LC-MS guided isolation of sinodamines A and B: Chimonanthine-type alkaloids from the endangered ornamental plant Sinocalycanthus chinensis

Abstract

Two previously undescribed chimonanthine-type [sinodamines A and B] and five related known dimeric tryptamine-derived alkaloids were isolated and characterized from the leaves of the endangered ornamental plant Sinocalycanthus chinensis under the guidance of LC-MS detection and dereplication analyses, along with conventional isolation procedures. Their structures were established on the basis of spectroscopic methods and chemical transformations. Sinodamine A can be regarded as the naturally occurring N-oxide derivative of its pseudo-mesomer sinodamine B. An acid-catalyzed Meisenheimer rearrangement from sinodamine A to its oxazine-form with a final equilibrium of 1:2 was observed by monitoring their NMR spectra. (-)-Folicanthine showed significant cytotoxicity against human lung carcinoma A549 and colorectal carcinoma HT29 cells, with IC₅₀ values of 7.76 and 6.16 μM, respectively.

Keywords: Calycanthaceae; Chimonanthine-type alkaloids; Cytotoxicity; Endangered plant; Sinocalycanthus chinensis.