Harvesting canthinones: identification of the optimal seasonal point of harvest of Zanthoxylum chiloperone leaves as a source of 5-methoxycanthin-6-one

References

• BaiJ, BaldwinE, PlottoA, MantheyJA, MccollumG, IreyM, LuzioG. 2009. Influence of harvest time on quality of ‘Valencia’ oranges and juice. Proc Fla Stare Hart Soc. 122:308–315.
   Google Scholar
• BapelaMJ, LallN, Isaza-MartinezJH, RegnierT, MeyerJJM. 2007. Variation in the content of naphthoquinones in seeds and seedlings of Euclea natalensis. S Afr J Bot. 73:606–610. doi:10.1016/j.sajb.2007.06.003.
   Web of Science ®Google Scholar
• Cebrián-TorrejónG, SpelmanK, LeblancK, Muñoz-DurangoK, Torijano GutiérrezS, FerreiraME, Rojas de AriasA, FigadèreB, FournetA, MaciukA, et al. 2011. The antiplasmodium effects of a traditional South American remedy: Zanthoxylum chiloperone var. angustifolium against chloroquine resistant and chloroquine sensitive strains of Plasmodium falciparum. Rev Bras Farmacogn. 21:652–661.
   Google Scholar
• CechNB, EleazerMS, ShoffnerLT, CrosswhiteMR, DavisAC, MortensonAM. 2006. High performance liquid chromatography/electrospray ionization mass spectrometry for simultaneous analysis of alkamides and caffeic acid derivatives from Echinacea purpurea extracts. J Chromatogr A. 1103:219–228. doi:10.1016/j.chroma.2005.11.008.
   PubMed Web of Science ®Google Scholar
• Doménech-CarbóA, Cebrián-TorrejónG, De MiguelL, TorderaV, RodriguesD, Assad-KahnS, FournetA, FigadèreB, VázquezR, PouponE. 2014. dsDNA, ssDNA, G-quadruplex DNA, and nucleosomal DNA electrochemical screening using canthin-6-one alkaloid-modified electrodes. Electrochim Acta. 115:546–552.
   Web of Science ®Google Scholar
• FerreiraME, Cebrián-TorrejónG, CorralesAS, de bilbaoNV, RolónM, GomezCV, LeblancK, YalufG, SchininiA, TorresS, et al. 2011. Zanthoxylum chiloperone leaves extract: first sustainable Chagas disease treatment. J. Ethnopharmacol. 133:986–993. doi:10.1016/j.jep.2010.11.032.
   PubMed Web of Science ®Google Scholar
• FerreiraME, NakayamaH, de ariasAR, SchininiA, de bilbaoNF, SernaE, LagoutteD, Soriano-AgatónF, PouponE, HocquemillerR, et al. 2007. Effects of canthin-6-one alkaloids from Zanthoxylum chiloperone On Trypanosoma cruzi-infected mice. Ethnopharmacol. 109:258–263. doi:10.1016/j.jep.2006.07.028.
   PubMed Web of Science ®Google Scholar
• FerreiraME, Rojas de AriasA, Torres de OrtizS, InchaustiA, NakayamaH, ThouvenelC, HocquemillerR, FournetA. 2002. Leishmanicidal activity of two canthin-6-one alkaloids, two major constituents of Zanthoxylum chiloperone var. angustifolium. J. Ethnopharmacol. 80:199–202. doi:10.1016/S0378-8741(02)00025-9.
   PubMed Web of Science ®Google Scholar
• Gobbo-NetoL, LopesNP. 2007. Plantas medicinais: fatores de influência no conteúdo de metabólitos secundários Quim. Nova. 30:374–381.
   Google Scholar
• HatanoT, InadaK, OgawaTO, ItoH, YoshidaT. 2004. Aliphatic acid amides of the fruits of Zanthoxylum piperitum. Phytochemistry. 65:2599–2604. doi:10.1016/j.phytochem.2004.08.018.
   PubMed Web of Science ®Google Scholar
• KashiwadaY, ItoC, KatagiriH, MaseI, KomatsuK, NambaT, IkeshiroY. 1997. Amides of the fruit of Zanthoxylum spp. Phytochemistry. 44:1125–1127. doi:10.1016/S0031-9422(96)00683-8.
   Web of Science ®Google Scholar
• LagoutteD, NicolasV, PouponE, FournetA, HocquemillerR, LibongD, ChaminadeP, LoiseauPM. 2008. Antifungal canthin-6-one series accumulate in lipid droplets and affect fatty acid metabolism in Saccharomyces cerevisiae. Biomed Pharmacother. 62:99–103. doi:10.1016/j.biopha.2007.07.014.
   PubMed Web of Science ®Google Scholar
• LiuZ, CarpenterSB, BourgeoisWJ, YuY, ConstantinRJ, FalconMWJ, AdamsJC. 1998. Variations in the secondary metabolite camptothecin in relation to tissue age and season in Camptotheca acuminata. Tree Phys. 18:265–270. doi:10.1093/treephys/18.4.265.
   PubMed Web of Science ®Google Scholar
• NegiJS, BishtVK, BhandariAK, SinghP, SundriyalRC. 2011. Chemical constituents and biological activities of the genus Zanthoxylum: a review. Afr J Pure Appl Chem. 5:412–416.
   Google Scholar
• RiipiM, HaukiojaE, LempaK, OssipovaV, OssipovS, PihlajaK. 2004. Ranking of individual mountain birch trees in terms of leaf chemistry: seasonal and annual variation. Chemoecology. 14:31–43. doi:10.1007/s00049-003-0256-y.
   Web of Science ®Google Scholar
• ScholzF, SchröderU, GulaboskiR, Doménech-CarbóA. 2014. Electrochemistry of immobilized particles and droplets. 2nd ed. Berlin: Springer.
   Google Scholar
• Soriano-AgatónF, LagoutteD, PouponE, RoblotF, FournetA, GantierJC, HocquemillerR. 2005. Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities. J Nat Prod. 68:1581–1587. doi:10.1021/np050250z.
   PubMed Web of Science ®Google Scholar
• SpelmanK, WetschlerMH, CechNB. 2009. Comparison of alkylamide yield in ethanolic extracts prepared from fresh versus dry Echinacea purpurea utilizing HPLC-ESI-MS. J Pharm Biomed Anal. 49:1141–1149. doi:10.1016/j.jpba.2009.02.011.
   PubMed Web of Science ®Google Scholar
• SpichigerR, Stutz de OrtegaL. 1987. Rutaceae. In: Spichiger R, editor. Flora del Paraguay. Ed. Conservatoire et Jardin botaniques de la Ville de Genève. St. Louis (MO): Missouri Botanical Garden; pp. 33–34.
   Google Scholar
• ThouvenelC, GantierJC, DuretP, FourneauC, HocquemillerR, FerreiraME, Rojas de AriasA, FournetA. 2003. Antifungal compounds from Zanthoxylum chiloperone var. angustifolium. Phytother Res. 17:678–680.
   PubMed Web of Science ®Google Scholar
• WallaceSK, EigenbrodeSD. 2002. Changes in the glucosinolate–myrosinase defense system in Brassica juncea cotyledons during seedling development. J Chem Ecol. 28:243–256. doi:10.1023/A:1017973005994.
   PubMed Web of Science ®Google Scholar
• YangX. 2008. Aroma constituents and alkylamides of red and green huajiao (Zanthoxylum bungeanum and Zanthoxylum schinifolium). J Agric Food Chem. 56:1689–1696. doi:10.1021/jf0728101.
   PubMed Web of Science ®Google Scholar