AU2021100536A4 - Method for simultaneously separating dihydromyricetin and myricetin from Snake grapes - Google Patents
Method for simultaneously separating dihydromyricetin and myricetin from Snake grapes Download PDFInfo
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- dihydromyricetin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/15—Preparation or pretreatment of starting material involving mechanical treatment, e.g. chopping up, cutting or grinding
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The sample of the present invention is dried and coarsely crushed (20-40 mesh), extracted twice
with boiling water, combined the extracts, filtered while hot, and the filtrate is left standing at
0-4°C to precipitate a white precipitate, filtered by suction or centrifugation, and filtered
precipitation with absolute ethanol Dissolve, stand and filter with suction, and concentrate the
filtrate under reduced pressure to obtain a thick liquid, evaporate the ethanol, and dry under
temperature control to obtain total flavonoids. The total flavonoids were extracted with acetone
reflux, the extract was concentrated to obtain crude dihydromyricetin, the insoluble residue
was extracted with ethanol-water (1:1) reflux, and the extract was concentrated to obtain crude
myricetin 1. When purifying dihydromyricetin by recrystallization from water
(recrystallization times > 3), filter by heating (temperature 85-95°C), the filtrate is a yellow
transparent solution, and there are a lot of yellow-green substances (myricetin 2) on the filter
paper. The dried myricetin 2 was collected. Detected by HPLC, the purity of myricetin 2 is
87.37%, and the purity of dihydromyricetin (white needle crystals) is 89.87%.
-1/2
Fig.1I
mV
-Detector A:294nm mth<-J
25
20
15
10
0.0 25 5.0 7.5 10.0 12.5 15.0 min
Fig. 2
Description
-1/2
Fig.1I
mV -Detector A:294nm mth<-J
0.0 25 5.0 7.5 10.0 12.5 15.0 min
Fig. 2
Method for simultaneously separating dihydromyricetin and myricetin from Snake
grapes
The invention relates to the technical field of extraction and separation of chemical
constituents from plants of the genus Snake grapes in the grape family, and can be used
for the simultaneous separation of myricetin and dihydromyricetin from the stems and
leaves of the Snake grapes plant and its processed vine tea.
The flavonoids myricetin and dihydromyricetin are contained in the plants of the grape
family Snake grapes. Among them, Ampelopsis-grossedentada contains the highest
content. The processed products of the stems and leaves of Snake grapes are commonly
known as vine tea. A variety of physiological activities, the main active ingredient is
flavonoids, and the content of dihydromyricetin is the highest, the main active ingredient
of flavonoids can be as high as 40%. In addition, it also contains myricetin, catechins,
gallic acid, amino acids, trace elements and other ingredients; the main components of
vine tea flavonoids are dihydromyricetin and myricetin. The US FDA has widely used
myricetin in medicine, food, Health products and cosmetics; and dihydromyricetin has
many functions such as scavenging free radicals, anti-oxidation, anti-thrombosis, anti
tumor, anti-inflammatory, etc. It is widely used in the treatment of respiratory tract
infections, alcoholism and Chinese patent medicine preparations. It has been preparing
anti-leukemia and the application field of nasopharyngeal cancer drugs has obtained
invention patents; it is a good product for protecting the liver, protecting the liver, and sobering up alcohol. It can be used as pharmaceutical raw materials. However, because dihydromyricetin and myricetin are both polyhydroxyflavonol compounds, their structure and physical and chemical properties are similar, and the content of myricetin and dihydromyricetin in Guizhou rattan tea is quite different, and the content of myricetin is
1-3 %, the content of dihydromyricetin can reach 1 8 - 2 5 %, so the efficient separation of
myricetin and dihydromyricetin in Tengcha has always been a technical problem
hindering its application in industrialization. According to current literature and patent
reports, classical extraction and separation methods such as ethanol reflux method and
decoction method are mostly used to separate and purify the higher content of
dihydromyricetin, such as a Chinese patent-a kind from rattan tea The method for
extracting dihydromyricetin (Patent No. 200510032918.5) proposes a method of solvent
soaking of dried vine tea leaves, microwave radiation treatment of wet vine tea leaves,
extraction with water bath heating, and then recrystallization and purification of
dihydromyricetin with cold water. The method is simple to operate, less impurity and low
cost, but it cannot separate myricetin at the same time. At present, high-efficiency
separation and purification methods involving dihydromyricetin or myricetin are matched
with various modern separation techniques, mainly various chromatographic
techniques.The published documents mainly include: "Separation and structure
identification of myricetin in the vine tea of Yao nationality" in the Chinese National
Medicine Journal; "simultaneous purification of dihydromyricetin and myricetin in vine
tea by high-speed countercurrent chromatography" in "Modem Chemical Industry"
;"Natural Products Development" "heating and dissolving, heating through the column,
temperature hydrolysis and absorption" to extract dihydromyricetin (1)"; "Separation of myricetin and dihydromyricetin in rattan tea" in "Journal of Harbin Medical University"
And anti-cardiomyocyte apoptosis". This kind of technology mainly uses water extraction
or alcohol extraction, and microwave or ultrasonic assisted extraction technology to
obtain high content of total flavonoids, and then cooperate with various chromatography
techniques such as silica gel column chromatography, polyamide column
Chromatography, macroporous resin adsorption chromatography, high-speed
countercurrent chromatography, etc., according to the needs of the purpose, use an
appropriate mobile phase system and appropriate operating conditions to separate
myricetin or dihydromyricetin. This method has high separation efficiency and high
purity, but this method Large investment in production, small preparation scale, and high
operation requirements are not conducive to industrial production.There are also domestic
reports on the simultaneous separation of myricetin and dihydromyricetin by solvent
extraction. The "Research on the Extraction Technology of Flavonoids in Guangxi
Tengcha" of "Modem Applied Pharmacy in China" proposed that by using the solubility
difference of myricetin and dihydromyricetin in acetone, the extracted crude flavonoids
can be extracted with acetone. The extract is concentrated and recrystallized with water to
obtain dihydromyricetin. The insoluble residue is then extracted with an ethanol-water
mixed solvent, concentrated, and left to stand for a few days to obtain myricetin crystals.
Although this method is simple and easy to operate, but the extracted myricetin contains
more impurities and the yield is low. With reference to domestic and foreign literature,
there has not been a separation method that can efficiently separate myricetin and
dihydromyricetin at the same time by a simple solvent method, and is expected to be
applied to industrial production.
The present invention is to solve the problem that myricetin and dihydromyricetin are
difficult to separate and are difficult to be applied to industrialization. A method for
simultaneously separating dihydromyricetin and myricetin from plants of the genus Vitis
is proposed.
The purpose of the present invention is achieved through the following technical
solutions.
1. A method for simultaneously separating dihydromyricetin and myricetin from Snake
grape genus plants, including (1) the steps of water extraction and alcohol-soluble refined
total flavonoids from crude samples of Snake grape genus plants, (2) reflux extraction
with acetone The initial separation of dihydromyricetin from total flavonoids, (3) the step
of extracting insoluble residue with ethanol-water to separate myricetin, and (4) the step
of purifying dihydromyricetin and myricetin by water recrystallization. It is characterized
in that when the dihydromyricetin is purified by water recrystallization, the myricetin and
the dihydromyricetin in the dihydromyricetin obtained by the preliminary separation are
separated by heating and filtering.
2. The method for simultaneously separating myricetin and dihydromyricetin according
to claim 1, characterized in that in the step (3) of separating myricetin from the ethanol
water extraction insoluble residue, the ratio of ethanol-water is 1: 1.
3. The method for simultaneously separating myricetin and dihydromyricetin according
to claim 1, characterized in that in the step (4) of purifying dihydromyricetin and myricetin by recrystallization, the heating and filtering operation temperature should be
-95°C and until the filtered solution is heated to yellow-green.
4. The method for simultaneously separating myricetin and dihydromyricetin according
to claim 1, characterized in that in the step of purifying dihydromyricetin by
recrystallization, (4) the number of recrystallizations of dihydromyricetin should be > 3
times.
Compared with previous separation methods, the present invention has the following
innovations:
1. Myricetin is obtained for thefirst time through recrystallization, heating and filtration;
2. Myricetin can be obtained in two ways;
3. Solvent method is used to separate high-purity myricetin and dihydromyricetin at the
same time.
Compared with previous separation methods, the present invention has the following
advantages:
1. Simple operation and low pollution;
2. The product has high purity and high output;
3. The equipment is simple, the cost is low, and it is suitable for industrial production.
The process is simple to operate and less pollution; Product purity is high, high yield;
Simple equipment, low cost, suitable for industrial production. The obtained products and
HPLC detection maps are as follows:
Figure 1 is the Dihydromyricetin white needle crystal (purity >95%).
Figure 2 is the HPLC chromatogram of dihydromyricetin.
Figure 3 is the yellow-green substance (recrystallized and filtered myricetin sample).
Figure 4 is the yellow brown precipitation (ethanol-water (1:1) extraction of myricetin
sample) .
Figure 5 is the HPLC chromatogram of myricetin.
Specific embodiment 1
1.Extraction and purification of total flavonoids in Ampelopsis-grossedentada (Hand
Mazz) W.T.Wang
Weigh 1OOg of dried and coarsely crushed Snake Snake grape stems and leaves, extract in
two boiling water, add 1000mL of water for the first time, heat and boil for 5-10 minutes,
pour out the decoction, add 500-10OOmL of water, heat and boil for 5- For 10 minutes,
combine the extracts, filter while hot, and let the filtrate stand at 0'C-4C to precipitate a
white precipitate. Filter with suction. Dissolve the precipitate with 100mL of absolute
ethanol. Let stand and filter with suction. The filtrate is concentrated under reduced pressure until the solution is concentrated. When it is thick, pour out the thick liquid, evaporate the ethanol to obtain a yellow mass (total flavonoids), dry at 50°C-65C, grind
2. Separation of dihydromyricetin
Take the total flavonoids obtained by the above extraction, use 200 mL of acetone as the
solvent for Soxhlet reflux extraction, reflux extraction until the extract in the paper tube
no longer appears yellow. When the extract is directly concentrated on a rotary
evaporator under reduced pressure and becomes thick, pour out the liquid, put it in a fume
hood, evaporate the acetone, transfer the mass to a beaker, add a certain amount of
distilled water, and stir with a glass rod A large amount of yellow-white precipitate
precipitated immediately.it with a mortar after drying, weigh it, and then pour it into a
paper tube for use Separate.
3. Myricetin separation
Take the insoluble residue from the filter paper cartridge and use 100 mL of ethanol
water (1:1) as the solvent to perform Soxhlet reflux extraction for 1 to 3 hours, and the
temperature of the water bath is 85 to 95°C. The color of the mixed solvent extract was
brownish yellow. When the extract was concentrated under reduced pressure to a small
volume, the solution turned red. Pour the solution into an Erlenmeyer flask and let it
stand for a few days in an environment of 0-4°C. A yellowish-brown precipitate
precipitates, which is filtered with a funnel, and the precipitate is dried and stored.
4. Recrystallization and purification
A large amount of yellow-white precipitate added with distilled water obtained after
separation is heated and dissolved in a water bath, and the temperature of the water bath is 85-95°C. When the solution is completely yellow-green, it is filtered while hot. The filtrate is a yellow transparent solution with a large amount of yellow-green substance on the filter paper, which is collected and dried. Pour the filtrate after suction filtration into an Erlenmeyer flask, label it, and let it stand at 0-4°C. The solution separated out white precipitate, which was flocculent. Suction the precipitate, discard the yellow-green filtrate, continue to recrystallize the precipitate with distilled water, collect the yellow green material on the filter paper, continue to stand the filtrate for crystallization at 0
4°C, follow this operation for the third and fourth recrystallization White needle crystals
are obtained every time, and the needle crystals are repeatedly washed with ice water in
the suction filtration operation, and then dried and stored to obtain dihydromyricetin at a
drying temperature of 60-65°C.
The yellow-brown precipitate and yellow-green substance obtained in the above
operation were identified as myricetin by thin-layer chromatography, and the white
needle crystal thin-layer chromatography was identified as dihydromyricetin. The content
of myricetin 1 (yellow-brown precipitate) obtained by this method is low, the purity of
myricetin 2 (yellow-green substance) is 87.37%, and the purity of dihydromyricetin
(white needle crystals) is 92.87%.
Specific embodiment 2
1. Extraction and purification of dihydromyricetin and myricetin from Guangdong snake
grape (Amplelopsis cantoniensis Planch)
Weigh 100g of dried and coarsely crushed Guangdong Snake grape stems and leaves
sample, extract in two boiling water, add 1OOOmL of water for the first time, heat and boil for 5-10 minutes, pour out the decoction, add 500-10OOmL of water, heat and boil for
~10 After 10 minutes, combine the extracts and filter while it is hot. The filtrate is
allowed to stand at 0 °C-4°C to precipitate a white precipitate. The filter precipitate is
dissolved in 100mL of absolute ethanol. After standing, the filtrate is concentrated under
reduced pressure until the solution is thick. When it is shaped, pour out the thick liquid
and evaporate the ethanol to obtain a yellow mass (total flavonoids), dry at 50°C-65C,
grind it with a mortar after drying, weigh it, and pour it into a paper tube for separation.
2. Separation of dihydromyricetin
Take the total flavonoids obtained by the above extraction, use 200 mL of acetone as the
solvent for Soxhlet reflux extraction, reflux extraction until the extract in the paper tube
no longer appears yellow. When the extract is directly concentrated on a rotary
evaporator under reduced pressure and becomes thick, pour out the liquid, put it in a fume
hood, evaporate the acetone, transfer the mass to a beaker, add a certain amount of
distilled water, and stir with a glass rod A large amount of yellow-white precipitate
precipitated immediately.
3. Myricetin separation
Take the insoluble residue from the filter paper cartridge and use 100 mL of ethanol
water (1:1) as the solvent for Soxhlet reflux extraction for 1 to 2 hours, and the
temperature of the water bath is 85-95°C. The color of the mixed solvent extract was
brownish yellow. When the extract was concentrated under reduced pressure to a small
volume, the solution turned red. Pour the solution into an Erlenmeyer flask and let it
stand for a few days in an environment of 0 to 4°C. A yellowish-brown precipitate is deposited, filtered with a funnel, and the precipitate is dried and stored to obtain myricetin.
4. Recrystallization and purification
A large amount of yellow-white precipitate added with distilled water obtained after
separation is heated and dissolved in a water bath, and the temperature of the water bath
is 85-95°C. When the solution is completely yellow-green, it is filtered while hot. The
filtrate is a yellow transparent solution with a large amount of yellow-green substance on
the filter paper, which is collected and dried. Pour the filtrate after suction filtration into
an Erlenmeyer flask, label it, and let it stand at 0-4°C. The solution separated out white
precipitate, which was flocculent. Suction the precipitate, discard the yellow-green
filtrate, continue to recrystallize the precipitate with distilled water, collect the yellow
green substance on the filter paper, continue to crystallize the filtrate at 0-4 °C, follow the
same operation in the third and fourth recrystallization White needle crystals are obtained
every time, and the needle crystals are repeatedly washed with ice water in the suction
filtration operation, and then dried and stored to obtain dihydromyricetin at a drying
temperature of 60-65°C.
The yellow-brown precipitate and yellow-green substance obtained in the above
operation were identified as myricetin by thin-layer chromatography, and the white
needle crystal thin-layer chromatography was identified as dihydromyricetin. The purity
of myricetin 1 (yellow-brown precipitate) obtained by this method is low, the purity of
myricetin 2 (yellow-green substance) is 85.3%, and the purity of dihydromyricetin (white
needle crystals) is 90.1%.
Claims (6)
1. A method for simultaneously separating myricetin and dihydromyricetin from the
stems and leaves of the Snake grape genus plant includes the following steps:(1) The step
of coarsely crushing the stems and leaves of Snake grape genus plants, and extracting and
alcohol-soluble refining total flavonoids in water;(2) The step of initially separating
dihydromyricetin by extracting total flavonoids with acetone reflux;(3) The step of
extracting the insoluble residue with ethanol and water to separate myricetin; (4) The step
of purifying dihydromyricetin and myricetin by water recrystallization.
2. It is characterized in that when the dihydromyricetin is purified by water
recrystallization, the myricetin and dihydromyricetin in the dihydromyricetin obtained by
the preliminary separation are separated by heating and filtering.
3. The method for simultaneously separating myricetin and dihydromyricetin according
to claim 1, characterized in that in the step (3) of separating myricetin from the insoluble
residue extracted from ethanol and water, the ratio of ethanol to water is 1: 1.
4. The method for separating myricetin and dihydromyricetin at the same time according
to claim 1, characterized in that in the step (4) of purifying dihydromyricetin and
myricetin by recrystallization, the heating and filtering operation temperature should be
-95°C and until the filtered solution is heated to yellow-green.
5. The method for simultaneously separating myricetin and dihydromyricetin according
to claim 1, characterized in that in the step (4) of purifying dihydromyricetin by
recrystallization, the number of recrystallizations of dihydromyricetin should be > 3
times.
6. The method of the present invention is not only suitable for the separation of myricetin
and dihydromyricetin from plants of the genus Snake grape, but also applicable to plants
of other genera containing myricetin and dihydromyricetin.
-1/2-
Fig. 2 Fig. 1
-2/2- 28 Jan 2021 2021100536
Fig. 3
Fig. 4
Fig. 5
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115844779A (en) * | 2022-11-30 | 2023-03-28 | 中国药科大学 | Total flavone and fruit acid part in citrus pulp as well as preparation method and application thereof |
-
2021
- 2021-01-28 AU AU2021100536A patent/AU2021100536A4/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115844779A (en) * | 2022-11-30 | 2023-03-28 | 中国药科大学 | Total flavone and fruit acid part in citrus pulp as well as preparation method and application thereof |
| CN115844779B (en) * | 2022-11-30 | 2024-05-28 | 中国药科大学 | Total flavone and fruit acid part in citrus pulp, and preparation method and application thereof |
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