Carotenoid-derived norsesquiterpenoids and sesquiterpenoids from Tagetes erecta L

Abstract

Tagetes erecta L. (marigold), a common landscaping flower widely cultivated in America, Africa, Asia and Europe, is the fundamental source of carotenoids (especially lutein) in food and pharmaceutical industry. Carotenoids are well-known to possess various healthy and beneficial biological activities such as eye protection, anti-aging, and anti-inflammatory. In our exploitation of carotenoid-derived products from T. erecta, nine previously undescribed compounds including seven megastigmane-type norsesquiterpenoids (1-7), one carotenoid-derived sesquiterpenoid (8), and one natural 3-hydroxyl-α-ionylideneacetic acid derivative (9), along with twelve known compounds (10-21), were afforded from the 95% ethanol extract of the petals of T. erecta. Their planar chemical structures and the absolute configurations were established by analysis of the extensive spectroscopic data including HRESI-MS, 1D/2D NMR and the simulation of ECD. Further, a plausible biosynthesis pathway for compounds 1-20 is proposed.

Keywords: Carotenoid-derived sesquiterpenoid; Megastigmane-type norsesquiterpenoid; Tagetes erecta L. Asteraceae; α-Ionylideneacetic acid derivative.