Jump to main content
Jump to site search


Alstolarines A and B, two unusual monoterpenoid indole alkaloids with an acetal moiety from Alstonia scholaris

Author affiliations

Abstract

Two novel monoterpenoid indole alkaloids, alstolarines A and B (1–2), were isolated from the leaves and twigs of Alstonia scholaris. Compound 1 is the first vobasinyl-type alkaloid with a 6/5/8/5/6/5 hexacyclic architecture featuring an unprecedented 21-oxa-4-azaspiro[4,4]nonane unit. Compound 2 is the first 21-nor-vobasinyl-type alkaloid with a unique 3-oxa-4-azatricyclo[5.1.1.13,20]undecane ring system. Their structures including absolute configurations were established by a combination of spectroscopic data analyses, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction analysis. The plausible biogenetic pathways of 1 and 2 were also proposed. Compounds 1 and 2 exhibited promising vasorelaxant activities with EC50 values of 4.6 and 6.7 μM, and compound 2 showed moderate acetylcholinesterase (AChE) inhibitory activity with an IC50 value of 19.3 μM.

Graphical abstract: Alstolarines A and B, two unusual monoterpenoid indole alkaloids with an acetal moiety from Alstonia scholaris

Back to tab navigation

Supplementary files

Article information


Submitted
28 Jun 2020
Accepted
02 Aug 2020
First published
18 Aug 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Alstolarines A and B, two unusual monoterpenoid indole alkaloids with an acetal moiety from Alstonia scholaris

J. Zhang, M. Song, Y. Ao, Y. Li, X. Zou, J. Xu, Y. Wang, D. Zhang, X. Zhang and W. Ye, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00751J

Social activity

Search articles by author

Spotlight

Advertisements