柚皮素

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
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，所有数据均出自一般条件（25 ℃，100 kPa）下。

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]

结构

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

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] [13] [14]希腊牛至，[15]水薄荷，[16]以及豆类。[17]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。[18]

服用葡萄柚汁后，柚皮素血浆浓度比服用橙汁更高。 [19]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。 [20]

生物合成与代谢

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。 [21]

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。 [22]

潜在的生物学影响

抗菌，抗真菌和抗病毒

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。 [23]进一步的研究增加了对乳酸乳球菌，[24]嗜酸乳杆菌，内氏放线菌，口腔普雷沃菌[25]嗜酸乳杆菌，黑色素丙酸杆菌，牙龈卟啉单胞菌[26]以及白色念珠菌，热带和克柔念珠菌等抗菌药物的证据。 [27]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。 [28]

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。 [29]柚皮苷的抗病毒作用目前正在临床研究中。 [30]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。 [31] [32]

抗炎

尽管有柚皮苷抗炎活性的证据， [33]但已观察到柚皮苷的抗炎活性很差或根本不存在。 [34] [35]

抗氧化剂

柚皮素已被证明具有显着的抗氧化性能。 [36] [37]在体外和动物研究中已证明它可以减少DNA的氧化损伤。 [38] [39]

抗肿瘤

据报道，柚皮素在乳腺癌，胃癌，肝癌，宫颈癌，胰腺癌和结肠组织癌细胞中以及白血病细胞中都可诱导细胞毒性。[40]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。[41]第一种假说是柚皮素抑制芳香化酶，从而减少了肿瘤生长。 [42]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。 [43]柚皮苷的新衍生物对多药耐药的癌症具有活性。 [44]

补充阅读

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。 . 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. . Analytical Chemistry. 2006-05-01, 78 (10): 3424–3433. ISSN 0003-2700. PMID 16689546. doi:10.1021/ac0600499.
Krause, Martin; Galensa, Rudolf. . 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. . 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. . Journal of Chromatographic Science. 2011-04-01, 49 (4): 316–320. ISSN 0021-9665. PMID 21439124. doi:10.1093/chrsci/49.4.316. 无效|subscription=free (帮助)
柚皮苷还在小鼠中产生BDNF依赖性抗抑郁剂样作用。 . 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 Journal of Nutritional Biochemistry. 2006, 17 (2): 89–95. PMID 16111881. doi:10.1016/j.jnutbio.2005.05.009. </ ref>
. 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. . 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。 . 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。 . 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. . 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. . 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. . Frontiers in Pharmacology. 19 June 2017, 8: 340. PMC 5474478. PMID 28674493. doi:10.3389/fphar.2017.00340.

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[pmid11093936-2] (PDF). Am. J. Physiol. Gastrointest. Liver Physiol. December 2000, 279 (6): G1148–54. PMID 11093936. doi:10.1152/ajpgi.2000.279.6.G1148.

[Yáñez_159–181-3] Yáñez, Jaime A.; Andrews, Preston K.; Davies, Neal M. . Journal of Chromatography B. 2007-04-01, 848 (2): 159–181. PMID 17113835. doi:10.1016/j.jchromb.2006.10.052.

[:0-4] Yáñez, Jaime A.; Remsberg, Connie M.; Miranda, Nicole D.; Vega-Villa, Karina R.; Andrews, Preston K.; Davies, Neal M. . Biopharmaceutics & Drug Disposition. 2008-01-01, 29 (2): 63–82. ISSN 1099-081X. PMID 18058792. doi:10.1002/bdd.588 （英语）.

[Krause_69–72-5] Krause, M.; Galensa, R. . Chromatographia. 1991-07-01, 32 (1–2): 69–72. ISSN 0009-5893. doi:10.1007/BF02262470 （英语）.

[6] Ho, Ping C; Saville, Dorothy J; Coville, Peter F; Wanwimolruk, Sompon. . Pharmaceutica Acta Helvetiae. 2000-04-01, 74 (4): 379–385. PMID 10812937. doi:10.1016/S0031-6865(99)00062-X.

[7] Gattuso, Giuseppe; Barreca, Davide; Gargiulli, Claudia; Leuzzi, Ugo; Caristi, Corrado. . Molecules. 2007-08-03, 12 (8): 1641–1673. PMC 6149096. PMID 17960080. doi:10.3390/12081641 （英语）. 无效|subscription=free (帮助)

[8] Gel-Moreto, Nuria; Streich, René; Galensa, Rudolf. . Electrophoresis. 2003-08-01, 24 (15): 2716–2722. ISSN 0173-0835. PMID 12900888. doi:10.1002/elps.200305486.

[9] Wang, H.; Nair, M. G.; Strasburg, G. M.; Booren, A. M.; Gray, J. I. . Journal of Agricultural and Food Chemistry. 1999-03-01, 47 (3): 840–844. ISSN 0021-8561. PMID 10552377. doi:10.1021/jf980936f.

[:1-10] Minoggio, M.; Bramati, L.; Simonetti, P.; Gardana, C.; Iemoli, L.; Santangelo, E.; Mauri, P. L.; Spigno, P.; Soressi, G. P. . Annals of Nutrition & Metabolism. 2003-01-01, 47 (2): 64–69. ISSN 0250-6807. PMID 12652057. doi:10.1159/000069277.

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