β-Elemene derivatives produced from SeO 2 -mediated oxidation reaction

Author:

He Xingrui1234ORCID,Zhuo Xiao-Tao123ORCID,Gao Yuan5ORCID,Bai Renren6ORCID,Ye Xiang-Yang1237ORCID,Xie Tian1237ORCID

Affiliation:

1. Key Laboratory of Elemene Class Anti-Cancer Chinese Medicine of Zhejiang Province, Hangzhou Normal University, Hangzhou, Zhejiang 311121, People's Republic of China

2. Engineering Laboratory of Development and Application of Traditional Chinese Medicine from Zhejiang Province, Hangzhou Normal University, Hangzhou, Zhejiang 311121, People's Republic of China

3. Holistic Integrative Pharmacy Institutes (HIPI), School of Medicine, Hangzhou Normal University, Hangzhou, Zhejiang 311121, People's Republic of China

4. School of Pharmacy, Liaocheng University, Shandong 252000, People's Republic of China

5. School of Clinical Medicine, Guangdong Pharmaceutical University, Guangzhou, Guangdong 510000, People's Republic of China

6. College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, People's Republic of China

7. Collaborative Innovation Center of Chinese Medicines from Zhejiang Province, Hangzhou Normal University, Hangzhou, Zhejiang 311121, People's Republic of China

Abstract

Herein, we report the first access of β-elemene derivatives through the SeO 2 -mediated oxidation reaction. Several new compounds were isolated through such a one-step reaction, and their structures were elucidated using various 2D-NMR techniques. This method provides easy access to multiple oxidative β-elemene derivatives in one single step and represents the first modifications on cyclohexyl ring of β-elemene. It is expected to open up the opportunity for future derivatization on cyclohexyl ring of β-elemene. The new compounds obtained above showed better anti-proliferation activities than β-elemene itself on several cancer cell lines. Among them, compound 17 shows the best activity in antiproliferation assays of A549 and U-87MG cell lines.

Funder

the open project of Shandong Collaborative Innovation Center for Antibody Drugs

The Natural Science Foundation of Shandong Province

Hangzhou Normal University startup fund

Key projects of National Natural Science Foundation of China

Publisher

The Royal Society

Subject

Multidisciplinary

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