柚皮素

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。 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。 S(-)-柚皮素的外消旋已显示相当快地发生。 柚皮素及其糖苷存在于多种草药和水果中，包括葡萄柚，佛手柑，酸橙，酸樱桃，西红柿， 可可， 希腊牛至，水薄荷，以及豆类。柚皮素与柚皮苷的比例因来源而异，对映体比例也是如此。 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。 服用葡萄柚汁后，柚皮素血浆浓度比服用橙汁更高。 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。 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。 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。 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。 进一步的研究增加了对乳酸乳球菌，嗜酸乳杆菌，内氏放线菌，口腔普雷沃菌嗜酸乳杆菌，黑色素丙酸杆菌，牙龈卟啉单胞菌以及白色念珠菌，热带和克柔念珠菌等抗菌药物的证据。 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。 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。 柚皮苷的抗病毒作用目前正在临床研究中。 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。 尽管有柚皮苷抗炎活性的证据， 但已观察到柚皮苷的抗炎活性很差或根本不存在。 柚皮素已被证明具有显着的抗氧化性能。 在体外和动物研究中已证明它可以减少DNA的氧化损伤。 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。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。 第一种假说是柚皮素抑制芳香化酶，从而减少了肿瘤生长。 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。 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。 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. 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