CN107868019A - Dihydro oat alkaloid compound, derivative and its preparation method and application - Google Patents
Dihydro oat alkaloid compound, derivative and its preparation method and application Download PDFInfo
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- CN107868019A CN107868019A CN201711096214.3A CN201711096214A CN107868019A CN 107868019 A CN107868019 A CN 107868019A CN 201711096214 A CN201711096214 A CN 201711096214A CN 107868019 A CN107868019 A CN 107868019A
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- oat alkaloid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/005—Preparations for sensitive skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- Cosmetics (AREA)
Abstract
The present invention relates to compound extraction, preparing technical field, and more particularly to dihydro oat alkaloid compound, derivative and its preparation method and application；The preparation method of the present invention is efficiently, gently, free from environmental pollution, moreover it is possible to reduce the cost of production；There is higher solubility in the compound and derivative water of the present invention, and it has many bioactivity such as anti-inflammatory, anti-oxidant, antipruritic skin of releiving, and can be applied in the cosmetics such as infant articles, sensitive skin nursing, eczema.
Description
Technical field
The present invention relates to compound extraction, preparing technical field, and more particularly to dihydro oat alkaloid compound, spread out
Biology and its preparation method and application.
Background technology
Oat alkaloid is a kind of material extracted from oat bran, is a kind of alkaloid containing phenolic hydroxyl group.Have
Many bioactivity such as anti-inflammatory, anti-oxidant, antipruritic skin of releiving, it is a kind of good cosmetic active ingredient, can be extensive
Applied to skin nursings such as infant articles, sensitive skin nursing, eczemas.
But there is the pendant double bonds being conjugated with phenolic hydroxyl group phenyl ring in the structure of natural oat alkaloid, therefore structure
Type is relatively fixed, and on space structure, is unfavorable for rotating freely for side chain, therefore the solubility in water is extremely low, and then is limited
Utilization of the oat alkaloid in cosmetics.
The content of the invention
The present invention first purpose be to provide a kind of dihydro oat alkaloid compound, its in water have it is higher
Solubility, and it is good cosmetic active ingredient.
Second object of the present invention is in providing a kind of dihydro oat alkaloid compound in cosmetics are prepared
Using dihydro oat alkaloid compound can be applied in skin care item, and it is living to fully play its many biology
Property.
Third object of the present invention is to provide a kind of cosmetics, and it, which has, anti-oxidant waits effect.
Fourth object of the present invention is to provide a kind of derivative of dihydro oat alkaloid compound, and it is in water
With higher solubility, and it is good cosmetic active ingredient.
The 5th purpose of the present invention is to provide a kind of derivative of dihydro oat alkaloid compound in preparationization
Application in cosmetic, the derivative of dihydro oat alkaloid compound can be applied in skin care item, and can be sufficient
Playing it has many bioactivity.
The present invention the 6th purpose be to provide another cosmetics, its have it is anti-oxidant wait effect.
The 7th purpose of the present invention is to provide a kind of preparation method of dihydro oat alkaloid compound, this method
Dihydro oat alkaloid compound can be efficiently produced, and working condition is gentle, it is free from environmental pollution, moreover it is possible to reduce production
Cost.
The 8th purpose of the present invention is to provide a kind of preparation side of the derivative of dihydro oat alkaloid compound
Method, this method can efficiently produce the derivative of dihydro oat alkaloid compound, and working condition is gentle, does not pollute ring
Border, moreover it is possible to reduce the cost of production.
The present invention is realized using following technical scheme.
The present invention proposes a kind of dihydro oat alkaloid compound, and the structure of the dihydro oat alkaloid compound is led to
Formula is
Wherein R is one kind in hydrogen, methoxyl group or hydroxyl.
The present invention proposes a kind of application of dihydro oat alkaloid compound in cosmetics are prepared；Preferably, make up
Product are with anti-inflammatory, anti-oxidant or itching-relieving action cosmetics；Preferably, cosmetics include one or more kinds of above-mentioned dihydros
Oat alkaloid compound；Preferably, cosmetics include two kinds of above-mentioned dihydro oat alkaloid compounds；Preferably,
Cosmetics include three kinds of above-mentioned dihydro oat alkaloid compounds.
The present invention also proposes a kind of cosmetics, and it includes at least one above-mentioned dihydro oat alkaloid compound；It is preferred that
Ground, cosmetics include one or more kinds of above-mentioned dihydro oat alkaloid compounds；Preferably, cosmetics are included on two kinds
The dihydro oat alkaloid compound stated；Preferably, cosmetics include three kinds of above-mentioned dihydro oat alkaloid compounds.
The present invention proposes a kind of derivative of dihydro oat alkaloid compound, the dihydro oat alkaloid compound
The general structure of derivative beWherein, R1For hydrogen, first
One kind in epoxide or hydroxyl, R2For Na+、K+、Li+、Ca2+、Zn2+、Mg2+、NH4 +, one kind in choline or amino acid.
The present invention proposes a kind of application of derivative of dihydro oat alkaloid compound in cosmetics are prepared；It is preferred that
Ground, cosmetics are with anti-inflammatory, anti-oxidant or itching-relieving action cosmetics；Preferably, cosmetics are included in one or more
The derivative for the dihydro oat alkaloid compound stated；Preferably, cosmetics include two kinds of above-mentioned dihydro oat alkaloids
The derivative of class compound；Preferably, cosmetics include the derivative of three kinds of above-mentioned dihydro oat alkaloid compounds.
The present invention also proposes a kind of cosmetics, and it includes the derivative of at least one above-mentioned dihydro oat alkaloid compound
Thing；Preferably, cosmetics include the derivative of one or more kinds of above-mentioned dihydro oat alkaloid compounds；Preferably,
Cosmetics include the derivative of two kinds of above-mentioned dihydro oat alkaloid compounds；Preferably cosmetics include three kinds it is above-mentioned
The derivative of dihydro oat alkaloid compound.
The invention also provides a kind of preparation method of dihydro oat alkaloid compound, including by oat alkaloid and
Palladium-carbon catalyst makes an addition to ethanol, stirring, then passes to hydrogen, then rotary evaporation.
The invention also provides a kind of preparation method of the derivative of dihydro oat alkaloid compound, including by dihydro
Oat alkaloid compound is dissolved in ethanol, and nitrogen, then dropwise reaction solution are passed through after addition, is neutralized to complete, complete
Continue to stir after neutralization；Wherein, reaction solution includes sodium hydroxide solution, potassium hydroxide solution, lithium hydroxide solution, hydroxide
One kind in calcium solution, zinc hydroxide solution, magnesium hydroxide solution, ammonium water, choline solution and Freamine Ⅲ.
The beneficial effect of the dihydro oat alkaloid compound of the embodiment of the present invention, derivative and its preparation method and application
Fruit is：The dihydro oat alkaloid compound of the present invention and the derivative of dihydro oat alkaloid compound have many
Bioactivity, it can be applied to by the active component as cosmetics in skin care item；The dihydro oat alkaloids of the present invention
Compound and the preparation method of derivative can efficiently produce dihydro oat alkaloid compound, and working condition temperature
With it is free from environmental pollution, moreover it is possible to reduce the cost of production.
Embodiment
, below will be in the embodiment of the present invention to make the purpose, technical scheme and advantage of the embodiment of the present invention clearer
Technical scheme be clearly and completely described.Unreceipted actual conditions person, builds according to normal condition or manufacturer in embodiment
The condition of view is carried out.Agents useful for same or the unreceipted production firm person of instrument, it is the conventional production that can be obtained by commercially available purchase
Product.
The dihydro oat alkaloid compound to the embodiment of the present invention, derivative and its preparation method and application enter below
Row illustrates.
The general structure of dihydro oat alkaloid compound of the present invention is
Above-mentioned R is one in hydrogen, methoxyl group or hydroxyl
Kind.
In detail, the dihydro oat alkaloid compound in the present invention includes following three kinds：
Specifically, it is many to be respectively provided with anti-inflammatory, anti-oxidant, antipruritic skin of releiving etc. for above-mentioned dihydro oat alkaloid compound
Bioactivity, can be applied in cosmetics as active material, and above-mentioned cosmetics for example can be：Infant articles, sensitivity
Skin nursing, eczema nursing etc..
It should be noted that above-mentioned dihydro oat alkaloid A, B, C are when being applied to cosmetics, can individually select
One of which, such as：Dihydro oat alkaloid A, dihydro oat alkaloid B or dihydro oat alkaloid C；Can also select two
Kind coordinates, such as following combined method：Dihydro oat alkaloid A and dihydro oat alkaloid B, dihydro oat alkaloid A and two
Hydrogen oat alkaloid C, dihydro oat alkaloid C and dihydro oat alkaloid B；It can also be that three kinds of dihydro oat alkaloids are same
When be applied to cosmetics in.
It should be further stated that above-mentioned dihydro oat alkaloid compound is employed cosmetics as active material
When middle, concentration can be 0.001 ‰ to 100%.When the dihydro oat alkaloid compound from more than one is as activity
When material is used for the preparation of cosmetics, the usage ratio between each dihydro oat alkaloid compound is not specifically limited,
Such as：Simultaneously with above-mentioned three kinds of dihydro oat alkaloid compounds collectively as certain cosmetics active material when amount ratio can
To be 1:1:1、1:2:1 or 2:2:1 etc..
The general structure of the derivative of dihydro oat alkaloid compound provided by the invention is
Wherein, R1For in hydrogen, methoxyl group or hydroxyl
One kind, R2For Na+、K+、Li+、Ca2+、Zn2+、Mg2+、NH4 +, one kind in choline or amino acid；Selected as preferably above-mentioned amino acid
From one kind in lysine and arginine.
In detail, the present invention provides the derivative of three kinds of dihydro oat alkaloid compounds, is respectively：
Dihydro oat alkaloid A derivative, structural formula are as follows：
The dihydro oat alkaloid A derivative
R in structural formula3Including Na+、K+、Li+、Ca2+、Zn2+、Mg2+、NH4 +, one kind in choline or amino acid, preferably, above-mentioned
The one kind of amino acid in lysine and arginine.
Dihydro oat alkaloid B derivatives, structural formula are as follows：
The dihydro oat alkaloid B derivatives
Structural formula in R4Including Na+、K+、Li+、Ca2+、Zn2+、Mg2+、NH4 +, one kind in choline or amino acid, preferably, on
State the one kind of amino acid in lysine and arginine.
Dihydro oat alkaloid C derivatives, structural formula are as follows：
Dihydro oat alkaloid C derives
R in the structural formula of thing5Including Na+、K+、Li+、Ca2+、Zn2+、Mg2+、NH4 +, one kind in choline or amino acid, preferably,
The one kind of above-mentioned amino acid in lysine and arginine.
Further, above-mentioned three kinds of dihydro oats alkaloid A, B, C derivative are respectively provided with anti-inflammatory, anti-oxidant, antipruritic releived
Many bioactivity such as skin, can be applied in cosmetics as active material, and above-mentioned cosmetics for example can be：Baby is virgin
Articles for use, sensitive skin nursing, eczema nursing etc..
It should be noted that above-mentioned dihydro oat alkaloid A, B, C derivative when being applied to cosmetics, can be single
One of which solely is selected, such as：Dihydro oat alkaloid A derivative, dihydro oat alkaloid B derivatives or dihydro oat biology
Alkali C derivatives；Can also be from two kinds of cooperations, such as following combined method：Dihydro oat alkaloid A derivative and dihydro swallow
Wheat alkaloid B derivatives, dihydro oat alkaloid A derivative and dihydro oat alkaloid C derivatives, dihydro oat alkaloid C
Derivative and dihydro oat alkaloid B derivatives；It can also be by three kinds of dihydro oat alcaloid-derivatives while applied to change
In cosmetic.
It should be further stated that the derivative of above-mentioned dihydro oat alkaloid compound is answered as active material
During in cosmetics, concentration can be 0.001 ‰ to 100%.When from more than one dihydro oat alkaloids chemical combination
When the derivative of thing is used for the preparation of cosmetics, the usage ratio between the derivative of each dihydro oat alkaloid compound
It is not specifically limited, such as：Simultaneously with dihydro oat alkaloid A derivative and dihydro oat alkaloid C derivatives collectively as
The amount ratio during active material of certain cosmetics can be 1:1、1:2、3:2 etc.；Or given birth to simultaneously with above-mentioned three kinds of dihydro oats
The derivative of thing alkaloid compound collectively as certain cosmetics active material when amount ratio can be 1:1:1、1:2:1 or
2:2:1 etc..
The preparation method of the dihydro oat alkaloid compound of the present invention can include：Oat alkaloid and palladium carbon are urged
Agent makes an addition to ethanol, stirring, then passes to hydrogen, then rotary evaporation.The rotating speed of above-mentioned stirring can be 400-600rpm, stir
The time mixed can be 3-5h.
In detail, above-mentioned dihydro oat alkaloid A, B, C can be manufactured separately, and preparation method difference is as follows：
Oat alkaloid A is dissolved in ethanol, adds palladium-carbon catalyst, under the conditions of room temperature (such as 0-40 DEG C), with
400-600rpm stir speed (S.S.) stirring 3-5h, then hydrogen is passed through into mixture so that oat alkaloid A side chain double bond selects
Property is hydrogenated to dihydro oat alkaloid A；Finally can also be by above-mentioned reacted product rotary evaporation, you can obtain gray solid
Product.It should be noted that amount ratio when above-mentioned oat alkaloid A mixes with ethanol can be according to every 0.45-0.55g oats
Alkaloid A makes an addition to 95-105mL absolute ethyl alcohols to be calculated；The addition of palladium-carbon catalyst can be oat alkaloid A weight
1/5 or so of amount.
Oat alkaloid B is dissolved in ethanol, adds palladium-carbon catalyst, under the conditions of room temperature (such as 0-40 DEG C), with
400-600rpm stir speed (S.S.) stirring 3-5h, then hydrogen is passed through into mixture so that oat alkaloid B side chains double bond selects
Property is hydrogenated to dihydro oat alkaloid B；Finally can also be by above-mentioned reacted product rotary evaporation, you can obtain brown solid
Product.It should be noted that amount ratio when above-mentioned oat alkaloid B mixes with ethanol can be according to every 0.25-0.35g oats
Alkaloid B makes an addition to 75-85mL absolute ethyl alcohols to be calculated；The addition of palladium-carbon catalyst can be oat alkaloid B weights
1/3 or so of amount.
Oat alkaloid C is dissolved in ethanol, adds palladium-carbon catalyst, under the conditions of room temperature (such as 0-40 DEG C), with
400-600rpm stir speed (S.S.) stirring 3-5h, then hydrogen is passed through into mixture so that oat alkaloid C side chains double bond selects
Property is hydrogenated to dihydro oat alkaloid C；Finally can also be by above-mentioned reacted product rotary evaporation, you can obtain brown solid
Product.It should be noted that amount ratio when above-mentioned oat alkaloid C mixes with ethanol can be according to every 0.35-0.45g oats
Alkaloid C makes an addition to 85-95mL absolute ethyl alcohols to be calculated；The addition of palladium-carbon catalyst can be oat alkaloid C weights
1/4 or so of amount.
It should be noted that the above-mentioned oat alkaloid for being used to prepare dihydro oat alkaloid compound can be various
Commercially available oat alkaloid or prepared with a kind of preparation method of oat alkaloid, this method can include：By swallow
Wheat bran skin is added in ethanol, stirs 10-15h, then stops stirring, and is soaked 45-50h, is again heated to 45-55 DEG C, and stir 10-
15h, centrifugal filtration after room temperature is cooled to, obtains filtrate；Filtrate is added into polymeric adsorbent ethanol elution, is being concentrated in vacuo,
Obtain extract；By extract chromatography.Above-mentioned chromatography can include above-mentioned extract passing through silicagel column in batches
Chromatography and hydroxypropyl sephadex chromatography (Sephadex LH-20 gel layers), you can obtain oat alkaloid A, B, C, and swallow
The weight ratio substantially 100 of wheat alkaloid A, oat alkaloid B and oat alkaloid C:46:45.
Above-mentioned oat bran can be that particle diameter is 80-120 mesh powders, oat bran powder and ethanol and weight ratio can
To be 4-5:50；The filter bag of 250-350 mesh can be used during above-mentioned centrifugal filtration；Above-mentioned polymeric adsorbent can be AB-8 trees
Fat, elute and carried out successively as follows for ethanol gradient elution, gradient elution program：The ethanol 10 of 20% column volume of ethanol 10 → 40%
Individual column volume → 60% ethanol, 10 column volumes → 100% ethanol, 10 column volumes, corresponding part is collected after gradient elution, on
The concentration for stating ethanol is mass concentration；Above-mentioned silica gel column chromatography and hydroxypropyl sephadex chromatography (Sephadex LH-20
Gel layer) elution requirement be 1:1 first alcohol and water, and at the uniform velocity elute；The temperature of above-mentioned vacuum concentration can be 40-55
℃。
The preparation method of the derivative of the dihydro oat alkaloid compound of the present invention can include giving birth to dihydro oat
Thing alkaloid compound is dissolved in ethanol, and being passed through nitrogen after addition is protected, then (at a slow speed be added dropwise) reaction solution is added dropwise, to complete
Neutralize, continue to stir with after in completely, last rotary evaporation, by ethanol and water evaporation；Wherein, reaction solution includes hydrogen
Sodium hydroxide solution, potassium hydroxide solution, lithium hydroxide solution, aqua calcis, zinc hydroxide solution, magnesium hydroxide solution,
One kind in ammonium water, choline solution and Freamine Ⅲ.
It should be noted that prepare foregoing dihydro oat alkaloid A derivative, dihydro oat alkaloid B derivatives, two
Hydrogen oat alkaloid C derivatives are respectively by dihydro oat alkaloid A, dihydro oat alkaloid B, dihydro oat alkaloid C
Prepared with the preparation method of the derivative of above-mentioned dihydro oat alkaloid compound.
It should be further stated that prepare the method for derivative above-mentioned, dihydro oat alkaloid compound and
Ethanol can be mixed according to following ratio：Dihydro oat alkaloid per 0.001-0.003mol can coordinate 3-7mL's
Ethanol, and ethanol can be heated to 40-50 DEG C；The mass concentration of above-mentioned various reaction solutions may each be 8-12%；It is above-mentioned
Neutralize completely and refer to that equivalent reacts；The time stirred after above-mentioned neutralization completely can be 0.5-1h.
Need further to illustrate, the ethanol being related in the present invention may each be absolute ethyl alcohol.
With reference to embodiments to the dihydro oat alkaloid compound of the present invention, derivative and preparation method thereof and should
With being described in further detail.
Embodiment 1
The oat bran powder 9.8kg of 100 mesh is added in 100kg absolute ethyl alcohols, stirs 12h, then stops stirring, is soaked
48h, 50 DEG C are again heated to, and stir 12h, be cooled to after room temperature with the filter bag centrifugal filtration of 300 mesh, obtain filtrate；Will filter
Liquid adds AB-8 resin ethanol gradient elutions, and elution program is：20% column volume of ethanol 10 → 40% ethanol, 10 cylinders
10 column volumes of → 60% ethanol of product → 100% ethanol, 10 column volumes, are concentrated in vacuo under the conditions of 40 DEG C, obtain extract；
By extract in batches by silica gel column chromatography and hydroxypropyl sephadex chromatography (Sephadex LH-20 gel layers), with 1:
1 first alcohol and water at the uniform velocity elutes, you can obtains oat alkaloid A, B, C.
The nuclear magnetic data of oat alkaloid A is as follows：
1H NMR(DMSO-d6):6.56 (1H, d, J=15.5Hz), 6.85 (2H, d, J=8.5Hz), 7.07 (1H, dd, J
=9.2Hz, J=3.0Hz), 7.42 (2H, d, J=8.5Hz), 7.49 (1H, d, J=3.0Hz), 7.55 (1H, d, J=
15.5Hz), 8.58 (1H, d, J=9.2Hz), 9.54 (1H, s), 9.86 (1H, s), 10.87 (1H, s), 13.27 (1H, brs).
13C NMR(DMSO-d6,100MHz):169.3,163.9,159.4,152.6,140.8,133.1,129.9,
125.7,122.5,121.0,119.1,118.5,116.6,115.8。
Structural formula is as follows：
Oat alkaloid B nuclear magnetic data is as follows：
1H NMR(DMSO-d6):3.77 (3H, s), 6.67 (1H, d, J=15.5Hz), 6.81 (1H, d, J=8.1Hz),
7.04 (1H, dd, J=9.0Hz, J=3.0Hz), 7.10 (1H, dd, J=8.1Hz, J=1.8Hz), 7.29 (1H, d, J=
1.8Hz), 7.41 (1H, d, J=3.0Hz), 7.49 (1H, d, J=15.5Hz), 8.40 (1H, d, J=9.0Hz), 9.44 (1H,
s),9.56(1H,s),10.77(1H,s),13.31(1H,brs)。
13C NMR(DMSO-d6,100MHz):169.5,164.1,152.8,149.1,148.1,141.4,133.3,
126.4,122.8,121.0,119.5,118.6,116.8,111.5,115.9,55.9。
Structural formula is as follows：
Oat alkaloid C nuclear magnetic data is as follows：
1H NMR(DMSO-d6):6.47 (1H, d, J=15.5Hz), 6.71 (1H, d, J=8.1Hz), 6.82 (1H, dd, J
=9.0Hz, J=3.0Hz), 6.90 (1H, dd, J=8.1Hz, J=1.8Hz), 7.04 (1H, d, J=1.8Hz), 7.31 (1H,
D, J=3.0Hz), 7.43 (1H, d, J=15.5Hz), 8.40 (1H, d, J=9.0Hz), 9.12 (1H, s), 9.44 (1H, s),
9.56(1H,s),10.77(1H,s),13.46(1H,brs)。
13C NMR(DMSO-d6,100MHz):169.6,164.1,153.0,148.2,146.1,141.5,133.3,
126.5,122.9,121.4,121.3,119.2,119.0,117.0,116.2,114.9。
Structural formula is as follows：
0.5g oat alkaloid As are dissolved in 100mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 4h is stirred with 500rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain gray solid product, dihydro oat alkaloid A.
The nuclear magnetic data of dihydro oat alkaloid A is as follows：
1H NMR(400MHz,DMSO-d6)δ(ppm):13.45(-COOH,br),10.69(-NH),9.57(-OH,br),
9.18 (- OH, br), 8.24 (1H, d), 7.36 (1H, d), 6.98~7.36 (3H, m), 6.68 (2H, d), 2.83 (2H, t),
2.60(2H,m)。
13C NMR(100MHz,DMSO-d6)δ(ppm):170.4,169.6,160.0,152.8,133.1,131.3,
129.6 (2C), 122.6,121.3,118.7,116.9,115.6 (2C), 39.9,30.4.
The structural formula of dihydro oat alkaloid A：
0.3g oat alkaloids B is dissolved in 80mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 4h is stirred with 500rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain brown solid, dihydro oat alkaloid B.
Dihydro oat alkaloid B nuclear magnetic data is as follows：
1H NMR(400MHz,DMSO-d6)δ(ppm):13.05(-COOH,br),10.19(-NH),9.32(-OH,br),
9.02 (- OH, br), 8.93 (1H, d), 7.70 (1H, d), 7.27 (1H, d), 6.71~6.79 (3H, m), 3.83 (3H, s), 2,
90(2H,t),2.84(2H,m)。
13C NMR(100MHz,DMSO-d6)δ(ppm):173.7,169.3,154.0,147.4,145.9,134.8,
133.0,122.9,122.8,122.5,121.3,118.3,115.5,113.2,56.1,35.2,31.4。
Dihydro oat alkaloid B structural formula：
0.4g oat alkaloids C is dissolved in 90mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 4h is stirred with 500rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain brown solid, dihydro oat alkaloid C.
Dihydro oat alkaloid C nuclear magnetic data is as follows：
1H NMR(400MHz,DMSO-d6)δ(ppm):12.35(-COOH,br),10.69(-OH,br),9.46(-OH,
Br), 9.37 (- OH, br), 8,93 (1H, d), 7.70 (1H), 7.36 (1H, d), 7.23 (- NH), 6.68~6.86 (3H, m),
2.90(2H,t),2.84(2H,m)。
13C NMR(100MHz,DMSO-d6)δ(ppm):173.7,169.3,154.0,145.6,144.5,133.4,
134.8,122.9,122.8,122.6,119.6,118.3,116.4,115.9,35.2,31.4.
Dihydro oat alkaloid C structural formula：
0.01mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 30mL is heated to 40 DEG C respectively, led to
Enter nitrogen protection, the sodium hydroxide solution that mass concentration is 10% is added dropwise, neutralized to complete, stir neutralization reaction 0.5h, then will
The rotation of second alcohol and water is evaporated, you can respectively obtains the dihydro oat alkaloid A, B, C sodium salt (derivative) of taupe, dihydro oat
The structural formula of alkaloid A sodium salt：Dihydro oat alkaloid
The structural formula of B sodium salts：Dihydro oat alkaloid C sodium
The structural formula of salt：
0.01mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 30mL is heated to 40 DEG C respectively, led to
Enter nitrogen protection, the zinc hydroxide solution that mass concentration is 10% is added dropwise, neutralized to complete, stir neutralization reaction 0.5h, then will
The rotation of second alcohol and water is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C zinc salt (derivative) of taupe, dihydro oat
The structural formula of alkaloid A zinc salt：Dihydro oat gives birth to
The structural formula of alkaloids B zinc salts：Dihydro oat gives birth to
The structural formula of alkaloids C zinc salts：
The alkaloid A of oat containing dihydro, the nursing lotion of B and C active components are prepared (formula table is as follows)：
At room temperature, after U20 (CARBOPOL ULTREZ 20) is swelled with 1,3-BDO, deionized water is added, is stirred
Mix more than 60min；Start slow heat to 75 DEG C, keep 30min, homogeneous 3 minutes；Start to be cooled to 55~60 DEG C or so；Add
Enter the B phases dissolved, mix slowly 30min；The C phase components dissolved are added, are stirred 60 minutes；Holding mixes slowly, and is down to
Room temperature, complete.
Embodiment 2
The oat bran powder 10kg of 120 mesh is added in 100kg absolute ethyl alcohols, stirs 15h, then stops stirring, is soaked
50h, 55 DEG C are again heated to, and stir 15h, be cooled to after room temperature with the filter bag centrifugal filtration of 350 mesh, obtain filtrate；Will filter
Liquid adds AB-8 resin ethanol gradient elutions, and elution program is：20% column volume of ethanol 10 → 40% ethanol, 10 cylinders
10 column volumes of → 60% ethanol of product → 100% ethanol, 10 column volumes, are concentrated in vacuo under the conditions of 55 DEG C, obtain extract；
By extract in batches by silica gel column chromatography and hydroxypropyl sephadex chromatography (Sephadex LH-20 gel layers), with 1:
1 first alcohol and water at the uniform velocity elutes, you can obtains oat alkaloid A, B, C (oat alkaloid A, B, C structural formula and nuclear magnetic data
It refer to embodiment 1).
0.45g oat alkaloid As are dissolved in 95mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 5h is stirred with 400rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain gray solid product (dihydro oat alkaloid A, its structural formula and nuclear magnetic data refer to embodiment 1).
0.25g oat alkaloids B is dissolved in 75mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 5h is stirred with 400rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain brown solid (dihydro oat alkaloid B, its structural formula and nuclear magnetic data refer to embodiment 1).
0.35g oat alkaloids C is dissolved in 85mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 5h is stirred with 400rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain brown solid (dihydro oat alkaloid C, its structural formula and nuclear magnetic data refer to embodiment 1).
0.005mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 25mL is heated to 50 DEG C respectively, led to
Enter nitrogen protection, the potassium hydroxide solution that mass concentration is 12% is added dropwise, neutralized to complete, stir neutralization reaction 1h, then by second
Alcohol and water rotation is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C sylvite (derivative) of taupe, the life of dihydro oat
The structural formula of alkaloids A sylvite：Dihydro oat alkaloid B
The structural formula of sylvite：Dihydro oat alkaloid C sylvite
Structural formula：
0.005mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 25mL is heated to 50 DEG C respectively, led to
Enter nitrogen protection, the magnesium hydroxide solution that mass concentration is 12% is added dropwise, neutralized to complete, stir neutralization reaction 1h, then by second
Alcohol and water rotation is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C magnesium salts (derivative) of taupe, the life of dihydro oat
The structural formula of alkaloids A magnesium salts：Dihydro oat biology
The structural formula of alkali B magnesium salts：Dihydro oat biology
The structural formula of alkali C magnesium salts：
Embodiment 3
The oat bran powder 8kg of 80 mesh is added in 100kg absolute ethyl alcohols, stirs 10h, then stops stirring, is soaked
45h, 45 DEG C are again heated to, and stir 10h, be cooled to after room temperature with the filter bag centrifugal filtration of 250 mesh, obtain filtrate；Will filter
Liquid adds AB-8 resin ethanol gradient elutions, and elution program is：20% column volume of ethanol 10 → 40% ethanol, 10 cylinders
10 column volumes of → 60% ethanol of product → 100% ethanol, 10 column volumes, are concentrated in vacuo under the conditions of 50 DEG C, obtain extract；
By extract in batches by silica gel column chromatography and hydroxypropyl sephadex chromatography (Sephadex LH-20 gel layers), with 1:
1 first alcohol and water at the uniform velocity elutes, you can obtains oat alkaloid A, B, C (oat alkaloid A, B, C structural formula and nuclear magnetic data
It refer to embodiment 1).
0.55g oat alkaloid As are dissolved in 105mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 3h is stirred with 600rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain gray solid product (dihydro oat alkaloid A, its structural formula and nuclear magnetic data refer to embodiment 1).
0.35g oat alkaloids B is dissolved in 85mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 3h is stirred with 600rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain brown solid (dihydro oat alkaloid B, its structural formula and nuclear magnetic data refer to embodiment 1).
0.45g oat alkaloids C is dissolved in 95mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 3h is stirred with 600rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain brown solid (dihydro oat alkaloid C, its structural formula and nuclear magnetic data refer to embodiment 1).
0.015mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 35mL is heated to 45 DEG C respectively, led to
Enter nitrogen protection, the lithium hydroxide solution that mass concentration is 8% is added dropwise, neutralized to complete, stir neutralization reaction 0.8h, then by second
Alcohol and water rotation is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C lithium salts (derivative) of taupe, the life of dihydro oat
The structural formula of alkaloids A lithium salts：Dihydro oat alkaloid B
The structural formula of lithium salts：Dihydro oat alkaloid C lithium salts
Structural formula：
0.015mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 35mL is heated to 45 DEG C respectively, led to
Enter nitrogen protection, the aqueous ammonium that mass concentration is 8% be added dropwise, neutralized to complete, stir neutralization reaction 0.8h, then by ethanol and
Water rotation is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C ammonium salt (derivative) of taupe, dihydro oat alkaloid
The structural formula of A ammonium salts：Dihydro oat alkaloid B ammonium salts
Structural formula：The structure of dihydro oat alkaloid C ammonium salts
Formula：
Embodiment 4
The oat bran powder 8.2kg of 90 mesh is added in 100kg absolute ethyl alcohols, stirs 13h, then stops stirring, is soaked
48h, 52 DEG C are again heated to, and stir 11h, be cooled to after room temperature with the filter bag centrifugal filtration of 270 mesh, obtain filtrate；Will filter
Liquid adds AB-8 resin ethanol gradient elutions, and elution program is：20% column volume of ethanol 10 → 40% ethanol, 10 cylinders
10 column volumes of → 60% ethanol of product → 100% ethanol, 10 column volumes, are concentrated in vacuo under the conditions of 48 DEG C, obtain extract；
By extract in batches by silica gel column chromatography and hydroxypropyl sephadex chromatography (Sephadex LH-20 gel layers), with 1:
1 first alcohol and water at the uniform velocity elutes, you can obtains oat alkaloid A, B, C (oat alkaloid A, B, C structural formula and nuclear magnetic data
It refer to embodiment 1).
0.52g oat alkaloid As are dissolved in 102mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 4.5h is stirred with 550rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally reacted product is rotated and steamed
Hair, you can obtain gray solid product (dihydro oat alkaloid A, its structural formula and nuclear magnetic data refer to embodiment 1).
0.31g oat alkaloids B is dissolved in 82mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 3.5h is stirred with 550rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally reacted product is rotated and steamed
Hair, you can obtain brown solid (dihydro oat alkaloid B, its structural formula and nuclear magnetic data refer to embodiment 1).
0.39g oat alkaloids C is dissolved in 89mL absolute ethyl alcohols, 0.1g palladium-carbon catalysts are added, in room temperature condition
Under, 3h is stirred with 450rpm stir speed (S.S.), then hydrogen is passed through into mixture, finally by reacted product rotary evaporation,
It can obtain brown solid (dihydro oat alkaloid C, its structural formula and nuclear magnetic data refer to embodiment 1).
0.012mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 30mL is heated to 47 DEG C respectively, led to
Enter nitrogen protection, the aqua calcis that mass concentration is 11% is added dropwise, neutralized to complete, stir neutralization reaction 0.6h, then will
The rotation of second alcohol and water is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C calcium salt (derivative) of taupe, dihydro oat
The structural formula of alkaloid A calcium salt：Dihydro oat gives birth to
The structural formula of alkaloids B calcium salts：Dihydro oat gives birth to
The structural formula of alkaloids C calcium salts：
0.012mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 30mL is heated to 47 DEG C respectively, led to
Enter nitrogen protection, the choline solution that mass concentration is 11% is added dropwise, neutralized to complete, stir neutralization reaction 0.6h, then by ethanol
It is evaporated with water rotation, you can respectively obtain dihydro oat alkaloid A, B, C choline salt (derivative) of taupe.
0.012mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 30mL is heated to 47 DEG C respectively, led to
Enter nitrogen protection, the lysine solution that mass concentration is 11% is added dropwise, neutralized to complete, stir neutralization reaction 0.6h, then by second
Alcohol and water rotation is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C lysine salt (derivative) of taupe.
0.012mol dihydro oat alkaloid A, B and C are dissolved in the absolute ethyl alcohol that 30mL is heated to 47 DEG C respectively, led to
Enter nitrogen protection, the arginine solution that mass concentration is 11% is added dropwise, neutralized to complete, stir neutralization reaction 0.6h, then by second
Alcohol and water rotation is evaporated, you can respectively obtains dihydro oat alkaloid A, B, C arginine salt (derivative) of taupe.
Embodiment 5
The dihydro oat alkaloid A prepared with embodiment 2 prepares itching-relieving cream, composition such as following table：
A phases (oil phase) are heated to 75 DEG C, stir more than 30 minutes；B phases (aqueous phase) are heated to 75 DEG C, stirring 60 minutes with
On；A phases are pumped at a slow speed in B phases, homogeneous 10 minutes, are stirred more than 30 minutes；Enoxolone in C phases is first used into 1,2- pentanediols
Dissolving, after dissolving, Sodium Aescinate and dihydro oat alkaloid A powder are added, is stirred；Deng AB emulsification systems, it is cooled to
55 degree, add C phases, homogeneous 5 minutes；Add the D phases dissolved, homogeneous 1 minute；Chuck leads to cooling water, is cooled at a slow speed
Cream, into cream after complete make.
Embodiment 6
Facial mask liquid, composition such as following table are prepared with the dihydro oat alkaloid A, B, C sodium salt of the preparation of embodiment 1：
Emulsify in pot, be pumped into deionized water, add Sodium Hyaluronate, card ripple 941, at room temperature swelling wetting 45 minutes with
On；75-80 DEG C is heated to, insulated and stirred more than 30 minutes；Oat beta-glucan and amino acid humectant are added, is stirred 15 minutes；
60 DEG C are cooled to, adds triethanolamine, homogeneous 1 minute；Add dihydro oat alkaloid A, B and C sodium salt and water soluble vitamin C phosphorus
Acid esters sodium, stir 15 minutes；After C phased solns are good, after material in pot is cooled to 45 DEG C, add；Stirring 30 minutes, complete system
Make.
Dihydro oat alkaloid A, B, C and the various derivatives provided embodiment 1-4 carries out grinding for antioxidation activity
Study carefully, research method includes the experiment of DPPH Scavenging activities and OH and O2-Scavenging activity is tested.
The method of DPPH Scavenging activities experiment is as follows：2mLDHHP solution is taken, adds the embodiment of the same solvent dissolvings of 2mL
Dihydro oat alkaloid A that 1-4 is provided, B, C and various derivative species it is any, be sufficiently mixed that (control group is vitamin E
Standard items).Its absorbance is determined after 30min at 517nm.DPPH clearance rate is calculated with following formula：K=[1- (Ai-Aj)/Ac]
× 100%, the absorbance of Ai-DPPH+2mL solution to be measured, Ai=2mL in formula；The absorbance of Aj- solution+2mL solvents to be measured
Value, Aj=2mL；The absorbance of Ac-DPPH+2mL solvents, Ac=2mL.
OH and O2-The method difference of Scavenging activity experiment is as follows：Using electron paramagnetic resonance (ESR) free agent for capturing.
By 50mmol/L, pH7.4 phosphate buffer (PBS), 1mmol/L ferrous sulfate amine aqueous solutions, 0.9mol/L DMPO's and 3%
H2O2Each 5 μ L are sequentially added and mixed, and are loaded immediately in quartz capillary.Then additional sample protection testing tube, is put into the lump
Scavenging activity of the measure to OH in ESR spectrometers.
Using ESR Active oxygen radical methods, using DMPO as spin traps.By 50mmol/L, pH7.4 phosphate buffer
(PBS), 1mmol/L xanthine saturated solution, 0.9mol/L DETAPAC solution, 0.9mol/L DMPO and 10% 5U's
Each 5 μ L of xanthine oxidase are sequentially added and mixed, and are loaded immediately in quartz capillary.Then additional sample protection testing tube,
It is put into ESR spectrometers and is determined to O in the lump2-Scavenging activity.
Clearance rate is calculated as follows：I=(ho-hx)/ho × 100%, ho- reference substances OH and O in formula2-Signal is high
Degree；Hx- adds OH and O after sample2-The height of signal；Control group is vitamin E standard items.
Vitamin E standard items reach corresponding concentration IC when 50% to the clearance rate of free radical50Value expression, IC50Value is got over
Small, expression understands that ability is bigger；On the contrary, IC50Value is bigger, then it represents that Scavenging activity is smaller.As a result see the table below.
It can be seen from upper table, the dihydro oat alkaloid A of 1-4 of embodiment of the present invention offer, B, C and various derivatives
Anti-oxidant activity be superior to the vitamin E of comparative example, i.e. dihydro oat alkaloid A of the invention, B, C and its derivative has
Stronger antioxidation activity.
In summary, the dihydro oat alkaloid compound of the embodiment of the present invention, derivative and preparation method thereof and should
Beneficial effect is：The dihydro oat alkaloid compound of the present invention and the derivative of dihydro oat alkaloid compound
Thing has many bioactivity, can be applied to by the active component as cosmetics in skin care item；The dihydro swallow of the present invention
The preparation method of wheat alkaloid compound and derivative can efficiently produce dihydro oat alkaloid compound, and
Working condition is gentle, free from environmental pollution, moreover it is possible to reduces the cost of production.
Embodiments described above is part of the embodiment of the present invention, rather than whole embodiments.The reality of the present invention
The detailed description for applying example is not intended to limit the scope of claimed invention, but is merely representative of the selected implementation of the present invention
Example.Based on the embodiment in the present invention, what those of ordinary skill in the art were obtained under the premise of creative work is not made
Every other embodiment, belongs to the scope of protection of the invention.
Claims (10)
- A kind of 1. dihydro oat alkaloid compound, it is characterised in that the structure of the dihydro oat alkaloid compound Formula isWherein R is in hydrogen, methoxyl group or hydroxyl It is any.
- 2. application of the dihydro oat alkaloid compound as claimed in claim 1 in cosmetics are prepared；Preferably, it is described Cosmetics are with anti-inflammatory, anti-oxidant or itching-relieving action cosmetics；Preferably, the cosmetics include one or more such as Dihydro oat alkaloid compound described in claim 1；Preferably, the cosmetics include two kinds such as claim 1 institute The dihydro oat alkaloid compound stated；Preferably, the cosmetics include three kinds of dihydro oats as claimed in claim 1 Alkaloid compound.
- 3. a kind of cosmetics, it is characterised in that including the dihydro oat alkaloids chemical combination described at least one claim 1 Thing；Preferably, the cosmetics include one or more kinds of dihydro oat alkaloid compounds as claimed in claim 1； Preferably, the cosmetics include two kinds of dihydro oat alkaloid compounds as claimed in claim 1；Preferably, it is described Cosmetics include three kinds of dihydro oat alkaloid compounds as claimed in claim 1.
- A kind of 4. derivative of dihydro oat alkaloid compound, it is characterised in that the dihydro oat alkaloids chemical combination The general structure of the derivative of thing isWherein, R1For hydrogen, Any of methoxyl group or hydroxyl, R2For Na+、K+、Li+、Ca2+、Zn2+、Mg2+、NH4 +, any of choline or amino acid； Preferably, the amino acid is any of lysine and arginine.
- 5. application of the derivative of dihydro oat alkaloid compound as claimed in claim 4 in cosmetics are prepared；It is excellent Selection of land, the cosmetics are with anti-inflammatory, anti-oxidant or itching-relieving action cosmetics；Preferably, the cosmetics include one kind Or the derivative of a variety of dihydro oat alkaloid compounds as claimed in claim 4；Preferably, the cosmetics include The derivative of two kinds of dihydro oat alkaloid compounds as claimed in claim 4；Preferably, the cosmetics include three kinds The derivative of dihydro oat alkaloid compound as claimed in claim 4.
- 6. a kind of cosmetics, it is characterised in that including the dihydro oat alkaloid compound described at least one claim 4 Derivative；Preferably, the cosmetics include one or more kinds of dihydro oat alkaloids as claimed in claim 4 The derivative of compound；Preferably, the cosmetics include two kinds of dihydro oat alkaloid compounds as claimed in claim 4 Derivative；Preferably described cosmetics include spreading out for three kinds of dihydro oat alkaloid compounds as claimed in claim 4 Biology.
- A kind of 7. preparation method of dihydro oat alkaloid compound, it is characterised in that including：Oat alkaloid and palladium-carbon catalyst are made an addition into ethanol, stirs, then passes to hydrogen, then rotary evaporation.
- 8. the preparation method of dihydro oat alkaloid compound according to claim 7, it is characterised in that the stirring Rotating speed be 400-600rpm, time 3-5h.
- 9. the preparation method of dihydro oat alkaloid compound according to claim 7, it is characterised in that the oat The preparation method of alkaloid includes：Oat bran is added in ethanol, stirs 10-15h, then soaks 45-50h, is again heated to 45- 55 DEG C, and 10-15h is stirred, then centrifugal filtration, obtain filtrate；The filtrate is added into polymeric adsorbent ethanol elution, then vacuum Concentration, obtains extract；By the extract chromatography, the method for the chromatography is included the extract in batches Pass through silica gel column chromatography and hydroxypropyl sephadex chromatography.
- 10. a kind of preparation method of the derivative of dihydro oat alkaloid compound, it is characterised in that including by dihydro oat Alkaloid compound is dissolved in ethanol, and nitrogen, then dropwise reaction solution are passed through after addition, is neutralized to complete, described complete Continue to stir after neutralization；Wherein, the reaction solution includes sodium hydroxide solution, potassium hydroxide solution, lithium hydroxide solution, hydrogen Any of calcium oxide solution, zinc hydroxide solution, magnesium hydroxide solution, ammonium water, choline solution and Freamine Ⅲ.
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| CN112315819A (en) * | 2020-11-20 | 2021-02-05 | 烟台新时代健康产业日化有限公司 | Bionic skin lipid membrane compound and application thereof in soothing cosmetics |
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| CN110981925A (en) * | 2019-11-18 | 2020-04-10 | 福州百草堂医药科技有限公司 | Dihydroartemisine D glucoside or salt compound thereof and application thereof in cosmetics |
| CN112315819A (en) * | 2020-11-20 | 2021-02-05 | 烟台新时代健康产业日化有限公司 | Bionic skin lipid membrane compound and application thereof in soothing cosmetics |
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