A pair of windmill-shaped enantiomers from Lindera aggregata with activity toward improvement of insulin sensitivity.
(+)-Linderaspirone A and (-)-linderaspirone A, a pair of natural windmill-shaped enantiomers, were isolated from the traditional Chinese medicine plant Lindera aggregate by HPLC using a chiral column, achieving over 98% ee. Their structures and absolute configurations were determined on the basis of extensive analysis of NMR spectra, crystal X-ray diffraction, and calculation of the optical rotations (OR). They have an unprecedented carbon skeleton and showed significant activity against glucosamine-induced insulin resistance.
Wang
Fei
F
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China.
Gao
Yuan
Y
Zhang
Ling
L
Bai
Bing
B
Hu
Ya Nan
YN
Dong
Ze Jun
ZJ
Zhai
Qi Wei
QW
Zhu
Hua Jie
HJ
Liu
Ji Kai
JK
D005944:Glucosamine / Q000494:pharmacology; D056945:Hep G2 Cells; D006801:Humans; D007328:Insulin / Q000378:metabolism*; D007333:Insulin Resistance; D007783:Lactones / Q000737:chemistry*; D027443:Lindera / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D007328:Insulin; D007783:Lactones; D010936:Plant Extracts; D013141:Spiro Compounds; C552578:linderaspirone A; D005944:Glucosamine