CN108774120B - 拉帕醌类化合物及其制备方法 - Google Patents
拉帕醌类化合物及其制备方法 Download PDFInfo
- Publication number
- CN108774120B CN108774120B CN201810435924.2A CN201810435924A CN108774120B CN 108774120 B CN108774120 B CN 108774120B CN 201810435924 A CN201810435924 A CN 201810435924A CN 108774120 B CN108774120 B CN 108774120B
- Authority
- CN
- China
- Prior art keywords
- compound
- fusarium
- fermentation
- hjt
- rhodiola
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 244000005700 microbiome Species 0.000 claims abstract description 12
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 241000223218 Fusarium Species 0.000 claims abstract description 11
- 239000002207 metabolite Substances 0.000 claims abstract description 8
- 241000327150 Rhodiola angusta Species 0.000 claims abstract description 5
- 241000083902 Rhodiola sachalinensis Species 0.000 claims abstract description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims abstract description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 lapachone compound Chemical class 0.000 claims abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000000855 fermentation Methods 0.000 claims description 18
- 230000004151 fermentation Effects 0.000 claims description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000001963 growth medium Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 241000196324 Embryophyta Species 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 6
- 241000209094 Oryza Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- 238000002137 ultrasound extraction Methods 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 3
- 239000002024 ethyl acetate extract Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 241001149959 Fusarium sp. Species 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 238000010828 elution Methods 0.000 claims 1
- QZPQTZZNNJUOLS-UHFFFAOYSA-N beta-lapachone Chemical class C12=CC=CC=C2C(=O)C(=O)C2=C1OC(C)(C)CC2 QZPQTZZNNJUOLS-UHFFFAOYSA-N 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 244000042430 Rhodiola rosea Species 0.000 abstract description 2
- 235000003713 Rhodiola rosea Nutrition 0.000 abstract description 2
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000012827 research and development Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000000638 solvent extraction Methods 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 241000997135 Rhodiola crenulata Species 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 241000044689 Actinomma boreale Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001165494 Rhodiola Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/66—Preparation of oxygen-containing organic compounds containing the quinoid structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明属于医药技术领域,具体涉及从镰刀霉属植物内生微生物代谢产物中提取得到三种新的拉帕醌类化合物,化合物Ⅰ1‑methoxylfusarnaphthoquinones A,化合物Ⅱ5‑dehydroxysolaninol,化合物Ⅲ1‑dehydroxysolaninol;本发明以采集自长白红景天(Rhodiola angusta Nakai)叶片部位的内生镰刀霉属微生物(Fusariumsp.HJT‑P‑5)的固体发酵产物为原料,经溶剂萃取和多种色谱方法分离,得到本发明三个新的拉帕醌类化合物;本发明这类新的拉帕醌类化合物及其制备方法在抗肿瘤药物研究开发上具有非常重要的意义。
Description
技术领域
本发明属于医药技术领域,具体涉及从镰刀霉属植物内生微生物代谢产物中提取得到三种新的拉帕醌类化合物,化合物Ⅰ1-methoxylfusarnaphthoquinones A,化合物Ⅱ5-dehydroxysolaninol ,化合物Ⅲ1-dehydroxysolaninol ,以及三种化合物的制备方法。
背景技术
目前从微生物代谢产物中分离得到50000种以上的天然产物,其中多种化合物生物活性良好,具有被开发成为新型药物的潜质。随着研究的深入,从传统陆生微生物代谢产物中获得新型先导化合物的概率逐渐降低,速度逐年减缓,故开发特境微生物资源成为当务之急。植物内生微生物由于其生境特殊,能够代谢产生结构特殊,活性良好的化合物,是目前的研究热点之一。
对长白红景天内生微生物Fusarium sp. HJT-P-5的研究表明,其代谢产物含有多种拉帕醌类化合物,该类化合物对人肺癌细胞A549和人结肠癌细胞HCT116有明显的抑制活性。
发明内容
本发明提供了采集自长白红景天(Rhodiola angusta Nakai)叶片部位的内生镰刀霉属微生物(Fusarium sp. HJT-P-5)的固体发酵产物中分离得到三个新型拉帕醌类化合物Ⅰ~Ⅲ,化合物Ⅰ命名为1- methoxylfusarnaphthoquinones A,化合物Ⅱ命名为5-dehydroxysolaninol,化合物Ⅲ名为1-dehydroxysolaninol, 化学结构式分别为:
药理活性表明这三个化合物对人肺癌细胞A549和人结肠癌细胞HCT116有明显的抑制活性。
这三种拉帕醌类化合物的制备方法是以采集自长白红景天(Rhodiola angustaNakai)叶片部位的内生镰刀霉属微生物(Fusarium sp. HJT-P-5)的固体发酵产物为原料,经溶剂萃取和多种色谱方法分离,得到三个新的拉帕醌类化合物;采用高分辨质谱,核磁共振等谱学技术,确定了这三个化合物的结构,其具体制备步骤如下:
(1)将采集自长白红景天(Rhodiola angusta Nakai)叶片部位的内生镰刀霉属微生物(Fusarium sp. HJT-P-5)进行固体发酵;
固体培养基配方:大米,纯净水;
发酵条件:将菌株HJT-P-5接种于真菌4号培养基发酵液的锥形瓶中摇床震荡培养,再将震荡培养的发酵液连同菌丝体接种于装有固体培养基的锥形瓶中静置发酵培养;
(2)代谢产物的提取:使用等体积丙酮对植物内生真菌HJT- P-5固体发酵产物进行超声提取,经8层纱布过滤,将提取液与菌丝体及大米分离,提取液浓缩至干,加水混悬,依次用等体积的乙酸乙酯、正丁醇萃取3次,减压回收溶剂得到乙酸乙酯萃取物和正丁醇萃取物;
(3)乙酸乙酯层用正相硅胶柱色谱分离纯化,采用体积比为氯仿:甲醇= 100:0、100:1、100:2、100:3、100:5、100:10的梯度洗脱,收集洗脱液;
(4)步骤(3)的洗脱液经高效液相色谱分离纯化,采用体积比为乙腈:水:四氢呋喃=15:80:5的溶液洗脱,浓缩后得化合物Ⅰ,采用体积比为乙腈:水=31:69的溶液洗脱得化合物Ⅱ、Ⅲ。
本发明的有益效果为:本发明的化合物为新的拉帕醌类化合物,本发明原料为植物内生微生物发酵产物,安全易得,方法简单易操作,不引入有毒物质,成本低廉,可大规模持续开发利用。本发明的化合物及制备方法在抗肿瘤药物研究开发上具有非常重要的意义。
具体实施方式
以下结合具体实施方式对本发明做进一步说明。
实施例1
化合物Ⅰ~Ⅲ的制备:
(1)将采集自长白红景天(Rhodiola angusta Nakai)叶片部位的内生镰刀霉属微生物(Fusarium sp. HJT-P-5)进行固体发酵;
固体培养基配方:大米80g,纯净水120ml;
发酵条件:将菌株HJT-P-5接种于4瓶装有200 mL真菌4号培养基发酵液的500 mL锥形瓶中摇床震荡培养2d(培养条件:28℃,120 r/min),再将震荡培养2d后的发酵液连同菌丝体按接种量10%的比例接种于40瓶装有固体培养基的500 mL锥形瓶中静置发酵培养40d,(培养条件:28℃);
(2)代谢产物的提取:使用等体积丙酮对植物内生真菌HJT- P-5固体发酵产物进行超声提取,15min ×3次,经8层纱布过滤,将提取液与菌丝体及大米分离,提取液浓缩至干,加2L水混悬,依次用等体积的乙酸乙酯、正丁醇萃取3次,减压回收溶剂得到乙酸乙酯萃取物(44.66g)和正丁醇萃取物(41.13g);
(3)乙酸乙酯层用正相硅胶柱色谱分离纯化,采用体积比为氯仿:甲醇= 100:0、100:1、100:2、100:3、100:5、100:10的梯度洗脱,收集洗脱液;
(4)步骤(3)的洗脱液经高效液相色谱分离纯化,采用体积比为乙腈:水:四氢呋喃=15:80:5的溶液洗脱,浓缩后得化合物1,采用体积比为乙腈:水=31:69的溶液洗脱得化合物Ⅱ、Ⅲ。
采用核磁共振(NMR)等波谱技术测定其结构,化合物Ⅰ~Ⅲ的波谱数据见下表1~表3。
表1 化合物Ⅰ氢谱(500 MHz)和碳谱(125 MHz)核磁数据(DMSO-d 6)
表2 化合物Ⅱ氢谱(500 MHz)和碳谱(125 MHz)核磁数据(DMSO-d 6)
表3 化合物Ⅲ氢谱(500 MHz)和碳谱(125 MHz)核磁数据(DMSO-d 6)
Claims (1)
1.拉帕醌类化合物的制备方法,其特征在于,拉帕醌类化合物具有下述化学结构式Ⅰ~Ⅲ:
所述方法步骤为:
(1)将采集自长白红景天(Rhodiola angusta Nakai)叶片部位的内生镰刀霉属微生物(Fusarium sp.HJT-P-5)进行固体发酵;
固体培养基配方:大米,纯净水;
发酵条件:将菌株HJT-P-5接种于真菌4号培养基发酵液的锥形瓶中摇床震荡培养,再将震荡培养的发酵液连同菌丝体接种于装有固体培养基的锥形瓶中静置发酵培养;
(2)代谢产物的提取:使用等体积丙酮对植物内生真菌HJT-P-5固体发酵产物进行超声提取,经8层纱布过滤,将提取液与菌丝体及大米分离,提取液浓缩至干,加水混悬,依次用等体积的乙酸乙酯、正丁醇萃取3次,减压回收溶剂得到乙酸乙酯萃取物和正丁醇萃取物;
(3)乙酸乙酯层用正相硅胶柱色谱分离纯化,采用体积比为氯仿:甲醇=100:0、100:1、100:2、100:3、100:5、100:10的梯度洗脱,收集洗脱液;
(4)洗脱液经高效液相色谱分离纯化,采用体积比为乙腈:水:四氢呋喃=15:80:5的溶液洗脱,浓缩后得化合物Ⅰ,采用体积比为乙腈:水=31:69的溶液洗脱得化合物Ⅱ、化合物Ⅲ。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810435924.2A CN108774120B (zh) | 2018-05-09 | 2018-05-09 | 拉帕醌类化合物及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810435924.2A CN108774120B (zh) | 2018-05-09 | 2018-05-09 | 拉帕醌类化合物及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108774120A CN108774120A (zh) | 2018-11-09 |
CN108774120B true CN108774120B (zh) | 2021-04-06 |
Family
ID=64026976
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810435924.2A Active CN108774120B (zh) | 2018-05-09 | 2018-05-09 | 拉帕醌类化合物及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108774120B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116041307A (zh) * | 2023-01-31 | 2023-05-02 | 三峡大学 | 一种自金丝楸中4, 9-二羟基-α-拉帕醌的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4837399A (en) * | 1988-05-10 | 1989-06-06 | The United States Of America As Represented By The Secretary Of Agriculture | Napthoquinone antibiotics from fuserium solani |
CN104274432A (zh) * | 2013-07-01 | 2015-01-14 | 上海来益生物药物研究开发中心有限责任公司 | 一种萘醌衍生物solaniol用于制备抗病毒药物的应用 |
CN105056230A (zh) * | 2015-08-03 | 2015-11-18 | 中国医学科学院医学生物学研究所 | β-拉帕醌的应用及含有β-拉帕醌的复合佐剂和疫苗 |
CN105294638A (zh) * | 2015-10-30 | 2016-02-03 | 成都科创佳思科技有限公司 | 一种去氢α-拉帕醌的催化合成方法 |
WO2017106624A1 (en) * | 2015-12-18 | 2017-06-22 | The Board Of Regents Of The University Of Texas System | Napthoquinones, pro-drugs, and methods of use thereof |
-
2018
- 2018-05-09 CN CN201810435924.2A patent/CN108774120B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4837399A (en) * | 1988-05-10 | 1989-06-06 | The United States Of America As Represented By The Secretary Of Agriculture | Napthoquinone antibiotics from fuserium solani |
CN104274432A (zh) * | 2013-07-01 | 2015-01-14 | 上海来益生物药物研究开发中心有限责任公司 | 一种萘醌衍生物solaniol用于制备抗病毒药物的应用 |
CN105056230A (zh) * | 2015-08-03 | 2015-11-18 | 中国医学科学院医学生物学研究所 | β-拉帕醌的应用及含有β-拉帕醌的复合佐剂和疫苗 |
CN105294638A (zh) * | 2015-10-30 | 2016-02-03 | 成都科创佳思科技有限公司 | 一种去氢α-拉帕醌的催化合成方法 |
WO2017106624A1 (en) * | 2015-12-18 | 2017-06-22 | The Board Of Regents Of The University Of Texas System | Napthoquinones, pro-drugs, and methods of use thereof |
Non-Patent Citations (2)
Title |
---|
Anthraquinone, Cyclopentanone, and Naphthoquinone Derivatives from the Sea Fan-Derived Fungi Fusarium spp. PSU-F14 and PSU-F135;Kongkiat Trisuwan等;《J. Nat. Prod.》;20100903;第73卷(第9期);1507-1511 * |
Chemical investigation of metabolites produced by an endophytic fungi Phialemonium curvatum from the leaves of Passiflora edulis;G.R.Nalin Rathnayake等;《Natural Product Research》;20171220;第32卷(第20期);2483-2486 * |
Also Published As
Publication number | Publication date |
---|---|
CN108774120A (zh) | 2018-11-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102936253B (zh) | 一种高纯度他克莫司的制备方法 | |
CN112592327A (zh) | 微生物拟盘多毛孢菌中分离出的聚酮类化合物及其分离方法和应用 | |
CN109134574B (zh) | 甾体化合物及其制备方法与应用和抗肿瘤的药物 | |
CN108774120B (zh) | 拉帕醌类化合物及其制备方法 | |
CN106518643A (zh) | 一种环戊烯酮类化合物及其制备方法和用途 | |
CN101367716B (zh) | 一类炭壳菌聚酮及其制法和用途 | |
CN113277998A (zh) | 一种聚酮类化合物及其制备方法 | |
CN113248369A (zh) | 具有抗新冠病毒活性的聚酮类化合物的制备及其应用 | |
CN115403556B (zh) | 戊酮噻吩类化合物及其制备方法和在抗炎药物中的应用 | |
CN108658911B (zh) | 一种呋喃萘醌类化合物及其制备方法 | |
CN114478685B (zh) | 一种吲哚二萜类化合物及其制备方法和应用 | |
CN112457196A (zh) | 镰刀霉属植物内生微生物中分离出的羟基苯乙酸酯化物及其分离方法和应用 | |
CN110698441B (zh) | 一类2-甲基-4-(1-丙三醇)-呋喃类化合物及其制备方法和应用 | |
CN109609568B (zh) | 一种采用固体发酵法制备苦马豆素的方法 | |
CN102452916B (zh) | 一类芳香聚酮及其提取方法和应用 | |
CN115894519B (zh) | 一种三肽生物碱化合物及其制备方法和应用 | |
CN106011190B (zh) | 一种天然对氨基苯甲酸及其衍生物的制备方法 | |
CN112592269A (zh) | 镰刀霉属植物内生微生物中分离出的链状萜类衍生物及其分离方法和应用 | |
CN115636869B (zh) | 具有肝癌细胞毒性和α-葡萄糖苷酶抑制活性的环cyclo色苏酪异亮苯丙肽及制备方法 | |
CN115651069B (zh) | 具有肝癌细胞毒性和α-葡萄糖苷酶抑制活性的环色-苏-酪-缬-苯丙肽及制备方法 | |
CN115636871B (zh) | 具有肝癌细胞毒性和α-葡萄糖苷酶抑制活性的环色-苏-酪-异亮-苯丙肽及制备方法 | |
CN111606796B (zh) | 两种土曲霉酮类化合物的制备方法及其作为抗肿瘤药物的应用 | |
CN112707890B (zh) | 吲哚二酮哌嗪衍生物及其制备方法和在制备抗炎药物中的应用 | |
CN101665814A (zh) | 去乙酰真菌环氧乙酯的制备方法 | |
CN103145667B (zh) | 8-羟基-2-丙基色原烷-4-酮和5,8-二羟基-2-丙基色原烷-4-酮及其制备方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20181109 Assignee: ZHEN-AO GROUP Co.,Ltd. Assignor: DALIAN University Contract record no.: X2023210000229 Denomination of invention: Rapaquinone compounds and their preparation methods Granted publication date: 20210406 License type: Common License Record date: 20231129 |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
OL01 | Intention to license declared |