KR20170106660A - Extraction method of paclitaxel using ultrasound-assisted extraction - Google Patents
Extraction method of paclitaxel using ultrasound-assisted extraction Download PDFInfo
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- KR20170106660A KR20170106660A KR1020160026542A KR20160026542A KR20170106660A KR 20170106660 A KR20170106660 A KR 20170106660A KR 1020160026542 A KR1020160026542 A KR 1020160026542A KR 20160026542 A KR20160026542 A KR 20160026542A KR 20170106660 A KR20170106660 A KR 20170106660A
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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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
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0261—Solvent extraction of solids comprising vibrating mechanisms, e.g. mechanical, acoustical
- B01D11/0265—Applying ultrasound
Abstract
Description
The present invention relates to a method for extracting paclitaxel from a biomass, and more particularly, to a method for extracting paclitaxel using an ultrasonic wave, And at the same time, we tried to drastically improve the process (device) complexity (danger), which was the limitation of microwave extraction process, and the high cost problem due to high energy consumption.
Paclitaxel is a diterpenoid-based anticancer substance found in the epidermis of the yew tree and is currently the most widely used anticancer drug. (US FDA) for the treatment of ovarian cancer, breast cancer, head and neck cancer, caposi's sarcoma, and non-small cell lung cancer. Demand for paclitaxel is expected to continue to grow due to continued indications (Alzheimer's treatment, rheumatoid arthritis) and treatment methods.
The main production methods of paclitaxel include direct extraction from a yew tree, a method of obtaining a precusor, and a method of culturing plant cells by inducing callus from a plant. Among these methods, the plant cell culture method is very advantageous for mass production because it can stably produce paclitaxel of constant quality in the bioreactor without being influenced by external factors (climate, environment) as compared with other methods. Most of the paclitaxel produced by plant cell cultures is contained in biomass (plant cells), and the production of paclitaxel consists of several stages of extraction and purification processes. From an economic point of view, it is very important to first recover the paclitaxel contained in the biomass in high yield.
Korean J. Biotechnol . According to Bioeng ., 15, 346-351 (2000), the recovery process is generally carried out by conventional solvent extraction and various kinds of organic solvents (methylene chloride, methyl-t-butyl ether, ethanol, isopropyl Alcohol, chloroform, diethyl ether, acetone, methanol, etc.). The results showed that methanol was the most effective for biomass extraction with the smallest recovery rate. Most of the paclitaxel in the biomass was recovered (~ 99%) by optimizing the main process parameters (methanol concentration, biomass / methanol mixture ratio, extraction time, extraction frequency, etc.).
However, conventional solvent extraction requires more than four extraction steps to recover most of the paclitaxel from the biomass, which has a drawback in that it takes a lot of organic solvent and time to recover the high paclitaxel. In 2008, most of the paclitaxel was recovered (~ 99%) by extraction with microwave only once from biomass. Microwave has shortened the number of extraction times. However, additional equipment and costs are incurred for high recovery, and the process is complicated (dangerous), troublesome, and consumes a lot of energy, which limits the application to industrial mass production processes. As a result, it is still necessary to develop a high-efficiency biomass extraction process that has both convenient facilities and feasibility as well as equipment savings and energy saving, while minimizing (simplifying) the equipment required to shorten the extraction frequency It is true.
SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide an extraction method that dramatically increases the recovery rate of paclitaxel, which is an anticancer substance, from biomass.
In order to solve the above-mentioned problems, the present invention provides a method for producing a taxane, comprising: a) obtaining a plant-derived biomass from Taxus genus comprising paclitaxel; b) mixing the biomass with an organic solvent; And c) treating the mixture of step b) with ultrasound to extract the paclitaxel.
According to a preferred embodiment of the present invention, the biomass of step a) may be a biomass derived from a plant belonging to the Taxus family, a cell thereof or a cell culture thereof.
According to another preferred embodiment of the present invention, the organic solvent in step b) may include at least one member selected from the group consisting of C 1 -C 4 alcohols and water.
According to another preferred embodiment of the present invention, the organic solvent and the biomass of step b) may be mixed at a ratio of 1: 1 to 1: 6 (w / v).
According to another preferred embodiment of the present invention, the ultrasound extraction in the step c) may be performed once.
According to another preferred embodiment of the present invention, the ultrasonic extraction may be performed at an ultrasonic power of 380 W to 530 W for 10 minutes to 16 minutes.
According to another preferred embodiment of the present invention, the recovery rate of paclitaxel after the ultrasonic extraction may be 99%.
The present invention provides a method of extracting paclitaxel using ultrasonic waves, which solves the problems of using a large amount of organic solvents and long extraction time which were limitations of the conventional solvent extraction process, and at the same time, ), It is possible to drastically improve the high cost problem caused by a lot of energy consumption. Therefore, the paclitaxel extraction method of the present invention is considered to be very useful for the commercial mass production of paclitaxel, an anticancer substance, from a plant-derived biomass of Taxus genus.
1 is a schematic diagram of an ultrasonic extraction process from a biomass.
FIG. 2 is a graphical representation of the effect of extraction times on the yield of paclitaxel using conventional solvent extraction. The biomass / MeOH ratio is 1: 1 (w / v) and the stirring rate is ~ 500 rpm.
Figure 3 shows a 3D response surface and contour plot for optimization of the extraction process from biomass with biomass / MeOH ratio of 1: 1 (w / v), stirring speed To 500 rpm.
Fig. 4 is an SEM image of a biomass sample dried by solvent extraction using different methods. Fig. (B) is a conventional solvent extraction method (one-time extraction); (C) shows an SEM image after extraction (once extraction) using ultrasonic waves.
Hereinafter, the present invention will be described in more detail.
As described above, conventional solvent extraction requires extraction of more than 4 times for recovery of most paclitaxel from biomass, which is disadvantageous in that it requires a lot of organic solvent and time for recovery of high paclitaxel. Extraction using microwave shortened the number of times of extraction, but the additional equipment and costs were incurred in order to obtain a high recovery rate, and the process was complicated (dangerous), cumbersome and consumes a lot of energy and was limited to industrial mass production process. Therefore, it is still necessary to develop a high-efficiency biomass extraction process that simplifies the equipment required to shorten the extraction frequency, simplifies equipment, saves energy, and is convenient and feasible. to be.
Accordingly, the present invention provides a method for producing a taxane, comprising: a) obtaining a taxoma genus plant-derived biomass comprising paclitaxel; b) mixing the biomass with an organic solvent; And c) ultrasonically treating the mixture of step b) with ultrasound to thereby solve the above-described problem by providing a paclitaxel extraction method. The paclitaxel extraction method of the present invention solves the problems of using a large amount of organic solvent and long extraction time, which were limitations of the conventional solvent extraction process, and at the same time, the complexity of the process (apparatus) It is possible to drastically improve the high cost problem.
First, a) step to obtain biomass derived from Taxus genus plant containing paclitaxel is described.
The biomass of step a) may include one or more selected from the group consisting of a plant belonging to the Taxus family, a cell thereof, a cell debris thereof, and a cell culture solution thereof.
In addition, the plant in the taxus is Taxus brevifolia , Taxus canadensis , Taxus cuspidata , Taxus baccata , Taxus globosa), Florida TAXUS I (Taxus floridana), TAXUS May Reach Ana (Taxus wallichiana , Taxus media , or Taxus chinensis ), and the like, but the present invention is not limited thereto.
The step of obtaining the biomass is not particularly limited as long as it is a method for obtaining biomass from a plant cell culture liquid.
Next, step b) of mixing the biomass with an organic solvent will be described.
Specifically, the organic solvent is not particularly limited as long as it is ordinarily used for extracting an active ingredient from a plant. Preferably, the organic solvent may include at least one selected from the group consisting of C 1 -C 4 alcohols and water.
Specific examples of the organic solvent include a mixture of one or more selected from the group consisting of methanol, ethanol, propanol, and methylene chloride. An organic solvent capable of recovering paclitaxel as much as possible from the biomass is preferably methanol Can be used.
The biomass of step b) and the organic solvent may be mixed at a ratio of 1: 1 to 1: 6 (w / v), but the present invention is not limited thereto. Generally, The ratio is not particularly limited. In an embodiment of the present invention, the biomass and the organic solvent are uniformly mixed at a ratio of 1: 1 (w / v) for optimum extraction efficiency.
Next, a description will be given of the step c) in which the mixture of step b) is subjected to ultrasonic wave processing for ultrasonic extraction.
The ultrasonic extraction in the step c) may be performed once.
In the ultrasonic extraction, the ultrasonic frequency can be selected without limitation as long as it is suitable for extracting the active ingredient from the plant. In one embodiment of the present invention, a 40 kHz ultrasonic cleaner was used.
The ultrasonic extraction may be performed at an ultrasonic power of 380 W to 530 W for 10 minutes to 16 minutes. When ultrasonic extraction is performed under such conditions, the yield of paclitaxel may be 99%.
If ultrasonic extraction is performed at an ultrasound power of less than 380 W, up to 97% of paclitaxel can be recovered. However, since the recovery rate of paclitaxel does not change even after 10 minutes of operation, all paclitaxel can not be recovered. When ultrasonic extraction is performed in excess of ultrasonic power, there is a difficulty in operation due to decomposition of paclitaxel due to excessive heat generation (deterioration of extraction efficiency).
In one embodiment of the present invention, the ultrasonic power (80, 180, 250, 380 and 530 W) and the operating time (1, 2, 4, 6, 8, 10, 12, 15 and 30 minutes) The mixture was subjected to one-time ultrasonic extraction under stirring (~500 rpm). The recovery rate of paclitaxel was calculated by the following equation (1), and the recovery rate of paclitaxel by various combinations of ultrasonic power and operating time is shown in FIG.
[Equation 1]
2 shows the recovery rate of paclitaxel according to the number of times of solvent extraction in order to compare the recovery rate of paclitaxel in the extraction method using the ultrasonic wave of the present invention with the recovery rate of paclitaxel in the conventional optimized solvent extraction.
When the ultrasonic extraction method is performed once in combination with various operating times and various ultrasonic powers, if the operation time is 10 minutes or longer even at the lowest 80 W ultrasonic power tested as shown in FIG. 3, When paclitaxel was recovered at a level equivalent to one solvent extraction (~ 64%) and once extracted at an ultrasonic power interval of 80 W to 530 W for 10 minutes, the ultrasound power was significantly higher than that of the conventional solvent extraction The recovery rate of paclitaxel was up to 99%.
Also, as shown in FIG. 3, even when the ultrasonic extraction is performed once for the shortest one minute of the test time, when the ultrasonic power is processed at 320 W, 64%) of paclitaxel was recovered. When the extract was extracted once at an ultrasonic power interval of 320 W to 530 W for 1 minute, the recovery rate of paclitaxel was significantly higher than that of the conventional solvent extraction as the ultrasonic power was increased. % Of paclitaxel could be recovered.
The present invention also discloses the conditions of an optimized ultrasonic extraction method capable of recovering most of the paclitaxel from the biomass with only a single extraction. In order to optimize the main process variables, the optimal biomass / methanol ratio (1: 1, w / v) was constant and the effects of ultrasonic power and operation time were investigated. (500 rpm) was changed by changing ultrasonic power (80, 180, 250, 380, 530 W) and operating hours (1, 2, 4, 6, 8, 10, Biomass extraction was performed.
As a result, as shown in FIG. 3, the yield was increased as the ultrasonic power was increased, and the highest yield (~ 99%) was obtained at 380 W. Also, as the operation time increased, the yield of paclitaxel increased and the highest yield (~ 99%) was obtained at the operating time of 10 minutes. The yield (~ 80%) did not change even after 10 minutes of operation in the section below the ultrasonic power of 250 W, but almost all of the paclitaxel was recovered (~ 99%) at the ultrasonic power of 380 W or more.
As a result, the optimum ultrasonic power and operation time were 380 W and 10 minutes, respectively. Most of the paclitaxel was recovered (~ 99%) by single extraction in the extraction process using ultrasound under optimal conditions.
From these results, it can be seen that the extraction method using the ultrasonic wave of the present invention significantly shortens the operating time compared with the conventional optimized solvent extraction and drastically increases the extraction efficiency according to the shortening of the operating time.
In the present invention, the biomass surface was also observed using a scanning electron microscope (MIRA LMH; Tescan, Czech Republic). In the case of the biomass before extraction, the biomass surface is very smooth as shown in FIG. 4 (A). In the case of conventional solvent extraction using methanol (once extraction), as shown in FIG. 4 (B) Respectively.
On the other hand, in the case of performing the extraction using the ultrasonic wave (once extraction), the biomass surface was very rough and crumbled (crushed) with a strong impact as shown in FIG. 4 (C). That is, the cell wall was disrupted by a strong impact, and a sufficiently crushed (crushed) surface was formed so that all of the paclitaxel contained in the cells could be extracted. As a result, the extraction efficiency was remarkably improved. From these results, it was confirmed that paclitaxel can be effectively extracted / recovered from biomass by extraction using ultrasonic waves.
Therefore, the optimized paclitaxel extraction method using the ultrasonic wave of the present invention solves the problem of using a lot of organic solvents and the long extraction time which were limitations of the conventional solvent extraction process, and at the same time, the complexity of the process (device) ), It is possible to drastically improve the high cost problem caused by a lot of energy consumption.
The present invention will now be described more specifically with reference to the following examples. However, the following examples should not be construed as limiting the scope of the present invention, but should be construed to facilitate understanding of the present invention.
Biomass Ready
The plant cell culture used in the present invention was cultured using a cell line obtained from leaves of Taxus chinensis . Taxus chinensis ) were cultured in a darkness condition at 24 ° C with stirring at 150 rpm. Suspension cells were cultured in a modified Gamborg's B5 medium, 30 g / L sucrose, 10 μM naphthaleneacetic acid, 0.2 μM 6-benzylaminopurine, 1 g / L casein hydrolysate, 1 g / (N-morpholino) ethanesulfonic acid. The cell culture was changed to a new medium every 2 weeks, and 1 to 2% (w / v) maltose was added on the days 7 and 21 to prolong the incubation time, and as an
Ultrasound-assisted extraction
(UC-10, Jeiotech, Korea and JAC-4020, KODO, Korea) with the ratio of the biomass recovered from the plant cell culture solution to methanol at 1: 1 (w / v) (500 rpm) by varying ultrasonic power (80, 180, 250, 380, 530 W) and operating hours (1, 2, 4, 6, 8, 10, And extracted once. After extraction, the filtrate was filtered with a filter paper (150 mm, Whatman) to collect the paclitaxel extraction filtrate. The filtrate was concentrated using a concentrator (CCA-1100, EYELA, Japan) and then completely dried under vacuum (40 ° C, overnight, 760 mmHg).
The paclitaxel purity and yield were determined using an HPLC system (Waters, USA) and a Capell Pak C 18 (250 × 4.6 mm, Shiseido, Japan) column for the crude paclitaxel. The mobile phase was flowed with a mixed solution of distilled water and acetonitrile (65/35 to 35/65, v / v, gradient solvent method) at a flow rate of 1.0 ml / min. Sample injection volume was 20 μl and detected by UV at 227 nm. A standard quantitative curve was used for HPLC analysis. A standard sample was a Sigma-Aldrich product (purity> 97%).
The process of extracting biomass using ultrasonic waves is shown in Fig. The yield of paclitaxel was calculated by the following equation (1).
[Equation 1]
The yield of paclitaxel according to various combinations of ultrasonic power and operating time is as shown in Fig.
Using conventional solvent extraction and ultrasonic Paclitaxel Comparison of extraction methods
Most of the paclitaxel produced by plant cell culture is contained in biomass (plant cell), and Korean J. Biotechnol . According to Bioeng ., 15, 346-351 (2000), extraction efficiency using various organic solvents was the most effective for methanol, and in Process Biochem ., 39, 1985-1991 (2004) As reported, the ratio of biomass / methanol was found to be an optimal ratio of 1: 1 (w / v).
Accordingly, in this embodiment, solvent extraction was performed using a biomass / methanol ratio of 1: 1 (w / v), which indicates the most effective extraction efficiency of the conventional solvent extraction. The extraction using the ultrasonic wave of Example 2 To evaluate the paclitaxel extraction efficiency of the present invention.
In the conventional solvent extraction without using ultrasonic waves, the biomass recovered in Example 1 was extracted four times in a batch manner using methanol. The mixing ratio of methanol and biomass was 1/1 (15 g biomass / 15 mL methanol) and the extraction time was 30 min.
As a result, as shown in FIG. 2, paclitaxel was recovered at 64% for one time extraction, 20% for 2 times extraction, 10% for 3 times extraction and 5% for 4 times extraction from biomass, Of paclitaxel (~ 99%) was possible.
On the other hand, when the ultrasonic extraction method is performed once in combination with various operating times and various ultrasonic powers as described in the second embodiment, as shown in FIG. 3, even when the ultrasonic power of the lowest tested 80W is used, (~ 64%) of paclitaxel was recovered at the same level as one of the optimized conventional solvent extraction, and when the extraction was performed once in the ultrasonic power interval of 80 W to 530 W for 10 minutes, as the ultrasonic power was increased The recovery rate of paclitaxel was significantly higher than that of the conventional solvent extraction, and up to 99% of paclitaxel could be recovered.
In addition, as shown in FIG. 3, even when the ultrasonic extraction is performed once during the shortest one minute of the tested operation time, when the ultrasonic power is processed at 320 W, %) Of paclitaxel was recovered and the paclitaxel recovery was remarkably higher than that of the conventional solvent extraction as the ultrasonic power was increased by 1 time in the ultrasonic power interval of 320 W to 530 W for 1 minute, Of paclitaxel was recovered.
The paclitaxel purity from the biomass extraction was ~ 0.5% with or without sonication (data not shown).
As a result, it has been confirmed that the extraction method using the ultrasonic wave of the present invention significantly shortens the operating time and drastically increases the extraction efficiency according to the shortening of the operating time as compared with the conventional solvent extraction.
Ultrasonic Paclitaxel Optimization of extraction method
In this embodiment, most of the paclitaxel was recovered from the biomass by extraction once by extraction using ultrasonic waves. In order to optimize the main process variables, the optimal biomass / methanol ratio (1: 1, w / v) was constant and the effects of ultrasonic power and operation time were investigated. The various ultrasonic powers (80, 180, 250, 380, 530 W) and operating times (1, 2, 4, 6, 8, 10, 12, 15, 30 minutes) were the same as described in Example 2, One biomass extraction was performed under agitation (~ 500 rpm) with varying power and operating time.
As a result, as shown in FIG. 3, the yield was increased as the ultrasonic power was increased, and the highest yield (~ 99%) was obtained at 380 W. In addition, the yield of paclitaxel increased with increasing the operating time, and the highest yield (~ 99%) was obtained at the operating time of 10 minutes. The yield (~ 80%) did not change even after 10 min of operation time in ultrasonic power 250 W or less. However, paclitaxel could be recovered (~ 99%) in ultrasonic power of 380 W or more.
In addition, as compared with the conventional organic solvent extraction, most of the paclitaxel was recovered (~ 99%) by four times extraction as shown in FIG. 2 in the conventional solvent extraction, but the ultrasonic extraction was performed for 10 minutes at 380 W of ultrasonic power Most of the paclitaxel was recovered (~ 99%) only by one extraction.
These results indicate that the extraction efficiency of the paclitaxel contained in the cells is effectively enhanced by breaking the cell wall by the ultrasonic wave. Thus, in the extraction using the ultrasonic wave of the present invention, the optimal ultrasonic power and operation time are 380
Therefore, the paclitaxel extraction method using the ultrasound of the present invention can remarkably shorten the operating time and dramatically increase the extraction efficiency as compared with the extraction method using the conventional solvent extraction.
Scanning microscope ( SEM ) analysis
Scanning electron microscopy (MIRA LMH; Tescan, Czech Republic) was used to observe the biomass surface. The type of biomass dried at an accelerating voltage of 10-15 kV was analyzed. In the case of the biomass before extraction, the biomass surface is very smooth as shown in FIG. 4 (A). In the case of conventional solvent extraction using methanol (once extraction), as shown in FIG. 4 (B) Respectively.
On the other hand, in the case of performing the extraction using the ultrasonic wave (once extraction), the biomass surface was very rough and crumbled (crushed) with a strong impact as shown in FIG. 4 (C). That is, the surface was sufficiently shrunken (crushed) so that all the paclitaxel contained in the cells could be extracted, and as a result, the extraction efficiency was effectively improved. From these results, it was confirmed that extraction with paclitaxel from biomass can be effectively extracted / recovered by ultrasonic extraction.
As a result, the optimized paclitaxel extraction method using the ultrasonic wave of the present invention solves the problem of using a long organic solvent and long extraction time, which were limitations of the conventional solvent extraction process, and at the same time, Risk), it was able to drastically improve the high cost problem caused by a lot of energy consumption.
Claims (7)
a) obtaining a plant-derived biomass from a taxus genus plant comprising paclitaxel;
b) mixing the biomass with an organic solvent; And
c) treating the mixture of step b) with ultrasound to ultrasonically extract the mixture.
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| CN108969566A (en) * | 2018-08-16 | 2018-12-11 | 临沂大学 | A kind of extraction element and its extracting method of clover general flavone |
| KR102090882B1 (en) * | 2018-11-26 | 2020-03-18 | 공주대학교 산학협력단 | Fractional precipitation method performed by ultrasound treatment in purifying paclitaxel |
| KR20220150101A (en) * | 2021-05-03 | 2022-11-10 | 공주대학교 산학협력단 | Extraction method of paclitaxel using negative pressure cavitation |
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| JP6333601B2 (en) | 2014-03-31 | 2018-05-30 | 大阪瓦斯株式会社 | Method for producing flaky carbon using plant extract |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108969566A (en) * | 2018-08-16 | 2018-12-11 | 临沂大学 | A kind of extraction element and its extracting method of clover general flavone |
| CN108969566B (en) * | 2018-08-16 | 2021-07-23 | 临沂大学 | Extraction device and extraction method of alfalfa total flavonoids |
| KR102090882B1 (en) * | 2018-11-26 | 2020-03-18 | 공주대학교 산학협력단 | Fractional precipitation method performed by ultrasound treatment in purifying paclitaxel |
| KR20220150101A (en) * | 2021-05-03 | 2022-11-10 | 공주대학교 산학협력단 | Extraction method of paclitaxel using negative pressure cavitation |
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