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CN113896702A - Quercetin-3-derivative and application thereof - Google Patents

Quercetin-3-derivative and application thereof Download PDF

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Publication number
CN113896702A
CN113896702A CN202111272595.2A CN202111272595A CN113896702A CN 113896702 A CN113896702 A CN 113896702A CN 202111272595 A CN202111272595 A CN 202111272595A CN 113896702 A CN113896702 A CN 113896702A
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Prior art keywords
quercetagetin
hydroxyl
quercetin
reaction
derivative
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程帅
赵剑
宋伟光
赵鹏宇
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Chenguang Biotech Group Co Ltd
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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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention provides a quercetagetin-3-derivative and application thereof. A quercetin-3-derivative has a structure shown in general formula (I), wherein R is1Is any group. The invention modifies the C-3 hydroxyl of the quercetagetin, and can achieve the purpose of optimizing the physicochemical property and the biological activity of the quercetagetin on the premise that the activity, such as the inoxidizability, is not influenced, thereby further widening the application scene of the quercetagetin and expanding the application range of the quercetagetin.

Description

Quercetin-3-derivative and application thereof
Technical Field
The invention relates to the technical field of chemistry, in particular to a quercetagetin-3-derivative and application thereof.
Background
Flavones are a class of polyhydroxyl phenolics widely found in plants. They have a certain content in the leaves, wood, bark, shell and pulp of plant, and the epidermis of fruit and grain contains high plant polyphenol. Researches show that the flavonoids have good biological activity, such as antioxidant, anti-inflammatory, antiallergic, hypotensive, antiarrhythmic, antitumor and other efficacies. The quercetagetin is the main component of marigold dregs generated after the lutein is extracted from marigold flowers, has the chemical name of 3,5,6,7,3 ', 4' -hexahydroxyflavone, has the structure close to that of the quercetagetin, has one more hydroxyl group on the C-6 position than the quercetagetin, and has good biological activity.
Due to the existence of a plurality of hydroxyl structures of the quercetagetin, the lipid solubility and the water solubility of the quercetagetin are low, so that the application of the quercetagetin is limited, and the effective antioxidant concentration threshold is difficult to reach. In addition, the lower fat solubility also causes that the quercetagetin molecules are not easy to permeate a cell membrane lipid bilayer, so that the bioavailability is lower, and the lower water solubility can limit the application of the quercetagetin molecules in various aspects such as beverages, animal drinking water and the like.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention researches and provides a quercetagetin-3-derivative and an application thereof, wherein the C-3 hydroxyl of the quercetagetin is modified, so that the activity of the quercetagetin is considered, and simultaneously, the purpose of optimizing the physicochemical property and the biological activity of the quercetagetin can be achieved.
The invention provides a quercetagetin-3-derivative, the structure of which is shown as the general formula (I):
Figure BDA0003329193750000021
wherein R is1Is any group.
Preferably, R1Is alkyl or heterocyclic radical.
Specifically, the "alkyl group" as referred to herein means a straight-chain and branched-chain and cyclic hydrocarbon group having 1 to 22 carbon atoms, for example, a C12-22 straight-chain or straight-chain alkyl group, further preferably an n-undecyl group, an n-tridecyl group, an n-pentadecyl group, an n-heptadecyl group, an n-nonadecyl group, an n-heneicosyl group or the like, or a substituted alkyl group such as a carboxyalkyl group.
The "heterocyclic group" according to the present invention is a heterocyclic group consisting of 3 to 8 atoms and means a monovalent or polyvalent, saturated or partially unsaturated, nonaromatic monocyclic ring containing 3 to 8 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, sulfur and oxygenAn atom. Unless otherwise specified, a heterocyclic group of 3 to 8 atoms may be carbon-based or nitrogen-based, and-CH2-the group may optionally be replaced by-C (═ O) -. The sulfur atom of the ring may optionally be oxidized to the S-oxide. The nitrogen atom of the ring may optionally be oxidized to an N-oxygen compound. For example, glucosyl, piperazinyl, C1-C6 substituted piperazinyl, such as methylpiperazinyl, ethylpiperazinyl and the like.
The invention provides a preparation method of the quercetagetin-3-derivative, which comprises the following steps:
1) carrying out selective hydroxyl protection reaction on quercetagetin and a hydroxyl protective agent to obtain a 3 ', 4', 6,7 hydroxyl protective compound;
2) under the action of an acid-binding agent, the 3 ', 4', 6,7 hydroxyl protecting compound and an acylating agent are subjected to acylation reaction to obtain a 3-ester-3 ', 4', 6,7 hydroxyl protecting compound;
3) and carrying out selective hydroxyl deprotection reaction on the 3-ester-3 ', 4', 6,7 hydroxyl protecting compound and a hydroxyl deprotection agent to obtain the target compound.
Specifically, in the step 1), the selective hydroxyl protection reaction is carried out in the absence of a solvent, and dichlorodiphenylmethane is used as a hydroxyl protective agent. After extensive research, the inventors found that the hydroxyl protecting agent can selectively react with the 3 ', 4' -hydroxyl and the 6, 7-hydroxyl of quercetagetin, and further protect the 3 ', 4' -hydroxyl and the 6, 7-hydroxyl, so that the C-3 hydroxyl can be more efficiently acylated with an acylating agent, thereby improving the yield of the target product.
And/or, the molar ratio of the quercetagetin to the hydroxyl protective agent is 1: (2-10).
And/or the temperature of the selective hydroxyl protection reaction is 20-200 ℃, preferably 80-100 ℃.
In the step 2), the acid binding agent is selected from one or more of tertiary ammonium, pyridine, DMAP and inorganic alkali.
And/or the acylating agent is R1COX, wherein R1Is as defined in claim 1, wherein R is in the formula (I)1In the definition of (1), X is halogen.
And/or the molar ratio of the 3 ', 4', 6,7 hydroxyl protecting compound to the acylating agent to the acid binding agent is 1: (1.5-3): (1.5-3).
And/or the temperature of the acylation reaction is 0-40 ℃.
And/or, the acylation reaction is carried out in the presence of an organic solvent, wherein the organic solvent is one or more selected from dichloromethane, DMF, THT, ethyl acetate, acetonitrile and acetone.
In the step 3), the hydroxyl deprotection agent is selected from one or more of hydrochloric acid, phosphoric acid, trifluoroacetic acid, glacial acetic acid and amino acid.
And/or, the temperature of the selective hydroxyl deprotection reaction is 0-100 ℃.
And/or, the selective hydroxyl deprotection reaction is carried out in the presence of a solvent, wherein the solvent is selected from one or more of tetrahydrofuran, DMF, dichloromethane, methanol, ethanol, ethyl acetate, acetone and water.
And/or the mass volume ratio of the 3-ester-3 ', 4', 6,7 hydroxyl protecting compound, the hydroxyl deprotection agent and the organic solvent is 1 g: (2-100) ml: (2-100) ml.
The invention also provides application of the quercetagetin-3-derivative in preparing functional food.
The invention also provides the application of the quercetagetin-3-derivative in preparing medicines.
The invention also provides application of the quercetagetin-3-derivative in preparing a feed additive.
Based on the scheme, the invention has the following beneficial effects:
the invention modifies the C-3 hydroxyl of the quercetagetin, and can achieve the purpose of optimizing the physicochemical property and the biological activity of the quercetagetin on the premise that the activity, such as the inoxidizability, is not influenced, thereby further widening the application scene of the quercetagetin and expanding the application range of the quercetagetin.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The following examples and comparative examples do not indicate any particular technique or condition, and are carried out according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or instruments used are conventional products available from regular distributors, not indicated by the manufacturer.
Example 1
Adding quercetin (32mg) and dichlorodiphenylmethane (90mg) into a 0.5ml glass reaction bottle, stirring at 90 ℃ for reaction for 12h, cooling to room temperature, adjusting to neutral with sodium bicarbonate aqueous solution, extracting with ethyl acetate and concentrating under reduced pressure, dissolving the obtained product in 0.5ml dichloromethane, adding palmitoyl chloride (45 muL) and triethylamine (20 muL), reacting at room temperature for 4h, adding glacial acetic acid (0.5ml) after the reaction is finished, refluxing for reaction for 12h, extracting with ethyl acetate after the reaction is finished, crystallizing with dichloromethane after the concentration, filtering and washing to obtain the marigold-3-palmitate (40mg), wherein the yield is 71%.
Marigold-3-palmitate nuclear magnetic data:
1HNMR(DMSO-d6):δ12.04(s,1H),10.68(br,1H),9.84(br,1H),9.50(br,1H),8.90(br,1H),7.30(d,J＝2.0Hz,1H),7.23(dd,J＝8.3,2.0Hz,1H),6.89(d,J＝8.3Hz,1H),6.56(s,1H),2.62(t,J＝7.4,2H),1.62(m,2H),1.22(m,24H),0.83(m,3H)。
13C NMR(DMSO-d6):175.059,170.612,155.738,153.922,149.095,149.051,146.397,145.457,129.387,129.168,120.368,119.886,115.854,114.957,103.787,93.908,33.142,31.312,29.073,29.044,28.950,28.862,28.738,28.643,28.293,24.327,22.118,13.959ppm。
the mass spectrum showed the composition as reduced hydrogen molecular ion peak 555.28.
Fat-soluble measurement:
at 20 ℃, the solubilities of the quercetagetin and the quercetagetin-3-palmitate in the soybean oil are respectively 10 mu g/ml and 500 mu g/ml, and compared with the quercetagetin, the lipid solubility of the quercetagetin-3-palmitate is improved by 50 times.
Determination of DPPH radical scavenging Capacity:
preparing 2 x 10 by using absolute ethyl alcohol-4A solution of DPPH in mol/L,preparing a sample solution of quercetagetin-3-palmitate, taking 2ml of DPPH solution and the sample solution, reacting at 30 ℃ in a dark place for 30min, testing absorbance at 519nm, and calculating half clearance rate, wherein the free radical DPPH clearance capacity is measured, tert-butyl hydroquinone (TBHQ) and quercetagetin are used as positive control, wherein IC of quercetagetin-3-palmitate is used as the positive control50A value of 18.74. mu. mol/ml; IC of TBHQ50A value of 34.53. mu. mol/ml; IC of quercetol marigold50The value was 17.57. mu. mol/ml, and the results showed that: the quercetagetin-3-palmitate has excellent free radical scavenging ability, and the 3-position substitution does not affect the free radical scavenging ability of the quercetagetin.
Example 2
Adding quercetagetin (32mg) and dichlorodiphenylmethane (90mg) into a 0.5ml glass reaction bottle, stirring and reacting at 90 ℃ for 12h, cooling to room temperature, adjusting to neutral with sodium bicarbonate water solution, extracting with ethyl acetate and concentrating under reduced pressure, dissolving the obtained product in 0.5ml dichloromethane, adding 4-methylpiperazine-1-formyl chloride (20mg) and triethylamine (20 μ L), reacting at room temperature for 4h, adding 250 μ L ethyl acetate and 250 μ L glacial acetic acid after the reaction is finished, reacting for 4h, extracting with ethyl acetate after the reaction is finished, crystallizing with dichloromethane after the concentration, filtering and washing to obtain quercetagetin 3-methylpiperazine (35.5mg) with the yield of 80%.
The mass spectrum showed the composition as reduced hydrogen molecular ion peak 443.12.
And (3) water solubility determination:
at 25 ℃, the solubilities of the quercetagetin and the quercetagetin 3-methylpiperazine in water are respectively 0.6mg/ml and 35mg/ml, and compared with the quercetagetin, the water solubility of the quercetagetin 3-methylpiperazine is improved by 58 times.
The radical DPPH scavenging ability of quercetagetin 3-methylpiperazine was measured according to the method described in example 1, and IC thereof50The value is 17.37 mu mol/ml, which is equivalent to the scavenging ability of the quercetagetin, and the result shows that the 3-position substitution does not influence the scavenging ability of the quercetagetin.
Example 3
Adding quercetagetin (32mg) into dichlorodiphenylmethane (90mg), stirring at 90 deg.C for reaction for 5 hr, cooling to room temperature, adding 0.5ml dichloromethane into the system for dilution and dissolution, then adding triethylamine (20 μ L) and malonyl chloride (50 μ L), reacting at room temperature for 2 hr, adding water (0.5ml) for hydrolysis for 1 hr, extracting with 0.5ml dichloromethane, adding trifluoroacetic acid (0.5ml) into dichloromethane, reacting at 25 deg.C for 4 hr, purifying the product with silica gel to obtain queretagetin 3-methyl acetate 30mg, yield 73.8%.
The mass spectrum showed the composition as reduced hydrogen molecular ion peak 403.0.
And (3) water solubility determination:
at 25 deg.C, the solubility of quercetagetin 3-propionic acid in water is 15 mg/ml.
Determination of DPPH radical scavenging Capacity:
the radical DPPH scavenging ability of quercetagetin 3-methylacetic acid was measured according to the method described in example 1, and IC thereof50The value was 19.42. mu. mol/ml.
Comparative example 1
Adding quercetagetin (32mg), palmitoyl chloride (45 μ L) and triethylamine (20 μ L) into ethyl acetate (1ml), reacting at room temperature for 4h, adding ethyl acetate and water into the reaction solution, extracting, drying ethyl acetate phase, spin-drying, and separating with silica gel, wherein the mobile phase is petroleum ether: ethyl acetate: the yield of 33mg of non-site-specific substituted quercetagetin palmitate was 58.6% with ethanol 15:5:1, and mass spectrometric detection showed that the ingredient was a hydrogen-reducing molecular ion peak 555.28.
Fat-soluble measurement:
the solubility of non-site-specific substituted quercetagetin palmitate in soybean oil was 550. mu.g/ml at 20 ℃.
The radical DPPH scavenging ability of non-site-specific substituted quercetin marigold palmitate was measured according to the method described in example 1, and the IC thereof was determined50The value was 27.42. mu. mol/ml. And (3) displaying data: the hydroxyl substitution on the A-ring and B-ring of quercetagetin results in a decrease in the radical scavenging ability of queretagetin.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.

Claims (10)

1. A quercetagetin-3-derivative is characterized in that the structure is shown as a general formula (I):
Figure FDA0003329193740000011
wherein R is1Is any group.
2. The quercetin marigold-3-derivative according to claim 1, wherein R is1Is alkyl or heterocyclic radical.
3. The quercetin marigold-3-derivative according to claim 1 or 2, wherein R is1Is a substituted or unsubstituted C1-C22 straight or branched chain alkyl.
4. The quercetin marigold-3-derivative according to claim 1 or 2, wherein R is1Is glucosyl, piperazinyl, or C1-C6 substituted piperazinyl.
5. A method of preparing the quercetagetin-3-derivative as defined in any one of claims 1 to 4, comprising the steps of:
1) carrying out selective hydroxyl protection reaction on quercetagetin and a hydroxyl protective agent to obtain a 3 ', 4', 6,7 hydroxyl protective compound;
2) under the action of an acid-binding agent, the 3 ', 4', 6,7 hydroxyl protecting compound and an acylating agent are subjected to acylation reaction to obtain a 3-ester-3 ', 4', 6,7 hydroxyl protecting compound;
3) and carrying out selective hydroxyl deprotection reaction on the 3-ester-3 ', 4', 6,7 hydroxyl protecting compound and a hydroxyl deprotection agent to obtain the target compound.
6. The method of claim 5, wherein the selective hydroxy-protecting reaction is performed in the absence of a solvent in step 1) and dichlorodiphenylmethane is used as a hydroxy-protecting agent.
7. The method for preparing quercetagetin-3-derivative according to claim 5 or 6, wherein the temperature of the selective hydroxy-protecting reaction is 20-200 ℃, preferably 80-100 ℃.
8. Use of the quercetin-3-derivative according to any one of claims 1 to 4 for the preparation of a functional food.
9. Use of the quercetin marigold-3-derivative according to any one of claims 1 to 4 for the preparation of a medicament.
10. Use of the quercetin marigold-3-derivative according to any one of claims 1 to 4 for the preparation of a feed additive.
CN202111272595.2A 2021-10-29 2021-10-29 Quercetin-3-derivative and application thereof Pending CN113896702A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819390A (en) * 2022-10-28 2023-03-21 晨光生物科技集团股份有限公司 Preparation method of quercetagetin fat-soluble derivative

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819390A (en) * 2022-10-28 2023-03-21 晨光生物科技集团股份有限公司 Preparation method of quercetagetin fat-soluble derivative
CN115819390B (en) * 2022-10-28 2024-06-14 晨光生物科技集团股份有限公司 Preparation method of quercetin marigold fat-soluble derivative

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