Synthesis and biological activities of petrosiols B and D

Jialin Geng; Qidong Ren; Caizhu Chang; Xinni Xie; Jun Liu; Yuguo Du

doi:10.1039/c9ra01166h

Synthesis and biological activities of petrosiols B and D

RSC Adv. 2019 Apr 1;9(18):10253-10263. doi: 10.1039/c9ra01166h. eCollection 2019 Mar 28.

Authors

Jialin Geng^{1

2}, Qidong Ren^{1

2}, Caizhu Chang^{1

3}, Xinni Xie¹, Jun Liu^{1

2}, Yuguo Du^{1

2

4}

Affiliations

¹ State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science Beijing 100085 China junliu@rcees.ac.cn.
² School of Chemical Sciences, University of Chinese Academy of Sciences Beijing 100049 China.
³ School of Chemistry and Environmental Engineering, Wuhan Institute of Technology Wuhan 430205 China.
⁴ National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University Nanchang 330022 China.

Abstract

A divergent total synthesis of natural diacetylenic tetraols, petrosiol B and petrosiol D, was accomplished by taking advantage of a carbohydrate chiral template. In particular, petrosiol B, which is the first total synthesis so far, was achieved in 13 linear steps with a 10% overall yield applying Ohira-Bestmann homologation, NaH-mediated dehydrobromination, and Cu(i)-catalyzed Cadiot-Chodkiewicz coupling as the key reaction steps. The synthetic petrosiols B and D were subjected to the study on differentiation activities toward neuronal progenitor PC12 cells. Our results suggested that both petrosiol B and petrosiol D could induce the differentiation of neuronal progenitor PC12 cells via the enhancement of Nrf2 activity. By comparing petrosiols B, D and their natural homologue E, petrosiol B displayed the most intensive cell differentiation activity and the highest Nrf2 activity enhancement as well.