Supplementary Material

Catechol-O-methyltransferase and UDP-glucuronosyltransferases in the metabolism of Baicalein in different species

Ruiya Zhang 1+, Yonglei Cui 1, Yan Wang 1,4, XianggeTian2*, Lu Zheng3, HaiJian Cong3, Bin Wu,3* XiaokuiHuo1, Chao Wang1, BaoJing Zhang1, Xiaobo Wang 1,4, Zhonghui Yu1*

1The Second Affiliated Hospital of Dalian Medical University, College of Pharmacy, Dalian Medical University, Dalian, 116044, China.

2College of Basic Medical Science, Dalian Medical University, Dalian, China.

3 Shanghai Haini Pharmaceutical Co. Ltd., No. 3999, Hunan Road of Pudong new district, Shanghai, China.

4 Department of Pharmacy and Traditional Chinese Medicine, Chinese People’s Liberation Army 210 Hospit.

*Correspondence author: XianggeTian and zhonghui Yu

Address: Dalian Medical University, 9 West Section, Lvshun South Road, Lvshunkou District, Dalian 116044, China.

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Tel: +86 0411-86118843.

Table S1. 1H NMR and 13C NMR Spectral Data for methylation of baicalein M-1 (DMSO-d6, 500, 125 MHz), and 1H NMR for glucuronidation metabolite M-2 (DMSO-d6, 500 MHz).

No. / M-1

1H NMR / 13C NMR / M-2
1H NMR
2 / -- / 163.2
3 / 6.96 s / 104.7 / 7.01s
4 / 182.2
5 / 152.7
6 / 131.5
7 / 157.6
8 / 6.65 s / 94.4 / 6.69 s
9 / 152.5
10 / 104.3
1' / 130.7
2' / 8.07 d (7.5) / 126.4 / 8.10 dd (8.0,2.0)
3' / 7.59 m / 129.1 / 7.63 m
4'
5'
6' / 7.61 m
7.59 m
8.07 d (7.5) / 132.0
129.1
126.4 / 7.63 m
7.63 m
8.10 dd (8.0, 2.0)
1'' / 5.01 d (5.0)
2''
3''
4''
5'' / 3.64 d (9.6)
6-OCH3 / 3.76 s / 59.9 / 3.90 (3H,s)

Fig. S1. Representative analysis of the metabolite M-1 of baicalein methylation in LC-MS/MS.

Fig. S2. The 1H NMR analysis of the metabolite M-1.

Fig. S3. The 13C NMR analysis of the metabolite M-1.

Fig. S4. The HMBC analysis of the metabolite M-1.

Fig. S5. The HSQC analysis of the metabolite M-1.

Fig. S6. The NOESY analysis of the metabolite M-1.

Fig. S7. Representative UV absorption (A), ESI-MS (B), and 1H NMR (C) spectra of glucuronidation metabolite oroxylin A-7-O-β-D-glucuronide, respectively.

Fig. S8. Representative HPLC chromatograms at 280nm for oroxylin A glucuronidation in different species, respectively.