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.

• Authors: Guang-Lei Ma, Juan Xiong, Ezzat E A Osman, Ting Huang, Guo-Xun Yang, Jin-Feng Hu
• Journal: Phytochemistry (Phytochemistry) Vol. 151 Pg. 61-68 (Jul 2018) ISSN: 1873-3700 [Electronic] England
• PMID: 29665477 (Publication Type: Journal Article)
• Copyright: Copyright © 2018 Elsevier Ltd. All rights reserved.

Chemical References

• Alkaloids
• sinodamine A
• sinodamine B

Topics

• Alkaloids (chemistry, isolation & purification, pharmacology)
• Calycanthaceae (chemistry)
• Cell Line, Tumor
• Cell Survival (drug effects)
• Chromatography, High Pressure Liquid
• Dose-Response Relationship, Drug
• Endangered Species
• HT29 Cells
• Humans
• Mass Spectrometry
• Molecular Structure
• Plant Leaves (chemistry)
• Structure-Activity Relationship