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Issue 34, 2016
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Isolation and characterization of related impurities in andrographolide sodium bisulphite injection

Ji-Qin Hou,ab  Bao-Lin Wang,abc  Xiao-Jun Huang,d  Xiao-Qi Zhang,d  Guo-Qiang Li,d  Hao Wang,*ab  Wen-Cai Yed  and  Ping Lia 
Author affiliations

* Corresponding authors

a State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China
E-mail: wanghao@cpu.edu.cn
Fax: +86 25 85301528
Tel: +86 25 86185376

b Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China

c Nanchang Institute for Food and Drug Control, Nanchang 330038, China

d Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China

Abstract

Andrographolide sodium bisulphite (ASB) injection was widely used in China for the treatment of infectious diseases. The chemical analysis of ASB injection resulted in the isolation of four new related impurities (2, 3, 5, 6), together with two known compounds (1, 4). The structures of the new compounds were elucidated by 1D and 2D NMR, high-resolution mass spectrometry, Mo2(OAc)4-induced circular dichroism and ECD calculation. Among them, 1 and 2 were two unprecedented photocyclization derivatives of isocopalane diterpene. The generation of the primary impurity 1 was proved to be an intramolucular 6-exo carbonyl radical cyclization of ASB through a novel sulfonyl group transfer. This finding furnished a facile photocyclization methodology to afford 1 in good yield with excellent regioselectivity. The possible mechanism for the formation of the related impurities was also discussed.

Graphical abstract: Isolation and characterization of related impurities in andrographolide sodium bisulphite injection

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Publication details

The article was received on 07 Jan 2016, accepted on 11 Mar 2016 and first published on 14 Mar 2016


Article type: Paper
DOI: 10.1039/C5RA28178D
Citation: RSC Adv., 2016,6, 28830-28837
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    Isolation and characterization of related impurities in andrographolide sodium bisulphite injection

    J. Hou, B. Wang, X. Huang, X. Zhang, G. Li, H. Wang, W. Ye and P. Li, RSC Adv., 2016, 6, 28830
    DOI: 10.1039/C5RA28178D

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