Aphamines A-C,dimeric acyclic diterpene enantiomers from Aphanamixis polystachya

摘要

Aphamines A-C(1-3),three pairs of acyclic diterpene dimer enantiomers with an unprecedent ploymerization pattern,were discovered from Aphanamixis polystachya by NMR-guided isolation and chiral resolution.The elucidation of their novel carbon skeletons was achieved based on spectroscopic analysis,exciton chirality,and calculated electronic circular dichroism(ECD).Plausible Claisen rearrangement,5-exo-trig cyclization,and reduction reactions may play important roles in the polymeric biosynthesis pathway.Compounds 1 and 3 showed inhibitory effects on nitric oxide(NO)production(IC_(50):6.71-15.36 μmol/L) and reduced the expression of iNOS in LPS-induced RAW 264.7 macrophages.