaneous determination of flavor substances in Chinese prickly ash and/or vine pepper and oil products thereof |
| CN109444284A (en) * | 2018-12-14 | 2019-03-08 | 成都中医药大学 | Method that is a kind of while measuring flavor substance in Chinese prickly ash and/or rattan green pepper and its oil product |
| CN109674012A (en) * | 2018-12-20 | 2019-04-26 | 四川大学 | Method that is a kind of while extracting fragrance matter and spicy components in Chinese prickly ash |
| CN109856346A (en) * | 2019-01-25 | 2019-06-07 | 峨眉山万佛绿色食品有限公司 | A kind of Tengjiao oil method of quality control |
| CN113040230A (en) * | 2019-12-27 | 2021-06-29 | 丰益(上海)生物技术研发中心有限公司 | Zanthoxylum oil capable of rapidly entering hemp |
| CN112881561A (en) * | 2021-01-22 | 2021-06-01 | 四川省食品药品检验检测院(四川省药品质量研究所、四川省医疗器械检测中心) | System and method for determining sanshool in rattan pepper |
| CN113816870A (en) * | 2021-08-25 | 2021-12-21 | 沈阳药科大学 | A method for rapidly extracting different sanshool monomers |
| CN113816870B (en) * | 2021-08-25 | 2023-10-31 | 沈阳药科大学 | A method for rapid extraction of different sanshool monomers |
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