柚皮素

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]

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  Y
PubChem	439246
ChemSpider	388383
SMILES	O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
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。

結構

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

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，其羥基緊挨着酮基。

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

它衍生自丙二酰基CoA和4-香豆酰基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

抗菌，抗真菌和抗病毒

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

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

柚皮素已被證明具有顯着的抗氧化性能。 ^{[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

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（英語：multiple drug resistance）的癌症具有活性。 ^[42]

補充閱讀

• 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>
• 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.
• 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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