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柚皮素

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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  checkY
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 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

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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

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柚皮素及其糖苷存在于多种草药水果中,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

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它衍生自丙二酰基CoA4-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

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抗菌,抗真菌和抗病毒

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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-1HSV-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

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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

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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

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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]柚皮苷的新衍生物多药耐药英语multiple drug resistance的癌症具有活性。 [42]

补充阅读

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参考文献

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