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Article(id=1218290946706428649, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1218290941232861879, articleNumber=1001-2494(2024)15-1366-09, orderNo=null, doi=10.11669/cpj.2024.15.002, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1709568000000, receivedDateStr=2024-03-05, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1768392796446, onlineDateStr=2026-01-14, pubDate=1723046400000, pubDateStr=2024-08-08, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1768392796446, onlineIssueDateStr=2026-01-14, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1768392796446, creator=13701087609, updateTime=1768392796446, updator=13701087609, issue=Issue{id=1218290941232861879, tenantId=1146029695717560320, journalId=1190317699101192196, year='2024', volume='59', issue='15', pageStart='1361', pageEnd='1452', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1768392795141, creator=13701087609, updateTime=1768394622953, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1218298607682376061, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1218290941232861879, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1218298607682376062, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1218290941232861879, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=1366, endPage=1374, ext={EN=ArticleExt(id=1218290947817919249, articleId=1218290946706428649, tenantId=1146029695717560320, journalId=1190317699101192196, language=EN, title=Research Progress on Quercetin Derivatives and Their Biological Activities, columnId=null, journalTitle=Chinese Pharmaceutical Journal, columnName=null, runingTitle=null, highlight=null, articleAbstract=

Quercetin, a natural polyphenol, is one of the most abundant flavonoids found in many plant foods. Quercetin is a natural antioxidant, which can protect cells from damage caused by free radicals. Quercetin is a lipophilic compound that can pass through the cell membrane and regulate many intracellular and extracellular signal pathways related to disease progression and chemoprevention. Quercetin has a wide range of pharmacological activities, anti-inflammatory, antibacterial, anti-cancer and prevention of cardiovascular and cerebrovascular diseases, but its low solubility and bioavailability limit its clinical application. In order to improve these drawbacks, people have carried out structural modifications on quercetin, such as modifying hydroxyl groups to generate esters or ethers, modifying carbonyl groups to generate hydrazone or carbonyl oxygen substituted products, 8-substituted products, and forming complexes with metal ions. Quercetin derivatives with good solubility, high bioavailability, improved activity and enhanced anti-cancer activity were obtained by optimizing the structure of quercetin. The research progress of quercetin derivatives in recent years is reviewed to provide reference for the further development of quercetin derivatives.

, correspAuthors=Guangyu ZHAI, authorNote=null, correspAuthorsNote=null, copyrightStatement=null, copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=Ke LI, Jinhai LIU, Guangyu ZHAI), CN=ArticleExt(id=1218290951903171556, articleId=1218290946706428649, tenantId=1146029695717560320, journalId=1190317699101192196, language=CN, title=槲皮素衍生物及其生物活性研究进展, columnId=1190352408384471863, journalTitle=中国药学杂志, columnName=综述, runingTitle=null, highlight=null, articleAbstract=

槲皮素是一种天然多酚,是多种植物性食品中发现最丰富的类黄酮类化合物之一。槲皮素是天然的抗氧化剂,可以保护细胞免受自由基造成的损害。槲皮素是一种亲脂性化合物,能够穿过细胞膜,调节众多与疾病进展、化学预防有关的细胞内和细胞外信号通路。槲皮素具有广泛的药理活性,抗炎、抗菌、抗癌和预防心脑血管疾病,但是它的低溶解度和生物利用度限制了其在临床上的应用。为了改善这些缺点,研究者对槲皮素进行了结构修饰,修饰羟基生成酯或者醚,修饰羰基生成腙或者羰基氧被取代的产物,8-位被取代的产物,与金属离子生成配合物等。对槲皮素的结构进行优化修饰获得了溶解性能好、生物利用度高、活性明显改善、抗癌活性增强的槲皮素衍生物。本研究综述了近年来槲皮素衍生物的研究进展,为槲皮素衍生物的进一步开发提供参考。

, correspAuthors=翟广玉, authorNote=null, correspAuthorsNote=
* 翟广玉,男,教授 研究方向:中草药提取及结构优化 Tel:(0371)69691670
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李珂,女,硕士,副教授 研究方向:中草药提取及结构优化

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李珂,女,硕士,副教授 研究方向:中草药提取及结构优化

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化合物 IC50/μmol·L-1
HCT116 MDA-MB-231
1c 4.29 3.60
1d 2.47 2.65
1e 1.53 1.51
1g 3.36 2.82
槲皮素 5.79 5.81
), ArticleFig(id=1218484899850403895, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1218290946706428649, language=CN, label=表1, caption=

槲皮素-5-O-酰基酯衍生物对不同肿瘤细胞的增殖抑制率(IC50)

, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 IC50/μmol·L-1
HCT116 MDA-MB-231
1c 4.29 3.60
1d 2.47 2.65
1e 1.53 1.51
1g 3.36 2.82
槲皮素 5.79 5.81
), ArticleFig(id=1218484899934289975, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1218290946706428649, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 IC50/μmol·L-1
6a 0.1<IC50<10
6b 0.62
6c 0.075
6d 0.4
6e 0.16
6f >100
6g 0.18
槲皮素 >100
), ArticleFig(id=1218484900022370360, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1218290946706428649, language=CN, label=表2, caption=

槲皮素三氮唑衍生物对REM-134肿瘤细胞的增殖抑制率(IC50)

, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 IC50/μmol·L-1
6a 0.1<IC50<10
6b 0.62
6c 0.075
6d 0.4
6e 0.16
6f >100
6g 0.18
槲皮素 >100
), ArticleFig(id=1218484900173365306, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1218290946706428649, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 IC50/μmol·L-1
MGC803 HCC827 OVCAR-3
10a 37.47 87.41 7.04
10f 16.75 20.51 4.84
10g 19.40 20.00 3.88
槲皮素 98.80 >100 >100
), ArticleFig(id=1218484900295000124, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1218290946706428649, language=CN, label=表3, caption=

部分8-取代槲皮素衍生物对癌症细胞活力的抑制作用

, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 IC50/μmol·L-1
MGC803 HCC827 OVCAR-3
10a 37.47 87.41 7.04
10f 16.75 20.51 4.84
10g 19.40 20.00 3.88
槲皮素 98.80 >100 >100
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槲皮素衍生物及其生物活性研究进展
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李珂 , 刘金海 , 翟广玉 *
中国药学杂志 | 综述 2024,59(15): 1366-1374
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中国药学杂志 | 综述 2024, 59(15): 1366-1374
槲皮素衍生物及其生物活性研究进展
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李珂, 刘金海, 翟广玉*
作者信息
  • 郑州工业应用技术学院药学与化学工程学院, 郑州 451100

    • 李珂,女,硕士,副教授 研究方向:中草药提取及结构优化

通讯作者:

* 翟广玉,男,教授 研究方向:中草药提取及结构优化 Tel:(0371)69691670
Research Progress on Quercetin Derivatives and Their Biological Activities
Ke LI, Jinhai LIU, Guangyu ZHAI*
Affiliations
  • College of Pharmacy and Chemical Engineering, Zhengzhou University of Industrial Technology, Zhengzhou 451100, China
出版时间: 2024-08-08 doi: 10.11669/cpj.2024.15.002
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摘要
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槲皮素是一种天然多酚,是多种植物性食品中发现最丰富的类黄酮类化合物之一。槲皮素是天然的抗氧化剂,可以保护细胞免受自由基造成的损害。槲皮素是一种亲脂性化合物,能够穿过细胞膜,调节众多与疾病进展、化学预防有关的细胞内和细胞外信号通路。槲皮素具有广泛的药理活性,抗炎、抗菌、抗癌和预防心脑血管疾病,但是它的低溶解度和生物利用度限制了其在临床上的应用。为了改善这些缺点,研究者对槲皮素进行了结构修饰,修饰羟基生成酯或者醚,修饰羰基生成腙或者羰基氧被取代的产物,8-位被取代的产物,与金属离子生成配合物等。对槲皮素的结构进行优化修饰获得了溶解性能好、生物利用度高、活性明显改善、抗癌活性增强的槲皮素衍生物。本研究综述了近年来槲皮素衍生物的研究进展,为槲皮素衍生物的进一步开发提供参考。

槲皮素  /  衍生物  /  抗氧化  /  抗炎  /  抗癌

Quercetin, a natural polyphenol, is one of the most abundant flavonoids found in many plant foods. Quercetin is a natural antioxidant, which can protect cells from damage caused by free radicals. Quercetin is a lipophilic compound that can pass through the cell membrane and regulate many intracellular and extracellular signal pathways related to disease progression and chemoprevention. Quercetin has a wide range of pharmacological activities, anti-inflammatory, antibacterial, anti-cancer and prevention of cardiovascular and cerebrovascular diseases, but its low solubility and bioavailability limit its clinical application. In order to improve these drawbacks, people have carried out structural modifications on quercetin, such as modifying hydroxyl groups to generate esters or ethers, modifying carbonyl groups to generate hydrazone or carbonyl oxygen substituted products, 8-substituted products, and forming complexes with metal ions. Quercetin derivatives with good solubility, high bioavailability, improved activity and enhanced anti-cancer activity were obtained by optimizing the structure of quercetin. The research progress of quercetin derivatives in recent years is reviewed to provide reference for the further development of quercetin derivatives.

quercetin  /  derivatives  /  anti-oxidation  /  anti-inflammation  /  anti-cancer
李珂, 刘金海, 翟广玉. 槲皮素衍生物及其生物活性研究进展. 中国药学杂志, 2024 , 59 (15) : 1366 -1374 . DOI: 10.11669/cpj.2024.15.002
Ke LI, Jinhai LIU, Guangyu ZHAI. Research Progress on Quercetin Derivatives and Their Biological Activities[J]. Chinese Pharmaceutical Journal, 2024 , 59 (15) : 1366 -1374 . DOI: 10.11669/cpj.2024.15.002
正文
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许多研究证实,多酚类化合物对健康有积极的影响[1]。槲皮素(quercetin,图1)是一种天然多酚,是多种植物性食品中发现的最丰富的类黄酮类化合物之一,如洋葱、芹菜、西兰花、葡萄、柑橘等。槲皮素具有多种药理活性,如抗氧化[2-3]、抗炎[4]、抗菌[5]、抗病毒[6]、抗癌[7-9]。槲皮素是一种亲脂性化合物,能够穿过细胞膜,启动与化学预防相关的多种细胞内信号通路[10]。补充槲皮素可增强抗氧化、抗炎、抗癌、抗糖尿病及免疫保护作用,可预防许多慢性病等。
槲皮素分子中有4个酚羟基、1个烯醇式羟基及1个羰基,是天然的抗氧化剂。然而,低溶解度和较低的生物利用度限制了其在临床上的应用。为了使天然化合物发挥其预防和治疗疾病的作用能尽快应用于临床,人们对槲皮素进行了结构修饰,如修饰羟基可以生成酯或者醚、修饰羰基生成腙或者羰基氧被取代的产物、8-位被取代的产物、与金属离子生成配合物等。通过优化修饰获得了溶解性能好、生物利用度高、活性明显改善、抗癌活性增强的槲皮素衍生物[11-13]。本研究综述了近年来槲皮素衍生物的研究进展。槲皮素的衍生物作为潜在的药物,在治疗多种疾病方面很有价值,为槲皮素衍生物的进一步开发提供参考。
1 槲皮素酯类衍生物
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研究表明,通过增加类黄酮的亲脂性,可使其具有更好的生物活性及生物利用度。槲皮素3、3'和4'位上的羟基对自由基清除活性有显著的贡献。槲皮素的5-O位是亲脂性衍生化的理想位置。Lo 等[14]合成了7个槲皮素-5-O-酰基酯(1a~1g),见图2,评估了对HCT116结肠癌和MDA-MB-231乳腺癌细胞系的抗增殖活性。部分化合物实验结果见表1,衍生物1d、1e和1g具有较好的总体活性。
翟广玉课题组[15-16]以廉价的芦丁为原料,合成了12种槲皮素-3-O-酰基酯衍生物,见图3。采用MTT法初步评价了12个槲皮素酰基酯衍生物对4种肿瘤细胞[人食管鳞癌细胞(EC109)、人食管鳞癌细胞(EC9706)、人胃癌细胞(SGC7901)和人前列腺癌细胞(PC-3)]的体外抗肿瘤活性。结果显示, 对槲皮素进行结构修饰后, 其体外抗肿瘤活性增强。11种槲皮素酯类衍生物对MGC-803细胞具有很好的抑制作用,其IC50值均小于55 μmol·L-1,明显优于槲皮素(>142.188 μmol·L-1);化合物2g、2k和2l对于4种癌细胞都表现出相对较好的抑制作用。化合物2b和2k对PC-3的IC50值分别达到了18.561和14.228 μmol·L-1,远小于槲皮素(>423.841 μmol·L-1)。
2 槲皮素醚类衍生物
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在槲皮素酚羟基上引入1个取代基,特别是长的或大的基团,可能是抗前列腺癌药物的最好策略[17]。在3',4'-二甲氧基黄酮醇的3-羟基上加入适当的氨基部分,在3种前列腺癌细胞系中的效力提高了292倍[18]。对2,3-脱氢水飞蓟宾(另一类黄酮类)的5-羟基进行修饰,得到了1种能够持续抑制前列腺癌细胞增殖的最佳衍生物[19]。Rajaram等[20]合成了16个5-O-氨基烷基四甲基槲皮素,见图4。用WST-1细胞增殖测定法测定对前列腺癌细胞系(PC-3、DU-145和LNCaP)的体外抗增殖活性。实验显示,3g被确定为PC-3、DU-145和LNCaP前列腺癌细胞的最佳衍生物,IC50值分别为0.55、2.82和1.16 μmol·L-1,是槲皮素的35~182倍,3g可以显著诱导PC-3细胞凋亡,将作为抗前列腺癌药物进一步开发。
选择3,3',4',7-O-四甲基槲皮素作为母体化合物,因为5-羟基上连接烷基,可以在一定程度上克服槲皮素中酚羟基引起的药动学限制。
修饰槲皮素不同位置的羟基是提高其对癌细胞细胞毒性的有效策略。Mukherjee等[21]修饰槲皮素C-3'和C-5位羟基合成了10个槲皮素衍生物(4a~4j),见图5,并考察了水溶性和抗肿瘤活性。结果显示, HCT116细胞中4j的IC50值为0.34 μmol·L-1,与槲皮素(IC50值为45.32 μmol·L-1)相比,细胞毒性提高约133倍,溶解度增加380倍; 4h的IC50值为0.48 μmol·L-1,细胞毒性提高94倍,溶解度增加约400倍;4h没有显示外周血单个核细胞的毒性,表明4h对癌细胞有选择性毒性。在CT-26荷瘤小鼠中的体内实验证实,与槲皮素治疗相比,4h的治疗存活率显著增加,肿瘤体积减小60%。这表明槲皮素衍生物具有应用于临床的巨大潜力。
肿瘤的多药耐药(multidrug resistance,MDR)是肿瘤化疗的主要障碍。MDR的一个重要原因是三磷酸腺苷结合盒(ATP binding cassette,ABC)转运蛋白的过度表达致使抗癌药物的细胞外流增加。在ABC转运蛋白中, P-糖蛋白(P-gp,ABCB1)、多药耐药相关蛋白1 (MRP1,ABCC1)和乳腺癌耐药蛋白(BCRP,ABCG2)是与MDR相关的3个主要外排转运蛋白。槲皮素五甲醚被发现具有很强的P-gp调节活性[22]。其他甲基化酚类化合物, 如全甲基儿茶素没食子酸酯及其类似物也显示了有效的P-gp调节活性。这些结果表明,一些天然酚类化合物的甲基化可以提高P-gp的调节活性,多甲氧基取代苯环可能是逆转MDR的重要药效团。因此, Yuan等[23]在黄酮类化合物上引入了碱性氮,以增加它们的亲脂性,合成了11种新型具有杂环或多甲氧基苯基的槲皮素衍生物5a~5k,见图6。实验发现, 5h具有最高的P-gp调节活性,5e和5h显示出良好的BCRP调节活性。5h被发现对P-gp和BCRP具有等效性,由于其双重调节活性,可能是一种很好的MDR逆转剂。研究表明, 合成的槲皮素衍生物可以作为P-gp或BCRP介导的癌细胞耐药安全有效的调节剂。
1,2,3-三氮唑单元是药物化学中非常重要的药效团,具有抗癌、抗菌和抗炎等药理作用。在过去的十年中,出现了各种各样含有1,2,3-三氮唑单元的化合物,其中大多数具有抗肿瘤活性[24]。为提高槲皮素的抗癌性能,Gastalho等[25]合成了含有1,2,3-三氮唑基团的槲皮素衍生物,见图7。新的衍生物作为人乳腺癌模型来评价其对REM-134犬乳腺癌细胞的抑制作用。实验结果显示,新的衍生物活性要好于槲皮素,见表2,将对犬类和人类乳腺癌的治疗产生重要影响。
3 槲皮素羰基氧被取代的衍生物
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羰基氧可以被硫或硒取代,伍林斯(Woollins)试剂[26]作为硒化还原环加成试剂,与非共轭酰胺基席夫碱通过扩环反应得到相应的六元1,3,4-硒二唑,同时羰基发生了硒化反应。Martins 等[27]利用伍林斯试剂合成了含硒的槲皮素衍生物(7c),见图8,MTT法评估了其对MCF-7(乳腺癌细胞)的生长抑制作用。硒基衍生物7c的细胞毒性高于其他硫族衍生物[对于MCF-7,IC50值分别是:7a >100 μmol·L-1,7c (3.08±1.98)μmol·L-1,7b无]。7c具有抑制克隆扩增的能力并可抑制硫氧蛋白还原酶(thioredoxin reductase,TrxT)活性导致细胞凋亡,对其他细胞无毒性。7c是开发潜在的癌症化疗候选化合物。
劳森(Sven-Olov Lawesson)试剂是一个温和的易于操作的氧硫交换试剂, 将羰基化合物转化为硫羰基化合物。Al-Anssari等[28]利用劳森试剂合成了5个槲皮素衍生物(7d~7h)。MTT法实验显示,化合物7d和7e都使细胞活力显著降低,分别降低至43.7%和38.1%。化合物7d和7e的 IC50值分别为2.042和1.838 μmol·L-1,表明它们具有针对三阴性乳腺癌类型的潜在抗癌活性。
上皮-间质转化(epithelial-to-mesenchymal transition,EMT)是肺癌等多种癌症转移的驱动因素[29]。过氧化物酶体增殖物激活受体(peroxisome proliferator-activated receptor,PPAR-γ)是一种配体激活的转录因子,控制多种基因的表达,涉及EMT、细胞分化及脂肪酸代谢等。合成的化合物作为PPAR-γ的强效激动剂,由于其严重的不良反应,限制了应用。之前的研究发现槲皮素及其衍生物对PPAR-γ具有良好的稳定作用[30]。在此基础上,Ballav等[31]合成了5种新的槲皮素腙类衍生物(8a~8e),见图9,并分析了它们通过PPAR-γ部分激活对肺癌细胞系EMT的调节作用。实验显示,与罗格列酮(RSG)相比,8a、8d和8e表现出部分激活的特性,显著下调间充质标记物(Snail, Slug和Zeb-1)的水平,上调上皮标记物(E-cadherin),抑制EMT过程。8a、8d和8e能协同激活蛋白质,其内在活性明显低于完全激动剂RSG和弱激动剂槲皮素。在PPAR-γ部分激活后,通过抑制迁移侵袭来调节EMT生化标志物。这些结果表明,8a、8d和8e是很有前景的PPAR-γ部分激动剂,可以作为抗转移药物使用。
4 槲皮素C-8位的取代衍生物
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Mannich反应是通过亲电取代引入氨基烷基的反应,经常用于药物设计和合成。Buravlev等[32]通过曼尼希反应合成了4个8-取代槲皮素衍生物(9a~9d),见图10。抗氧化活性实验结果显示,在抗坏血酸/Fe2+β诱导的脑匀浆脂质过氧化模型中,所有衍生物均具有较高的抗氧化活性,9c在低浓度下显示出最高的活性。小鼠红细胞氧化性溶血研究表明, 具有吗啉代甲基或硫代吗啉代甲基的衍生物具有保护原始细胞免受急性氧化应激的能力和抗自由基活性,9c和9d在保护红细胞免受H2O2诱导的急性氧化应激的能力上超过了槲皮素。9c具有较好的抗炎作用,可用于治疗胃溃疡。
槲皮素是一种亲脂性化合物,能够穿过细胞膜,启动与化学预防相关的多种细胞内信号通路,抑制不同类型癌细胞的增殖。氟原子可以影响芳环的电子效应,从而影响分子与药物靶标的相互作用[33],据此,Shi等[34]设计合成了11个8-取代槲皮素衍生物(10a~10k),见图11。实验显示,10f和10g总体效果较好,对MGC803(人胃癌细胞)、HCC827(人非细胞肺癌细胞)和OVCAR-3(人卵巢癌细胞)的抑制作用见表3。
5 槲皮素配位化合物
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利什曼病是由利什曼原虫属的一种细胞内寄生虫引起的,主要表现在内脏和皮肤。槲皮素、山柰酚、芦丁已被认为是潜在的抗利什曼药物[35]。治疗利什曼病的药物主要有五价锑、两性霉素B和帕罗霉素。Abdeyazdan等[36]合成了Sb(V)槲皮素衍生物配合物(11a和11b),见图12。实验显示,亲脂性较强的11a抗无鞭毛虫作用最强,IC50值为(14.93±2.21)μmol·L-1。槲皮素Sb(V)配合物的抗无鞭毛虫活性高于泛影葡胺。在宿主巨噬细胞内,通过将该复合体分解成锑和槲皮素类似物,观察到的抗寄生虫作用可能与Sb(V)/Sb(Ⅲ)转化和黄酮类抗利什曼活性有关。
金属及其配合物的药用和临床上的应用具有重要的意义。Refat等[37]合成的槲皮素锌Zn(Ⅱ) (12)配合物见图13。实验显示,通过注射链脲佐菌素(STZ)诱导大鼠糖尿病。70只雄性白化大鼠分为7组:对照组、糖尿病未治疗组和糖尿病治疗组。结果表明,使用12和骨髓间充质干细胞(mesenchymal stem cells,MSCs)治疗胰腺和肺组织受到诱导的实验性糖尿病大鼠,可改善胰岛素分泌,减少细胞炎症,并有助于改善胰腺和糖代谢并发症,比单独使用 MSCs 或12时效果更好。结果证实12对治疗高血糖、遗传毒性非常有效和安全,开辟了治疗糖尿病及其相关并发症的新途径。
6 小结和展望
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槲皮素具有C6-C3-C6碳骨架的苯并γ-吡喃酮结构,由两个苯环A和B组成,并通过三碳吡喃环C连接。在槲皮素分子中,B环存在邻二酚结构,A环有间二酚结构,C环有1个烯醇式羟基酮结构,这些结构使得槲皮素具有一些特殊的生物活性。槲皮素的3个环是平面的,在该体系中,分子间形成3个氢键:两个氢键通过羰基建立,另一个在B环的羟基基团之间形成。修饰不同基团,得到的衍生物具有不同的生物活性和功效。
通过比较槲皮素及其衍生物的活性,可以发现衍生物的构效关系主要取决于取代基的位置和性质。槲皮素的3'-羟基是非常重要的位置,引入N-甲基-N-丙基哌嗪(4h),油水分配系数增大,水溶性提高,细胞穿透能力增强,细胞毒性活性增加了96倍,IC50值为0.48 μmol·L-1,在结肠癌模型中,治疗17只CT-26荷瘤小鼠,可显著提高存活率,并且肿瘤质量减少60%[21]。对槲皮素的3-羟基或者5-羟基进行修饰,可提高其抗病毒、抗糖尿病、抗癌和抗炎能力[14-15,20,23,25]。在槲皮素中引入羧基或酯基,可提高脂溶性、生物利用度,抗肿瘤活性增强[14-15,21]。槲皮素的羰基氧被硫或硒取代,抗肿瘤活性增强[27-28]。槲皮素金属配合物有较好的抗寄生虫、抗糖尿病活性[36-37]。在槲皮素8位引入不同的基团,可以改善口服利用度,用于治疗胃溃疡和提高抗癌活性[32,34]。
槲皮素是一种有价值的天然黄酮类化合物,由于能够调节多种靶点和信号通路而得到了广泛的研究。然而,槲皮素的低溶解性和生物利用度限制了其应用。因此,设计和合成新的槲皮素衍生物来改变其局限性势在必行。目前,对槲皮素的结构进行优化修饰,已经合成了许多溶解性能好,生物利用度高的槲皮素衍生物,在抗癌/抗增殖、抗氧化/抗衰老、抗病毒、抗炎、降糖等方面有许多优势,应用前景广阔。
基金
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  • 河南省教育厅高等学校重点科研项目(23B350002)
  • 郑州市高等学校名师技术技能工作室(郑教高[2015]70号)
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参考文献 引证文献
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2024年第59卷第15期
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doi: 10.11669/cpj.2024.15.002
  • 接收时间：2024-03-05
  • 首发时间：2026-01-14
  • 出版时间：2024-08-08
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  • 收稿日期：2024-03-05
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河南省教育厅高等学校重点科研项目(23B350002)
郑州市高等学校名师技术技能工作室(郑教高[2015]70号)
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    郑州工业应用技术学院药学与化学工程学院, 郑州 451100

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* 翟广玉,男,教授 研究方向:中草药提取及结构优化 Tel:(0371)69691670
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2种不同金属材料的力学参数
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Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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