WO2020042250A1 - 一种查尔酮类化合物及其制备方法 - Google Patents

一种查尔酮类化合物及其制备方法 Download PDF

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WO2020042250A1
WO2020042250A1 PCT/CN2018/106841 CN2018106841W WO2020042250A1 WO 2020042250 A1 WO2020042250 A1 WO 2020042250A1 CN 2018106841 W CN2018106841 W CN 2018106841W WO 2020042250 A1 WO2020042250 A1 WO 2020042250A1
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methanol
water
extract
chalcone
tetrahydroxy
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French (fr)
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杨宝
蒋跃明
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中国科学院华南植物园
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Priority to US16/626,906 priority Critical patent/US11186533B2/en
Publication of WO2020042250A1 publication Critical patent/WO2020042250A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the invention relates to the field of natural product chemistry, in particular to a chalcone compound and a preparation method thereof.
  • Mulberry belongs to the mulberry evergreen tree and is widely planted in tropical and subtropical areas.
  • Mulberry fruit is sweet and delicious, has high nutritional value and health care function, and has the effects of treating white hair and anti-inflammatory, and is deeply loved by consumers.
  • Mulberry leaf is a new resource vegetable food with a fresh taste and has gradually been accepted by consumers.
  • Studies have found that mulberry leaves are rich in flavonoids and have biological activities such as anti-oxidation, anti-cancer and immune regulation.
  • the current research on the active ingredients of mulberry leaves is extremely limited, and the composition of related active substances remains to be studied.
  • the purpose of the present invention is to provide a method for preparing chalcones, specifically 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -Alkenyl) chalcone preparation method.
  • the method for preparing 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -alkenyl) chalcone includes the following steps: Mulberry leaves are extracted by a fraction of 40 to 100% methanol or ethanol aqueous solution, the extract is concentrated to remove methanol or ethanol, and then dissolved in water, followed by extraction with petroleum ether and ethyl acetate in order, and the ethyl acetate extract is concentrated to obtain an extract.
  • the paste was subjected to silica gel column chromatography, using chloroform / methanol as eluent, and eluting from a volume ratio of 100/0 to 60/40.
  • the mulberry leaf is mulberry leaf powder, which is obtained by drying fresh mulberry leaf and pulverizing it into powder.
  • the mulberry leaf is leached with a volume fraction of 40 to 100% methanol or ethanol aqueous solution.
  • the amount of the methanol or ethanol aqueous solution is 5 to 20 mL / g mulberry leaf (that is, 5-20 ml of methanol or ethanol aqueous solution per gram of mulberry leaf).
  • the extraction temperature is 25 to 80 ° C, and the extraction time is 1 to 72 hours.
  • the method of condensing the extract solution to remove methanol or ethanol is to dissolve the extract solution by concentrating the extract solution at 40 to 80 ° C to remove methanol or ethanol, and then adding 1 to 5 times the volume of water to dissolve the extract.
  • the sequential extraction with petroleum ether and ethyl acetate is firstly extracted with petroleum ether 3-12 times, and then with ethyl acetate 3-12 times.
  • the invention confirms that the compound 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -alkenyl) chalcone has good freedom Base scavenging ability, the IC 50 value of the compound for DPPH free radical scavenging is 21.6 ⁇ M. It indicates that the compound 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -formaldehyde) provided by the present invention Butyl-3 ′′ -alkenyl) chalcone has excellent antioxidant properties and can be used to prepare antioxidant skin care products, medicines or health products.
  • 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -alkenyl) chalcone is prepared and isolated from mulberry leaves.
  • the compound The yield is 10 to 120 mg / kg (purity 85 to 95%).
  • the present invention is of great significance for promoting the deep processing and utilization of mulberry leaves, enhancing the added value of mulberry leaves products, and promoting the sustainable development of the industry.
  • a new method for the preparation of 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -alkenyl) chalcone is provided.
  • Drying and pulverizing drying or drying mulberry leaves and pulverizing them into powder with a pulverizer
  • the components eluted with a volume ratio of chloroform / methanol of 95/5 were collected, and then subjected to C18 reversed-phase column chromatography, using methanol / water as an eluent, and eluted from a volume ratio of 10/90 to 100/0, and collected
  • the component eluting with a methanol / water volume ratio of 60/40 was evaporated to dryness at 60 ° C to obtain compound 1 (2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -Methylbutyl-3 "-alkenyl) chalcone).
  • Drying and pulverizing drying or drying mulberry leaves and pulverizing them into powder with a pulverizer
  • the yield of 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -alkenyl) chalcone obtained by this method is 70-120 mg / kg, purity is 85-95%.
  • Drying and pulverizing drying or drying mulberry leaves and pulverizing them into powder with a pulverizer
  • Drying and pulverizing drying or drying mulberry leaves and pulverizing them into powder with a pulverizer
  • the yield of 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -alkenyl) chalcone obtained by this method is 50-100 mg / kg, purity is 85-95%.
  • DPPH is a stable long-lived free radical.
  • a free radical scavenger When a free radical scavenger is present, DPPH light absorption is weakened due to its single-electron pairing, thereby evaluating the ability of the substance to scavenge free radicals, and thereby assessing its antioxidant capacity.
  • the DPPH radical neutralization test is used to determine the absorbance and detect the compound 2,2 ', 4,4'-tetrahydroxy-3- (2 ′′ -hydroxy-3 ′′ -methylbutyl-3 ′′ -alkenyl) Chalcone's ability to scavenge DPPH free radicals to evaluate the antioxidant capacity of the compound, the test method specifically includes the following steps:

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Abstract

一种制备2,2',4,4'-四羟基-3-(2"-羟基-3"-甲基丁基-3"-烯基)查尔酮的方法，该方法的步骤为：用体积分数40～100％甲醇或乙醇水溶液浸提桑叶，将浸提液浓缩去除甲醇或乙醇后用水溶解，然后依次用石油醚、乙酸乙酯萃取，将乙酸乙酯萃取液浓缩得浸膏，浸膏经硅胶柱层析，以氯仿/甲醇为洗脱剂，收集氯仿/甲醇体积比为95/5洗脱的馏分，该馏分再经反相柱层析，以甲醇/水为洗脱剂，收集甲醇/水体积比为60/40洗脱的馏分，即得。本发明对于推动桑叶的深加工利用，提升桑叶产品附加值，促进该行业的可持续发展具有重要的意义。

Description

一种查尔酮类化合物及其制备方法 技术领域
本发明涉及天然产物化学领域，具体涉及一种查尔酮类化合物及其制备方法。
背景技术
桑树属于桑科常绿乔木，广泛种植于热带与亚热带地区。桑椹果实香甜可口，营养价值和保健功能较高，具有治疗白发、消炎等功效，深受广大消费者的喜爱。桑叶属于新资源蔬菜食品，口感鲜嫩，已逐渐为消费者所接受。研究发现，桑叶富含黄酮类化合物，具有抗氧化、抗癌、调节免疫等生物活性。然而，目前关于桑叶活性成分的研究极为有限，相关活性物质组成仍有待研究。
发明内容
本发明的目的是提供一种查尔酮类化合物的制备方法，具体为2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的制备方法。
本发明的2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮，该化合物是从桑叶中提取分离得到，其结构式如下式(I)所示：
Figure PCTCN2018106841-appb-000001
所述的2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的制备方法包括以下步骤：用体积分数40～100％甲醇或乙醇水溶液浸提桑叶，将浸提液浓缩去除甲醇或乙醇后用水溶解，然后依次用石油醚、乙酸乙酯萃取，将乙酸乙酯萃取液浓缩得浸膏，浸膏经硅胶柱层析，以氯仿/甲醇为洗脱剂，从体积比100/0～60/40梯度洗脱，收集氯仿/甲醇体积比为95/5洗脱的馏分，该馏分再经反 相柱层析，以甲醇/水为洗脱剂，从体积比10/90～100/0梯度洗脱，收集甲醇/水体积比为60/40洗脱的馏分，即得到2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮。
所述的桑叶为桑叶粉末，其是将新鲜的桑叶干燥后粉碎成粉末。
所述的用体积分数40～100％甲醇或乙醇水溶液浸提桑叶，甲醇或乙醇水溶液的用量是5～20mL/g桑叶(即每克桑叶用5-20ml甲醇或乙醇水溶液)，浸提的温度为25～80℃，浸提时间为1～72小时。
所述的将浸提液浓缩去除甲醇或乙醇后用水溶解，是将浸提液在40～80℃下浓缩除去甲醇或乙醇，再加入1～5倍体积的水溶解。
所述的依次用石油醚、乙酸乙酯萃取，是先用石油醚萃取3～12次，再用乙酸乙酯萃取3～12次。
本发明证实，所述的化合物2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮具有良好的自由基清除能力，该化合物对DPPH自由基清除的IC 50值为21.6μM。表明本发明提供的化合物2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮具有优异的抗氧化性能，可用于制备抗氧化护肤品、药品或保健品。
与现有技术相比，本发明的优势在于：
本发明从桑叶中制备分离得到2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮，该化合物的产率为10～120mg/kg(纯度为85～95％)。本发明对于推动桑叶的深加工利用，提升桑叶产品附加值，促进该行业的可持续发展具有重要的意义。同时也为2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的制备提供了一种新的方法。
具体实施方式
以下实施例是对本发明的进一步说明，而不是对本发明的限制。
实施例1
一、2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的制备分离
1)选料：选择新鲜桑叶，清水洗涤；
2)干燥粉碎：将桑叶晒干或烘干，采用粉碎机粉碎成粉末；
3)浸提：按5mL/g桑叶粉末的投料量(即每克桑叶粉末加5mL甲醇水溶液)， 往桑叶粉末中加入体积分数40％的甲醇水溶液，在25℃浸提1小时，过滤，收集过滤液；
4)有机溶剂分级：将上述过滤液在40℃下浓缩除去甲醇，得浓缩液，加入浓缩液1倍体积的水，先后用等体积的石油醚、乙酸乙酯分别萃取3次；选择乙酸乙酯相萃取液进行浓缩，将得到的浸膏用于后续纯化；
5)取乙酸乙酯相萃取液浓缩后得到的浸膏，采用硅胶柱(100～200目)层析，以氯仿/甲醇为洗脱溶剂，从体积比100/0～60/40梯度洗脱，收集氯仿/甲醇体积比为95/5洗脱的组分，再经C18反相柱层析，以甲醇/水为洗脱剂，从体积比10/90～100/0梯度洗脱，收集甲醇/水体积比为60/40洗脱的组分，在60℃蒸发浓缩干燥，即得到化合物1(2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮)。
采用该方法获得的2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的产率为10～40mg/kg，纯度为85～95％。
二、化合物1(2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮)的结构鉴定
化合物1(2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮)易溶于甲醇，质谱结果表明：该化合物分子量为564。该化合物的 1H NMR(500MHz，CD 3OD)和 13C NMR(125MHz，CD 3OD)见表1。
表1化合物1的 13C与 1H谱化学位移
位置 1H 13C
1   115.8
2   163.2
3 6.33 103.8
4   163.1
5 6.35 109.3
6 7.50 132.5
1'   114.3
2'   165.7
3'   118.1
4'   160.9
5' 6.40 109.4
6' 7.77 131.0
1″ 2.88,3.05 30.2
2″ 4.37 77.0
3″   149.1
4″ 4.71,4.82 110.9
5″ 1.83 18.1
α 7.71 118.0
β 8.07 141.8
羰基   194.6
综上所述，鉴定该化合物1的结构式如式(I)所示，名称为：2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮，该化合物易溶于甲醇。
Figure PCTCN2018106841-appb-000002
实施例2
1)选料：选择新鲜桑叶，清水洗涤；
2)干燥粉碎：将桑叶晒干或烘干，采用粉碎机粉碎成粉末；
3)浸提：按20mL/g桑叶粉末的投料量(即每克桑叶粉末加20mL甲醇水溶液)，往桑叶粉末中加入体积分数100％的甲醇水溶液(即完全是甲醇)，在80℃浸提72小时，过滤，收集过滤液；
4)有机溶剂分级：将上述过滤液在60℃浓缩除去甲醇，得浓缩液，加入浓缩液5倍体积的水，先后用等体积的石油醚、乙酸乙酯分别萃取12次；选择乙 酸乙酯相萃取液进行浓缩，将得到的浸膏用于后续纯化；
后续纯化步骤与实施例1相同，由此得到化合物1并鉴定为2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮。
采用该方法获得的2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的产率为70～120mg/kg，纯度为85～95％。
实施例3
1)选料：选择新鲜桑叶，清水洗涤；
2)干燥粉碎：将桑叶晒干或烘干，采用粉碎机粉碎成粉末；
3)浸提：按20mL/g桑叶粉末的投料量(即每克桑叶粉末加20mL乙醇水溶液)，往桑叶粉末中加入体积分数40％的乙醇水溶液，在55℃浸提24小时，过滤，收集过滤液；
4)有机溶剂分级：将上述过滤液在60℃浓缩除去乙醇，得浓缩液，加入浓缩液3倍体积的水，先后用等体积的石油醚、乙酸乙酯分别萃取6次；选择乙酸乙酯相萃取液进行浓缩，将得到的浸膏用于后续纯化；
后续纯化步骤与实施例1相同，得到化合物1并鉴定为2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮。
采用该方法获得的2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的产率为30～80mg/kg，纯度为85～95％。
实施例4
1)选料：选择新鲜桑叶，清水洗涤；
2)干燥粉碎：将桑叶晒干或烘干，采用粉碎机粉碎成粉末；
3)浸提：按5mL/g桑叶粉末的投料量(即每克桑叶粉末加5mL乙醇水溶液)，往桑叶粉末中加入体积分数100％的乙醇水溶液(即是乙醇)，在80℃浸提48小时，过滤，收集过滤液；
4)有机溶剂分级：将上述过滤液在80℃浓缩除去乙醇，得浓缩液，加入浓缩液1倍体积的水，先后用与等体积的石油醚、乙酸乙酯分别萃取6次；选择乙酸乙酯相萃取液进行浓缩，将得到的浸膏用于后续纯化；
后续纯化步骤与实施例1相同，得到化合物1并鉴定为2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮。
采用该方法获得的2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮的产率为50～100mg/kg，纯度为85～95％。
实施例5
DPPH是一种稳定的长寿命自由基，当有自由基清除剂存在时，由于与其单电子配对而使DPPH光吸收减弱，借此评价物质清除自由基的能力，从而评定其抗氧化能力。本发明通过DPPH自由基中和试验，测定吸光度，检测化合物2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮对DPPH自由基清除能力，以评价该化合物的抗氧化能力，所述的测试方法具体包括以下步骤：
将1,1-二苯基-2-三硝基苯肼(DPPH)溶于无水乙醇配制成浓度为0.2mM的溶液；将化合物2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮溶于无水乙醇；取80μL的2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮乙醇溶液和160μL浓度为0.2mM的DPPH乙醇溶液混合，避光室温下放置30min，在光吸收酶标仪(SpectraMax 190,Molecular Devices,USA)于517nm波长下测定吸光度值。结果表明，化合物2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮对DPPH自由基清除的IC 50值为21.6μM。表明本发明提供的化合物2,2',4,4'-四羟基-3-(2″-羟基-3″-甲基丁基-3″-烯基)查尔酮具有优异的抗氧化性能，可用于制备抗氧化护肤品、药品或保健品。
以上仅是本发明的优选实施方式，应当指出的是，上述优选实施方式不应视为对本发明的限制，本发明的保护范围应当以权利要求所限定的范围为准。对于本技术领域的普通技术人员来说，在不脱离本发明的精神和范围内，还可以做出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。

Claims (8)

  1. 2,2',4,4'-四羟基-3-(2”-羟基-3”-甲基丁基-3”-烯基)查尔酮，其结构式如下式(I)所示：
    Figure PCTCN2018106841-appb-100001
  2. 一种制备权利要求1所述的2,2',4,4'-四羟基-3-(2”-羟基-3”-甲基丁基-3”-烯基)查尔酮的方法，其特征在于，是从桑叶中制备分离得到的。
  3. 根据权利要求2所述的制备方法，其特征在于，包括以下步骤：用体积分数40～100％甲醇或乙醇水溶液浸提桑叶，将浸提液浓缩去除甲醇或乙醇后用水溶解，然后依次用石油醚、乙酸乙酯萃取，将乙酸乙酯萃取液浓缩得浸膏，浸膏经硅胶柱层析，以氯仿/甲醇为洗脱剂，从体积比100/0～60/40梯度洗脱，收集氯仿/甲醇体积比为95/5洗脱的馏分，该馏分再经反相柱层析，以甲醇/水为洗脱剂，从体积比10/90～100/0梯度洗脱，收集甲醇/水体积比为60/40洗脱的馏分，即得到2,2',4,4'-四羟基-3-(2”-羟基-3”-甲基丁基-3”-烯基)查尔酮。
  4. 根据权利要求3所述的制备方法，其特征在于，所述的桑叶为桑叶粉末，其是将新鲜的桑叶干燥后粉碎成粉末。
  5. 根据权利要求3所述的制备方法，其特征在于，所述的用体积分数40～100％甲醇或乙醇水溶液浸提桑叶，甲醇或乙醇水溶液的用量是5～20mL/g桑叶，浸提的温度为25～80℃，浸提时间为1～72小时。
  6. 根据权利要求3所述的制备方法，其特征在于，所述的将浸提液浓缩去除甲醇或乙醇后用水溶解，是将浸提液在40～80℃下浓缩除去甲醇或乙醇，再加入1～5倍体积的水溶解。
  7. 根据权利要求3所述的制备方法，其特征在于，所述的依次用石油醚、乙酸乙酯萃取，是先用石油醚萃取3～12次，再用乙酸乙酯萃取3～12次。
  8. 权利要求1所述的2,2',4,4'-四羟基-3-(2”-羟基-3”-甲基丁基-3”-烯基)查尔酮在制备抗氧化护肤品、药品或保健品中的应用。
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