Antibacterial Alkaloids from Zanthoxylum rhoifolium

Abstract

Two new dihydrobenzophenanthridine-type alkaloids, 6-methoxy [1] [3]dioxolo[4′,5′:4,5]benzo[c][1] [3]dioxolo[4,5-j]phenanthridine (1) and 2,3,13-trimethoxy-5,11a-dihydro[1] [3]dioxolo[4′,5′:4,5]benzo[c]phenanthridine (2) were isolated from the stem bark of Zanthoxylum rhoifolium, together with four other previously known benzophenanthridine alkaloids, 6-acetonyldihydronitidine (3) {= 8-acetonyldihydronitidine}, 6-acetonyldihydroavicine (4) {= 8-acetonyldihydroavicine}, 6-acetonyldihydrochelerythrine (5) and xanthoxyline (6). The structures were elucidated mainly by spectroscopic methods, including 1D and 2D NMR spectroscopy. For alkaloids 1 and 2 we propose the trivial names rhoifolines A and B. The crude plant extracts and the alkaloids 3, 4 and 6 showed activity against Gram (±) bacteria, while the new alkaloids 1 and 2 were inactive.

References

• 1 Tin-Wa M, Bell C L, Bevelle C, Fong H HS, Farnsworth N R. Potential anticancer agents I: Confirming evidence for the structure of fagaronine.  Journal of Pharmaceutical Sciences. 1974;  63 1476-7
• 2 Odebiyl O O, Sofowora E A. Antimicrobial alkaloids from a Nigerian chewing stick (Fagara zanthoxyloides).  Planta Medica. 1979;  36 204-7
• 3 Lenfeld J, Kroutil M, Marsálek E, Slavic J, Preininger V, Simánek V. Anti-inflammatory activity of quaternary benzophenanthridine alkaloids from Chelidonium majus .  Planta Medica. 1981;  43 161-5
• 4 Nowick W. Diagnostic and therapeutic treatment of tumors and/or infections diseases of all types using alkaloid compositions or their salts.  Chemical Abstracts. 1983;  99 P71067g
• 5 Cushman M, Mohan P, Smith E CR. Synthesis and biological activity of structural analogues of the anticancer benzophenanthridine alkaloid nitidine chloride.  Journal of Medicinal Chemistry. 1984;  27 544-7
• 6 Morel A F, Moura N F, Ribeiro H B, Machado E CSM, Ethur E M, Zanatta N. Benzophenanthridine alkaloids from Zanthoxylum rhoifolium .  Phytochemistry. 1997;  46 1443-6
• 7 Waterman G P, Khalid S A. The biochemical systematics of Fagaropsis angolensis and its significance in the Rutales.  Biochemical Systematics and Ecology. 1981;  9 45-51
• 8 Ajith P KN, Veranja K, Bandara B MR, Viajaya K, Tsutomu N, Masatoshi N, Akira I, Tillekeratne L MV, Wijesundara D SA, Gunatilaka A AL. Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum .  Phytochemistry. 2001;  56 857-61
• 9 Decaudain N, Kunesch K, Poison J. Alcaloïdes de Zanthoxylum tsihanimposa .  Phytochemistry. 1974;  13 505-7
• 10 Hamburger O M, Cordell A G. Direct bioautography TLC assay for compounds possessing antibacterial activity.  Journal of Natural Products. 1987;  50 19-22
• 11 Rahalison L, Hamburger M, Hostettmann K, Monod M, Frenk E. A bioautographic agar overlay method for the detection of antifungal compounds from higher plants.  Phytochemical Analysis. 1991;  2 199-203