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Updated: Aug 29, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Cytotoxic alkaloids from the flowers of Senna spectabilis
Lawan Sriphong1, Uthai Sotanaphun, Siripan Limsirichaikul
1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Silpakorn University, Nakorn Prathom, Thailand. lawan@email.pharm.su.ac.th
Abstract:
Three new alkaloids, 3(R)-benzoyloxy-2(R)-methyl-6(R)-(11'-oxododecyl)-piperidine (3), 5-hydroxy-2-methyl-6-(11'-oxododecyl)-pyridine (4) and 5-hydroxy-2-methyl-6-(11'-oxododecyl)-pyridine N-oxide (5), together with a known alkaloid, (-)-cassine (1), were isolated from the flowers of Senna spectabilis. A derivative, N,O-diacetylcassine (2), was semisynthesized. Their structures and stereochemistry were established on the basis of spectroscopic analysis. Cytotoxic activity and brine shrimp lethality of these compounds were evaluated. Compounds 2, 3 and 5 exhibited cytoxicity against KB cell lines with IC50 values of 5.2, 3.7 and 2.0 microg/mL, respectively.
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