CAS: 6199-67-3; (R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-Pentamethyl-3,11-Dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-1H-Cyclopenta[a]Phenanthren-17-yl)-6-Hydroxy-2-Methyl-5-Oxohept-3-En-2-Yl Acetate
该化合物是从curbitaceous 植物中提取的生物活性化合物,具有强大的抗炎和抗氧化性特性,该化合物在各种疾病中的潜在治疗用途得到了广泛研究.Ccurbitacin B的结构独特性和生物活动使它成为宝贵的研究工具,是药物开发的有希望的候选工具.
- 英文名称(R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-Pentamethyl-3,11-Dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-1H-Cyclopenta[a]Phenanthren-17-yl)-6-Hydroxy-2-Methyl-5-Oxohept-3-En-2-Yl Acetate
- 中文名称葫芦素 B
- IUPAC名称(R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
- 其它别名Cuc B; Cucurbitacin B; Cucurbitacine (B); Cucurbitacin R - Datisca Principle B; (R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-Pentamethyl-3,11-Dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-
- CAS编号6199-67-3
- MFCD编号:MFCD07778083
- EINECS号:683-121-7
- FDA UNII编号:0115W5MABF
- 分子式:C32H46O8
- 分子量:558.71
- 产品CID: 1602132
- 产品分类生物化工 → 中草药成分
物理性质
- 熔点184-186 °C
- 沸点699.3±55.0 °C at 760 mmHg
- 闪点218.8±25.0 °C
- 密度1.2±0.1 g/cm3
- PH:D25 +88° (c = 1.55 in ethanol)
- pKa:12.60±0.29(预测)
- PSA:138.2
- LogP:2.31
- 折射率1.568
- 蒸汽压0.0±5.0 mmHg at 25°C
- 溶解性DMSO: Soluble10mg/mL, Clear
- 外观形态白色至米色粉末
- 储存条件置于阴暗处,密封干燥,2-8°C
- 产品应用该化合物用于抗体受体(ECR)对抗体注射,以降低20--羟氧基酮(20E)在蝴蝶中的信号水平.以确定其对细胞对胰腺癌细胞线的耐受力的影响.
MSDS等安全信息
欧盟法规
ECHA物质C&L通报上下游产品
(10Alpha)-25-(乙酰氧基)-2Beta,16Alpha,20-三羟基-9Beta-甲基-19-去甲羊毛甾-5-烯-3,11,22-三酮 23,24-Dihydrocucurbitacin B 13201-14-4合成工艺路线路线简述
[(E,6R)-6-Hydroxy-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-16-Hydroxy-4,4,9,13,14-Pentamethyl-3,11-Dioxo-2-[(2R,3R,5R,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-2,7,8,10,12,15,16,17-octahydro-1H-Cyclopenta[a]Phenanthren-17-Yl]-2-Methyl-5-Oxohept-3-En-2-Yl] Acetate 反应生成 葫芦素 B
参考文献:Mata,Rachel;Castaneda,Perla;Gamacho,Maria-Del-Rayo;Delgado,Guillermo,J. Natur. Prod.,51,(1988) N 5,C. 836-839
标题:Mata,Rachel;Castaneda,Perla;Gamacho,Maria-Del-Rayo;Delgado,Guillermo,J. Natur. Prod.,51,(1988) N 5,C. 836-839
专利信息
专利号:CN-117363495-A
优先权日:2023-09-26
标题:Aspergillus and its application in the synthesis of α-pyrones
专利号:CN-106749572-B
优先权日:2016-12-08
标题 :Transcription factor participating in regulation and control of synthesis of muskmelon bitter principle and application thereof
专利号:CN-106749572-A
优先权日:2016-12-08
标 题 :Transcription factor participating in regulation and control of synthesis of muskmelon bitter principle and application thereof
专利号:CN-110317829-B
优先权日:2016-12-08
标 题:Transcription factor participating in regulation and control of synthesis of muskmelon bitter principle and application thereof
专利号:CN-103483435-B
优先权日:2013-08-26
标题:Gene Clusters Involved in the Synthesis of Cucurbitacin C in Cucumber and Its Application
专利号:CN-103483435-A
优先权日:2013-08-26
标题 :Gene Clusters Involved in the Synthesis of Cucurbitacin C in Cucumber and Its Application
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主要参考文献
1: Luo WW, Zhao WW, Lu JJ, Wang YT, Chen XP. Cucurbitacin B suppresses metastasis mediated by reactive oxygen species (ROS) via focal adhesion kinase (FAK) in breast cancer MDA-MB-231 cells. Chin J Nat Med. 2018 Jan;16(1):10-19. doi: 10.1016/S1875-5364(18)30025-6. doi: 10.18632/oncotarget.21704. eCollection 2017 Nov 28.
4: Sallam AM, Esmat A, Abdel-Naim AB. Cucurbitacin-B attenuates CCl(4) -induced hepatic fibrosis in mice through inhibition of STAT-3. Chem Biol Drug Des. 2017 Dec 17. doi: 10.1111/cbdd.13160. [Epub ahead of print] doi: 10.4103/pm.pm_397_16. Epub 2017 Oct 11.
7: Garg S, Kaul SC, Wadhwa R. Cucurbitacin B and cancer intervention: Chemistry, biology and mechanisms (Review). Int J Oncol. 2018 Jan;52(1):19-37. doi: 10.3892/ijo.2017.4203. Epub 2017 Nov 10. doi: 10.1016/j.jchromb.2017.09.024. Epub 2017 Sep 18. doi: 10.3892/ol.2017.6148. Epub 2017 May 10.
合成参考文献
摘要:Zhongcaoyao. Chinese Traditional and Herbal Medicine., 23(605), 1992
摘要:LE-MEN J ET AL; RELATION BETWEEN STRUCTURE OF CUCURBITACINS AND THEIR TOXICITY AND LAXATIVE ACTIVITY; CHIM THER 4(6) 459 (1969)
参考文献:10.1016/s0024-3205(99)00200-3
摘要:Peters RR, Saleh TF, Lora M, Patry C, de Brum-Fernandes AJ, Farias MR, Ribeiro-do-Valle RM. Anti-inflammatory effects of the products from Wilbrandia ebracteata on carrageenan-induced pleurisy in mice. Life Sci. 1999;64(26):2429–37. doi: 10.1016/s0024-3205(99)00200-3.
参考文献:10.3390/ijms11125323
摘要:Duangmano S, Dakeng S, Jiratchariyakul W, Suksamrarn A, Smith DR, Patmasiriwat P. Antiproliferative effects of cucurbitacin B in breast cancer cells: down-regulation of the c-Myc/hTERT/telomerase pathway and obstruction of the cell cycle. Int J Mol Sci. 2010;11(12):5323–38.
参考文献:10.1007/s11356-014-3021-6
摘要:Krzyśko-Łupicka T, Cybulska K, Wieczorek A, Możdżer E, Nowak MJ. The effect of spent bleaching earth ageing process on its physicochemical and microbial composition and its potential use as a source of fatty acids and triterpenes. Environmental Science and Pollution Research. 2014 May 31;21(18):10765–74. doi: 10.1007/s11356-014-3021-6.
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