JP2013510127A5 - - Google Patents
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- Publication number
- JP2013510127A5 JP2013510127A5 JP2012537406A JP2012537406A JP2013510127A5 JP 2013510127 A5 JP2013510127 A5 JP 2013510127A5 JP 2012537406 A JP2012537406 A JP 2012537406A JP 2012537406 A JP2012537406 A JP 2012537406A JP 2013510127 A5 JP2013510127 A5 JP 2013510127A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- triptolide
- medium
- days
- iii
- 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
- 238000000034 method Methods 0.000 claims description 17
- DFBIRQPKNDILPW-CIVMWXNOSA-N Triptolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](O)[C@]21[C@H]3O1 DFBIRQPKNDILPW-CIVMWXNOSA-N 0.000 claims description 13
- YKUJZZHGTWVWHA-UHFFFAOYSA-N triptolide Natural products COC12CC3OC3(C(C)C)C(O)C14OC4CC5C6=C(CCC25C)C(=O)OC6 YKUJZZHGTWVWHA-UHFFFAOYSA-N 0.000 claims description 13
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 12
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 10
- GEWDNTWNSAZUDX-UHFFFAOYSA-N methyl 7-epi-jasmonate Natural products CCC=CCC1C(CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-UHFFFAOYSA-N 0.000 claims description 9
- NKBASRXWGAGQDP-UHFFFAOYSA-N 5-chlorosalicylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1O NKBASRXWGAGQDP-UHFFFAOYSA-N 0.000 claims description 8
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 claims description 7
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims description 7
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005792 Geraniol Substances 0.000 claims description 6
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 6
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 6
- 229940043259 farnesol Drugs 0.000 claims description 6
- 229930002886 farnesol Natural products 0.000 claims description 6
- 229940113087 geraniol Drugs 0.000 claims description 6
- 230000006698 induction Effects 0.000 claims description 6
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 230000024245 cell differentiation Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 5
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical compound OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 claims description 4
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 claims description 4
- 229930191978 Gibberellin Natural products 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 claims description 4
- 239000004062 cytokinin Substances 0.000 claims description 4
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003448 gibberellin Substances 0.000 claims description 4
- 230000037361 pathway Effects 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 150000003505 terpenes Chemical class 0.000 claims description 4
- 235000007586 terpenes Nutrition 0.000 claims description 4
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 3
- 229960004249 sodium acetate Drugs 0.000 claims description 3
- 229940054269 sodium pyruvate Drugs 0.000 claims description 3
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Substances [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 claims description 3
- 239000002609 medium Substances 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000002028 Biomass Substances 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 claims 3
- 238000004113 cell culture Methods 0.000 claims 3
- 230000012447 hatching Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 241000894007 species Species 0.000 claims 3
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 claims 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 2
- 229930192334 Auxin Natural products 0.000 claims 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 2
- 239000002363 auxin Substances 0.000 claims 2
- 230000000779 depleting effect Effects 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000005556 hormone Substances 0.000 claims 2
- 229940088597 hormone Drugs 0.000 claims 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 206010020649 Hyperkeratosis Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 241000545405 Tripterygium Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 239000012228 culture supernatant Substances 0.000 claims 1
- 239000001963 growth medium Substances 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229940107700 pyruvic acid Drugs 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- HYVABZIGRDEKCD-UHFFFAOYSA-N N(6)-dimethylallyladenine Chemical compound CC(C)=CCNC1=NC=NC2=C1N=CN2 HYVABZIGRDEKCD-UHFFFAOYSA-N 0.000 description 2
- FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 1
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0957847A FR2952072B1 (fr) | 2009-11-05 | 2009-11-05 | Procede de production de triptolide |
| FR0957847 | 2009-11-05 | ||
| PCT/EP2010/066916 WO2011054929A2 (fr) | 2009-11-05 | 2010-11-05 | Procede de production de triptolide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013510127A JP2013510127A (ja) | 2013-03-21 |
| JP2013510127A5 true JP2013510127A5 (cg-RX-API-DMAC7.html) | 2015-07-02 |
| JP5951491B2 JP5951491B2 (ja) | 2016-07-13 |
Family
ID=42316019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537406A Expired - Fee Related JP5951491B2 (ja) | 2009-11-05 | 2010-11-05 | トリプトリドの製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9228209B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2496708B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5951491B2 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2952072B1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011054929A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159822B (zh) * | 2013-03-04 | 2016-05-18 | 华侨大学 | 雷公藤甲素及其衍生物组合物的制备方法 |
| ES2806553T3 (es) * | 2013-12-02 | 2021-02-18 | Phyton Holdings Llc | Producción de tapsigarginas por cultivo en suspensión de células de Thapsia |
| FR3031900A1 (fr) | 2015-01-22 | 2016-07-29 | Pf Medicament | Triptolide et ses derives dans le traitement des tumeurs et pathologies pre-cancereuses cutanees |
| US10406232B2 (en) * | 2015-06-29 | 2019-09-10 | Vets Plus, Inc. | Oral delivery compositions for treating dermatitis disorders in mammals |
| CN109311930B (zh) * | 2016-03-31 | 2023-02-24 | 伯克利之光生命科技公司 | 核酸稳定试剂、试剂盒及其使用方法 |
| FR3051116B1 (fr) * | 2016-05-12 | 2019-06-07 | Pierre Fabre Dermo-Cosmetique | Procede de production du celastrol et de derives triterpeniques pentacycliques |
| CN111132685A (zh) * | 2017-04-25 | 2020-05-08 | 瑞阳公司 | 五味子提取物的组合物和其方法 |
| WO2022081767A1 (en) * | 2020-10-13 | 2022-04-21 | Phytotech Labs, Inc. | Methods and compositions for axillary shoot micropropagation of cannabis and related plants |
| CN114642171B (zh) * | 2022-03-30 | 2023-04-25 | 华侨大学 | 一种高活性雷公藤代谢产物的诱导方法及雷公藤活性代谢组合物 |
| CN119386082A (zh) * | 2024-11-05 | 2025-02-07 | 广西壮族自治区亚热带作物研究所（广西亚热带农产品加工研究所） | 睡莲提取物在制备抗硫酸铜诱导的斑马鱼氧化和炎症损伤产品中的应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5940440B2 (ja) * | 1980-06-05 | 1984-09-29 | 協和醗酵工業株式会社 | 抗腫瘍性物質の製造法 |
| US4328309A (en) * | 1980-07-02 | 1982-05-04 | The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Method for producing tripdiolide, triptolide and celastrol |
| JPS585196A (ja) * | 1981-06-30 | 1983-01-12 | Kyowa Hakko Kogyo Co Ltd | 抗腫瘍性物質の製造法 |
| HU223267B1 (hu) * | 1996-05-24 | 2004-04-28 | Phyton, Inc. | Eljárás taxánok elõállítására Taxus fajok sejtjeinek tenyésztésével |
| EP1007066B1 (en) | 1996-09-27 | 2005-11-16 | The Board Of Regents, The University Of Texas System | Screening methods for glucocorticoid receptor binding substances using trypterygium wilfordii preparations |
| ATE258594T1 (de) * | 1997-02-19 | 2004-02-15 | Phytobiotech Inc | Verfahren zur steigerung des wachstums von pflanzenzellkulturen |
| US6303589B1 (en) * | 1998-12-08 | 2001-10-16 | Micro Flo Company | Pentacyclic triterpenes |
| CN1184309C (zh) * | 2002-01-25 | 2005-01-12 | 北京达科豪科技有限公司 | 植物悬浮培养细胞生产雷公藤总生物碱的方法 |
| AU2003903909A0 (en) * | 2003-07-25 | 2003-08-07 | Albright & Wilson (Australia) Limited | Production methods |
| US7879369B2 (en) * | 2007-09-18 | 2011-02-01 | Selvamedica, Llc | Combretum laurifolium Mart. extract and methods of extracting and using such extract |
| CN100593367C (zh) * | 2008-03-13 | 2010-03-10 | 西北农林科技大学无公害农药研究服务中心 | 一种由雷公藤悬浮细胞诱导不定根的方法 |
| CN101358180B (zh) | 2008-08-25 | 2010-09-08 | 西北农林科技大学无公害农药研究服务中心 | 一种由雷公藤细胞培养法生产雷公藤甲素和生物碱的方法 |
-
2009
- 2009-11-05 FR FR0957847A patent/FR2952072B1/fr not_active Expired - Fee Related
-
2010
- 2010-11-05 JP JP2012537406A patent/JP5951491B2/ja not_active Expired - Fee Related
- 2010-11-05 US US13/508,068 patent/US9228209B2/en not_active Expired - Fee Related
- 2010-11-05 EP EP10781460.0A patent/EP2496708B1/fr not_active Not-in-force
- 2010-11-05 WO PCT/EP2010/066916 patent/WO2011054929A2/fr not_active Ceased
-
2015
- 2015-11-24 US US14/950,685 patent/US20160143975A1/en not_active Abandoned
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