(±)-Sativamides A and B, Two Pairs of Racemic Nor-Lignanamide Enantiomers from the Fruits of Cannabis sativa

May 22, 2018

Title

(±)-Sativamides A and B, Two Pairs of Racemic Nor-Lignanamide Enantiomers from the Fruits of Cannabis sativa

Author

Guo-Yuan Zhu, Ji Yang, Xiao-Jun Yao, Xing Yang, Jing Fu, Xin Liu, Li-Ping Bai, Liang Liu, Zhi-Hong Jiang

Year

2018

Journal

The Journal of Organic Chemistry

Abstract

(±)-Sativamides A (1) and B (2), two pairs of nor-lignanamide enantiomers featuring a unique benzo-angular triquinane skeleton, were isolated from the fruits of Cannabis sativa (hemp seed). Their structures were elucidated by detailed spectroscopic analysis and ECD calculations. The resolution of (+)- and (−)-sativamides A and B were achieved by chiral HPLC. Pretreatment of neuroblastoma cells with 1 and 2 significantly reduced the endoplasmic reticulum (ER) stress-induced cytotoxicity.

Instrument

J-1500

Keywords

Circular dichroism, Absolute configuration, Natural products, Medicinal