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 |
|
| 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。 | |
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] [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
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
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。 [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
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
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
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细胞毒性。[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的癌症具有活性。 [42]
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。 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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