CAS: 2306-27-6; 2-(3,4-Dimethoxyphenyl)-5,6,7-Trimethoxy-4H-Chromen-4-One

该化合物是柑橘水果,特别是某些橙色品种的皮果中自然发现的聚甲基苯氧氟拉夫酮(PMF),具有显著的生物活动,包括抗氧化剂,抗炎和潜在的抗癌特性.在结构上,它具有多种甲氧基组,与其他氟化物相比,它更稳定,更具有生物利用率.研究表明,辛森锡可能调节细胞信号路径,如NF-B和MAPK, 有助于其治疗潜力.它的亲脂性可以有效地吸收细胞,使它成为有前途的食疗和药物应用的候选产品.HPLC和LC-MS等分析方法通常因其独特的化学特征而用于鉴定和量化.

结构式图片

欧盟法规

C&L通报

上下游产品

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one 3,6-dihydroxy-2,4-dimethoxyacetophenone 3,4-dimethoxybenzoic anhydride 3',4',5,6,7-pentahydroxyflavone3',4',5,6,7-pentahydroxyflavone Veratric acid 1-(2,3,4,6-tetramethoxyphenyl)ethanone 5-desmethylsinensetin

合成工艺路线路线简述

  • 合成目标产物 Sinensetin 主要起始原料 3,4-Dimethoxybenzoyl Chloride And 3,4,5-Trimethoxy Benzoic Acid
  • (文献来源)合成步骤主要原料 3,4-Dimethoxybenzoyl Chloride 和 3,4,5-Trimethoxy Benzoic Acid
📜3,4,5-三甲氧基苯酚置于三氟化硼乙醚,Potassium Tert-Butylate,碘体系中,用 乙醇,二甲基亚砜 用作溶剂,化学反应 6.5H,反应生成甜橙黄酮
参考文献:大鼠血浆,尿液和粪便中正念珠菌素及其代谢物的生物转化和定量
标题:大鼠血浆,尿液和粪便中正念珠菌素及其代谢物的生物转化和定量
摘要:据报道,作为柑橘皮中主要的多甲氧基黄酮之一,Sinensetin (Sin) 具有多种生物活性.然而,其详细的体内代谢命运尚未被发现.在本研究中,合成了 Sin 的可能代谢物,并通过超高效液相色谱-串联质谱 (Uplc-Ms/ms) 分析在喂食 100 Mg/(Kg.bw) 的大鼠中成功鉴定了所有五种单去甲基化代谢物) 罪.然后进行排泄和药代动力学研究,以定量研究它们在尿液,粪便和血浆样品中的含量随时间的变化.结果表明,4'-去甲基sinensetin,6-Demethylsinensetin和3'-Demethylsinensetin是上述生物样品中产生的三种最丰富的代谢物.此外,尿液中的 Sin 及其代谢物的总量显着高于粪便中的含量,表明 Sin 可能很容易在小肠中被吸收.
Doi:10.1021/acs.Jafc.1C05024

海关参考信息

专利信息


专利号:US-2007232495-A1
优先权日:2006-03-24
标题:Compositions and methods to add value to plant products, increasing the commercial quality, resistance to external factors and polyphenol content thereof
发明人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
权利人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
摘要:The invention is related to compositions and methods that naturally protect plant tissues against ultraviolet radiation and temperature, thus giving protection against sunburn to plants, plant parts, fruits and/or flowers during their development. The invention is also related to compositions and methods to naturally improve the color of plants, plant parts, fruits and/or flowers by inducing the natural synthesis of flavonoids and anthocyanins present in plants. Likewise, the present invention is directed to improving the nutritional value of plants, plant parts, fruits and/or flowers by increasing the normal levels of polyphenolic compounds, especially flavonoids, present therein. Additionally, the present invention is related to compositions and methods that give more resistance to plants, plant parts, fruits and/or flowers against pathogens as bacteria and fungi. Finally, the present invention is related to plants, plant parts, fruits, flowers and/or propagating material treated with the compositions described in the present document.

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主要参考文献


1: Kang SI, Shin HS, Kim SJ. Sinensetin enhances adipogenesis and lipolysis by increasing cyclic adenosine monophosphate levels in 3T3-L1 adipocytes. Biol Pharm Bull. 2015;38(4):552-8. doi: 10.1248/bpb.b14-00700. Epub 2015 Jan 24. doi: 10.1002/ptr.4683. Epub 2012 Mar 22. doi: 10.1016/j.jams.2012.05.005. Epub 2012 Jun 15. doi: 10.1021/jf3046768. Epub 2013 May 16. doi: 10.1055/s-0031-1298458. Epub 2012 Apr 19. doi: 10.4103/jpbs.JPBS_253_17. Review.
8: Shin HS, Kang SI, Yoon SA, Ko HC, Kim SJ. Sinensetin attenuates LPS-induced inflammation by regulating the protein level of IκB-α. Biosci Biotechnol Biochem. 2012;76(4):847-9. Epub 2012 Apr 7. doi: 10.1038/s41440-018-0083-8. Epub 2018 Aug 15. Chinese. doi: 10.1186/1472-6882-12-176.
12: Lam IK, Alex D, Wang YH, Liu P, Liu AL, Du GH, Lee SM. In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: identifying sinensetin as a novel antiangiogenesis agent. Mol Nutr Food Res. 2012 Jun;56(6):945-56. doi: 10.1002/mnfr.201100680. doi: 10.1097/CAD.0000000000000756. doi: 10.1016/j.phymed.2010.04.010. Epub 2010 Jun 23. pii: E973. doi: 10.3390/nu9090973.

合成参考文献


参考文献:10.1021/np960057s
摘要:Lale A, Herbert JM, Augereau JM, Billon M, Leconte M, Gleye J. Ability of different flavonoids to inhibit the procoagulant activity of adherent human monocytes. J Nat Prod. 1996 Mar;59(3):273–6. doi: 10.1021/np960057s.
参考文献:10.1016/s0278-6915(02)00007-8
摘要:Delaney B, Phillips K, Vasquez C, Wilson A, Cox D, Wang HB, Manthey J. Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones. Food Chem Toxicol. 2002 May;40(5):617–24. doi: 10.1016/s0278-6915(02)00007-8.
参考文献:10.1016/s0278-6915(01)00058-8
摘要:Delaney B, Phillips K, Buswell D, Mowry B, Nickels D, Cox D, Wang HB, Manthey J. Immunotoxicity of a standardized citrus polymethoxylated flavone extract. Food Chem Toxicol. 2001 Nov;39(11):1087–94. doi: 10.1016/s0278-6915(01)00058-8.
参考文献:10.1186/s12906-015-0884-0
摘要:Saidan NH, Hamil MSR, Memon AH, Abdelbari MM, Hamdan MR, Mohd KS, Majid AMSA, Ismail Z. Selected metabolites profiling of Orthosiphon stamineus Benth leaves extracts combined with chemometrics analysis and correlation with biological activities. BMC Complementary Medicine and Therapies. 2015 Oct 07;15(1):350. doi: 10.1186/s12906-015-0884-0.
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