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Alstolarines A and B, two unusual monoterpenoid indole alkaloids with an acetal moiety from Alstonia scholaris
- Source :
- Organic Chemistry Frontiers. 7:3468-3473
- Publication Year :
- 2020
- Publisher :
- Royal Society of Chemistry (RSC), 2020.
-
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.
Details
- ISSN :
- 20524129
- Volume :
- 7
- Database :
- OpenAIRE
- Journal :
- Organic Chemistry Frontiers
- Accession number :
- edsair.doi...........56a76b0147e40d6116c52cc94bd8e1c5