柚皮素
| 柚皮素 | |
|---|---|
| |
| IUPAC名 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one | |
| 別名 | Naringetol; Salipurol; Salipurpol; 4',5,7-Trihydroxyflavanone |
| 識別 | |
| CAS號 | 480-41-1 
|
| PubChem | 439246 |
| ChemSpider | 388383 |
| SMILES |
|
| ChEBI | 50202 |
| DrugBank | DB03467 |
| 性質 | |
| 化學式 | C15H12O5 |
| 摩爾質量 | 272.25 g·mol−1 |
| 熔點 | 251 °C（524 K） |
| 溶解性（水） | 475 mg/L [1] |
| 若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。 | |
柚皮素是一種無味，顏色由白色至淡黃的黃烷酮，是一種類黃酮。它是葡萄柚中的主要黃烷酮，[2]並存在於多種水果與草藥中。 [3]
結構
[編輯]柚皮素具有黃烷酮的骨架結構，其4'，5和7位碳原子處有三個羥基。柚皮素可以單體存在，亦有糖苷形式即柚皮苷，其具有加入的二糖新橙皮糖與7位碳原子連接而成。
像大多數黃烷酮一樣，柚皮素在碳2上有一個手性中心，儘管光學純度是可變的。 [3] [4] S(-)-柚皮素的外消旋已顯示相當快地發生。 [5]
來源和生物利用度
[編輯]柚皮素及其糖苷存在於多種草藥和水果中，包括葡萄柚，[6]佛手柑，[7]酸橙，[8]酸櫻桃，[9]西紅柿，[10] [11]可可，[12] [11] [12]希臘牛至，[13]水薄荷，[14]以及豆類。[15]柚皮素與柚皮苷的比例因來源而異，對映體比例也是如此。 [4]
柚皮苷-7-葡萄糖苷形式的生物利用度似乎低於聚乙二醇形式。[16]
服用葡萄柚汁後，柚皮素血漿濃度比服用橙汁更高。 [17]在葡萄柚中還發現了相關的化合物山柰酚，其羥基緊挨著酮基。
柚皮素可以從煮熟的番茄醬中吸收。 每10克番茄醬中含有253毫克柚皮素。 [18]
生物合成與代謝
[編輯]它衍生自丙二醯基CoA和4-香豆醯基CoA 。後者衍生自苯丙氨酸。將所得丁烯酮通過作用於查耳酮合成酶，得到查耳酮。查爾酮隨後經歷閉環，生成柚皮素。 [19]
柚皮素-8-二甲基烯丙基轉移酶使用二甲基烯丙基二磷酸和(−)- (2S)-柚皮素以產生二磷酸和8-戊基柚皮素 。雅致小克銀漢霉（Cunninghamella elegans）是一種哺乳動物新陳代謝的真菌模型生物，它可用於研究柚皮素的硫酸化。 [20]
潛在的生物學影響
[編輯]抗菌，抗真菌和抗病毒
[編輯]柚皮素對表皮葡萄球菌，金黃色葡萄球菌，枯草芽孢桿菌，黃球菌和大腸桿菌具有抗菌作用。 [21]進一步的研究增加了對乳酸乳球菌，[22]嗜酸乳桿菌，內氏放線菌，口腔普雷沃菌[22]嗜酸乳桿菌，黑色素丙酸桿菌，牙齦卟啉單胞菌[23]以及白色念珠菌，熱帶和克柔念珠菌等抗菌藥物的證據。 [24]儘管沒有證明柚皮苷對微生物的脲酶活性有任何抑制作用，但有證據證明其對幽門螺桿菌具有抗菌作用。 [25]
柚皮素可以減少體外培養的HCV感染的肝細胞病毒的產生。這可能繼發於柚皮素抑制極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臨床研究中。 [27]關於脊髓灰質炎病毒， HSV-1和HSV-2的抗病毒作用的報道也已經發表，儘管病毒的複製並未受到抑制。 [28] [29]
抗炎
[編輯]儘管有柚皮苷抗炎活性的證據， [30]但已觀察到柚皮苷的抗炎活性很差或根本不存在。 [31] [32]
抗氧化劑
[編輯]柚皮素已被證明具有顯著的抗氧化性能。 [33] [34]在體外和動物研究中已證明它可以減少DNA的氧化損傷。 [35] [36]
抗腫瘤
[編輯]研究指出，柚皮素在乳腺癌、胃癌、肝癌、宮頸癌、胰腺癌、結腸組織癌細胞中以及白血病細胞中都可誘導細胞毒性。[37]柚皮素抑制人類乳腺癌生長的機制已被證實，在此基礎上提出了兩種柚皮素抗癌的假說。[38][39] 第一種假說是柚皮素抑制芳香化酶，從而減少了腫瘤生長。 [40]第二種假說提出與雌激素受體的互作是其調節腫瘤生長的原因。 [41]柚皮苷的新衍生物對多藥耐藥的癌症具有活性。 [42]
補充閱讀
[編輯]- 對人細胞色素P450同工型[[CYP1A2]]具有抑制作用，導致原本無害的物質致癌。 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 （英語）.
- 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.
- 柚皮苷還在小鼠中產生BDNF依賴性抗抑鬱劑樣作用。 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>
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- 據報道，柚皮素可誘導前脂肪細胞凋亡。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.
- 柚皮素似乎可以保護LDLR缺陷型小鼠免受高脂飲食的肥胖影響。 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.
- 柚皮素通過抑制高膽固醇飲食的大鼠中的HMG-CoA還原酶和ACAT降低血漿和肝膽固醇的濃度。 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.
- 在一項使用阿爾茨海默氏病小鼠模型的研究中，柚皮苷已被證明可以改善記憶力並減少澱粉樣蛋白和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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