New neoclerodane diterpenoids isolated from the leaves of Salvia divinorum and their binding affinities for human kappa opioid receptors.
Bioactivity-guided fractionation of the leaves of Salvia divinorum has resulted in the isolation of three new neoclerodane diterpenoids: divinatorin D (1), divinatorin E (2), and salvinorin G (3), together with 10 known terpenoids, divinatorin C (4), hardwickiic acid (5), salvinorin-A (6), -B (7), -C (8), -D (9), -E (10), and -F (11), presqualene alcohol (12), and (E)-phytol (13). The structures of these three new compounds were characterized by spectroscopic methods. All these compounds were evaluated for their binding affinities to the human kappa opioid receptors. In comparison with divinatorin D (1), divinatorin E (2), and salvinorin G (3), salvinorin A (6) is still the most potent kappa agonist.
Lee
David Y W
DY
Bio-Organic and Natural Products Laboratory, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, MA 02478, USA.
Ma
Zhongze
Z
Liu-Chen
Lee-Yuan
LY
Wang
Yulin
Y
Chen
Yong
Y
Carlezon
William A
WA
Cohen
Bruce
B
D001667:Binding, Competitive / Q000187:drug effects*; D045785:Diterpenes, Clerodane / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry*; D017473:Receptors, Opioid, kappa / Q000037:antagonists & inhibitors*; D027544:Salvia / Q000737:chemistry*; D013329:Structure-Activity Relationship
D045785:Diterpenes, Clerodane; D010936:Plant Extracts; D017473:Receptors, Opioid, kappa