Unprecedented Quassinoids from Eurycoma longifolia: Biogenetic Evidence and Antifeedant Effects

Six new quassinoids (1-6) were isolated from the roots of Eurycoma longifolia, and their structures with absolute configurations were determined unambiguously by spectroscopic analyses and single-crystal X-ray crystallographic experiments. Compounds 1 and 2 are the first members of a new class of quassinoids with an unusual C₂₆ carbon skeleton. Compound 6 features a C₂₀ cage-like scaffold with an unprecedented densely functionalized 2,5-dioxatricyclo[5.2.2.0^4,8]undecane core. The discovery of the two C₂₆ quassinoids 1 and 2 has provided firm evidence for the better understanding the biogenetic process from C₃₀ triterpenoid precursors to quassinoids. Compound 5 exhibited significant antifeedant activity on the diamondback moth (DBM) larvae and excellent systemic absorption and accumulated properties in Brassica chinensis.