WO2020087688A1 - 一种二氢呋喃查尔酮类化合物及其制备方法 - Google Patents

一种二氢呋喃查尔酮类化合物及其制备方法 Download PDF

Info

Publication number
WO2020087688A1
WO2020087688A1 PCT/CN2018/121636 CN2018121636W WO2020087688A1 WO 2020087688 A1 WO2020087688 A1 WO 2020087688A1 CN 2018121636 W CN2018121636 W CN 2018121636W WO 2020087688 A1 WO2020087688 A1 WO 2020087688A1
Authority
WO
WIPO (PCT)
Prior art keywords
methanol
dihydrofuran
chalcone
water
preparation
Prior art date
Application number
PCT/CN2018/121636
Other languages
English (en)
French (fr)
Inventor
杨宝
蒋跃明
Original Assignee
中国科学院华南植物园
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 中国科学院华南植物园 filed Critical 中国科学院华南植物园
Priority to US16/626,943 priority Critical patent/US11161829B1/en
Publication of WO2020087688A1 publication Critical patent/WO2020087688A1/zh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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

Definitions

  • the invention relates to the field of natural product chemistry, and relates to a dihydrofuran chalcone and a preparation method thereof.
  • the mulberry belongs to the evergreen tree of the mulberry family and is widely planted in tropical and subtropical regions.
  • Mulberry fruit is sweet and delicious, with high nutritional value and health care function. It has the effects of treating white hair and anti-inflammatory, and is popular among consumers.
  • Mulberry leaf is a new resource vegetable food with a fresh and tender taste, which has gradually been accepted by consumers.
  • the study 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 is still to be studied.
  • the object of the present invention is to provide a dihydrofuran chalcone and its preparation method.
  • the dihydrofuran chalcone of the present invention is extracted and separated from mulberry leaves, and its structural formula is shown as the following formula (I):
  • the preparation method of dihydrofuran chalcone includes the following steps: extracting mulberry leaves with a volume fraction of 40-100% methanol or ethanol aqueous solution, concentrating the extract to remove methanol or ethanol, dissolving with water, and then sequentially using petroleum ether 1.
  • Ethyl acetate extraction the ethyl acetate extract is concentrated to obtain an extract, the extract is subjected to silica gel column chromatography, using chloroform / methanol as the eluent, and the gradient is eluted from the volume ratio of 100/0 to 60/40, and the chloroform is collected
  • the fraction eluted with a volume ratio of 95% in methanol / methanol was subjected to reversed-phase column chromatography, using acetonitrile / water as the eluent, and the gradient was eluted from the volume ratio of 5/95 to 100/0 to collect acetonitrile / water.
  • the fraction eluted at a volume ratio of 30/70 gives dihydrofuran chalcone.
  • the mulberry leaf is a mulberry leaf powder, which is obtained by drying fresh mulberry leaves into powder.
  • the mulberry leaves are extracted with a volume fraction of 40-100% methanol or ethanol aqueous solution.
  • the amount of methanol or ethanol aqueous solution is 5-20 mL / g mulberry leaves (that is, 5-20 mL of methanol or ethanol aqueous solution per gram of mulberry leaves).
  • the extraction temperature is 25 to 70 ° C, and the extraction time is 1 to 72 hours.
  • the concentration of the leaching solution to remove methanol or ethanol and dissolution with water is to concentrate the leaching solution at 40 to 80 ° C to remove methanol or ethanol, and then add 1 to 5 times the volume of water to dissolve.
  • the above mentioned extraction with petroleum ether and ethyl acetate is carried out by first extracting with petroleum ether 3-12 times, and then extracting with ethyl acetate 3-12 times.
  • the invention also provides an antioxidant skin care product, medicine or health care product, which contains the above-mentioned dihydrofuran chalcone as an active ingredient.
  • the present invention demonstrates that, according dihydrofuran chalcones having a good free radical scavenging capacity, the DPPH radical scavenging compound IC 50 value of 32.7 ⁇ M, significantly better than the positive control of vitamin C (Vc) of the IC 50 value 100 ⁇ M. It shows that the dihydrofuran chalcone provided by the present invention has excellent antioxidant properties and can be used for preparing antioxidant skin care products, medicines or health products.
  • dihydrofuran chalcone is prepared and separated from mulberry leaves, and the yield of the compound is 23 to 157 mg / kg (purity is 85 to 95%).
  • the invention has important 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. It also provides a new method for the preparation of dihydrofuran chalcone.
  • the yield of dihydrofuran chalcone obtained by this method is 23-49 mg / kg, and the purity is 85-95%.
  • the yield of dihydrofuran chalcone obtained by this method is 115-157 mg / kg, and the purity is 85-95%.
  • the yield of dihydrofuran chalcone obtained by this method is 55-104 mg / kg, and the purity is 85-95%.
  • the yield of dihydrofuran chalcone obtained by this method is 48-96 mg / kg, and the purity is 85-95%.
  • DPPH is a stable long-life 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, thereby assessing its antioxidant capacity.
  • the DPPH free radical neutralization test is used to determine the absorbance and detect the DPPH free radical scavenging ability of dihydrofuran chalcone to evaluate the antioxidant capacity of the compound.
  • the test method specifically includes the following steps:
  • the dihydrofuran chalcone had an IC 50 value of 32.7 ⁇ M for DPPH free radical scavenging, and the IC 50 value of Vc for DPPH free radical scavenging was 100 ⁇ M. It shows that the dihydrofuran chalcone provided by the present invention has excellent antioxidant performance, which is obviously superior to the positive control Vc, and can be used for preparing antioxidant skin care products, medicines or health products.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

一种制备二氢呋喃查尔酮类化合物的方法，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，以乙腈/水为洗脱剂，收集乙腈/水体积比为30/70洗脱的馏分，即得二氢呋喃查尔酮。本方法能够推动桑叶的深加工利用，提升桑叶产品附加值。

Description

一种二氢呋喃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，涉及一种二氢呋喃查尔酮及其制备方法。
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二氢呋喃查尔酮及其制备方法。
本发明的二氢呋喃查尔酮是从桑叶中提取分离得到，其结构式如下式(I)所示：
Figure PCTCN2018121636-appb-000001
所述的二氢呋喃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，以乙腈/水为洗脱剂，从体积比5/95～100/0梯度洗脱，收集乙腈/水体积比为30/70洗脱的馏分，即得到二氢呋喃查尔酮。
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25～70℃，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。
本发明还提供一种抗氧化护肤品、药品或保健品，其含有上述二氢呋喃查尔酮作为活性成分。
本发明证实，所述的二氢呋喃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32.7μM，明显优于阳性对照维生素C(Vc)的IC 50值100μM。表明本发明提供的二氢呋喃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二氢呋喃查尔酮，该化合物的产率为23～157mg/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。同时也为二氢呋喃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、二氢呋喃查尔酮的制备分离
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，以乙腈/水为洗脱剂，从体积比5/95～100/0梯度洗脱，收集乙腈/水体积比为30/70洗脱的组分，在60℃蒸发浓缩干燥，即得到化合物1(二氢呋喃查尔酮)。
采用该方法获得的二氢呋喃查尔酮的产率为23～49mg/kg，纯度为85～95％。
二、化合物1(二氢呋喃查尔酮)的结构鉴定
化合物1(二氢呋喃查尔酮)易溶于甲醇，质谱结果表明：该化合物分子量为356。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   115.1
2   160.5
3 6.35 103.7
4   161.1
5 6.37 109.2
6 7.52 132.4
1'   114.7
2'   168.1
3'   114.6
4'   162.1
5' 6.37 109.0
6' 7.89 133.1
1″ 3.13 27.9
2″ 4.74 92.6
3″   72.2
4″ 1.28 25.1
5″ 1.24 25.3
α 7.73 117.4
β 8.09 142.1
羰基   194.1
综上所述，鉴定该化合物1的结构式如式(I)所示，属于一种二氢呋喃查尔酮，该化合物易溶于甲醇。
Figure PCTCN2018121636-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60℃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并鉴定为二氢呋喃查尔酮。
采用该方法获得的二氢呋喃查尔酮的产率为115～157mg/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并鉴定为二氢呋喃查尔酮。
采用该方法获得的二氢呋喃查尔酮的产率为55～104mg/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70℃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并鉴定为二氢呋喃查尔酮。
采用该方法获得的二氢呋喃查尔酮的产率为48～96mg/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，检测二氢呋喃查尔酮对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；将二氢呋喃查尔酮溶于无水乙醇；取80μL的二氢呋喃查尔酮的乙醇溶液和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(SpectraMax190,Molecular Devices,USA)于517nm波长下测定吸光度值，并以Vc作为阳性对照。结果表明，二氢呋喃查尔酮对DPPH自由基清除的IC 50值为32.7μM，Vc对DPPH自由基清除的IC 50值为100μM。表明本发明提供的二氢呋喃查尔酮具有优异的抗氧化性能，明显优于阳性对照Vc，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 (9)

  1. 一种二氢呋喃查尔酮，其结构式如下式(I)所示：
    Figure PCTCN2018121636-appb-100001
  2. 一种制备权利要求1所述的二氢呋喃查尔酮的方法，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，以乙腈/水为洗脱剂，从体积比5/95～100/0梯度洗脱，收集乙腈/水体积比为30/70洗脱的馏分，即得到二氢呋喃查尔酮。
  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 25～70℃，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所述的二氢呋喃查尔酮在制备抗氧化护肤品、药品或保健品中的应用。
  9. 一种抗氧化护肤品、药品或保健品，其特征在于，其含有权利要求1所述的二氢呋喃查尔酮作为活性成分。
PCT/CN2018/121636 2018-11-01 2018-12-18 一种二氢呋喃查尔酮类化合物及其制备方法 WO2020087688A1 (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US16/626,943 US11161829B1 (en) 2018-11-01 2018-12-18 Dihydrofuran chalcone compound and preparation method thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201811296972.4A CN109369582B (zh) 2018-11-01 2018-11-01 一种二氢呋喃查尔酮类化合物及其制备方法
CN201811296972.4 2018-11-01

Publications (1)

Publication Number Publication Date
WO2020087688A1 true WO2020087688A1 (zh) 2020-05-07

Family

ID=65391414

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2018/121636 WO2020087688A1 (zh) 2018-11-01 2018-12-18 一种二氢呋喃查尔酮类化合物及其制备方法

Country Status (3)

Country Link
US (1) US11161829B1 (zh)
CN (1) CN109369582B (zh)
WO (1) WO2020087688A1 (zh)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0998939A1 (en) * 1998-09-09 2000-05-10 The School Of Pharmacy, University Of London Chalcone plant extracts for use in therapy
CN102579644A (zh) * 2012-03-13 2012-07-18 河南中医学院 复方山楂叶总黄酮滴丸及其制备方法
DE102012105613A1 (de) * 2012-06-27 2014-01-23 Herbert Riepl Raffinationsverfahren
CN104643083A (zh) * 2015-03-05 2015-05-27 山西金科海生物科技有限公司 一种具有抗氧化降血脂功效的组方及其加工工艺
CN105001068A (zh) * 2015-06-23 2015-10-28 江南大学 一步绿色合成羟基查尔酮和二氢黄酮的方法
CN106008172A (zh) * 2016-05-18 2016-10-12 江南大学 桑枝中具酪氨酸酶抑制作用有效部位制备方法及其应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102161650B (zh) * 2011-03-13 2013-08-07 浙江大学 桑叶中多酚类次生代谢产物及制备方法与用途
CN102161649B (zh) * 2011-03-13 2012-07-04 浙江大学 桑叶中提取的多酚类衍生物及制备方法与用途
CN102153534B (zh) * 2011-03-13 2013-03-13 浙江大学 具酪氨酸酶抑制活性的化合物及制备方法与用途
CN102525853B (zh) * 2011-12-23 2013-06-05 广州市娇兰化妆品有限公司 具有祛斑功能的复方天然植物提取物及其制备方法与应用
CN102924421B (zh) * 2012-11-04 2014-12-03 浙江大学 一类具酪氨酸酶抑制活性的化合物的制备方法与用途

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0998939A1 (en) * 1998-09-09 2000-05-10 The School Of Pharmacy, University Of London Chalcone plant extracts for use in therapy
CN102579644A (zh) * 2012-03-13 2012-07-18 河南中医学院 复方山楂叶总黄酮滴丸及其制备方法
DE102012105613A1 (de) * 2012-06-27 2014-01-23 Herbert Riepl Raffinationsverfahren
CN104643083A (zh) * 2015-03-05 2015-05-27 山西金科海生物科技有限公司 一种具有抗氧化降血脂功效的组方及其加工工艺
CN105001068A (zh) * 2015-06-23 2015-10-28 江南大学 一步绿色合成羟基查尔酮和二氢黄酮的方法
CN106008172A (zh) * 2016-05-18 2016-10-12 江南大学 桑枝中具酪氨酸酶抑制作用有效部位制备方法及其应用

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BRANDT, D. R. ET AL.: "The synthetic preparation of naturally-occurring aromatase inhibitors, morachalcone A, isogemichalcone B, and isogemichalcone C", TETRAHEDRON, vol. 69, no. 47, 27 September 2013 (2013-09-27), XP028756328, ISSN: 0040-4020, DOI: 20190715210404X *
WANG, YIHAI ET AL.: "Antidiabetic and Antioxidant Effects and Phytochemicals of Mulberry Fruit (Morus alba L.) Polyphenol Enhanced Extract", PLOS ONE, vol. 8, no. 7, 30 July 2013 (2013-07-30), pages 1 - 10, XP055700028, ISSN: 1932-6203, DOI: 10.1371/journal.pone.0071144 *
YANG, YAN: "Studies on the Chemical Constituents and Bioactivities of Leaves of Morus Alba L.", CHINA MASTER'S THESES FULL-TEXT DATABASE, 15 October 2010 (2010-10-15), pages 1 - 133, XP055699971, ISSN: 1674-0246 *

Also Published As

Publication number Publication date
US11161829B1 (en) 2021-11-02
CN109369582A (zh) 2019-02-22
CN109369582B (zh) 2021-12-10
US20210332022A1 (en) 2021-10-28

Similar Documents

Publication Publication Date Title
WO2020087687A1 (zh) 一种异戊烯基查尔酮类化合物及其制备方法
CN109293572A (zh) 一种提取榆黄菇中麦角硫因与多糖的方法
CN110467528A (zh) 一种从迷迭香中提取鼠尾草酸的方法
KR101404286B1 (ko) 신선초 녹즙 부산물로부터 칼콘 고함유 추출물 제조방법
CN108069930B (zh) 一种从高良姜中联合提取高良姜挥发油及高良姜素的方法
KR101737556B1 (ko) 법제 하수오 추출물을 유효성분으로 포함하는 산화적 스트레스 개선용 조성물
WO2017103838A1 (en) A solvent free sesamin complex 90% and a method of synthesizing the same
WO2020042250A1 (zh) 一种查尔酮类化合物及其制备方法
CN111171106A (zh) 一种24-羟基硬脂醇甘草亭酸酯的制备方法
WO2016110216A1 (zh) 一种提取茋类化合物的方法
WO2020087688A1 (zh) 一种二氢呋喃查尔酮类化合物及其制备方法
JP3925828B2 (ja) アクテオシドの抽出法
KR102025349B1 (ko) 더덕에서 유래한 란세마사이드 a의 추출 방법
CN104926823B (zh) 一种汉防己中生物碱的提取方法
CN105748569A (zh) 紫藤花总黄酮的提取分离方法
CN102718650B (zh) 2-(2-羟基-5-(甲氧羰基)苯氧基)苯甲酸及其制备方法和应用
CN104004034B (zh) 一种制备开环异落叶松脂素9’-O-β-木糖苷的方法
CN104003999B (zh) 一种制备cinnamtannin B1的方法
KR102413699B1 (ko) 아세토제닌 성분이 분리된 포포나무 잎 추출물로부터 항염증 활성을 가진 분리물의 제조방법
CN109589340B (zh) 蝼蛄提取物在制备治疗三阴乳腺癌药物中的应用
CN105254691B (zh) 一种制备2”-O-β-D-xylosylvitexin的方法
JP5441433B2 (ja) カムカムフルーツ果汁含有肝機能改善剤
CN109589341B (zh) 蝼蛄提取物及其制备方法
CN104003854B (zh) 一种制备愈创木基丙三醇-(8-o-4’)-愈创木基丙三醇的方法
CN113058001A (zh) 一种从薤白中提取化疗药物增敏的制备方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18938403

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18938403

Country of ref document: EP

Kind code of ref document: A1