Macdentichalcone, a unique polycyclic dimeric chalcone from Macaranga denticulata. Issue 49 (7th December 2016)

• Record Type: Journal Article
• Authors: Lei, Chun; Zhang, Lai-Bin; Yang, Jing; Gao, Li-Xin; Li, Jing-Ya; Li, Jia; Hou, Ai-Jun
• Is Part Of: Tetrahedron letters. Volume 57:Issue 49(2016)
• Page Start: 5475
• Page End: 5478
• Publication Date: 2016-12-07
• Subjects: Macaranga denticulata -- Euphorbiaceae -- Dimeric chalcone -- Macdentichalcone -- Protein tyrosine phosphatase 1B; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.10.090
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Macdentichalcone (1 ) is an unprecedented polycyclic dimeric chalcone. Both1 and its proposed biosynthetic precursor2 showed PTP1B inhibition. The structure of1 was established by extensive NMR methods and 13 C NMR calculation. Abstract: Macdentichalcone (1 ), an unprecedented polycyclic dimeric chalcone featuring a unique quinonoid moiety, was isolated from Macaranga denticulata, together with 1-(5, 7-dihydroxy-2, 2, 6-trimethyl-2 H -1-benzopyran-8-yl)-3-phenyl-2-propen-1-one (2 ), a known monomeric chalcone proposed as a biosynthetic precursor of1 . The structure of1 was elucidated by extensive spectroscopic analysis including NMR and MS data, as well as calculation of 13 C NMR chemical shifts. Both compounds1 and2 showed inhibitory activity against PTP1B in vitro .