CN109069456A - Anti-oxidant, anti-inflammatory composition with and application thereof - Google Patents
Anti-oxidant, anti-inflammatory composition with and application thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/191—Carboxylic acids, e.g. valproic acid having two or more hydroxy groups, e.g. gluconic acid
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
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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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/889—Arecaceae, Palmae or Palmaceae (Palm family), e.g. date or coconut palm or palmetto
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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Abstract
Composition and its purposes for being used to enhance anti-oxidant and anti-inflammatory characteristic including oil palm phenols and shikimic acid or its derivative.
Description
Technical field
The present invention relates to the compounds with anti-oxidant and anti-inflammatory cooperative characteristics.More particularly it relates to enhance anti-
The compound of the characteristic of oxidant and anti-inflammatory agent.
Background technique
The normal function of life entity is in particular for the appropriate balance between the formation and elimination of harmful substance.Such as:
Oxidative stress represents the imbalance of damaging oxidation material (such as active oxygen (ROS), active nitrogen (RNS)) level.Biosystem is fast
In fast ground and/or eliminates the scarce capacity of the oxidation material and will lead to harmful modification of cell protein, lipid and DNA.
Oxidative stress and inflammation and metabolic disease, diabetes, obesity, dyslipidemia and the painstaking effort being associated with
The pathogenesis of pipe complication is related.Oxidative stress is also related for example to various diseases and other medical conditions: Ah
Disease, Parkinson disease, rheumatoid arthritis, neurodegenerative disease, bronchitis and high response write from memory (as roared in Wurz sea
Asthma) and some skin diseases such as leucoderma correlation.In addition to pathological conditions, it is believed that oxidative stress also with some agings not
Desired constituents are related.
For inflammation clinical research show acute hyperglycemia cause circulation inflammatory cytokine for example: TNFa, IL6 with
And the increase of IL8 level.In hyperglycemia and/or hyperlipidemia, activity and line grain of the mitochondria by tricarboxylic acids (TCA) circulation
The associated electrical transfer chain of internal film generates cellular energy.Although mitochondria is same however, mitochondria generates a large amount of ATP
Also significant active oxygen (ROS) and active nitrogen (RNS) can be generated.
Cell contains several antioxidases to neutralize ROS and RNS.Although cell there are many available Antioxidation Mechanism,
If ROS is excessive and/or the overload of anti-oxidant approach is likely to damage.
Reducing oxidative stress in many cases, leads to the performance for accelerating disease.In many other cases, oxidation is reduced
It stress perhaps can prevent illness outbreak.
In our Prior efforts, we have delivered the phenol of caffeoyl shikimic acid, P-hydroxybenzoic acid composition
Class antioxidant is such as: oil palm phenols (OPP) has anti-oxidant and anti-inflammatory activity.Such as phenol generalization is had shown in many experiments
Close object compared to many known reproducibility molecules be powerful antioxidant (Bala Balasundram et.al (2005):
“Antioxidant properties of palm fruit extracts”,Asia Pacific Journal of
Clinical Nutrition,14(4),319-324).Gene expression research shows that oil palm phenols has in mammalian cells
There is anti-oxidant and anti-inflammatory effect (Sarnbanthamurthi R.et al. (2013): " OPP attenuate changes
caused by an atherogcnic diet in mice”,European Journal of Nutrition,52(2),
443-456)。
But there is still a need for enhance metabolism by improving inflammation relevant to these diseases and oxidation process in the art
The treatment of property disease.
Summary of the invention
Multiple embodiments of the invention provide a kind of composition, the composition include oil palm phenols and shikimic acid or
Its derivative.
Invention further provides use shikimic acid or its derivative to enhance the anti-oxidation characteristics of antioxidant.
Invention further provides a kind of improvement oxidative stress or the methods of inflammation, including give the effective therapeutic dose of patient
The composition including oil palm phenols and shikimic acid or its derivative.
Improving oxidation using the composition for including shikimic acid and 3- dehydroshikimate invention further provides a kind of
Stress, the application in inflammation or related disease.
Detailed description of the invention
Other purposes, feature and advantage of the present invention are obvious from being described below of reference attached drawing.
Fig. 1 is in cell base NO2 -Scavenging capacity test (Ge Lisi (Griess) test, RAW macrophage, be averaged ±
SE the diagram of the Bioaugnentation effect of the Chemical composition that of the main compound of oil palm phenols in).
Specific embodiment
Referring now to attached drawing, the present invention will be described in detail.
Many embodiments of the invention provide a kind of composition, the composition include oil palm phenols and shikimic acid or
Its derivative.
An embodiment shikimic acid derivative according to the present invention includes 3- dehydroshikimate.
Another embodiment according to the present invention, oil palm phenols are selected from: protocatechuic acid, P-hydroxybenzoic acid, 4- caffeoyl
Shikimic acid, 3- caffeoyl shikimic acid, 5- caffeoyl shikimic acid or its mixture.
Another embodiment according to the present invention, the composition optionally include bioactive compound, which is selected from
Group including following substance, i.e. peptide, minerals, oligosaccharide and its mixture.
An embodiment according to the present invention, the composition further include pharmaceutically acceptable carrier.
According to an embodiment, the composition optionally includes one or more diluents.The non-limiting reality of diluent
Applying example includes glucose, maltodextrin, physiological saline, buffer, water, glycerol and ethyl alcohol.
Composition of the invention includes oil palm phenols, can also include other at least one anti-oxidation stress and/or anti-inflammatory
The component of reagent is such as: drug, quasi drug, food or beverage for the purpose.
Composition of the invention can be configured to any form.Its preparation can be prepared into ejection preparation (true solution, suspension
Agent or emulsion), oral preparation (tablet, capsule, soft capsule, aqua, pill, granule), topical preparation's (ointment
Agent, patch, spray, solution) etc..
According to an embodiment, the composition is used as a kind of skin patch, a kind of skin spraying agent or a kind of nose
Solution, a kind of parenteral solutions local application.
According to an embodiment, the present invention relates to use shikimic acid or its derivative to enhance the antioxygen of antioxidant
Change characteristic.
Another embodiment according to the present invention, the antioxidant are the oil palm phenol selected from the group including following compound
Class, the group of the compound include protocatechuic acid, P-hydroxybenzoic acid, 4- caffeoyl shikimic acid, 3- caffeoyl shikimic acid, 5- coffee
Coffee acyl shikimic acid and its mixture.
According to another embodiment, the present invention relates to use shikimic acid or derivative to enhance the anti-inflammatory spy of anti-inflammatory agent
Property.
Another embodiment according to the present invention, the anti-inflammatory agent are the oil palm phenol selected from the group including following compound
Class, the compound are protocatechuic acid, P-hydroxybenzoic acid, 4- caffeoyl shikimic acid, 3- caffeoyl shikimic acid, 5- caffeoyl thick grass
Acid and its mixture.
According further to another embodiment, the present invention provides a kind of improvement oxidative stress or the methods of inflammation, including
Give the composition described in claim 1 of the effective therapeutic dose of patient.
An embodiment according to the present invention, the composition inhibit nitrite in biosystem.
An embodiment according to the present invention, the composition inhibit ROS (active oxygen) in biosystem.
An embodiment according to the present invention, the composition as skin patch, skin spraying agent or nose solution,
Parenteral solutions local application.
According to an embodiment, the invention further relates to use the composition including shikimic acid and 3- dehydroshikimate
Improving the application in oxidative stress, inflammation or related disease.
Following embodiment is for illustrating certain special characteristics and/or embodiment.These embodiments are not construed as it
Disclosure is limited in the special characteristic or disclosed embodiment.
Embodiment
For convenience, following embodiments will use following abbreviation.
Abbreviation
Protocatechuic acid (P)
P-hydroxybenzoic acid (H)
3- dehydroshikimate (D)
Caffeoyl shikimic acid (C)
4- caffeoyl shikimic acid (4)
3- caffeoyl shikimic acid (3)
5- caffeoyl shikimic acid (5)
Shikimic acid (S)
The Chemical composition that (PH435S) of PH435 and S
The Chemical composition that (PH435D) of PH435 and D
Inhibit NO2 -Mathematics and % (PH435+S)
Inhibit NO2 -Mathematics and % (PH435+D)
Embodiment 1
Nitrous nitrification (sodium nitroprussiate test, SNP test)
SNP aqueous solution spontaneous generation nitric oxide under physiology PH, the nitric oxide and oxygen effect generate can be by lattice
The nitrite ion of this (Griess) agent assessments.
In the test, shikimic acid and 3- dehydroshikimate show the weak effect for inhibiting nitrite ion.
But when a large amount of existing compound P-hydroxybenzoic acid are added in OPP together, which is not shown
Any enhancing.3- dehydroshikimate shows the effect similar with shikimic acid in the chemical system.The result may be due to
The test only measures chemical activity.
It was found that the nitrite that 4 kinds of compositions OPP, PH435, PH435S, PH435D show similar percentage inhibits
Rate, shikimic acid and 3- dehydroshikimate are without any humidification.
Cell base experiment
Embodiment 2
H2O2Measurement (cell base anti-oxidation protection is tested in red blood cell, CAP-e test)
Red blood cell can be used as the cell model for evaluating active oxygen (ROS).Because these cells are in hemocytoblast
Its core of stage disappears, they are unable to transcription and translation to bring the variation of gene and protein level.Therefore, ROS is surveyed
Surely indicate that anti-oxidizing compounds enter the ability of cytosol and the ability of free radical is quenched.
In the method, shikimic acid does not show any effect for reducing ROS.However, other all compounds can be with
Inhibit H202Oxidation.The effect of HCS composition is all larger than H+C+S, and HCD composition, which acts on, is greater than H+C+D, therefore HCS composition and HCD
Composition all has synergistic effect.One interesting phenomenon, Chemical composition that HCS (main compound of OPP) can illustrate to lead to
Cross the ROS inhibiting rate that ON only has 78%.However, 3- dehydroshikimate adds together with H and C, reach pair compared to OPP
The inhibiting rate of ROS93%.The result such as the following table 1:
1 cell base ROS scavenging capacity of table (CAP-e test)
# is according to the concentration of the OPP of 10mg/mL in table come addO-on therapy.
* all data show to count compared to OPP (test of P ﹤ 0.01, Tukey-Kramer loyalty significant difference)
Conspicuousness.
Embodiment 3
H2O2Measurement (cell base anti-oxidation protection is tested in multicore granulocyte, PMN cell tests)
Shikimic acid shows inhibitory activity in two tests in following measurement is anti-inflammatory and antioxidant activity is tested.The measurement is anti-
Scorching and antioxidant activity test are as follows: 1) cell base Ge Lisi (Griess) is tested；2) cell base PMN test and nitrous acid
Salt removes test；3) chemical fundamentals SNP is tested.However it can only enhance in two cell base tests (Griess and PMN)
The anti-inflammatory and antioxidant activity of other components.Activity is not showed since it lacks direct antioxidant activity in RBC cell.
3- dehydroshikimate shows inhibitory activity in three tests in following measurement is anti-inflammatory and antioxidant activity is tested.It should
Measure the test of anti-inflammatory and antioxidant activity are as follows: 1) 2) cell base PMN test 3) cell base for cell base Griess test
CAP-e test and nitrite remove test, and 4) chemical fundamentals SNP is tested.However, only in following Germicidal efficacy to its enhancing effect
Fruit: 1) 2) cell base PMN test 3) cell base CAP-e test 4) chemical fundamentals ORAC survey for cell base Griess test
Examination.
Fig. 1 and table 2 are the synergistic effects of composition in the nitrite scavenging capacity for indicate cell base.
In order to study, composition PH435 is prepared according to the concentration of 800 μ g/mL oil palm phenols (OPP) in table.From Fig. 1 and
Table 2 is (as follows) it can be seen that protocatechuic acid, P-hydroxybenzoic acid, 4- caffeoyl shikimic acid, 3- caffeoyl shikimic acid, 3- caffeoyl
Shikimic acid is much larger than oil palm phenols (OPP) with the nitrite elimination activity of 3- dehydroshikimate and the composition of shikimic acid respectively
Composition.
Table 2
Composition is added according to the concentration of 800 μ g/mL OPP in table.
* using Tukey-Kramer loyalty significant difference test (HSD), all components in addition to PH435S relative to
OPP shows statistical significance (P ﹤ 0.05)).
Existing AMP (Adenosine acid) its part-structure, which can be reasoned out, may is that shikimic acid to show by force
Structure required for change acts on.It is only likely to obtain the structure in cell system.It is also possible in RBC cell, due to
Lack GDH and shikimic acid can not be made to be converted into its activated form 3- dehydroshikimate, but in more granular cells the conversion be can
Can.It is also likely to be the result for the anti-inflammatory and oxidation resistant signal path that shikimic acid combines to activate with other components.
As long as, it is to be understood that without departing from purpose and scope of the present invention carry out various structural modifications and variation or
Various standard/the conventional programs that can be taken all need to be to be understood as included in the scope of the present invention.
Claims (15)
1. a kind of composition includes oil palm phenols and shikimic acid or its derivative.
2. composition according to claim 1, wherein shikimic acid derivative includes 3- dehydroshikimate.
3. composition according to claim 1, wherein oil palm phenols is selected from: protocatechuic acid, P-hydroxybenzoic acid, 4- coffee
Acyl shikimic acid, 3- caffeoyl shikimic acid, 5- caffeoyl shikimic acid or its mixture.
4. composition according to claim 1, wherein the composition optionally includes bioactive compound, the chemical combination
Object is selected from the group including following substance, i.e. peptide, minerals, oligosaccharide and its mixture.
5. composition according to claim 1, further includes pharmaceutically acceptable carrier.
6. composition according to claim 1, wherein the composition is used as skin patch, skin spraying agent or nose
Solution, parenteral solutions local application.
7. a kind of purposes for the anti-oxidation characteristics for enhancing antioxidant with shikimic acid or its derivative.
8. purposes according to claim 8, wherein the antioxidant is the oil palm selected from the group including following compound
Phenols, the group of the compound include protocatechuic acid, P-hydroxybenzoic acid, 4- caffeoyl shikimic acid, 3- caffeoyl shikimic acid, 5-
Caffeoyl shikimic acid and its mixture.
9. a kind of purposes for the anti-inflammatory property for enhancing anti-inflammatory agent with shikimic acid or its derivative.
10. purposes according to claim 10, wherein the anti-inflammatory agent is the oil palm selected from the group including following compound
Phenols, the group of the compound include for protocatechuic acid, P-hydroxybenzoic acid, 4- caffeoyl shikimic acid, 3- caffeoyl shikimic acid,
5- caffeoyl shikimic acid and its mixture.
11. a kind of method for improving oxidative stress or inflammation, including giving the described in claim 1 of bacterium
Composition.
12. according to the method for claim 12, wherein the composition inhibits nitrite in biosystem.
13. according to the method for claim 12, wherein the composition inhibits ROS (active oxygen) in biosystem.
14. according to the method for claim 12, the composition is as skin patch, skin spraying agent or nose with molten
Vena axillaris injects solution local application.
15. using including the composition of shikimic acid and 3- dehydroshikimate in improving oxidative stress, inflammation or related disease
Application.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2017/000237 WO2018165780A1 (en) | 2017-03-17 | 2017-03-17 | Antioxidant, anti-inflammatory compositions and uses thereof |
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| CN109069456A true CN109069456A (en) | 2018-12-21 |
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| CN201780000807.7A Pending CN109069456A (en) | 2017-03-17 | 2017-03-17 | Anti-oxidant, anti-inflammatory composition with and application thereof |
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| WO (1) | WO2018165780A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109620820A (en) * | 2019-01-30 | 2019-04-16 | 桂林医学院 | Application of the P-hydroxybenzoic acid in preparation treatment inflammatory bowel medicine |
| CN111840266A (en) * | 2019-12-09 | 2020-10-30 | 桂林医学院 | Application of sodium p-hydroxybenzoate in preparing medicine for treating or preventing inflammatory bowel disease |
| CN114867533A (en) * | 2019-10-16 | 2022-08-05 | 美斯蒂克制药集团有限公司 | Cosmetic composition and use thereof |
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| CN102448925A (en) * | 2009-05-26 | 2012-05-09 | 马来西亚棕榈油协会 | Composition comprising caffeoylshikimic acids, protocatechuic acid, hydroxytyrosol, hydroxybenzoic acid and their derivatives and method of preparation thereof |
| WO2012067491A2 (en) * | 2010-11-16 | 2012-05-24 | Malaysian Palm Oil Board | Compositions comprising extracts obtained from oil palm based materials for providing anti -inflammatory effects and method of producing thereof |
| CN103097334A (en) * | 2010-06-16 | 2013-05-08 | 马来西亚棕榈油协会 | Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof |
| WO2014129884A2 (en) * | 2013-02-21 | 2014-08-28 | Malaysian Palm Oil Board | Composition with inhibitory effect on viral integrase activity |
| CN109152807A (en) * | 2015-12-31 | 2019-01-04 | 马来西亚棕榈油委员会 | Oil palm phenol component for protecting human body, organ, cell and tissue to influence from being exposed to the damaging of ionising radiation |
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| EP2953639B1 (en) * | 2013-02-06 | 2021-06-02 | Brandeis University | Treatment of dna damage and mitochondrial dysfunction using palm fruit juice |
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Cited By (4)
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|---|---|---|---|---|
| CN109620820A (en) * | 2019-01-30 | 2019-04-16 | 桂林医学院 | Application of the P-hydroxybenzoic acid in preparation treatment inflammatory bowel medicine |
| CN109620820B (en) * | 2019-01-30 | 2021-03-30 | 桂林医学院 | Application of p-hydroxybenzoic acid in preparing medicine for treating inflammatory bowel disease |
| CN114867533A (en) * | 2019-10-16 | 2022-08-05 | 美斯蒂克制药集团有限公司 | Cosmetic composition and use thereof |
| CN111840266A (en) * | 2019-12-09 | 2020-10-30 | 桂林医学院 | Application of sodium p-hydroxybenzoate in preparing medicine for treating or preventing inflammatory bowel disease |
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| Publication number | Publication date |
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| WO2018165780A1 (en) | 2018-09-20 |
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Application publication date: 20181221 |