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Cite This: J. Org. Chem. 2018, 83, 2376−2381
(±)-Sativamides A and B, Two Pairs of Racemic Nor-Lignanamide Enantiomers from the Fruits of Cannabis sativa Guo-Yuan Zhu,*,† Ji Yang,† Xiao-Jun Yao,† Xing Yang,‡ Jing Fu,† Xin Liu,† Li-Ping Bai,† Liang Liu,† and Zhi-Hong Jiang*,† †
State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Macau, China ‡ Department of Chemistry, Lanzhou University, Lanzhou 730000, China S Supporting Information *
ABSTRACT: (±)-Sativamides A (1) and B (2), two pairs of norlignanamide 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) stressinduced cytotoxicity.
Cannabis sativa L. (Cannabaceae), an annual herbaceous plant, is native of western and central Asia and now cultivated commercially all over the world. It has been used by humans as food, fiber, medicine, and a psychoactive drug for thousands of years.1 It is currently recognized as a highly variable species in the Cannabis genus. Two major varieties of C. sativa are marijuana (drug type) and hemp (nondrug type). Marijuana has psychoactivity because of the existence of a high content of Δ9-tetrahydrocannabinol (THC, ranging from 1 to 20%) and is prohibited worldwide, whereas hemp with low THC content (
