CN109053641B - 一种二新木脂素类化合物及分离制备方法和应用 - Google Patents
一种二新木脂素类化合物及分离制备方法和应用 Download PDFInfo
- Publication number
- CN109053641B CN109053641B CN201810959131.0A CN201810959131A CN109053641B CN 109053641 B CN109053641 B CN 109053641B CN 201810959131 A CN201810959131 A CN 201810959131A CN 109053641 B CN109053641 B CN 109053641B
- Authority
- CN
- China
- Prior art keywords
- dineolignan
- separating
- compound
- hemlock
- ethanol
- 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
- CECWJTLAPIRAPJ-UHFFFAOYSA-N Dineolignan Natural products O1C2=CC=C(C=CC)C=C2C(C)=C1C1=CC=C(O)C(OC=2C=CC=C(C=2)C=2OC3=CC=C(C=C3C=2C)C=CC)=C1 CECWJTLAPIRAPJ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000000926 separation method Methods 0.000 title abstract description 8
- 241000218685 Tsuga Species 0.000 claims abstract description 19
- 235000007173 Abies balsamea Nutrition 0.000 claims abstract description 18
- 238000002953 preparative HPLC Methods 0.000 claims abstract description 10
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 239000000499 gel Substances 0.000 claims abstract description 5
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000000259 anti-tumor effect Effects 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 235000011613 Pinus brutia Nutrition 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 9
- 241000018646 Pinus brutia Species 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 8
- 238000001514 detection method Methods 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000469 ethanolic extract Substances 0.000 claims description 6
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 2
- 238000000605 extraction Methods 0.000 description 4
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 2
- 238000000990 heteronuclear single quantum coherence spectrum Methods 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000012306 spectroscopic technique Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000218641 Pinaceae Species 0.000 description 1
- 241001116459 Sequoia Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930182783 neolignan Natural products 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810959131.0A CN109053641B (zh) | 2018-08-22 | 2018-08-22 | 一种二新木脂素类化合物及分离制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810959131.0A CN109053641B (zh) | 2018-08-22 | 2018-08-22 | 一种二新木脂素类化合物及分离制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109053641A CN109053641A (zh) | 2018-12-21 |
CN109053641B true CN109053641B (zh) | 2022-06-24 |
Family
ID=64686833
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810959131.0A Active CN109053641B (zh) | 2018-08-22 | 2018-08-22 | 一种二新木脂素类化合物及分离制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109053641B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109846876B (zh) * | 2019-04-18 | 2021-05-25 | 济宁医学院附属医院 | 木脂素类化合物在抗肿瘤中的应用及其药物制备 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107056800A (zh) * | 2017-05-31 | 2017-08-18 | 遵义医学院 | 一种长苞铁杉中新成分及其分离方法和应用 |
-
2018
- 2018-08-22 CN CN201810959131.0A patent/CN109053641B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107056800A (zh) * | 2017-05-31 | 2017-08-18 | 遵义医学院 | 一种长苞铁杉中新成分及其分离方法和应用 |
Non-Patent Citations (4)
Title |
---|
Photodiscoloration of western hemlock (Tsuga heterophylla) sapwood III Early stage of photodiscoloration reaction with lignans.;Fumio Kawamura等;《J Wood Sci》;19980201;第44卷;第47-55页 * |
云南铁杉中一个新的倍半木脂素(英文);赵友兴等;《云南植物研究》;20050430;第27卷(第2期);第217-222页 * |
云南铁杉中的木脂素成分(英文);赵友兴等;《云南植物研究》;20040430;第26卷(第2期);第229-233页 * |
长苞铁杉中木脂素类化学成分研究(英文);刘贵园等;《有机化学》;20200731;第40卷(第7期);第2120-2126页 * |
Also Published As
Publication number | Publication date |
---|---|
CN109053641A (zh) | 2018-12-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108707133B (zh) | 一种木脂素类化合物及其从老鹰茶中提取分离的方法与应用 | |
CN111704544B (zh) | 一种半日花烷型二萜类化合物及其分离方法和应用 | |
CN115160337B (zh) | 1α-烷基瑞香烷型二萜类化合物及其制备方法和应用 | |
CN113754533A (zh) | 氧化半日花烷型二萜类化合物及其分离方法和应用 | |
CN110818669B (zh) | 沉香四氢2-(2-苯乙基)色酮类化合物及其分离方法和应用 | |
CN108912086B (zh) | 一种活性黄酮类化合物及其制备方法与应用 | |
CN109096232B (zh) | 一种联苄基二聚体类化合物及其从金钗石斛中提取分离的方法与应用 | |
CN109053641B (zh) | 一种二新木脂素类化合物及分离制备方法和应用 | |
CN108912091B (zh) | 一种金钗石斛联苄基成分及提取分离和手性拆分方法 | |
CN107056800B (zh) | 一种长苞铁杉中的二聚体黄酮类成分及其分离方法和应用 | |
CN114276364B (zh) | 蒙古蒿中的倍半萜类化合物及制备方法和用途 | |
CN112794832B (zh) | 一个从牛蒡叶中提取的具有抗炎活性的化合物nby-10及其制备方法与应用 | |
CN112898357B (zh) | 金莲花中一种二萜苷类新化合物及其分离纯化方法和应用 | |
CN111606801B (zh) | 一种裂环半日花烷型二萜类化合物及其分离方法和应用 | |
CN109651233B (zh) | 一种生物碱类化合物及其从棒节石斛中提取分离的方法与应用 | |
CN110804083B (zh) | 醋栗叶醇的制备方法及其作为降糖药物的用途 | |
CN112194690B (zh) | 钩毛茜草中3个化合物及提取分离方法 | |
CN108314669B (zh) | 带有两个醇羟基的异黄酮化合物及其制备方法和应用 | |
CN116003238B (zh) | 茉莉根中倍半萜类化合物及其提取方法和用途 | |
CN114106070B (zh) | 连翘中的二聚体环烯醚萜化合物及其提取分离方法和应用 | |
CN113024494B (zh) | 一种菲类化合物、制备方法及应用 | |
CN111606787B (zh) | 一种脂肪醇类化合物及其制备方法 | |
CN114478683B (zh) | 一种球蕊五味子内酯a及其制备与应用 | |
CN108329287B (zh) | 大果榕中带有环氧基的化合物及其制备方法和应用 | |
CN109897079B (zh) | 一种香豆素糖苷类化合物的制备方法及其应用 |
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 | ||
CB02 | Change of applicant information |
Address after: 563000 No. 201, Dalian Road, Zunyi, Guizhou Applicant after: ZUNYI MEDICAL University Address before: 563000 No. 201, Dalian Road, Huichuan District, Zunyi City, Guizhou Province Applicant before: ZUNYI MEDICAL University |
|
CB02 | Change of applicant information | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240415 Address after: 200025 Building 1, 2 and 3, No. 105 Sinan Road, Huangpu District, Shanghai (centralized registration place) Patentee after: Anjie Tai Biotechnology (Shanghai) Co.,Ltd. Country or region after: China Address before: 563000 No. 201, Dalian Road, Zunyi, Guizhou Patentee before: ZUNYI MEDICAL University Country or region before: China |
|
TR01 | Transfer of patent right |