Furoquinoline Alkaloids and Cytotoxic Constituents from the Leaves of Melicope semecarpifolia

Abstract

Three new furoquinoline alkaloids, melicarpine, semecarpine, and (±)-8-methoxyplatydesmine, together with a known flavone, ayanin, were isolated from the leaves of Melicope semecarpifolia. The structures of the three alkaloids were determined through spectral analyses. Of the nineteen isolates obtained here and during earlier work, twelve exhibited cytotoxic activity against P-388, HT-29, or A549 cell lines in vitro. Among them, confusameline is the most cytotoxic isolate, and exhibited more potent cytotoxicity (ED₅₀ value = 0.03 μg/mL) against the P-388 cell line than the reference compound mithramycin (ED₅₀ value = 0.06 μg/mL).

Melicope semecarpifolia - Rutaceae - leaves - alkaloids - furoquinolines - melicarpine - semecarpine - (±)-8-methoxyplatydesmine - cytotoxicity

References

• 1 Tsai I L, Wun M F, Teng C M, Ishikawa T, Chen I S. Anti-platelet aggregation constituents from Formosan Toddalia asiatica .  Phytochemistry. 1998;  48 1377-82
• 2 Chen I S, Wu S J, Leu Y L, Tsai I W, Wu T S. Alkaloids from root bark of Zanthoxylum simulans .  Phytochemistry. 1996;  42 217-9
• 3 Zhao W, Wolfender J L, Hostettmann K, Xu R, Qin G. Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus .  Phytochemistry. 1998;  47 7-11
• 4 Higa T, Scheuer P J. Alkaloids from Pelea barbigera .  Phytochemistry. 1974;  13 1269-72
• 5 Setzer W N, Setzer M C, Schmidt J M, Moriarity D M, Vogler B, Reeb S, Holmes A M, Haber W A. Cytotoxic components from the bark of Stauranthus perforatus from Monteverde, Costa Rica.  Planta Medica. 2000;  66 493-4
• 6 Yang T H, Lu S T, Wang S J, Wang T W, Lin J H, Chen I S. Alkaloids of Melicope confusa .  Yakugaku Zasshi. 1971;  91 782-6
• 7 Tsai I L, Wu S J, Ishikawa T, Seki H, Yan S T, Chen I S. Evomerrine from Melicope semecarpifolia .  Phytochemistry. 1995;  40 1561-2
• 8 Chen K S, Chang Y L, Teng C M, Chen C F, Wu Y C. Furoquinolines with antiplatelet aggregation activity from leaves of Melicope confusa .  Planta Medica. 2000;  66 80-1
• 9 Chang C E, Hartley T G. Rutaceae in Flora of Taiwan. 2nd edition. Editorial Committee of the Flora of Taiwan Taipei, Taiwan; 1993 Vol. 3: 510-44
• 10 Kan W S. Manual of Medicinal Plants in Taiwan. National Research Institute of Chinese Medicine Taipei, Taiwan; 1970 Vol. 2: 374
• 11 Chen J J, Chang Y L, Teng C M, Su C C, Chen I S. Quinoline alkaloids and anti-platelet aggregation constituents from the leaves of Melicope semecarpifolia .  Planta Medica. 2002;  68 790-3
• 12 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  Journal of Immunological Methods. 1983;  65 55-63
• 13 Tillequin F, Baudouin G, Koch M. Synthesis of dutadrupine.  Heterocycles. 1982;  19 507-9
• 14 Muyard F, Bevalot F, Laude B, Vaquett J. Alkaloids from stem bark of Dutaillyea baudouinii .  Phytochemistry. 1992;  31 1087-9
• 15 Barr S A, Boyd D R, Sharma N D, Evans T A, Malone J F, Mehta V D. Resolution of prenyl bromohydrin esters and derivatives: Synthesis of the quinoline alkaloid (+)-(R)- and (-)-(S)-lunacridine.  Tetrahedron. 1994;  50 11 219-34
• 16 Bowman R M, Collins J F, Grundon M F. Quinoline alkaloids. Part XIV. Asymmetric synthesis by the peroxyacid-olefin reaction. The absolute stereochemistry of balfourodine, isobalfourodine, and related compounds, and the biosynthesis of isomeric dihydrofuro- and dihydropyrano-derivatives. Journal of the Chemical Society, Perkin Transactions I 1973;: 626-32