Identification of flavone glucuronide isomers by metal complexation and tandem mass spectrometry: regioselectivity of uridine 5'-diphosphate-glucuronosyltransferase isozymes in the biotransformation of flavones.
Identification of flavone glucuronide isomers by metal complexation and tandem mass spectrometry: regioselectivity of uridine 5'-diphosphate-glucuronosyltransferase isozymes in the biotransformation of flavones.
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DOI：
10.1021/jf304853j
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发表时间：
2013-02-20
影响因子：
6.1
通讯作者：
Brodbelt JS
中科院分区：
文献类型：
--
作者：
Robotham SA;Brodbelt JS
用[Co（II）（flavone-H）（4，7-diphenyl-1，10-phenanthroline）2]+配合物的碰撞诱导解离（CID）方法，区分了白杨素、芹菜素、毛地黄黄酮、黄芩素和黄芩素等5种黄酮的葡糖苷酸异构体。通过柱后添加金属/配体溶液，在分离每种黄酮与UDP-葡萄糖醛酸基转移酶（UGT）同工酶阵列孵育后产生的葡萄糖醛酸苷产物后，生成复合物。葡萄糖醛酸苷异构体的解析允许对12种人UDP-葡萄糖醛酸基转移酶（UGT）同工酶（包括8种UGT 1A和4种UGT 2B同工酶）的区域选择性进行系统研究。7-OH位的葡萄糖醛酸化是所有黄酮类化合物的优选位点，除了毛地黄黄酮，毛地黄黄酮在B环上具有相邻的羟基。对于所有黄酮和UGT同工酶，从未观察到5-OH位置的葡萄糖醛酸化。正如金属络合/MS/MS策略所证实的，当与三种UGT同工酶孵育时，仅发生黄芩素和黄芩素的6-OH位置的葡萄糖醛酸化。
Flavone Glucuronide isomers of five flavones (chrysin, apigenin, luteolin, baicalein, and scutellarein) were differentiated by collision induced dissociation (CID) of [Co(II) (flavone-H) (4,7-diphenyl-1,10-phenanthroline)2]+ complexes. The complexes were generated via post-column addition of a metal/ligand solution after separation of the glucuronide products generated upon incubation of each flavone with an array of UDP-glucuronosyl-transferase (UGT) isozymes. Elucidation of the glucuronide isomers allowed a systematic investigation of the regioselectivity of twelve human UDP-glucuronosyl-transferase (UGT) isozymes, including eight UGT1A and four UGT2B isozymes. Glucuronidation of the 7-OH position was the preferred site for all the flavones except for luteolin, which possessed adjacent hydroxyl groups on the B ring. For all flavones and UGT isozymes, glucuronidation of the 5-OH position was never observed. As confirmed by the metal complexation/MS/MS strategy, glucuronidation of the 6-OH position only occurred for baicalein and scutellarein when incubated with three of the UGT isozymes.
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影响因子：
7.4
作者：
Davis, BD;Brodbelt, JS
通讯作者：
Brodbelt, JS
影响因子：
2.4
作者：
Graf, BA;Milbury, PE;Blumberg, JB
通讯作者：
Blumberg, JB
DOI：
10.1016/j.jasms.2003.07.002
发表时间：
2003-12-01
影响因子：
3.2
作者：
Pikulski, M;Brodbelt, JS
通讯作者：
Brodbelt, JS
DOI：
10.3109/00498254.2012.663515
发表时间：
2012-08
期刊：
Xenobiotica; the fate of foreign compounds in biological systems
影响因子：
--
作者：
Dong D;Ako R;Hu M;Wu B
通讯作者：
Wu B
影响因子：
1.8
作者：
Chen, YK;Chen, SQ;Zeng, S
通讯作者：
Zeng, S