Phytochemical evaluation of Zanthoxylum monophyllum has led to the isolation of the alkaloid 4-methoxy-N-methyl-2-quinolone (1) with a significant activity against methicillin-resistant Staphylococcus aureus (MRSA), with an IC50 value of 1.5 (μg /mL. Xenobiotic biotransformation of 1 has been conducted with the general goal of increasing the bioactivity of the compound and contributing new leads for further pharmacological research. Twenty-nine microorganisms were used for screening and two (Aspergillus flavus and Cunninghamella echinulata var.echinulata) were able to transform compound 1 to 4-methoxy-2-quinolone (2). Structural identification of the compounds was based on NMR, IR, and MS data.
CucaSL, MartinezVJ, DelleMF. (1998) Chemical constituents of Zanthoxylum monophyllum. Revista Colombiana de Quimica, 27, 17–27;
2.
De GarciaLA, CalleJ, RegueroMT, NathanJP. (1989) Phtychemical study ofZanthoxylum monophyllum Fitoterapia, 60, 447–450;
3.
StermitzFR, SharifiIA. (1977) Alkaloids from Zanthoxylum monophyllum and Zanthoxylum punctatum. Phytochemistry, 16, 2003–2006;
4.
Mata-GreenwoodE, ItoA, WesternburgH, CuiB, MethaRG, KinghornAD, PizzutoJM. (2001) Discovery of novel inducers of cellular differentiation using HL-60 Promyelocytis cells. Anticancer Research, 21, 1763–1770;
5.
ItoA, ShamonLA, YuB, Mata-GreenwoodE, LeeSK. (1998) Antimutagenic constituents of Casimiroa edulis with potential cancer chemopreventive activity. Journal of Agriculture and Food Chemistry, 46, 3509–3516.
6.
DarawalaAB, GearienGJ, DunnJW, BenoitSP, BauerL. (1974) β-Amino ketones. Synthesis and some biological activities in mice of 3,3-dialkyl-1,2,3,4-tetrahhydro-4-quinolinones and related Mannich base. Journal of Medicinal Chemistry, 7, 819–824;
7.
ItoC, ItoigawaM, OtsukaT, TokudaH, NishinoH, FurukawaH. (2000) Constituents of Boronia pinata. Journal of Natural Products, 63, 1344–1348;
8.
CamachoMR, PhillipsonJD, CroftSL, YardleyV, SolisPN. (2004) In-vitro antiprotozaoal and cytotoxic activities of some alkaloids, quinones, flavonoids and coumarins. Planta Medica, 70, 70–72;
9.
HardtmannGE. (1980) Pharmaceutical preparation and use of 4-hydroxy-2-quinolinone-3-carboxylic acid esters. US patent4,190,659, February 26.
10.
HansonJR. (1992) The microbial transformation of diterpenoids. Natural Product Reports, 9, 139–151;
YangW, JiangT, AcostaD, DavisPJ. (1993) Microbail models of mamamalian metabolism: Involvement of cytochrom P450 in the N-methycarbazol by Cunninghamella echinulata. Xenobiotica, 23, 973–982;
13.
YangW, DavisPJ. (1992) Microbial models of mammalian metabolism. Biotransformations of N-methylcarbazole using the fungus Cunninghamella echinulata. Drug Metabolism and Disposition, 20, 38–46.
14.
AbourashedEA, ClarkAM, HuffordCD. (1999) Microbial models of mammalian metabolism of xenobiotics: an updated review. Current Medicinal Chemistry, 6, 359–374;
15.
HerathW, KhanI. (2010) Microbial metabolism. Part 11. Metabolism of flutamide. Chemical and Pharmaceutical Bulletin, 58, 562–564;
16.
CoppolaGM, KahleAD, ShapiroMJ. (1981) 13C NMR investigation of some hetero-ring substituted 2- and 4- quinolone systems. Organic Magnetic Resonance, 17, 242–245.
MadyasthaKM, ReddyGV. (1994) Use of Mucor piriformis as an efficient N-dealkylating reagent for thebaine and its N-variants. Journal of Chemical Society Perkin Transactions1, 911–912;
19.
AbelAM, CantrellAJ, DavisJA, PaylorM.Synthesis of potential buprenorphine intermediate by selective microbial N- and O-demethylation. (2002) Biotechnology Letters, 24, 1291–1294;
20.
IliasM, Xing-CongLi, DunbarC, El SohlyMA, KhanIA. (2003) Antimalarial (+)-trans-hexahydrobenzopyran derivatives from Machaerium multiflorum. Journal of Natural Products, 66, 804–809.
