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维基百科

柚皮素

一月 01, 1970

柚皮素是一种无味，颜色由白色至淡黄的黄烷酮，是一种类黄酮。它是葡萄柚中的主要黄烷酮，[2]并存在于多种水果与草药中。 [3]

柚皮素
IUPAC名
5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
别名 Naringetol; Salipurol; Salipurpol; 4',5,7-Trihydroxyflavanone
识别
CAS号 480-41-1  Y
PubChem 439246
ChemSpider 388383
SMILES
 
  • O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
ChEBI 50202
DrugBank DB03467
性质
化学式 C15H12O5
摩尔质量 272.25 g·mol−1
熔点 251 °C（524 K）
溶解性（水） 475 mg/L [1]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

结构 编辑

柚皮素具有黄烷酮的骨架结构，其4'，5和7位碳原子处有三个羟基。柚皮素可以单体存在，亦有糖苷形式即柚皮苷，其具有加入的二糖新橙皮糖与7位碳原子连接而成。

像大多数黄烷酮一样，柚皮素在碳2上有一个手性中心，尽管光学纯度是可变的。 [3] [4] S(-)-柚皮素的外消旋已显示相当快地发生。 [5]

来源和生物利用度 编辑

柚皮素及其糖苷存在于多种草药和水果中，包括葡萄柚，[6]佛手柑，[7]酸橙，[8]酸樱桃，[9]西红柿，[10] [11]可可，[12] [11] [12]希腊牛至，[13]水薄荷，[14]以及豆类。[15]柚皮素与柚皮苷的比例因来源而异，对映体比例也是如此。 [4]

柚皮苷-7-葡萄糖苷形式的生物利用度似乎低于聚乙二醇形式。[16]

服用葡萄柚汁后，柚皮素血浆浓度比服用橙汁更高。 [17]在葡萄柚中还发现了相关的化合物山柰酚，其羟基紧挨着酮基。

柚皮素可以从煮熟的番茄酱中吸收。 每10克番茄酱中含有253毫克柚皮素。 [18]

生物合成与代谢 编辑

它衍生自丙二酰基CoA和4-香豆酰基CoA 。后者衍生自苯丙氨酸。将所得丁烯酮通过作用于查耳酮合成酶，得到查耳酮。查尔酮随后经历闭环，生成柚皮素。 [19]

柚皮素-8-二甲基烯丙基转移酶使用二甲基烯丙基二磷酸和(−)- (2S)-柚皮素以产生二磷酸和8-戊基柚皮素 。雅致小克银汉霉（Cunninghamella elegans）是一种哺乳动物新陈代谢的真菌模型生物，它可用于研究柚皮素的硫酸化。 [20]

潜在的生物学影响 编辑

抗菌，抗真菌和抗病毒 编辑

柚皮素对表皮葡萄球菌，金黄色葡萄球菌，枯草芽孢杆菌，黄球菌和大肠杆菌具有抗菌作用。 [21]进一步的研究增加了对乳酸乳球菌，[22]嗜酸乳杆菌，内氏放线菌，口腔普雷沃菌[22]嗜酸乳杆菌，黑色素丙酸杆菌，牙龈卟啉单胞菌[23]以及白色念珠菌，热带和克柔念珠菌等抗菌药物的证据。 [24]尽管没有证明柚皮苷对微生物的脲酶活性有任何抑制作用，但有证据证明其对幽门螺杆菌具有抗菌作用。 [25]

柚皮素可以减少体外培养的HCV感染的肝细胞病毒的产生。这可能继发于柚皮素抑制极低密度脂蛋白分泌的作用。 [26]柚皮苷的抗病毒作用目前正在临床研究中。 [27]关于脊髓灰质炎病毒， HSV-1和HSV-2的抗病毒作用的报道也已经发表，尽管病毒的复制并未受到抑制。 [28] [29]

抗炎 编辑

尽管有柚皮苷抗炎活性的证据， [30]但已观察到柚皮苷的抗炎活性很差或根本不存在。 [31] [32]

抗氧化剂 编辑

柚皮素已被证明具有显着的抗氧化性能。 [33] [34]在体外和动物研究中已证明它可以减少DNA的氧化损伤。 [35] [36]

抗肿瘤 编辑

研究指出，柚皮素在乳腺癌、胃癌、肝癌、宫颈癌、胰腺癌、结肠组织癌细胞中以及白血病细胞中都可诱导細胞毒性。[37]柚皮素抑制人类乳腺癌生长的机制已被证实，在此基础上提出了两种柚皮素抗癌的假说。[38][39] 第一种假说是柚皮素抑制芳香化酶，从而减少了肿瘤生长。 [40]第二种假说提出与雌激素受体的互作是其调节肿瘤生长的原因。 [41]柚皮苷的新衍生物对多药耐药（英语：multiple drug resistance）的癌症具有活性。 [42]

补充阅读 编辑

  • 对人细胞色素P450同工型[[CYP1A2]]具有抑制作用，导致原本无害的物质致癌。 Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. Br J Clin Pharmacol. April 1993, 35 (4): 431–6. PMC 1381556  . PMID 8485024. doi:10.1111/j.1365-2125.1993.tb04162.x. 
  • Wistuba, Dorothee; Trapp, Oliver; Gel-Moreto, Nuria; Galensa, Rudolf; Schurig, Volker. Stereoisomeric Separation of Flavanones and Flavanone-7-O-glycosides by Capillary Electrophoresis and Determination of Interconversion Barriers. Analytical Chemistry. 2006-05-01, 78 (10): 3424–3433. ISSN 0003-2700. PMID 16689546. doi:10.1021/ac0600499. 
  • Krause, Martin; Galensa, Rudolf. High-performance liquid chromatography of diastereomeric flavanone glycosides in Citrus on a β-cyclodextrin-bonded stationary phase (Cyclobond I). Journal of Chromatography A. 1991, 588 (1–2): 41–45. doi:10.1016/0021-9673(91)85005-z （英语）. 
  • Gaggeri, Raffaella; Rossi, Daniela; Collina, Simona; Mannucci, Barbara; Baierl, Marcel; Juza, Markus. Quick development of an analytical enantioselective high performance liquid chromatography separation and preparative scale-up for the flavonoid Naringenin. Journal of Chromatography A. 2011-08-12, 1218 (32): 5414–5422. PMID 21397238. doi:10.1016/j.chroma.2011.02.038. 
  • Wan, Lili; Sun, Xipeng; Li, Yan; Yu, Qi; Guo, Cheng; Wang, Xiangwei. A Stereospecific HPLC Method and Its Application in Determination of Pharmacokinetics Profile of Two Enantiomers of Naringenin in Rats. Journal of Chromatographic Science. 2011-04-01, 49 (4): 316–320. ISSN 0021-9665. PMID 21439124. doi:10.1093/chrsci/49.4.316. 
  • 柚皮苷还在小鼠中产生BDNF依赖性抗抑郁剂样作用。 BDNF signaling is necessary for the antidepressant-like effect of naringenin. Prog. Neuropsychopharmacol. Biol. Psychiatry. October 2013, 48C: 135–141. PMID 24121063. doi:10.1016/j.pnpbp.2013.10.002. 
  • Gao, K; Henning, S; Niu, Y; Youssefian, A; Seeram, N; Xu, A; Heber, D. The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells. The Journal of Nutritional Biochemistry. 2006, 17 (2): 89–95. PMID 16111881. doi:10.1016/j.jnutbio.2005.05.009.  </ ref>
  • Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships. J. Nat. Prod. August 2007, 70 (8): 1278–82. PMC 2265593  . PMID 17685652. doi:10.1021/np070194x. 
  • 据报道，柚皮素可诱导前脂肪细胞凋亡。Hsu, Chin-Lin; Huang, Shih-Li; Yen, Gow-Chin. Inhibitory Effect of Phenolic Acids on the Proliferation of 3T3-L1 Preadipocytes in Relation to Their Antioxidant Activity. Journal of Agricultural and Food Chemistry. 2006-06-01, 54 (12): 4191–4197. ISSN 0021-8561. PMID 16756346. doi:10.1021/jf0609882. 
  • 柚皮素似乎可以保护LDLR缺陷型小鼠免受高脂饮食的肥胖影响。 Naringenin prevents dyslipidemia, apolipoprotein B overproduction, and hyperinsulinemia in LDL receptor-null mice with diet-induced insulin resistance. Diabetes. October 2009, 58 (10): 2198–210. PMC 2750228  . PMID 19592617. doi:10.2337/db09-0634. 
  • 柚皮素通过抑制高胆固醇饮食的大鼠中的HMG-CoA还原酶和ACAT降低血浆和肝胆固醇的浓度。 Cholesterol-lowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A:cholesterol acyltransferase in rats. Ann. Nutr. Metab. 1999, 43 (3): 173–80. PMID 10545673. doi:10.1159/000012783. 
  • 在一项使用阿尔茨海默氏病小鼠模型的研究中，柚皮苷已被证明可以改善记忆力并减少淀粉样蛋白和tau蛋白。Ghofraniab, Saeed; Joghataei, Mohammad-Taghi; Mohsenia, Simin; Baluchnejadmojaradd, Tourandokht; Bagheriac, Maryam; Khamsee, Safoura; Roghani, Mehrdad. Naringenin improves learning and memory in an Alzheimer's disease rat model: Insights into the underlying mechanisms. European Journal of Pharmacology. 5 October 2015, 764: 195–201. PMID 26148826. doi:10.1016/j.ejphar.2015.07.001. Yang, Zhiyou; Kuboyama, Tomoharu; Tohda, Chihiro. Naringenin promotes microglial M2 polarization and Aβ degradation enzyme expression. Phytotherapy Research. 2019-02-15, 33 (4): 1114–1121. ISSN 1099-1573. PMID 30768735. doi:10.1002/ptr.6305. Yang, Zhiyou; Kuboyama, Tomoharu; Tohda, Chihiro. A Systematic Strategy for Discovering a Therapeutic Drug for Alzheimer's Disease and Its Target Molecule. Frontiers in Pharmacology. 19 June 2017, 8: 340. PMC 5474478  . PMID 28674493. doi:10.3389/fphar.2017.00340. 

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  39. ^ Hermawan A, Ikawati M, Jenie RI, Khumaira A, Putri H, Nurhayati IP, Angraini SM, Muflikhasari HA. Identification of potential therapeutic target of naringenin in breast cancer stem cells inhibition by bioinformatics and in vitro studies (PDF). Saudi Pharmaceutical Journal. January 2021, 29 (1): 12–26. PMC 7873751  . PMID 33603536. doi:10.1016/j.jsps.2020.12.002. （原始内容 (PDF)于2021-10-18）. 
  40. ^ van Meeuwen, J. A.; Korthagen, N.; de Jong, P. C.; Piersma, A. H.; van den Berg, M. (Anti)estrogenic effects of phytochemicals on human primary mammary fibroblasts, MCF-7 cells and their co-culture. Toxicology and Applied Pharmacology. 2007-06-15, 221 (3): 372–383. PMID 17482226. doi:10.1016/j.taap.2007.03.016. 
  41. ^ Harmon, Anne W.; Patel, Yashomati M. Naringenin Inhibits Glucose Uptake in MCF-7 Breast Cancer Cells: A Mechanism for Impaired Cellular Proliferation. Breast Cancer Research and Treatment. 2004-05-01, 85 (2): 103–110. ISSN 0167-6806. PMID 15111768. doi:10.1023/B:BREA.0000025397.56192.e2 （英语）. 
  42. ^ Ferreira, Ricardo J; Baptista, Rafael; Moreno, Alexis; Madeira, Patricia G; Khonkarn, Ruttiros; Baubichon-Cortay, Hélène; Santos, Daniel JVA dos; Falson, Pierre; Ferreira, Maria-José U. Optimizing the flavanone core toward new selective nitrogen-containing modulators of ABC transporters. Future Medicinal Chemistry. 2018-03-23, 10 (7): 725–741. PMID 29570361. doi:10.4155/fmc-2017-0228 （英语）. 

一月 01, 1970
柚皮素, 是一种无味, 颜色由白色至淡黄的黄烷酮, 是一种类黄酮, 它是葡萄柚中的主要黄烷酮, 并存在于多种水果与草药中, iupac名5, dihydroxy, hydroxyphenyl, chroman, 别名, naringetol, salipurol, salipurpol, trihydroxyflavanone, 识别, cas号, pubchem, 439246, chemspider, 388383, smiles, c2c3c, c1ccc, cc3o, chebi, 50202, drugb. 柚皮素是一种无味 颜色由白色至淡黄的黄烷酮 是一种类黄酮 它是葡萄柚中的主要黄烷酮 2 并存在于多种水果与草药中 3 柚皮素 IUPAC名5 7 Dihydroxy 2 4 hydroxyphenyl chroman 4 one 别名 Naringetol Salipurol Salipurpol 4 5 7 Trihydroxyflavanone 识别 CAS号 480 41 1 Y PubChem 439246 ChemSpider 388383 SMILES O C2c3c O C H c1ccc O cc1 C2 cc O cc3O ChEBI 50202 DrugBank DB03467 性质 化学式 C15H12O5 摩尔质量 272 25 g mol 1 熔点 251 C 524 K 溶解性 水 475 mg L 1 若非注明 所有数据均出自标准状态 25 100 kPa 下 目录 1 结构 2 来源和生物利用度 3 生物合成与代谢 4 潜在的生物学影响 4 1 抗菌 抗真菌和抗病毒 4 2 抗炎 4 3 抗氧化剂 4 4 抗肿瘤 5 补充阅读 6 参考文献结构 编辑柚皮素具有黄烷酮的骨架结构 其4 5和7位碳原子处有三个羟基 柚皮素可以单体存在 亦有糖苷形式即柚皮苷 其具有加入的二糖新橙皮糖与7位碳原子连接而成 像大多数黄烷酮一样 柚皮素在碳2上有一个手性中心 尽管光学纯度是可变的 3 4 S 柚皮素的外消旋已显示相当快地发生 5 来源和生物利用度 编辑柚皮素及其糖苷存在于多种草药和水果中 包括葡萄柚 6 佛手柑 7 酸橙 8 酸樱桃 9 西红柿 10 11 可可 12 11 12 希腊牛至 13 水薄荷 14 以及豆类 15 柚皮素与柚皮苷的比例因来源而异 对映体比例也是如此 4 柚皮苷 7 葡萄糖苷形式的生物利用度似乎低于聚乙二醇形式 16 服用葡萄柚汁后 柚皮素血浆浓度比服用橙汁更高 17 在葡萄柚中还发现了相关的化合物山柰酚 其羟基紧挨着酮基 柚皮素可以从煮熟的番茄酱中吸收 每10克番茄酱中含有253毫克柚皮素 18 生物合成与代谢 编辑它衍生自丙二酰基CoA和4 香豆酰基CoA 后者衍生自苯丙氨酸 将所得丁烯酮通过作用于查耳酮合成酶 得到查耳酮 查尔酮随后经历闭环 生成柚皮素 19 柚皮素 8 二甲基烯丙基转移酶使用二甲基烯丙基二磷酸和 2S 柚皮素以产生二磷酸和8 戊基柚皮素 雅致小克银汉霉 Cunninghamella elegans 是一种哺乳动物新陈代谢的真菌模型生物 它可用于研究柚皮素的硫酸化 20 潜在的生物学影响 编辑抗菌 抗真菌和抗病毒 编辑 柚皮素对表皮葡萄球菌 金黄色葡萄球菌 枯草芽孢杆菌 黄球菌和大肠杆菌具有抗菌作用 21 进一步的研究增加了对乳酸乳球菌 22 嗜酸乳杆菌 内氏放线菌 口腔普雷沃菌 22 嗜酸乳杆菌 黑色素丙酸杆菌 牙龈卟啉单胞菌 23 以及白色念珠菌 热带和克柔念珠菌等抗菌药物的证据 24 尽管没有证明柚皮苷对微生物的脲酶活性有任何抑制作用 但有证据证明其对幽门螺杆菌具有抗菌作用 25 柚皮素可以减少体外培养的HCV感染的肝细胞病毒的产生 这可能继发于柚皮素抑制极低密度脂蛋白分泌的作用 26 柚皮苷的抗病毒作用目前正在临床研究中 27 关于脊髓灰质炎病毒 HSV 1和HSV 2的抗病毒作用的报道也已经发表 尽管病毒的复制并未受到抑制 28 29 抗炎 编辑 尽管有柚皮苷抗炎活性的证据 30 但已观察到柚皮苷的抗炎活性很差或根本不存在 31 32 抗氧化剂 编辑 柚皮素已被证明具有显着的抗氧化性能 33 34 在体外和动物研究中已证明它可以减少DNA的氧化损伤 35 36 抗肿瘤 编辑 研究指出 柚皮素在乳腺癌 胃癌 肝癌 宫颈癌 胰腺癌 结肠组织癌细胞中以及白血病细胞中都可诱导細胞毒性 37 柚皮素抑制人类乳腺癌生长的机制已被证实 在此基础上提出了两种柚皮素抗癌的假说 38 39 第一种假说是柚皮素抑制芳香化酶 从而减少了肿瘤生长 40 第二种假说提出与雌激素受体的互作是其调节肿瘤生长的原因 41 柚皮苷的新衍生物对多药耐药 英语 multiple drug resistance 的癌症具有活性 42 补充阅读 编辑对人细胞色素P450同工型 CYP1A2 具有抑制作用 导致原本无害的物质致癌 Inhibitory effect of grapefruit juice and its bitter principal naringenin on CYP1A2 dependent metabolism of caffeine in man Br J Clin Pharmacol April 1993 35 4 431 6 PMC 1381556 nbsp PMID 8485024 doi 10 1111 j 1365 2125 1993 tb04162 x Wistuba Dorothee Trapp Oliver Gel Moreto Nuria Galensa Rudolf Schurig Volker Stereoisomeric Separation of Flavanones and Flavanone 7 O glycosides by Capillary Electrophoresis and Determination of Interconversion Barriers Analytical Chemistry 2006 05 01 78 10 3424 3433 ISSN 0003 2700 PMID 16689546 doi 10 1021 ac0600499 Krause Martin Galensa Rudolf High performance liquid chromatography of diastereomeric flavanone glycosides in Citrus on a b cyclodextrin bonded stationary phase Cyclobond I Journal of Chromatography A 1991 588 1 2 41 45 doi 10 1016 0021 9673 91 85005 z 英语 Gaggeri Raffaella Rossi Daniela Collina Simona Mannucci Barbara Baierl Marcel Juza Markus Quick development of an analytical enantioselective high performance liquid chromatography separation and preparative scale up for the flavonoid Naringenin Journal of Chromatography A 2011 08 12 1218 32 5414 5422 PMID 21397238 doi 10 1016 j chroma 2011 02 038 Wan Lili Sun Xipeng Li Yan Yu Qi Guo Cheng Wang Xiangwei A Stereospecific HPLC Method and Its Application in Determination of Pharmacokinetics Profile of Two Enantiomers of Naringenin in Rats Journal of Chromatographic Science 2011 04 01 49 4 316 320 ISSN 0021 9665 PMID 21439124 doi 10 1093 chrsci 49 4 316 柚皮苷还在小鼠中产生BDNF依赖性抗抑郁剂样作用 BDNF signaling is necessary for the antidepressant like effect of naringenin Prog Neuropsychopharmacol Biol Psychiatry October 2013 48C 135 141 PMID 24121063 doi 10 1016 j pnpbp 2013 10 002 Gao K Henning S Niu Y Youssefian A Seeram N Xu A Heber D The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells The Journal of Nutritional Biochemistry 2006 17 2 89 95 PMID 16111881 doi 10 1016 j jnutbio 2005 05 009 lt ref gt Flavonoids as opioid receptor ligands identification and preliminary structure activity relationships J Nat Prod August 2007 70 8 1278 82 PMC 2265593 nbsp PMID 17685652 doi 10 1021 np070194x 据报道 柚皮素可诱导前脂肪细胞凋亡 Hsu Chin Lin Huang Shih Li Yen Gow Chin Inhibitory Effect of Phenolic Acids on the Proliferation of 3T3 L1 Preadipocytes in Relation to Their Antioxidant Activity Journal of Agricultural and Food Chemistry 2006 06 01 54 12 4191 4197 ISSN 0021 8561 PMID 16756346 doi 10 1021 jf0609882 柚皮素似乎可以保护LDLR缺陷型小鼠免受高脂饮食的肥胖影响 Naringenin prevents dyslipidemia apolipoprotein B overproduction and hyperinsulinemia in LDL receptor null mice with diet induced insulin resistance Diabetes October 2009 58 10 2198 210 PMC 2750228 nbsp PMID 19592617 doi 10 2337 db09 0634 柚皮素通过抑制高胆固醇饮食的大鼠中的HMG CoA还原酶和ACAT降低血浆和肝胆固醇的浓度 Cholesterol lowering activity of naringenin via inhibition of 3 hydroxy 3 methylglutaryl coenzyme A reductase and acyl coenzyme A cholesterol acyltransferase in rats Ann Nutr Metab 1999 43 3 173 80 PMID 10545673 doi 10 1159 000012783 在一项使用阿尔茨海默氏病小鼠模型的研究中 柚皮苷已被证明可以改善记忆力并减少淀粉样蛋白和tau蛋白 Ghofraniab Saeed Joghataei Mohammad Taghi Mohsenia Simin Baluchnejadmojaradd Tourandokht Bagheriac Maryam Khamsee Safoura Roghani Mehrdad Naringenin improves learning and memory in an Alzheimer s disease rat model Insights into the underlying mechanisms European Journal of Pharmacology 5 October 2015 764 195 201 PMID 26148826 doi 10 1016 j ejphar 2015 07 001 Yang Zhiyou Kuboyama Tomoharu Tohda Chihiro Naringenin promotes microglial M2 polarization and Ab degradation enzyme expression Phytotherapy Research 2019 02 15 33 4 1114 1121 ISSN 1099 1573 PMID 30768735 doi 10 1002 ptr 6305 Yang Zhiyou Kuboyama Tomoharu Tohda Chihiro A Systematic Strategy for Discovering a Therapeutic Drug for Alzheimer s Disease and Its Target Molecule Frontiers in Pharmacology 19 June 2017 8 340 PMC 5474478 nbsp PMID 28674493 doi 10 3389 fphar 2017 00340 参考文献 编辑 Naringenin ChemIDplus 原始内容存档于2015 12 20 Bioavailability of the flavanone naringenin and its glycosides in rats PDF Am J Physiol Gastrointest Liver Physiol December 2000 279 6 G1148 54 2020 09 29 PMID 11093936 doi 10 1152 ajpgi 2000 279 6 G1148 原始内容存档 PDF 于2020 11 07 3 0 3 1 Yanez Jaime A Andrews Preston K Davies Neal M Methods of analysis and separation of chiral flavonoids Journal of Chromatography B 2007 04 01 848 2 159 181 PMID 17113835 doi 10 1016 j jchromb 2006 10 052 4 0 4 1 Yanez Jaime A Remsberg Connie M Miranda Nicole D Vega Villa Karina R Andrews Preston K Davies Neal M Pharmacokinetics of selected chiral flavonoids hesperetin naringenin and eriodictyol in rats and their content in fruit juices Biopharmaceutics amp Drug Disposition 2008 01 01 29 2 63 82 ISSN 1099 081X PMID 18058792 doi 10 1002 bdd 588 英语 Krause M Galensa R Analysis of enantiomeric flavanones in plant extracts by high performance liquid chromatography on a cellulose triacetate based chiral stationary phase Chromatographia 1991 07 01 32 1 2 69 72 ISSN 0009 5893 doi 10 1007 BF02262470 英语 Ho Ping C Saville Dorothy J Coville Peter F Wanwimolruk Sompon Content of CYP3A4 inhibitors naringin naringenin and bergapten in grapefruit and grapefruit juice products Pharmaceutica Acta Helvetiae 2000 04 01 74 4 379 385 PMID 10812937 doi 10 1016 S0031 6865 99 00062 X Gattuso Giuseppe Barreca Davide Gargiulli Claudia Leuzzi Ugo Caristi Corrado Flavonoid Composition of Citrus Juices Molecules 2007 08 03 12 8 1641 1673 PMC 6149096 nbsp PMID 17960080 doi 10 3390 12081641 英语 Gel Moreto Nuria Streich Rene Galensa Rudolf Chiral separation of diastereomeric flavanone 7 O glycosides in citrus by capillary electrophoresis Electrophoresis 2003 08 01 24 15 2716 2722 ISSN 0173 0835 PMID 12900888 doi 10 1002 elps 200305486 Wang H Nair M G Strasburg G M Booren A M Gray J I Antioxidant polyphenols from tart cherries Prunus cerasus Journal of Agricultural and Food Chemistry 1999 03 01 47 3 840 844 ISSN 0021 8561 PMID 10552377 doi 10 1021 jf980936f Minoggio M Bramati L Simonetti P Gardana C Iemoli L Santangelo E Mauri P L Spigno P Soressi G P Polyphenol pattern and antioxidant activity of different tomato lines and cultivars Annals of Nutrition amp Metabolism 2003 01 01 47 2 64 69 ISSN 0250 6807 PMID 12652057 doi 10 1159 000069277 11 0 11 1 Vallverdu Queralt A Odriozola Serrano I Oms Oliu G Lamuela Raventos RM Elez Martinez P Martin Belloso O Changes in the polyphenol profile of tomato juices processed by pulsed electric fields J Agric Food Chem 2012 60 38 9667 9672 PMID 22957841 doi 10 1021 jf302791k 12 0 12 1 Sanchez Rabaneda Ferran Jauregui Olga Casals Isidre Andres Lacueva Cristina Izquierdo Pulido Maria Lamuela Raventos Rosa M Liquid chromatographic electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa Theobroma cacao Journal of Mass Spectrometry 2003 01 01 38 1 35 42 Bibcode 2003JMSp 38 35S ISSN 1076 5174 PMID 12526004 doi 10 1002 jms 395 Exarchou Vassiliki Godejohann Markus van Beek Teris A Gerothanassis Ioannis P Vervoort Jacques LC UV Solid Phase Extraction NMR MS Combined with a Cryogenic Flow Probe and Its Application to the Identification of Compounds Present in Greek Oregano Analytical Chemistry 2003 11 01 75 22 6288 6294 ISSN 0003 2700 PMID 14616013 doi 10 1021 ac0347819 Olsen Helle T Stafford Gary I van Staden Johannes Christensen Soren B Jager Anna K Isolation of the MAO inhibitor naringenin from Mentha aquatica L Journal of Ethnopharmacology 2008 05 22 117 3 500 502 PMID 18372132 doi 10 1016 j jep 2008 02 015 Hungria M Johnston A W Phillips D A Effects of flavonoids released naturally from bean Phaseolus vulgaris on nodD regulated gene transcription in Rhizobium leguminosarum bv phaseoli Molecular Plant Microbe Interactions 1992 05 01 5 3 199 203 ISSN 0894 0282 PMID 1421508 doi 10 1094 mpmi 5 199 Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation Biochem Biophys Res Commun November 1999 265 2 410 5 PMID 10558881 doi 10 1006 bbrc 1999 1695 Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice J Nutr February 2001 131 2 235 41 PMID 11160539 doi 10 1093 jn 131 2 235 Naringenin from cooked tomato paste is bioavailable in men J Nutr November 2002 132 11 3349 52 PMID 12421849 doi 10 1093 jn 132 11 3349 Wang Chuanhong Zhi Shuang Liu Changying Xu Fengxiang Zhao Aichun Wang Xiling Ren Yanhong Li Zhengang Yu Maode Characterization of Stilbene Synthase Genes in Mulberry Morus atropurpurea and Metabolic Engineering for the Production of Resveratrol in Escherichia coli Journal of Agricultural and Food Chemistry 2017 65 8 1659 1668 PMID 28168876 doi 10 1021 acs jafc 6b05212 Ibrahim AR Sulfation of naringenin by Cunninghamella elegans Phytochemistry January 2000 53 2 209 12 PMID 10680173 doi 10 1016 S0031 9422 99 00487 2 Rauha Jussi Pekka Remes Susanna Heinonen Marina Hopia Anu Kahkonen Marja Kujala Tytti Pihlaja Kalevi Vuorela Heikki Vuorela Pia Antimicrobial effects of Finnish plant extracts containing flavonoids and other phenolic compounds International Journal of Food Microbiology 2000 05 25 56 1 3 12 PMID 10857921 doi 10 1016 S0168 1605 00 00218 X 22 0 22 1 Mandalari G Bennett R N Bisignano G Trombetta D Saija A Faulds C B Gasson M J Narbad A Antimicrobial activity of flavonoids extracted from bergamot Citrus bergamia Risso peel a byproduct of the essential oil industry Journal of Applied Microbiology 2007 12 01 103 6 2056 2064 ISSN 1364 5072 PMID 18045389 doi 10 1111 j 1365 2672 2007 03456 x Koru Ozgur Toksoy Fulya Acikel Cengiz Han Tunca Yasar Meric Baysallar Mehmet Uskudar Guclu Aylin Akca Eralp Ozkok Tuylu Asli Sorkun Kadriye In vitro antimicrobial activity of propolis samples from different geographical origins against certain oral pathogens Anaerobe 2007 06 01 13 3 4 140 145 ISSN 1075 9964 PMID 17475517 doi 10 1016 j anaerobe 2007 02 001 Uzel Atac Sorkun Kadri ye Oncag Ozant Cogulu Dilsah Gencay Omur Sali h Beki r Chemical compositions and antimicrobial activities of four different Anatolian propolis samples Microbiological Research 2005 04 25 160 2 189 195 PMID 15881836 doi 10 1016 j micres 2005 01 002 Bae Eun Ah Han Myung Kim Dong Hyun In vitroAnti Helicobacter pylori Activity of Some Flavonoids and Their Metabolites Planta Medica 1999 65 5 442 443 PMID 10454900 doi 10 1055 s 2006 960805 Apolipoprotein B dependent hepatitis C virus secretion is inhibited by the grapefruit flavonoid naringenin Hepatology May 2008 47 5 1437 45 PMC 4500072 nbsp PMID 18393287 doi 10 1002 hep 22197 A Pilot Study of the Grapefruit Flavonoid Naringenin for HCV Infection Full Text View ClinicalTrials gov clinicaltrials gov 原始内容存档于2010 10 01 Mucsi I Pragai B M Inhibition of virus multiplication and alteration of cyclic AMP level in cell cultures by flavonoids Experientia 1985 07 01 41 7 930 931 ISSN 0014 4754 PMID 2989000 doi 10 1007 BF01970018 英语 Lyu Su Yun Rhim Jee Young Park Won Bong Antiherpetic activities of flavonoids against herpes simplex virus type 1 HSV 1 and type 2 HSV 2 in vitro Archives of Pharmacal Research 2005 11 01 28 11 1293 1301 ISSN 0253 6269 PMID 16350858 doi 10 1007 BF02978215 英语 Kawaguchi K Kikuchi S Hasunuma R Maruyama H Ryll R Kumazawa Y Suppression of Infection Induced Endotoxin Shock in Mice by aCitrusFlavanone Naringin Planta Medica 2004 70 1 17 22 PMID 14765287 doi 10 1055 s 2004 815449 Gutierrez Venegas Gloria Kawasaki Cardenas Perla Rita Arroyo Cruz Santa Maldonado Frias Silvia Luteolin inhibits lipopolysaccharide actions on human gingival fibroblasts European Journal of Pharmacology 2006 07 10 541 1 2 95 105 PMID 16762341 doi 10 1016 j ejphar 2006 03 069 Olszanecki R Gebska A Kozlovski V I Gryglewski R J Flavonoids and nitric oxide synthase Journal of Physiology and Pharmacology 2002 12 01 53 4 Pt 1 571 584 ISSN 0867 5910 PMID 12512693 Gorinstein Shela Leontowicz Hanna Leontowicz Maria Krzeminski Ryszard Gralak Mikolaj Delgado Licon Efren Martinez Ayala Alma Leticia Katrich Elena Trakhtenberg Simon Changes in Plasma Lipid and Antioxidant Activity in Rats as a Result of Naringin and Red Grapefruit Supplementation Journal of Agricultural and Food Chemistry 2005 04 01 53 8 3223 3228 ISSN 0021 8561 PMID 15826081 doi 10 1021 jf058014h Yu Jun Wang Limin Walzem Rosemary L Miller Edward G Pike Leonard M Patil Bhimanagouda S Antioxidant Activity of Citrus Limonoids Flavonoids and Coumarins Journal of Agricultural and Food Chemistry 2005 03 01 53 6 2009 2014 ISSN 0021 8561 PMID 15769128 doi 10 1021 jf0484632 Sumit Kumar amp Ashu Bhan Tiku Biochemical and Molecular Mechanisms of Radioprotective Effects of Naringenin a Phytochemical from Citrus Fruits J Agric Food Chem 2016 64 8 1676 1685 PMID 26881453 doi 10 1021 acs jafc 5b05067 Chandra Jagetia Ganesh Koti Reddy Tiyyagura Venkatesha V A Kedlaya Rajendra Influence of naringin on ferric iron induced oxidative damage in vitro Clinica Chimica Acta 2004 09 01 347 1 2 189 197 PMID 15313158 doi 10 1016 j cccn 2004 04 022 Kanno Syu ichi Tomizawa Ayako Hiura Takako Osanai Yuu Shouji Ai Ujibe Mayuko Ohtake Takaharu Kimura Katsuhiko Ishikawa Masaaki Inhibitory Effects of Naringenin on Tumor Growth in Human Cancer Cell Lines and Sarcoma S 180 Implanted Mice Biological and Pharmaceutical Bulletin 2005 01 01 28 3 527 530 PMID 15744083 doi 10 1248 bpb 28 527 So Felicia V Guthrie Najla Chambers Ann F Moussa Madeleine Carroll Kenneth K Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices Nutrition and Cancer 1996 01 01 26 2 167 181 ISSN 0163 5581 PMID 8875554 doi 10 1080 01635589609514473 Hermawan A Ikawati M Jenie RI Khumaira A Putri H Nurhayati IP Angraini SM Muflikhasari HA Identification of potential therapeutic target of naringenin in breast cancer stem cells inhibition by bioinformatics and in vitro studies PDF Saudi Pharmaceutical Journal January 2021 29 1 12 26 PMC 7873751 nbsp PMID 33603536 doi 10 1016 j jsps 2020 12 002 原始内容存档 PDF 于2021 10 18 van Meeuwen J A Korthagen N de Jong P C Piersma A H van den Berg M Anti estrogenic effects of phytochemicals on human primary mammary fibroblasts MCF 7 cells and their co culture Toxicology and Applied Pharmacology 2007 06 15 221 3 372 383 PMID 17482226 doi 10 1016 j taap 2007 03 016 Harmon Anne W Patel Yashomati M Naringenin Inhibits Glucose Uptake in MCF 7 Breast Cancer Cells A Mechanism for Impaired Cellular Proliferation Breast Cancer Research and Treatment 2004 05 01 85 2 103 110 ISSN 0167 6806 PMID 15111768 doi 10 1023 B BREA 0000025397 56192 e2 英语 Ferreira Ricardo J Baptista Rafael Moreno Alexis Madeira Patricia G Khonkarn Ruttiros Baubichon Cortay Helene Santos Daniel JVA dos Falson Pierre Ferreira Maria Jose U Optimizing the flavanone core toward new selective nitrogen containing modulators of ABC transporters Future Medicinal Chemistry 2018 03 23 10 7 725 741 PMID 29570361 doi 10 4155 fmc 2017 0228 英语 取自 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