New and Bioactive Aromatic Compounds from Zanthoxylum zanthoxyloides

Abstract

In the course of a study of medicinal plants from Mali, the root bark of Zanthoxylum zanthoxyloides Lam. (Rutaceae) was investigated. The root bark of this plant is used as a toothbrush by West African people. Phytochemical investigation of the MeOH extract of Zanthoxylum zanthoxyloides Lam. (Rutaceae) led to the isolation of different biologically active compounds. The separation of acetylcholinesterase inhibitors was performed by centrifugal partition chromatography (CPC). The fractions were monitored by direct TLC bioautographic assays. The bio-guided isolation led to the isolation of a new peroxide derivative. In addition, LC/UV/MS analysis performed on the crude MeOH extract allowed on-line identification of some known compounds. The structures of the isolated compounds were elucidated by classical spectroscopic methods including UV, NMR, MS and HR-MS.

Zanthoxylum zanthoxyloides - Rutaceae - acetylcholinesterase inhibitors - Cladosporium cucumerinum - Candida albicans - Bacillus subtilis - free radical scavengers

References

• 1 Kerharo J, Adam J G. La Pharmacopée sénégalaise traditionnelle. Paris; Vigot Frères 1971: p 713-5
• 2 Chaaib F, Queiroz E F, Ndjoko K, Diallo D, Hostettmann K. Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides .  Planta Med. 2003;  69 316-20
• 3 Marston A, Kissling J, Hostettmann K. A rapid TLC bioautographic method for the detection of acetylcholinesterase and butyrylcholinesterase inhibitors in plants.  Phytochem Anal. 2002;  13 51-4
• 4 Cuendet M, Hostettmann K, Potterat O, Dyatmiko W. Iridoid glucosides with free radical scavenging properties from Fagraea blumei .  Helv Chim Acta. 1997;  80 1144-51
• 5 Homans A L, Fuchs A. Direct bioautography on thin-layer chromatograms as a method for detecting fungitoxic substances.  J Chromatogr. 1970;  51 327-9
• 6 Rahalison L, Hamburger M, Hostettmann K, Monod M, Frenk E. A bioautographic agar overlay method for the detection of antifungal compounds from higher plants.  Phytochem Anal. 1991;  2 199-203
• 7 Godin P. A new spray reagent for paper chromatography of polyols and cetoses.  Nature. 1954;  174 134
• 8 Guinaudeau H, Leboeuf M, Cave A. Aporphine alkaloids.  Lloydia. 1975;  38 275-338
• 9 Garg A, Garg S, Zaneveld L , Singla A . Chemistry and pharmacology of the citrus biflavonoid hesperidin.  Phytother Res. 2001;  15 655-69
• 10 Messmer W , Tinwa , Trojanek J, Abraham D J, Bevelle C, Fong H HS. et al . Fagaronine, a new tumor inhibitor isolated from Fagara zanthoxyloides Lam (Rutaceae).  J Pharm Sci. 1972;  61 858-9
• 11 Wu S J, Chen I S. Alkaloids from Zanthoxylum simulans .  Phytochemistry. 1993;  34 1659-61
• 12 Paris R, Moyse-Mignon H. Recherches sur les Fagaras africaines. 3. Étude du Fagara macrophylla Engler.  Ann Pharm Fr. 1951;  9 479-93
• 13 Bruins A P, Covey T R, Henion J T. Ion spray for combined liquid chromatography mass spectrometry/atmospheric pressure chemical ionization mass spectrometry.  Anal Chem. 1987;  59 2642-6
• 14 Waldron K W, Parr A J, Ralph J. Cell wall esterified phenolic dimers: identification and quantification by RP HPLC and DAD.  Phytochem Anal. 1996;  7 305-12
• 15 Ouattara B, Angenot L, Guissou P, Fondu P, Dubois J, Frédérich M. et al . Direct LC/MS/NMR analysis of isomeric divanilloylquinic acids from the root bark of Fagara zanthoxyloides Lam.  Phytochemistry. 2004;  65 1-7
• 16 Markham K R. Techniques of flavonoid identification. London; Academic Press 1982
• 17 Sharma P N, Shoeb A, Kapil R S, Popli S P. 8-hydroxydrochelerythrine and arnottianamide from the roots of Toddalia asiatica .  Phytochemistry. 1982;  21 252-3
• 18 Krane B D, Fagbule M O, Sharma M. The benzophenanthridine alkaloids.  J Nat Prod. 1984;  47 1-43
• 19 Berova N, Nakanishi K. Circular dichroism principles and applications. 2nd edition New York; Wiley & Sons 2000: p 337-82
• 20 Ulrichova J, Walterova D, Preininger V, Slavik J, Lenfeld J, Cushman M. et al . Inhibition of acetylcholinesterase activity by some isoquinoline alkaloids.  Planta Med. 1983;  48 111-5