Cytotoxic Alkaloids from the Flowers of Senna spectabilis

Lawan Sriphong; Uthai Sotanaphun; Siripan Limsirichaikul; Penpan Wetwitayaklung; Chaiyo Chaichantipyuth; Sunibhond Pummangura

doi:10.1055/s-2003-45156

Planta Med 2003; 69(11): 1054-1056
DOI: 10.1055/s-2003-45156

Letter

Cytotoxic Alkaloids from the Flowers of Senna spectabilis

Lawan Sriphong¹ , Uthai Sotanaphun¹ , Siripan Limsirichaikul¹ , Penpan Wetwitayaklung¹ , Chaiyo Chaichantipyuth² , Sunibhond Pummangura²

¹Faculty of Pharmacy, Silpakorn University, Nakorn Prathom, Thailand
²Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand

This work was financially supported by Graduated School, Chulalongkorn University, and the Research Institution of Silpakorn University

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 μg/mL, respectively.

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References

1 Chritofidis I, Watter A, Jadot J. Spectaline and iso-6-cassine, two new piperidin-3-ol alkaloids from the leaves of Cassia spectabilis . Tetrahedron. 1977; 33 377-9
2 Christofidis I, Walter A, Jadot J. Spectalinine and iso-6-carnavaline, two unprecedented piperidine alkaloids from the seeds of Cassia spectabilis . Tetrahedron. 1977; 33 3005-6
3 Freyer A J, Patil A D, Killlmer L, Troupe N, Mentzer M, Carte B, Faucette L, Johnson R K. Three new pseudodistomin, piperidine alkaloids from ascidian Pseudodistoma megalarva . Journal of Natural Products. 1997; 60 986-90
4 Charan R D, Garson M J, Brereton I M, Willis A C, Hooper J NA. Haliclonacyclamines A and B, cytotoxic alkaloids from the tropical marine sponge Haliclona sp. Tetrahedron. 1996; 52 9111-20
5 Rice W Y, Coke J L. Structure and configuration of alkaloids. II. Cassine. Journal of Organic Chemistry. 1966; 31 1010-2
6 Premaratne bandara K AN, Kumar V, Jacobson U, Molleyers L P. Insecticidal piperidine alkaloid from Microcos paniculata stem bark. Phytochemistry. 2000; 54 29-32
7 Pavia D L, Lampman G M, Kriz G S. Introduction to organic laboratory techniques. Philadelphia; W.B. Saunders company 1976: pp 25-30
8 Meyer B N, Ferrigni N R, Putnam J E, Jacobsen L B, McLaughlin J L, et al. Brine shrimp: convenient general bioassay for active plant constituents. Planta Medica. 1982; 45 31-4
9 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D. et al . New colorimetric cytotoxicity assay for anticancer drug screening. Journal of the National Cancer Institute. 1990; 82 1107-12

Associate Professor Lawan Sriphong

Department of Pharmaceutical Chemistry

Faculty of Pharmacy

Silpakorn University

Nakorn-Pathom 73000

Thailand

Phone: +66-34-255800

Fax: +66-34-255801

Email: lawan@email.pharm.su.ac.th