KR20180124422A - Methods for Extracting Aromatic Compounds of Aromatic plants - Google Patents

Abstract

The present invention relates to a method for extracting aromatic components of aromatic plants, and specifically, the method comprises the following steps: freeze-drying the aromatic plants (S1); pulverizing the freeze-dried aromatic plants in the presence of a refrigerant (S2); and placing the pulverized aromatic plants in a container, placing an adsorbent having a fixed bed on which the aromatic components can be adsorbed in an upper space in the container and blocking external air inflow into the container to adsorb the aromatic components (S3). The present invention provides an extraction method having excellent degree of extraction of unstable aromatic plant fragrance components, and thus it is possible to provide the method for extracting the aromatic components capable of providing analysis results with high efficiency and accuracy of analysis of the aromatic components using the same.

Description

Methods for Extracting Aromatic Compounds of Aromatic Plants [

The present invention relates to a method for extracting aromatic plant fragrance components.

A variety of oriental plants with a unique aroma are not only unique fragrances but also have many functional materials, making them highly useful as spices and other functional food materials. In the West, not only are the fragrance ingredients obtained from plant materials processed into spices and used for cooking, but also various functionalities such as digestion promotion, antiseptic, antibacterial, .

The aroma components present in these oriental plants have been studied in various ways such as distillation method, solvent extraction method, adsorption method and the like for the analysis and use. Stir bar sorptive extraction (SBSE) was first introduced in 1999, 10 years after the advent of solid-phase microextraction (SPME). The stirring rod adsorption extraction method and the solid phase microextraction method are basically based on the principle of performing the sample pretreatment without a solvent basically and separating and extracting the analyte between the adsorption layer and the liquid sample layer. However, it has been reported that the adsorption efficiency of the stirring rod adsorption extraction method is 250 times or more as compared with the solid phase microextraction method (Non-Patent Document 1), and has a relatively large amount of extraction phase and consequently has a lower detection limit. In addition, the stir bar adsorption extraction method has been applied to liquid samples such as whiskey, juice, wine and the like since it is expected to be more advantageous in analyzing the components of liquid food samples compared to the solid phase microextraction method.

However, fragrance components are present in a minor amount compared to other major components, and are not only large in terms of threshold values among the compounds, but also are very diverse and complex in their properties, large in reactivity and unstable, not. In addition, the directional plant including the above-mentioned fragrance component has a completely different state of the sample for performing the extraction method according to the part such as leaf, fruit, stem, root, etc., and is complicated and has a mixed state of aliphatic, It is not easy to find an optimal extraction method.

Furthermore, since the above methods often use a sample of an aqueous solution as an object to be measured, it is often the case that the extract of the oriental plant, rather than the fruit or leaf itself, is analyzed. In the case of liquefaction, if the fruit or leaf of the plant is directly used, the amount of extraction and adsorption of the component of the plant is not sufficient. If the plant is liquefied, the volatile component A change or a loss of a perfume component occurs due to this influence. Therefore, an optimal extraction method for various fragrance components is desired.

1. Korean Patent Publication No. 10-217-0000280 2. Korean Patent No. 10-0643177

1. Frank David, Bart Tienpont, Pat Sandra, Stir-bar sorptive extraction of trace organic compounds from aqueous matrices, LCGC North America, 21: 21-27 (2003)

The present invention relates to a method for extracting aromatic plant fragrance components, and provides an extraction method having an excellent extraction efficiency of fragrance components in the analysis of aroma components of oriental plants, and provides analysis results with high efficiency and accuracy in analyzing fragrance components And a method for extracting fragrance components.

In order to achieve the above-mentioned object, the present invention provides a method for producing a plant, (S2) pulverizing the freeze-dried oriental plant in the presence of a refrigerant; And (S3) placing the pulverized aroma plant in a container, placing an adsorbent coated with a stationary phase on which a perfume component can be adsorbed in an upper space in the container, blocking external air from entering the container, and adsorbing the perfume component And a method for extracting aromatic plant fragrance components.

In the aroma component extraction method of the present invention, the refrigerant in step (S2) may be any one or more selected from nitrogen, ammonia, chlorofluorocarbon, hydrogen fluoride, hydrogen fluoride, hydrogen fluoride, .

In the aromatic plant aroma component extraction method of the present invention, 0 to 8 캜 is maintained from the end of the step (S1) to the start of the step (S2).

In the aromatic plant aroma component extraction method of the present invention, the step (S2) is characterized by pulverizing at 0 to 200 캜.

In the aromatic plant aroma component extraction method of the present invention, the step (S3) is characterized in that it adsorbs at 30 to 50 ° C.

In the aroma component extraction method of the present invention, the step (S3) is characterized by adsorption for 0.5 to 2.5 hours.

In the aroma component extraction method of oriental plant of the present invention, the oriental plant is characterized in that it is at least one selected from the group consisting of Lamiaceae and Plants, Acanthopods and Plants, Asteraceae Plants, Poppy Plants, Rosaceae Plants and Omiza Plants.

In the aromatic plant fragrance component extraction method of the present invention, the orienting plant may be at least one selected from leaves, fruits, stem, roots and shells.

In the aroma component extraction method of the present invention, the fixed phase to which the perfume component can be adsorbed is characterized by being polydimethylsiloxane, ethylene glycol-silicone, or a mixture thereof.

In the aromatic plant fragrance component extraction method of the present invention, the aromatic plant fragrance component extraction method of the present invention is a method of extracting aroma components from oriental plants by extracting ylangene, cymene, terpinene, limonene, myrcene, The compounds of formula (I) are preferably selected from the group consisting of sabinene, pinene, camphene, ethyl acetate, thujene, methylcarvacrol, himachalene, cerene, phellandrene, terpinolene, terpineol, germacrene, elemene, ocimene, terpinene, farnesene, hexenol ( wherein at least one of the fragrance components selected from the group consisting of hexenol, hexanol, pentenol, hexenal and hexanal is extracted.

The aroma component extraction method of oriental plant according to the present invention can improve the extraction degree of aroma component of the aroma component of the aroma component of oriental plants and provide the analysis result with high efficiency and accuracy of aroma component analysis.

Fig. 1 is a photograph showing a container containing a sample (aroma plant, example omija) according to the present invention and a perfume component adsorbent mounted on the upper part of the container in an upper space.
2 is a photograph of a directional plant prepared for Example 1. Fig. (a): As the Schizosaccharomyces cerevisiae, the freeze-dried powder samples on the left, raw whey samples on the center, and raw samples on the right. (b): As the leaves of omija, the freeze-dried powder samples on the left side, the raw whey samples on the center, and the raw samples on the right side.
FIG. 3 is a result of analysis of fragrance components according to pretreatment of the Omiza fruit sample according to Example 1. FIG. Fig. 3a: raw sample, Fig. 3b: raw pulverization sample, Fig. 3c: freeze-dried pulverized sample.
FIG. 4 is a result of analysis of fragrance components according to the pretreatment of the sample of Omija leaf according to Example 1. FIG. Fig. 4a: raw sample, Fig. 4b: raw pulverization sample, Fig. 4c: freeze-dried pulverized sample.
FIG. 5 is a graph showing the result of analysis of main fragrance components according to the pretreatment method of the sample performed according to Example 1. FIG. Fig. 5a: Omiza fruit, Fig. 5b: Omiza leaf.
6 is a graph showing the result of analyzing major fragrance components according to the adsorbed fixed bed phase of the perfume component according to Example 2. Fig. Figure 6a: Schizophyllum, Figure 6b: Schizandra chinensis.
7 is a graph showing the results of analysis of major fragrance components according to the amount of samples performed according to Example 3. FIG. Fig. 7a: Omiza fruit, Fig. 7b: Omiza leaf.
8 is a graph showing the results of analysis of main fragrance components according to adsorption temperature according to Example 4. Fig. Fig. 8a: Omiza fruit, Fig. 8b: Omiza leaf.
9 is a graph showing the result of analyzing the main fragrance component according to the adsorption time according to Example 5. Fig. Fig. 9a: Omiza fruit, Fig. 9b: Omiza leaf.
FIG. 10 is a graph showing results of analysis of perfume components performed under the optimum conditions according to Example 6. FIG. Fig. 10a: Omiza fruit, Fig. 10b: Omiza leaf.

According to an aspect of the present invention, (S2) pulverizing the freeze-dried oriental plant in the presence of a refrigerant; And (S3) placing the pulverized aroma plant in a container, placing an adsorbent coated with a stationary phase on which a perfume component can be adsorbed in an upper space in the container, blocking external air from entering the container, and adsorbing the perfume component And a method for extracting fragrance components of a directional plant. BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail with reference to the drawings.

The present invention relates to a method for producing a plant, (S2) pulverizing the freeze-dried oriental plant in the presence of a refrigerant; And (S3) placing the pulverized aroma plant in a container, placing an adsorbent coated with a stationary phase on which a perfume component can be adsorbed in an upper space in the container, blocking external air from entering the container, and adsorbing the perfume component And a method for extracting aromatic plant fragrance components.

Accordingly, the present invention includes the first step (Sl) of lyophilizing the oriental plant.

In the present invention, " orienting plant " means a plant containing a perfume component, and various parts such as leaves, fruits, roots, and stems thereof are used as spices, tea, and the like. For example, it may be at least one selected from the group consisting of Lamiaceae, Acanthopelops, Asteraceae, Papaveraceae, Rosaceae and Omiza, and may be any one or more selected from the group consisting of Cinnamon, Nutmeg, Clove, Turmeric, Allspice, Vanilla, Lavender, Rosemary, Basil, Oregano, , Mint, pepper, ginger, mustard, horseradish and the like. The above-mentioned Lamiaceae plants include, for example, catnip, hwakwi, lupine, perilla, lavender, rosemary, peppermint, thyme, motherwort, etc. Herbaceous plants include herbs, coriander, oilseed, angelica, carrot, , Wormwood, lettuce, vetch, plant, wormwood, chrysanthemum, thistle, thistle, fossil, sunflower, etc. And Omija is a plant. For example, the aroma component of the present invention can be analyzed.

The oriental plants used in the present invention can be any of the fragrance components, for example, one or more selected from leaves, fruits, stem, roots and shells.

In the present invention, "freeze-drying" or freeze-drying refers to a process in which water is removed from the product after it has been frozen and placed under vacuum, thereby directly changing the ice from the solid to the steam without passing through the liquid phase. The sub-process consists of three separate process-freezing, primary drying (sublimation), and secondary drying (desorption), each of which is a unique and interdependent process.

The temperature can be maintained at a suitable temperature from the end of the step (S1) of the present invention to the start of the following step (S2), for example, from 0 to 8 캜, more preferably from 2 to 4 Lt; 0 > C. Thus, the loss or change of the fragrance component of the present invention to be extracted can be minimized.

The present invention then comprises a step (S2) of grinding said lyophilized oriental plant in the presence of a refrigerant.

In the present invention, the term " refrigerant " means all substances which cause a cooling action in a broad sense and include, for example, nitrogen, ammonia, chlorofluorocarbon, hydrogen fluoride, hydrogen fluoride, hydrogen fluoride, It can be any one or more. Preferably, dry ice can be used.

In the present invention, " pulverization " can be carried out by using a method known to a person skilled in the art by applying a mechanical force such as cutting, compression, impact, shearing or the like to a solid to reduce its particle size without changing the chemical composition. For example, the leaves and fruits of plants are pulverized when they are put into a grinder or a blender.

It was confirmed that when the freeze-dried and pulverized samples according to the present invention were used, the perfume extraction efficiency was higher than that of direct use of raw leaves such as oriental plant leaves or fruit or raw pulverization.

Since the step (S2) of the present invention is performed in the presence of a refrigerant, it is maintained at a low temperature and the loss or change of the fragrance component due to frictional heat generated by pulverization or the like can be minimized. For example, the pulverization process may be performed at 0 to -100 deg. C, preferably 0 to -80 deg. C, and more preferably -20 to -60 deg.

Next, the present invention is characterized in that the pulverized aroma plant is placed in a container, an adsorbent having a stationary phase on which a perfume component is adsorbed is placed in the upper space of the container, (S3).

In order to carry out the step (S3), the pulverized aromatic plant sample prepared in the step (S2) may be put in a suitable container. The container may be sealed by sealing the container itself It is preferable to have a structure that can be used. For example, Twister ™ headspace vials can be used. In addition, the amount of the plant sample in the direction of the container contained in the container is not particularly limited as long as it is capable of adsorbing and extracting the perfume component, and is 0.01 to 5 g, preferably 0.1 to 1.0 g, more preferably 0.1 to 0.5 g, g can be used in containers.

An adsorbent having a fixed bed coated with a perfume component is placed in an upper space of a directional plant specimen contained in the appropriate container. It is desirable to have an upper space of suitable height so that the aroma component can reach without direct contact with the oriental plant sample.

In the method of extracting aroma components according to the present invention, it is possible to have a suitable insert portion for placing an adsorbent in an upper space of a container for containing the sample, and it may be placed in the insert portion. For example, in the Twister ™ headspace vial inlet, (See Fig. 1).

In the present invention, the stationary phase to which the perfume component can be adsorbed is a substance capable of adsorbing a volatile perfume component, for example, polydimethylsiloxane, ethylene glycol-silicone, or a mixture thereof. More preferred is ethylene glycol-silicone. The stationary phase may be coated on a suitable object and used in the present invention, for example an ethylene glycol-silicone coated stir bar.

In the perfume extracting method of the present invention, the adsorbent may exist in a state in which the adsorbent is not stirred or stirred in the inserting portion, that is, in a fixed state.

In the present invention, the step (S3) is not particularly limited as long as it is a temperature and a time suitable for adsorbing and extracting a perfume component. For example, the step (S3) is carried out at 30 to 50 DEG C for 0.5 to 2.5 hours, preferably at 40 to 50 DEG C for 2 to 2.5 The fragrance component can be adsorbed and extracted for a period of time. If the extraction temperature is lower than the extraction temperature or the extraction time is short, the adsorption extraction efficiency of the fragrance component is insufficient. On the other hand, if the extraction temperature is higher than the extraction temperature or the extraction time is longer,

The aroma component extraction method of the present invention is a method for extracting aroma components from omija, such as ylangene, cymene, terpinene, limonene, myrcene, sabinene, pinene, but are not limited to, camphene, ethyl acetate, thujene, methylcarvacrol, himachalene, cerene, phellandrene, terpinolene, But are not limited to, terpineol, germacrene, elemene, ocimene, terpinene, farnesene, hexenol, hexanol, pentenol, one or more fragrance components selected from the group consisting of pentenol, hexenal and hexanal may be extracted.

In addition, the kinds and contents of the fragrance components vary depending on the directional plant to be extracted and the extraction site of the plant. For example, in the case of Schizandra chinensis, the alpha-ylangene, p-cymene, gamma-terpinene, limonene, alpha-terpinene, Beta -myrcene, sabinene, alpha-pinene, beta-pinene, camphene, ethyl acetate, alpha-toluene, but are not limited to, α-thujene, methylcarvacrol, β-himachalene, 3-cerene, α-phellandrene, terpinolene, 4-terpineol, and the like. In the case of the omija leaves, germacrene D, beta-elemene, beta-ocimene, alpha-terpinene, gamma-terpinene, terpinene, alpha-phellandrene, sabinene, beta-pinene, alpha-pinene, limonene, p-cymene, Alpha-farnesene, 3-hexen-1-ol, 1-hexanol, 1-hexanol, Penten-3-ol, 2-hexenal, hexanal, and the like.

In addition, the present invention can further analyze the components by desorbing and analyzing the fragrance components adsorbed and extracted by the above-described fragrance component extraction method. For example, the analysis step may be a step of performing heat desorption, followed by cold condensation and performing gas chromatography and mass spectrometry.

The analysis step may be performed by a suitable technician or a suitable machine or system known to be capable of performing the process. For example, the desorption step may be thermo-desorbed by a thermal desorption unit (TDU), followed by chro- matography and mass spectrometry by injection into an analytical machine while cooling and condensing with a Cooled Injection System (CIS) .

This step may be carried out at a temperature and for a time sufficient to minimize the loss and variation of the aroma component. For example, thermal desorption can be carried out at 180 to 220 ° C for 0.5 to 7 minutes, preferably 200 to 210 ° C for 4 to 6 minutes. For example, the cooling condensation can be carried out at a temperature of 10 to -100 ° C, preferably 0 to -50 ° C, and for this, the refrigerants nitrogen, ammonia, carbon tetrafluoride, hydrogen fluoride, hydrogen fluoride At least one selected from carbon monoxide, carbon tetrachloride, carbon tetrachloride, hydrogen fluoride, olefin, and carbon dioxide. For example, liquid nitrogen can be used.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, these are only for the purpose of illustrating the present invention in more detail, but the scope of the present invention is not limited thereto.

[Example 1] Sample preparation setting optimum for aroma component extraction

1-1. Preparation of sample

Omiza leaves and fruits were supplied from Hyojongwon Co., Ltd., and each of them was pretreated with the above raw material, raw material (ground powder) and freeze-dried powder (freeze-dried powder) ). The pulverization of the samples was carried out by adding dry ice, followed by pulverization and homogenization using a blender. The prepared state of the Omija samples is shown in Fig.

On the other hand, the lyophilized samples were subjected to lyophilization, and the lyophilized samples of the same weight for the raw samples were used for the experiment. In the case of Schizandra chinensis, the amounts of the fruit and leaf samples recovered after freeze drying were 18.07 ± 0.17% and 17.16 ± 0.94%, respectively.

1-2. Adsorption and extraction of fragrance components

5 g of the raw Schizandra chinensis extract, 5 g of the raw wheat bran of Schizandra chinensis L., 5 g of the raw wheat bran of Schizophyllum lanceolata, 0.93 g of the lyophilized Schizandra chinensis extract, 2.5 g of the Schizandra chinensis extract, 5 g of the Schizandra chinensis extract and 0.43 g of the Schizo- After mounting Twister ™ headspace vial inserts (inserts) into the vials, the inserts were filled with an ethylene glycol-silicone glycol (EG) -silicone stirrer bar, 10 mm, 32 ㎕ phase volume), sealed with a dedicated crimp cap, and then extracted at 50 ° C for 2 hours and 30 minutes.

1-3. Analysis of aroma components

In order to analyze the components of the fragrance component of the adsorbent extracted from the above, HP 6890 gas chromatograph equipped with a thermal desorption unit (Cooled Injection System: TDU-CIS) and HP 5973 mass selective detector (Agilent Technologies, Palo Alto, Calif.) Were used. Extracted materials were analyzed on a DB-WAX column (60 m × 0.25 mm id, 0.25 μm film thickness, Agilent Technologies).

The thermal desorption unit (TDU) was set to the splitless mode and the temperature programming was ramped up to 205 ° C at 50 ° C / 60 ° C / min and held for 5 minutes. The desorption rate of the thermal desorption unit was set to 50 ml / min, the cooling rate of the cooling injection system was maintained at 20: 1, the temperature was lowered to -20 ° C using liquid nitrogen, Lt; RTI ID = 0.0 > 220 C < / RTI > and held for 2 minutes.

The flow rate of the helium gas was set at 1.4 ml / min, and the gas chromatography oven programming was maintained at 50 ° C for 1 minute and then increased to 210 ° C at 3 ° C / min. The transfer line, MSD source and quadrupole temperature of the mass spectrometer were maintained at 250 ° C, 230 ° C and 150 ° C respectively, and the mass spectra were recorded in the range of 35-400 m / z in all modes.

Each data was analyzed by one-way ANOVA followed by Duncan's multiple range test for significance in the range of P <0.05. For statistical analysis, SigmaPlot v12.5 (Systat Software, Chicago, IL, USA) was used.

1-4. Experiment result

3, 4, 5, and Table 1 and Table 2 show the results of analyzing the fragrance components of pretreatment of the Omija samples. The above results are obtained by repeating a total of 3 repetitions.

FIG. 3 shows experimental results of each pretreatment of Omiza fruit samples. In all pretreatment samples, fragrance components alpha-ylangene, p-cymene, gamma-terpinene, limonene it is confirmed that the main component is limonene, alpha-terpinene, beta -myrcene, sabinene, beta-pinene, and camphene I could.

FIG. 4 shows experimental results of each pretreatment of Omija leaf samples. In all pretreatment samples, fragrance components germacrene D, β-elemene, β-ocimene, gamma -Terpinene, alpha-phellandrene, sabinene, beta-pinene, and alpha-pinene are the main common components. I could confirm.

Table 1 and FIG. 5 show the results of specific preparation of the main fragrance components of Schizandra chinensis and leaves in each of the pretreatments (FIG. 5A: Schizandra chinensis, FIG. 5B: Schizandra chinensis).

Major fragrance ingredients Retention time
(minute) Raw sample
(a) Raw pulverization sample
(b) A freeze-dried pulverized sample
(c) Average ^* Standard Deviation Average Standard Deviation Average Standard Deviation Omiza fruit camphene 10.87 20 4 601 360 3,073 762 β-pinene 12.25 473 77 433 132 7,042 814 sabinene 12.58 1,618 187 201 91 2,774 378 β-myrcene 14.15 4,147 238 1,912 463 17,828 582 alpha-terpinene 14.78 215 16 279 117 6,903 673 limonene 15.49 618 56 373 151 6,061 441 gamma-terpinene 17.49 483 31 1,108 501 25,589 1,989 p-Cymene 18.33 275 27 606 249 10,667 713 α-ylangene 27.45 35 30 1,948 1,011 31,415 2,193 Omiza leaf alpha-pinene 9.64 90 12 283 42 362 10 β-pinene 12.13 49 24 287 19 523 8 sabinene 12.56 320 128 856 126 1,914 36 alpha-phellandrene 14.14 60 16 57 12 113 4 gamma-terpinene 17.17 60 6 104 14 164 10 (E) -β-ocimene 17.33 1,025 152 1,466 228 2,127 115 (-) -? - elemene 31.22 45 2 475 103 632 94 germacrene D 35.91 60 8 496 164 893 131

^{*) Unit: peak area / 1000}

Based on the peak area of the fragrant components extracted through the above three pretreatment methods, the extraction efficiencies of the common fragrance components of each of the pretreatment of the freeze-dried crushed Schizo- Was about 40 to 90% higher than that in the case of extraction.

In summary, it was found that extracting aroma components from freeze-dried pulverized material rather than raw or raw pulverized material was effective in extracting aroma components from Omiza.

[ Example  2] It is the best Adsorbate  Stationary phase setting

2-1. Experimental Method

Polydimethylsiloxane (PDMS) and ethylene glycol (EG) -silicone (EG) were compared and analyzed to select the optimal adsorbent stationary phase for aroma components.

0.9 g of the lyophilized and ground Omiza leaf sample prepared in the same manner as in Example 1, and 0.4 g of the lyophilized powdered Omiza fruit sample were each placed in a Twister ™ headspace vial, and the Twister ™ headspace insert was mounted on the vial , An ethylene glycol-silicone stir bar and polydimethylsiloxane stir bar (10 mm, 32 μl phase volume) were placed in the insert, sealed with a special crimp cap, and then extracted at 50 ° C. for 2 hours and 30 minutes. The extracted stirrer bar was immersed in a twister desorption liner, injected into a thermal desorption unit (TDU), thermally desorbed, and analyzed by gas chromatography. The specific conditions for the performance are the same as those in the first to third embodiments.

2-2. Experiment result

The results of extracting fragrance components of the adsorbent immobilized phase of the Omija sample as described above are shown in Table 2 and FIG. The above results are obtained by repeating a total of 3 repetitions.

Fragrance component Retention time
(minute) Polydimethylsiloxane
Stir bar Ethylene glycone -silicon
Stir bar Average* Standard Deviation Average Standard Deviation Omiza fruit sabinene 12.58 2,774 378 2,337 399 α-ylangene 27.45 31,415 2,193 27,417 3,364 alpha-thujene 9.71 - - 1,010 117 Acetic acid 25.43 - - 170 14 Omiza leaf 1-penten-3-ol 13.70 31 3 84 8 1-hexanol 21.44 48 5 80 6 (Z) -3-hexen-1-ol 22.80 304 32 538 55 (-) -? - elemene 31.25 455 70 602 29 (E, E) -α-farnesene 37.07 20 3 36 9

^{*) Unit: peak area / 1000}

In summary, in the case of Schizandra chinensis, major fragrance components such as alpha-ylangene and sabinene were extracted with polydimethylsiloxane and ethylene glycol-silicone stir bar, but acetic acid and alpha Components such as α-thujene were detected only when extracted with ethylene glycol-silicone stir bar, but not with polydimethylsiloxane stir bar.

For the Schizophyllum lanceolata, alpha-farnesene, beta-elemene, 3-hexenol, 1-hexanol, 1-pentene- (1-penten-3-ol) were all detected by using polydimethylsiloxane and ethylene glycol-silicone stirrer. However, the extraction efficiency with ethylene glycol-silicone stirrer was higher than that of polydimethylsiloxane Extraction efficiency was about 20-60% higher than peak area.

In summary, it can be seen that ethylglycon-silicone (EG (ethylene glycol) -silicone) stirring bars are more preferable in extracting the fragrance components of the freeze-dried powdered omija samples.

[ Example  3] It is most suitable for extraction of fragrance ingredient Amount of sample  Set

3-1. Experimental Method

In order to select the optimum amount of sample for analysis of fragrance components, freeze-dried powder samples of each of the fruits of Omiza berries and leaves were tested at various weights and compared and analyzed

0.3 g and 0.6 g of 0.9 g of the freeze-dried powder of the lyophilized powder obtained in the same manner as in Example 1, 0.1 g, 0.2 g, 0.4 g and 0.6 g of each of the lyophilized and ground Schizandra chinensis samples were placed in a Twister ™ headspace The Twister ™ headspace insert was then placed in the vial, the ethylene glycol-silicone stir bar was placed in the insert, sealed with a dedicated crimp cap, and then incubated at 50 ° C. for 2 hours and 30 minutes And extracted. The extracted stirring rod was injected into a thermal desorption unit in a twister desorption liner, packed, thermally desorbed and analyzed by gas chromatography. The specific conditions for the performance are the same as those in the first to third embodiments.

3-2. Experiment result

The results of analysis of fragrance components of each of the stirrer bars of the Omiza samples as described above are shown in Table 3 (Omija fruit), Table 4 (Omija leaf), and Fig. The above results are obtained by repeating a total of 3 repetitions.

Omiza fruit
Fragrance component Retention time
(minute) 0.3 g of freeze-dried pulverized sample 0.6 g of freeze-dried pulverized sample 0.9 g of a freeze-dried pulverized sample Average* Standard Deviation Average Standard Deviation Average Standard Deviation β-pinene 12.21 4,571 388 5,088 875 4,131 371 sabinene 12.57 2,337 399 2,264 298 2,792 616 p-Cymene 18.29 7,962 464 8,163 939 8,108 373 methylcarvacrol 31.33 4,418 143 , 3952 502 3,385 450

^{*) Unit: peak area / 1000}

Omiza leaf
Fragrance component Retention time (minutes) 0.1 g of the freeze-dried pulverized sample Freeze-dried powder 0.2 g 0.4g of the freeze-dried powder sample 0.6 g of freeze-dried pulverized sample Average* Standard Deviation Average Standard Deviation Average Standard Deviation Average Standard Deviation β-pinene 12.17 289 6 450 43 684 31 698 73 Sabinene 12.57 1,015 50 1,545 139 2,223 85 2,246 213 β-myrcene 13.93 602 40 927 41 1,269 82 1,405 98 (E) -2-Hexenal 16.11 761 95 1,000 107 1,137 163 1,228 165 gamma-terpinene 17.17 158 16 208 12 261 22 260 30 (E) -β-ocimene 17.31 878 81 1,193 40 1,482 112 1,594 119 (Z) -3-hexen-1-ol 22.79 379 30 476 24 538 55 571 20 (-) -? - elemene 31.25 611 98 602 86 602 29 549 23 germacrene D 35.94 558 111 604 134 537 71 592 25

^{*) Unit: peak area / 1000}

As a result of comparing the main fragrance components of methylcarvacrol, p-cymene, sabinene, β-pinene, 0.3 g, 0.6 g, and 0.9 g, respectively. There was no significant difference (p <0.05) for each sample weight.

In the case of the omija leaves, germacrene D, β-elemene, 3-hexen-1-ol, β-ocimene, , Gamma-terpinene, 2-hexenal, beta-myrcene, sabinene, and beta-pinene. There was no significant difference (p <0.05) between 0.4g and 0.6g sample weight, although there was significant difference (p <0.05) by 0.1g, 0.2g and 0.4g sample weight. 0.4g is considered suitable for efficiency.

[ Example  4] Optimum extraction temperature for aroma component extraction

4-1. Experimental Method

In order to determine the optimal extraction temperature in the analysis of aroma components, freeze-dried powder samples of each of the fruits of Omiza berries and leaves were extracted and analyzed at various temperatures

0.3 g of each of the freeze-dried powdered omisa fruit samples prepared in the same manner as in Example 1, and 0.4 g of each of the freeze-dried and ground omiga leaf samples were placed in a Twister headspace vial, and the Twister headspace insert was mounted on the vial, An ethylene glycol-silicone stir bar was inserted into the insert, sealed with a dedicated crimp cap, and then extracted at 30 ° C, 40 ° C and 50 ° C for 2 hours and 30 minutes, respectively. The extracted stirring rod was immersed in a twister desorption liner, injected into a thermal desorption unit, thermally desorbed, and analyzed by gas chromatography. The specific conditions for the performance are the same as those in the first to third embodiments.

4-2. Experiment result

The results of analyzing the fragrance components of the Omiza samples by the extraction temperature are shown in Table 5 and FIG. The above results are obtained by repeating a total of 3 repetitions.

Fragrance component Retention time (minutes) 30 ℃ extraction 40 ℃ extraction 50 ℃ extraction Average* Standard Deviation Average Standard Deviation Average Standard Deviation Omiza fruit β-myrcene 14.03 3,291 363 5,468 89 6,157 367 alpha-terpinene 14.72 2,143 252 3,358 46 4,191 327 limonene 15.44 1,873 206 3,263 36 3,699 264 gamma-terpinene 17.42 8,280 1,056 14,809 320 17,533 1,322 p-Cymene 18.27 2,545 261 4,613 181 5,272 413 α-ylangene 27.50 8,647 2,008 18,315 1,014 27,417 3,364 Omiza leaf alpha-pinene 9.63 259 17 387 13 537 22 hexanal 11.28 117 13 224 18 313 34 β-pinene 12.17 446 47 706 37 952 48 sabinene 12.61 1,484 133 2,292 70 3,043 115 β-myrcene 13.96 604 58 1,040 32 1,455 75 (E) -2-hexenal 16.12 348 45 766 78 1,046 157 (E) -β-ocimene 17.34 557 44 1,072 73 1,556 99 (Z) -3-hexen-1-ol 22.80 88 9 257 25 463 46

^{*) Unit: peak area / 1000}

As a result, the extraction rate of aroma components at 50 ℃ was the highest in Omiza fruit. The extraction rate of the fragrant components extracted at 40 ℃ from the pulverized fruit after freeze - drying was about 1.8 times higher than the extraction rate at 30 ℃ and the extraction rate of the fragrant components extracted at 40 ℃ was about 1.25 times higher than the extraction rate at 50 ℃.

In the case of Schizandra chinensis, the extraction rate of the fragrance component was the highest at 50 ℃. The extraction rate of the fragrant components extracted from the crushed leaves after lyophilization was about 1.8 times higher than the extraction rate at 30 ° C and the extraction rate of the fragrance components extracted at 50 ° C was about 1.4 times higher than the extraction rate at 40 ° C.

These results suggest that the optimum temperature for extraction of fragrant components from freeze-dried crushed omija samples is 50 ℃ for both fruit and leaves.

[ Example  5] Optimum extraction time for aroma component extraction

5-1. Experimental Method

In order to determine the optimal extraction time for the fragrance component analysis, freeze - dried powder samples of each of Schizandra chinensis and leaves were extracted and analyzed at various times.

0.3 g of each of the freeze-dried powdered omisa fruit samples prepared in the same manner as in Example 1, and 0.4 g of each of the freeze-dried and ground omiga leaf samples were placed in a Twister ™ headspace vial, and Twister ™ headspace inserts , And an ethylene glycol-silicone stir bar was placed in the insert. The insert was sealed with a dedicated crimp cap and then extracted at 50 ° C for 0.5 hour, 1 hour, 1.5 hours, 2 hours, and 2.5 hours, respectively. The extracted stirring rod was immersed in a twister desorption liner, then injected into a thermal desorption unit to be thermally desorbed, and analyzed by gas chromatography. The specific conditions for the performance are the same as those in the first to third embodiments.

5-2. Experiment result

The fragrance component analysis results of the above-mentioned Omiza samples at the extraction time are shown in Table 6 and FIG. The above results are obtained by repeating a total of 3 repetitions.

Fragrance component Retention time (minutes) Extraction 0.5 hours 1 hour extraction 1.5 hours of extraction 2 hours of extraction 2.5 hours of extraction Average* Standard Deviation Average Standard Deviation Average Standard Deviation Average Standard Deviation Average Standard Deviation Omiza fruit β-pinene 12.18 1,517 257 2,087 394 2,266 309 2,316 307 2,557 183 sabinene 12.57 1,207 241 1,670 454 1759 183 1669 240 2485 203 β-myrcene 14.03 2,377 313 3,794 755 4,702 526 4,855 439 6,157 367 alpha-terpinene 14.72 1,413 208 2,366 394 2,985 181 3,159 224 4,191 327 limonene 15.44 1,266 163 2,106 370 2,653 186 2,776 205 3,699 264 gamma-terpinene 17.42 5,930 841 9,555 1,225 12,324 132 12,974 1,187 17,533 1,322 p-cymene 18.27 1,864 171 3,127 646 4,013 500 4,168 334 5,272 413 α-ylangene 27.5 7,007 3,182 11,881 2,623 16,335 3,796 17,457 6,605 27,417 3,364 Omiza leaf alpha-pinene 9.64 149 18 235 4 318 9 429 27 428 79 hexanal 11.28 167 27 233 31 258 32 323 23 305 49 β-pinene 12.15 206 33 340 11 481 16 647 80 666 167 sabinene 12.61 801 125 1,263 38 1,759 71 2,282 217 2,328 572 β-myrcene 13.98 669 90 1,090 58 1,484 97 1,856 187 1,874 328 limonene 15.36 66 10 108 6 154 13 196 21 205 46 (E) -2-hexenal 16.13 508 119 748 103 907 160 1,071 118 1,025 171 gamma-terpinene 17.18 57 8 96 7 140 14 183 28 212 58 (E) -β-ocimene 17.37 759 117 1,266 91 1,807 179 2,205 273 2,200 327 (Z) -3-hexen-1-ol 22.8 143 24 232 19 332 34 405 45 437 58 (-) -? - elemene 31.26 153 32 262 23 458 53 532 77 597 71 germacrene D 35.96 178 52 331 40 552 155 744 167 765 106

^{*) Unit: peak area / 1000}

As a result, the extraction rate of aroma components was the highest in 2.5 hours (p <0.05). The extraction rate of fragrant components for 1 hour from the pulverized fruit after freeze drying was about 1.5 times higher than the extraction rate for 0.5 hour and the extraction rate for 2.5 hours and 2 hours was 1.3 times higher than that for 1 hour. The extraction rate for 2.5 hours was about 1.3 times higher than the extraction rate for 1.5 hours and 2 hours.

In addition, the extraction rate of aroma components for 2 hours was the highest (p <0.05). The extraction rate of fragrant components gradually increased from 0.5 to 2 hours after the lyophilization, but the extraction rate for 2.5 hours was not significantly different from the extraction rate for 2 hours (p <0.05).

As a result, the optimal extraction time for the extraction of aroma components from the freeze-dried crushed omija samples is 150 minutes for fruit and 120 minutes for leaves.

[ Example  6] Quantitative and Qualitative Analysis of Extracted Flavor Components

6-1. Experimental Method

The fragrance components were extracted from Schizandra chinensis and leaves with optimum conditions set by the above experiment and quantitatively and qualitatively analyzed.

In order to select the internal reference material for quantitative analysis, phenethyl alcohol, methyl octanoate, tetradecane, ethyl nonanoate, 1-hexanol (1- hexanoic acid, hexanol, hexyl butanoate, hexyl 2-methyl butanoate, hexyl isobutyrate, and hexyl hexanoate. As a result, the retention times of the fragrant component peaks from the fruit and leaf were overlapped or the influence of the overall peak area was observed with respect to the internal standard materials except for phenethyl alcohol, And it was more suitable for the extraction method used in this experiment, and phenethyl alcohol was selected as the internal standard material.

0.3 g of each of the freeze-dried powdered omisa fruit samples prepared in the same manner as in Example 1, and 0.4 g of each of the freeze-dried and ground omiga leaf samples were placed in a Twister ™ headspace vial, and Twister ™ headspace inserts The insert was sealed with an ethylene glycol-silicone stirrer and sealed with a special crimp cap, and then extracted at 50 ° C for 2.5 hours. Phenetyl alcohol was added to the sample and measured by a thermal desorption unit-gas chromatography-mass spectrometer (TDU-GC-MS), and the fragrance components were quantitatively measured by the peak area ratio of phenol alcohol and phenetyl alcohol. Repeated.

The fractions of Kovats gas chromatographic retention index and actual fragrance components were compared with each other for mass spectrometry fragmentation and Wiley 6th edition MS spectra library.

As a result of the experiment, as shown in Fig. 10 and Table 7, 35 kinds of aroma components were found in the omiza fruit and 40 kinds of fragrance components in the omiza leaf were qualitatively determined.

Peak No. Retention time (minutes) RI Fragrance component Peak area ratio ^a Omiza fruit Omiza leaf Average Standard Deviation Average Standard Deviation One 7.03 884 ethyl acetate 0.7 0.0 - - 2 7.46 914 2-methylbutanal - - 0.5 0.1 3 7.51 916 3-methylbutanal - - 0.5 0.1 4 8.63 977 pentanal - - 0.6 0.1 5 9.63 1022 alpha-pinene 39.8 1.2 39.7 6.8 6 9.70 1024 alpha-thujene 20.1 1.1 9.4 1.3 7 10.82 1066 camphene 29.3 1.0 2.6 0.4 8 11.26 1082 hexanal - - 4.9 0.7 9 12.16 1112 β-pinene 47.0 1.3 25.3 4.1 10 12.53 1123 sabinene 18.3 1.4 89.8 14.3 11 13.04 1137 1,4-dimethylbenzene (= p-xylene) 0.9 0.0 - - 12 13.51 1151 3-carene 14.7 0.7 3.1 0.5 13 13.70 1156 1-penten-3-ol 3.0 0.7 14 14.07 1167 β-myrcene 110.5 5.1 517.0 79.0 15 14.13 1169 alpha-phellandrene 25.5 10.1 - - 16 14.69 1185 alpha-terpinene 64.7 3.2 4.6 0.7 17 15.41 1205 limonene 56.7 3.0 15.2 2.3 18 15.76 1214 β-phellandrene 14.8 0.8 4.6 0.7 19 15.84 1216 1,8-cineole 7.9 0.3 3.1 0.5 20 16.10 1223 (E) -2-hexenal - - 44.5 6.4 21 16.64 1237 (Z) -β-ocimene 7.5 0.5 49.7 7.0 22 17.17 1250 gamma-terpinene 276.6 15.3 21.0 3.4 23 17.39 1256 (E) -β-ocimene - - 243.8 36.4 24 18.23 1277 p-cymene 94.5 5.0 7.8 1.1 25 18.73 1290 terpinolene 24.0 1.3 3.8 0.6 26 19.94 1320 (Z) -3-hexenyl acetate - - 0.3 0.1 27 20.80 1341 6-methyl-5-heptene-
2-one 0.5 0.0 1.6 0.2 28 21.43 1356 1-hexanol - - 0.5 0.1 29 22.77 1389 (Z) -3-hexen-1-ol - - 11.2 1.5 30 22.97 1394 2-nonanone 3.4 0.2 - - 31 24.97 1443 1-isopropenyl-4-methylbenzene 1.2 0.1 - - 32 25.58 1457 aceticacid 0.8 0.1 - - 33 26.39 1477 δ-elemene - - 2.2 0.2 34 27.28 1499 α-ylangene 273.5 30.9 - - 35 27.38 1502 alpha-Copaene 3.8 0.3 5.2 0.7 36 28.27 1523 α-bourbonene - - 0.5 0.1 37 28.49 1529 β-bourbonene - - 6.0 0.9 38 28.54 1530 benzaldehyde 4.9 0.3 - - 39 29.22 1547 β-cubebene 0.8 0.1 1.6 0.4 40 31.26 1597 (-) -? - elemene - - 45.9 4.1 41 31.29 1598 4-isopropyl-2-methoxy-1-methylbenzene 49.3 5.0 - - 42 31.46 1602 2-undecanone 2.9 0.4 - - 43 31.66 1608 β-caryophyllene - - 4.5 0.7 44 31.77 1610 4-terpineol 10.4 0.9 - - 45 34.45 1682 α-humulene - - 4.1 1.1 46 35.08 1699 γ-curcumene 2.0 0.3 - - 47 35.11 1700 alpha-muurolene - - 1.4 0.3 48 35.92 1722 germacrene D - - 86.9 20.6 49 36.45 1736 (-) -? - bisabolene 9.4 1.9 - - 50 36.49 1737 alpha-selinene - - 1.5 0.1 51 37.07 1751 β-himachalene * 85.7 14.5 - - 52 37.07 1753 (E, E) -α-farnesene - - 3.6 1.0 53 37.64 1769 (+) - [delta] -cadinene 3.6 0.5 2.2 0.7 54 37.78 1773 γ-cadinene - - 2.8 0.4 55 38.02 1779 β-sesquiphellandrene 0.8 0.1 - - 56 39.35 1817 2-tridecanone 2.5 0.5 - -

^{a (peak area of each compound / peak area of the internal standard) x 100,}

The major fragrant components of Schizandra chinensis are beta-myrcene, alpha-terpinene, limonene, gamma-terpinene, p- cymene, alpha-ylangene, beta-himachalene and the like were detected for the ovid leaves and sabinene, beta-myrcene, Various major fragrance components such as beta-ocimene ((E) -β-ocimene), (-) - β-elemene and germacrene D were detected .

While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, Should be interpreted as belonging to the scope.

Claims (10)

Lyophilizing the plant in the (S1) direction;
(S2) pulverizing the freeze-dried oriental plant in the presence of a refrigerant; And
(S3) placing the pulverized aroma plant in a container, placing an adsorbent having a fixed bed on which a perfume component can be adsorbed in the upper space of the container, blocking the inflow of external air into the container, and adsorbing the perfume component A method for extracting aroma components from a plant containing directional fractions.
The method according to claim 1,
Wherein the refrigerant in step (S2) is at least one selected from the group consisting of nitrogen, ammonia, chlorofluorocarbon, hydrogen fluoride, hydrogen fluoride, hydrogen fluorinated olefin, and carbon dioxide.
The method according to claim 1,
Wherein the temperature is maintained at 0 to 8 占 폚 from the end of the step (S1) to the start of the step (S2).
The method according to claim 1,
Wherein the step (S2) is pulverized at 0 to -100 ° C.
The method according to claim 1,
Wherein the aromatic component is adsorbed at 30 to 50 DEG C in step (S3).
The method according to claim 1,
Wherein the aromatic component is adsorbed for 0.5 to 2.5 hours in the step (S3).
The method according to claim 1,
Wherein the oriental plant is at least one selected from the group consisting of Lamiaceae plants, Acanthopods and Plants, Asteraceae plants, Poppy plants, Rosaceae plants and Omiza plants.
The method according to claim 1,
Wherein the orienting plant is at least one selected from leaves, fruits, stem, roots and shells.
The method according to claim 1,
Wherein the fixed phase to which the perfume component is adsorbed is polydimethylsiloxane, ethylene glycol-silicone, or a mixture thereof.
The method according to claim 1,
The fragrance component may be selected from the group consisting of ylangene, cymene, terpinene, limonene, myrcene, sabinene, pinene, camphene, ethyl acetate but are not limited to, ethyl acetate, thujene, methylcarvacrol, himachalene, cerene, phellandrene, terpinolene, terpineol, But are not limited to, germacrene, elemene, ocimene, terpinene, farnesene, hexenol, hexanol, pentenol, wherein the extract is at least one selected from the group consisting of hexenal and hexanal.

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