柚皮苷的人肠内菌生物转化

doi:10.5246/jcps.2013.04.047

柚皮苷的人肠内菌生物转化

冉丽, 吴帅, 徐嵬, 张友波, 杨秀伟^*

北京大学医学部天然药物及仿生药物国家重点实验室; 药学院天然药物学系, 北京 100191

收稿日期:2013-01-06 修回日期:2013-01-16 出版日期:2013-07-10 发布日期:2013-07-10
通讯作者: 杨秀伟*

Biotransformation of naringin by human intestinal flora

Li Ran, Shuai Wu, Wei Xu, Youbo Zhang, Xiuwei Yang^*

State Key Laboratory of Natural and Biomimetic Drugs; Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2013-01-06 Revised:2013-01-16 Online:2013-07-10 Published:2013-07-10
Contact: Xiuwei Yang*

摘要/Abstract

摘要：

柚皮苷(1)是酸橙中含量最高的二氢黄酮苷类化合物, 将其与人肠内菌丛共温孵, 从温孵物中通过色谱方法得到原形化合物1和四个转化产物 (2–5), 根据谱学数据确定它们分别为柚皮苷-6"-乙酰物(2)、柚皮素(3)、根皮酸(4)和间苯三酚(5)。在1的糖苷链葡萄糖基6位能够特异性地发生乙酰化作用。1口服难以吸收。本文结果为阐明其生物利用度低提供了实验依据, 推测表现其生物活性的物质基础主要是其肠内菌生物转化产物3。肠内菌丛所致1的生物转化的继发结果, 是它的转化产物吸收进入体循环发挥生物学作用, 此结果为进一步或再评价其体内过程、作用或毒性及其生物利用度提供了有用的信息。

关键词: 柚皮苷, 柚皮素, 柚皮苷-6"-乙酰物, 生物转化, 人肠内菌丛

Abstract: Naringin (1), the highest-content flavanone glycoside in sour oranges, was incubated with human intestinal flora, and four biotransformation products (2-5) were obtained from the incubated mixture by chromatographic methods. The chemical structures of the four products were elucidated as naringin-6"-acetate (2), naringenin (3), phloretic acid (4), and phloroglucinol (5) on the basis of their spectroscopic data. Naringin-6"-acetate was specifically formed by acetylation at C6-OH of glucosyl group of 1. The result obtained in the present research could account for the lower bioavailability of 1 after oral administration, suggesting that some biological properties of 1 in vivo may be mediated by its intestinal flora converted product 3. The biotransformation of 1 by intestinal flora leading to their systemic absorption deserves further attention and may provide valuable insights into pre-systemic drug metabolism, delivery or toxicity.

Key words: Naringin, Naringenin, Naringin-6"-acetate, Biotransformation, Human intestinal flora

中图分类号:

R284

Supporting: Foundation items: National Sciences and Technology Program of China (Grant No. 2011BAI07B08) and "Major New Medicine Project" in Mega-projects of Science Research of China (Grant No. 2009ZX-09301-010).

^*Corresponding author. Tel.: 86-10-62070317

冉丽, 吴帅, 徐嵬, 张友波, 杨秀伟^*. 柚皮苷的人肠内菌生物转化[J]. , DOI: 10.5246/jcps.2013.04.047.

Li Ran, Shuai Wu, Wei Xu, Youbo Zhang, Xiuwei Yang^*. Biotransformation of naringin by human intestinal flora[J]. , DOI: 10.5246/jcps.2013.04.047.

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