CN106366153B - The method that hydrolysis madecassoside prepares brahmic acid - Google Patents
The method that hydrolysis madecassoside prepares brahmic acid Download PDFInfo
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- CN106366153B CN106366153B CN201610728601.3A CN201610728601A CN106366153B CN 106366153 B CN106366153 B CN 106366153B CN 201610728601 A CN201610728601 A CN 201610728601A CN 106366153 B CN106366153 B CN 106366153B
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- madecassoside
- hydrolysis
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- brahmic acid
- acid
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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Abstract
The invention discloses a kind of method for hydrolyzing madecassoside and preparing brahmic acid, comprise the following steps：1) madecassoside, lauryl sodium sulfate and NaOH are mixed, are dissolved in water, hydrolyze 10~15min at normal temperatures；2) hydrolyzate pH value is adjusted to 2~5, is stood, filtering, is collected precipitation；3) precipitation is dissolved in ethanol, filters, filtrate plus water are crystallized, filtered, crystallized, dried, produce brahmic acid.This method can quickly disconnect glycosidic bond at normal temperatures and pressures, and hydrolytic process is gentle, and hydrolysis is thorough, and will not produce the change of configuration of brahmic acid.
Description
Technical field
The invention belongs to technical field of biological extraction, and in particular to one kind hydrolysis madecassoside prepares madacasso grass
The method of acid.
Background technology
Centella (Centella asiatica (L.) Urban) is Umbelliferae centella tree plant, because its leaf exactly likes horse
Shoes or half of copper coin, so also known as membranaceous marshmarigold herb, Longtube Ground Ivy Herb etc., it is among the people also to there is place to be called pennyroyal mint, marchantia grass etc..Accumulated snow
Applicating history of the grass in the traditional medicine field of many countries and regions is long, China's traditional Chinese medicine to for oral administration of centella and
External application has bimillennium history, earliest quilt《Sheng Nong's herbal classic》One book is recorded.According to《Compendium of Materia Medica》Record, centella bitter,
It is pungent, it is cold in nature, it is nontoxic, return liver,spleen,kidney, stomach, its effect is promoting blood circulation, swelling and pain relieving, and has clearing heat and detoxicating, diuresis etc..Centella
Chemical composition mainly have triterpenes, flavonoids, polyyne alkenes and volatile oil etc..Triterpenes mainly has triterpene saponin, such as
Asiaticosid, madecassoside etc., and triterpene acids, such as asiatic acid, brahmic acid.It is generally believed that centella
In play the mainly triterpene saponin material such as asiaticosid and madecassoside of active function, but also there is data to grind in recent years
Study carefully and show, the bioavilability of the aglycon such as asiatic acid, brahmic acid substantially will height compared with its corresponding glycoside in organism.
Research shows, madecassoside is absorbed in jejunum and ileal segment and slightly improved in duodenum and poor colonic absorption, hydroxyl product
Asiaticoside is absorbed after large intestine is partially converted into aglycon, dramatically increases, and madecassoside member can be directly rapidly absorbed into
In animal blood, saponin(e then needs to be hydrolyzed into aglycon in vivo now and can just be absorbed and used.
Recent studies indicate that asiatic acid and brahmic acid have necessarily in anti-oxidant, anticancer etc.
Effect, and also have part curative effect for cerebral ischemia.Content of the aglycons such as brahmic acid in centella compares madacasso
Careless glycosides is much lower, and saponin content is generally 1.8~5% in centella, and sapogenin with saponin(e content than usually 1：2.5
Therefore by asiaticoside hydrolysis come to obtain asiaticoside member be an effective approach.Routine hydrolysis madacasso grass soap
The method that glycosides prepares brahmic acid is：Madecassoside is dissolved in ethanol solution, adds 1mol/L NaOH solution
As catalyst, 2~10h is hydrolyzed at 80 DEG C, after hydrolysis terminates, cools down hydrolyzate, adjusts pH value to be staticly settled, filtering is received to 2
Collection precipitation, is dissolved in ethanol by sediment, adds water and crystallized, and filters, as creamy white crystals.The above method uses high-temperature water
Solution, it can cause brahmic acid that the changes such as dehydration, cyclization, double-bond shift, substituent displacement, configuration conversion occur, drop significantly
The yield and purity of low target composition.
The content of the invention
Present invention solves the technical problem that it is to provide a kind of method for hydrolyzing madecassoside and preparing brahmic acid,
This method can quickly disconnect glycosidic bond at normal temperatures and pressures, and hydrolytic process is gentle, and hydrolysis is thorough, and will not produce madacasso
The change of configuration of oxalic acid.
Technical scheme provided by the invention is to provide a kind of method for hydrolyzing madecassoside and preparing brahmic acid,
Comprise the following steps：
1) madecassoside, lauryl sodium sulfate and NaOH are mixed, are dissolved in water, hydrolysis 10 at normal temperatures~
15min；
2) hydrolyzate pH value is adjusted to 2~5, is stood, filtering, is collected precipitation；
3) precipitation is dissolved in ethanol, filters, filtrate plus water are crystallized, filtered, crystallized, dried, produce hydroxyl
Base asiatic acid.
In step 1), concentration 3.44~4.3 × 10 of the lauryl sodium sulfate in mixed solution-2mol/L.Due to 12
The critical micelle concentration of sodium alkyl sulfate is 0.86 × 10-2Mol/L, when the concentration of surfactant molecule is higher than its critical micelle
During concentration, surfactant molecule will be internally formed a large amount of micelles in solution, but due to lauryl sodium sulfate in water it is dense
When degree is more than critical micelle concentration, it is bar-shaped micelle easily to form Thermodynamically stable shape, when the concentration of lauryl sodium sulfate
When continuing to improve to 4~5 times of critical micelle concentration, i.e., 3.44~4.3 × 10-2During mol/L, bar-shaped micelle phase in aqueous
Mutually wriggle, and then form stratiform micelle structure, be greatly improved the package action to hydrophobic grouping.
Madecassoside is amphiprotic substance, is to be combined by brahmic acid with glucose and rhamnose by glycosidic bond
Material, glucose and rhamnose are hydrophilic radical, and brahmic acid is hydrophobic grouping, and hydrophilic radical part has micella
Group surface, and hydrophobic grouping is then interspersed between the surfactant molecule to form rod-shaped micelle, due to the presence of stratiform micelle, is dredged
Water base group is then fully inserted among stratiform micelle, and now, hydrophilic radical is exposed at surface, is advantageous to OH-It is quick and complete
Face attack glycosidic bond so that elimination reaction occurs for glycosidic bond and the glycosidic bond that ftractures, hydrolysis are quick and thorough.Therefore, NaOH is being mixed
Concentration in solution is that 0.01~0.02mol/L is that hydrolyzable is complete, and hydrolysis time only needs 10~15min.
In step 2), pH value is adjusted using HCl.
In step 3), the precipitation and the solid-liquid ratio of ethanol are 1g：5~30ml.The volumetric concentration of the ethanol be 50~
70%.
In step 3), the dosage of water is 8~16 times of ethanol volume.
Compared with prior art, the present invention can quickly disconnect glycosidic bond at normal temperatures and pressures, and hydrolytic process is gentle, water
Solution is thorough, and will not produce the change of configuration of brahmic acid.
Embodiment
The present invention is further elaborated for specific examples below, but not as a limitation of the invention.
Madecassoside is provided by Guangxi Chang Zhou pharmaceutical Co. Ltds in following examples, purity 90%.
Embodiment 1
1) by 1g madecassosides, 3.44 × 10-2Mol lauryl sodium sulfate and 0.01mol NaOH mixing, add water
To 1L, stirring and dissolving, mixed solution is obtained, hydrolyze 10~15min at normal temperatures and pressures, obtain hydrolyzate；
2) hydrolyzate pH value is adjusted to 2 using HCl, stands, filtering, collect precipitation；
3) it is 1g by solid-liquid ratio by precipitation：5ml's is dissolved in volumetric concentration in 50% ethanol, filtering, filtrate to be added into second
The water that 8 times of alcohol volume is crystallized, and filtering, is crystallized, and is dried, is produced brahmic acid, and weigh 0.451g, through HPLC points
Its purity is analysed as 98.0%.Yield is 95.05%.
Embodiment 2
1) by 1g madecassosides, 4.3 × 10-2Mol lauryl sodium sulfate and 0.02mol NaOH mixing, are added water to
1L, stirring and dissolving, mixed solution is obtained, hydrolyzes 15min at normal temperatures and pressures, obtains hydrolyzate；
2) hydrolyzate pH value is adjusted to 5 using HCl, stands, filtering, collect precipitation；
3) it is 1g by solid-liquid ratio by precipitation：30ml's is dissolved in volumetric concentration in 70% ethanol, filtering, filtrate to be added into second
The water that 16 times of alcohol volume is crystallized, and filtering, is crystallized, and is dried, is produced brahmic acid, weigh 0.449g, through HPLC
Its purity is analyzed as 98.6%.Yield is 95.21%.
Embodiment 3
1) by 1g madecassosides, 3.87 × 10-2Mol lauryl sodium sulfate and 0.015mol NaOH mixing, add water
To 1L, stirring and dissolving, mixed solution is obtained, hydrolyzes 12min at normal temperatures and pressures, obtains hydrolyzate；
2) hydrolyzate pH value is adjusted to 3 using HCl, stands, filtering, collect precipitation；
3) it is 1g by solid-liquid ratio by precipitation：15ml's is dissolved in volumetric concentration in 60% ethanol, filtering, filtrate to be added into second
The water that 12 times of alcohol volume is crystallized, and filtering, is crystallized, and is dried, is produced brahmic acid, weigh 0.452g, through HPLC
Its purity is analyzed as 98.1%.Yield is 95.36%.
Embodiment 4
1) by 1g madecassosides, 3.44 × 10-2Mol lauryl sodium sulfate and 0.02mol NaOH mixing, add water
To 1L, stirring and dissolving, mixed solution is obtained, hydrolyzes 10min at normal temperatures and pressures, obtains hydrolyzate；
2) hydrolyzate pH value is adjusted to 5 using HCl, stands, filtering, collect precipitation；
3) it is 1g by solid-liquid ratio by precipitation：5ml's is dissolved in volumetric concentration in 70% ethanol, filtering, filtrate to be added into second
The water that 8 times of alcohol volume is crystallized, and filtering, is crystallized, and is dried, is produced brahmic acid, and weigh 0.456g, through HPLC points
Its purity is analysed as 98.15%.Yield is 96.25%.
Claims (5)
1. the method that hydrolysis madecassoside prepares brahmic acid, it is characterised in that：Comprise the following steps：
1) madecassoside, lauryl sodium sulfate and NaOH are mixed, is dissolved in water, obtains mixed solution, at normal temperatures
Hydrolyze 10~15min；Concentration 3.44~4.3 × 10 of the lauryl sodium sulfate in mixed solution-2mol/L；NaOH is being mixed
Concentration in solution is 0.01~0.02mol/L；
2) hydrolyzate pH value is adjusted to 2~5, is stood, filtering, is collected precipitation；
3) precipitation is dissolved in ethanol, filters, filtrate plus water are crystallized, filtered, crystallized, dried, produce hydroxyl product
Avenge oxalic acid.
2. the method that hydrolysis madecassoside according to claim 1 prepares brahmic acid, it is characterised in that：Step
It is rapid 2) in, using HCl adjust pH value.
3. the method that hydrolysis madecassoside according to claim 1 prepares brahmic acid, it is characterised in that：Step
It is rapid 3) in, the precipitation and the solid-liquid ratio of ethanol are 1g：5~30ml.
4. the method that hydrolysis madecassoside according to claim 3 prepares brahmic acid, it is characterised in that：Institute
The volumetric concentration for stating ethanol is 50~70%.
5. the method that hydrolysis madecassoside according to claim 1 prepares brahmic acid, it is characterised in that：Step
It is rapid 3) in, the dosage of water is 8~16 times of ethanol volume.
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| CN101456892A (en) * | 2008-12-29 | 2009-06-17 | 浙江大学 | Method for preparing madecassic acid by hydroxyl asiatic centella glycosides basic hydrolysis |
| CN102558142A (en) * | 2010-12-23 | 2012-07-11 | 重庆药友制药有限责任公司 | Preparation method of alpha-lipoic acid bulk pharmaceutical |
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Effective date of registration: 20180521 Address after: 530603 Zhou Lu Street cattle Road, Zhou Lu Town, Mashan County, Nanning, the Guangxi Zhuang Autonomous Region Patentee after: Guangxi Nanning Li Chuang Biological Technology Co.,Ltd. Address before: 541004 B303, room B, business building, five building, District five, New District, Guilin, Qixing District, the Guangxi Zhuang Autonomous Region. Patentee before: GUILIN BATURAL INGREDIENTS Corp. |
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Effective date of registration: 20221010 Address after: Room 212, Building B, No. 51 Congyun Road, Huangshi Street, Baiyun District, Guangzhou City, Guangdong Province, 510000 Patentee after: Guangzhou Shenye Biotechnology Co.,Ltd. Address before: 530603 Zhou Lu Street cattle Road, Zhou Lu Town, Mashan County, Nanning, the Guangxi Zhuang Autonomous Region Patentee before: Guangxi Nanning Li Chuang Biological Technology Co.,Ltd. |