CN102659547A - 一种蛇孢假壳素类二倍半萜化合物及其制备和应用 - Google Patents
一种蛇孢假壳素类二倍半萜化合物及其制备和应用 Download PDFInfo
- Publication number
- CN102659547A CN102659547A CN201210084361XA CN201210084361A CN102659547A CN 102659547 A CN102659547 A CN 102659547A CN 201210084361X A CN201210084361X A CN 201210084361XA CN 201210084361 A CN201210084361 A CN 201210084361A CN 102659547 A CN102659547 A CN 102659547A
- Authority
- CN
- China
- Prior art keywords
- ophiobolin
- class
- sesquiterpene compound
- preparation
- dimeric sesquiterpene
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- MWYYLZRWWNBROW-UHFFFAOYSA-N 6-epiophiobolin A Natural products CC1CC(C=C(C)C)OC11C2CC=C(C=O)C(C(=O)CC3(C)O)C3CC2(C)CC1 MWYYLZRWWNBROW-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229930184030 ophiobolin Natural products 0.000 title claims abstract description 10
- -1 Ophiobolin sesterterpene compound Chemical class 0.000 title abstract description 6
- 229930002368 sesterterpene Natural products 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- MWYYLZRWWNBROW-BDZRSQQBSA-N ophiobolin A Chemical compound C[C@H]1C[C@H](C=C(C)C)O[C@]11[C@@H]2C\C=C(C=O)/[C@@H](C(=O)C[C@@]3(C)O)[C@@H]3C[C@@]2(C)CC1 MWYYLZRWWNBROW-BDZRSQQBSA-N 0.000 claims abstract description 37
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 241000122818 Aspergillus ustus Species 0.000 claims abstract description 19
- 241000233866 Fungi Species 0.000 claims abstract description 10
- 238000000855 fermentation Methods 0.000 claims abstract description 8
- 230000004151 fermentation Effects 0.000 claims abstract description 8
- 239000000575 pesticide Substances 0.000 claims abstract description 5
- 238000000746 purification Methods 0.000 claims abstract description 3
- 229930003839 sesquiterpene dimer Natural products 0.000 claims description 32
- 238000004809 thin layer chromatography Methods 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 13
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003208 petroleum Substances 0.000 claims description 12
- 238000010898 silica gel chromatography Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000000287 crude extract Substances 0.000 claims description 8
- 238000010828 elution Methods 0.000 claims description 8
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000001641 gel filtration chromatography Methods 0.000 claims description 6
- 230000000968 intestinal effect Effects 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- 238000004811 liquid chromatography Methods 0.000 claims description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000638 solvent extraction Methods 0.000 claims description 4
- 230000003068 static effect Effects 0.000 claims description 4
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 235000008504 concentrate Nutrition 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 235000014666 liquid concentrate Nutrition 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 abstract description 7
- 238000002474 experimental method Methods 0.000 abstract description 6
- 230000003385 bacteriostatic effect Effects 0.000 abstract description 4
- 230000000749 insecticidal effect Effects 0.000 abstract description 4
- 231100000111 LD50 Toxicity 0.000 abstract description 3
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 241001672739 Artemia salina Species 0.000 abstract 1
- 241001474374 Blennius Species 0.000 abstract 1
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000238582 Artemia Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 241000238426 Anostraca Species 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000595940 Notostraca Species 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 108010021006 Tyrothricin Proteins 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 208000031513 cyst Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 231100000225 lethality Toxicity 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006273 synthetic pesticide Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GSXRBRIWJGAPDU-BBVRJQLQSA-N tyrocidine A Chemical compound C([C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@H](C(N[C@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N1)=O)CC(C)C)C(C)C)C1=CC=C(O)C=C1 GSXRBRIWJGAPDU-BBVRJQLQSA-N 0.000 description 2
- 229960003281 tyrothricin Drugs 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000196222 Codium fragile Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 238000005276 aerator Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 210000001136 chorion Anatomy 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 229930002995 diterpene alkaloid Natural products 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 229940049547 paraxin Drugs 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210084361.XA CN102659547B (zh) | 2012-03-27 | 2012-03-27 | 一种蛇孢假壳素类二倍半萜化合物及其制备和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210084361.XA CN102659547B (zh) | 2012-03-27 | 2012-03-27 | 一种蛇孢假壳素类二倍半萜化合物及其制备和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102659547A true CN102659547A (zh) | 2012-09-12 |
CN102659547B CN102659547B (zh) | 2014-04-16 |
Family
ID=46769160
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201210084361.XA Expired - Fee Related CN102659547B (zh) | 2012-03-27 | 2012-03-27 | 一种蛇孢假壳素类二倍半萜化合物及其制备和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102659547B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103193743A (zh) * | 2013-03-22 | 2013-07-10 | 中国科学院微生物研究所 | 一种化合物、该化合物的制备方法以及该化合物在制备抗肿瘤药物中的应用 |
CN107893090A (zh) * | 2017-10-20 | 2018-04-10 | 国家海洋局第三海洋研究所 | 土曲霉h768的发酵化合物在制备抗过敏药物中的应用 |
CN108383707A (zh) * | 2018-04-23 | 2018-08-10 | 中国科学院烟台海岸带研究所 | 一种胡萝卜烷倍半萜类化合物及其制备和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005132787A (ja) * | 2003-10-31 | 2005-05-26 | Nippon Kayaku Co Ltd | 生理活性物質6−epiophiobolinN及び6−epiophiobolinG、並びにそれらの類縁物質の用途 |
CN101591314A (zh) * | 2008-10-24 | 2009-12-02 | 中国海洋大学 | 蛇孢假壳素(ophiobolin)类二倍半萜烯化合物及其制备方法和用途 |
-
2012
- 2012-03-27 CN CN201210084361.XA patent/CN102659547B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005132787A (ja) * | 2003-10-31 | 2005-05-26 | Nippon Kayaku Co Ltd | 生理活性物質6−epiophiobolinN及び6−epiophiobolinG、並びにそれらの類縁物質の用途 |
CN101591314A (zh) * | 2008-10-24 | 2009-12-02 | 中国海洋大学 | 蛇孢假壳素(ophiobolin)类二倍半萜烯化合物及其制备方法和用途 |
Non-Patent Citations (2)
Title |
---|
HONG-BING LIU ET AL: "Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge-Derived Fungus Aspergillus ustus", 《HELVETICA CHIMICA ACTA》 * |
卢圳域: "《特殊环境微生物的次生代谢产物研究》", 23 September 2009 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103193743A (zh) * | 2013-03-22 | 2013-07-10 | 中国科学院微生物研究所 | 一种化合物、该化合物的制备方法以及该化合物在制备抗肿瘤药物中的应用 |
CN103193743B (zh) * | 2013-03-22 | 2015-11-18 | 中国科学院微生物研究所 | 一种化合物、该化合物的制备方法以及该化合物在制备抗肿瘤药物中的应用 |
CN107893090A (zh) * | 2017-10-20 | 2018-04-10 | 国家海洋局第三海洋研究所 | 土曲霉h768的发酵化合物在制备抗过敏药物中的应用 |
CN107893090B (zh) * | 2017-10-20 | 2020-05-15 | 国家海洋局第三海洋研究所 | 土曲霉h768的发酵化合物在制备抗过敏药物中的应用 |
CN108383707A (zh) * | 2018-04-23 | 2018-08-10 | 中国科学院烟台海岸带研究所 | 一种胡萝卜烷倍半萜类化合物及其制备和应用 |
CN108383707B (zh) * | 2018-04-23 | 2020-11-03 | 中国科学院烟台海岸带研究所 | 一种胡萝卜烷倍半萜类化合物及其制备和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN102659547B (zh) | 2014-04-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102643167B (zh) | 一种海藻内生真菌倍半萜类化合物及其制备和应用 | |
CN102187870B (zh) | 一种海藻内生真菌次生代谢产物二萜生物碱类化合物的应用 | |
CN104277982B (zh) | 一种三环系倍半萜类化合物及其制备方法和用途 | |
CN102659521B (zh) | 一种海藻溴代倍半萜类化合物及其制备和应用 | |
CN106434783A (zh) | 一种苯并吡喃酮化合物及其制备方法和在制备抗菌药物中的应用 | |
CN102659912B (zh) | 一种多氧二倍半萜类化合物及其制备和应用 | |
CN103937678A (zh) | 一株海洋壳青霉、其衍生的喹啉酮类化合物及其制备和应用 | |
CN103255061A (zh) | 灰黄青霉、由其产生的抗菌活性化合物及应用 | |
CN102659547B (zh) | 一种蛇孢假壳素类二倍半萜化合物及其制备和应用 | |
CN102875551A (zh) | 一种氯代生物碱类化合物及其制备和应用 | |
CN106632230B (zh) | 一种海洋真菌爪曲霉溴代缩酚环酸醚类化合物及其制备方法和应用 | |
CN103613490B (zh) | 一种降二萜类化合物及其制备和应用 | |
CN102701935B (zh) | 一种四环二萜类化合物及其制备和应用 | |
CN102786528B (zh) | 一种多氧生物碱类化合物及其制备和应用 | |
CN109400444B (zh) | 抑制植物病源真菌的倍半萜类化合物及其制备方法 | |
CN104804071B (zh) | 一种缩酚酸肽类化合物及其制备方法和应用 | |
CN103045488B (zh) | 一种白僵菌as-70菌株及其应用 | |
CN102816717A (zh) | 一株孔氏葡萄球菌及其制备5-氨基乙酰丙酸的方法 | |
CN102190612B (zh) | 一种天然海藻内生真菌二萜生物碱类化合物及其制备和应用 | |
CN115725420A (zh) | 一株产黄酮类化合物的工业大麻内生真菌及其应用 | |
CN106566782B (zh) | 一株产7-羟基环庚三烯酚酮的假单胞菌及其应用 | |
CN102190698B (zh) | 一种海藻内生真菌二萜生物碱类化合物及其制备和应用 | |
CN102675293A (zh) | 一种吲哚二酮哌嗪类衍生物及其制备方法和应用 | |
CN108640841B (zh) | 一种缩酚酸环醚类化合物及其制备方法和应用 | |
CN102190614B (zh) | 一种天然海藻内生真菌二萜生物碱类化合物的应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: BEIHAI SOUTHERN OCEAN SCIENCE AND TECHNOLOGY DEVEL Free format text: FORMER OWNER: YANTAI INSTITUTE OF COASTAL ZONE RESEARCH, CHINESE ACADEMY OF SCIENCES Effective date: 20141204 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 264003 YANTAI, SHANDONG PROVINCE TO: 536000 BEIHAI, GUANGXI ZHUANG AUTONOMOUS REGION |
|
TR01 | Transfer of patent right |
Effective date of registration: 20141204 Address after: 536000, the Guangxi Zhuang Autonomous Region Beihai Beihai Avenue science and technology building, 5 floor Patentee after: Beihai Nanfang marine science and Technology Development Co.,Ltd. Address before: Chunhui road Laishan District 264003 Shandong city of Yantai province No. 17 Patentee before: Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140416 |
|
CF01 | Termination of patent right due to non-payment of annual fee |