Oxyprenylated ferulic acid derivatives in Italian citrus liqueurs

https://doi.org/10.17221/524/2014-CJFSCitation:Fiorito S., Epifano F., Taddeo V.A., Genovese S. (2015): Oxyprenylated ferulic acid derivatives in Italian citrus liqueurs. Czech J. Food Sci., 33: 237-241.
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4’-Geranyloxyferulic and boropinic acid have been recently found as phytochemicals exerting promising pharmacological effects as cancer chemopreventive, anti-inflammatory, neuroprotective, and anti-Helicobacter pylori agents. An RP HPLC-UV/Vis method for the qualitative and quantitative analysis of these oxyprenylated derivatives in handmade citrus-based typical Italian liqueurs like limoncello, arancello, and mandarinetto was successfully performed. Concentration values showed a great variation between the different liquors, limoncello, from Abruzzo region, being the richest one both in 4’-geranyloxyferulic acid (1.68 ± 0.03 µg/ml of liquor) and boropinic acid (0.16 ± 0.01 µg/ml). Only in two cases boropinic acid was not detected.
References:
Curini M., Genovese S., Menghini L., Marcotullio M.C., Epifano F. (2008): Phytochemistry and pharmacology of Boronia pinnata Sm. Natural Product Communications, 3: 2145–2152.
 
Dugo Paola, Mondello Luigi, Cogliandro Eugenia, Cavazza Antonella, Dugo Giovanni (1998): On the genuineness of citrus essential oils. Part LIII. Determination of the composition of the oxygen heterocyclic fraction of lemon essential oils (Citrus limon (L.) Burm. F.) by normal-phase high performance liquid chromatography. Flavour and Fragrance Journal, 13, 329-334  https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<329::AID-FFJ754>3.0.CO;2-1
 
Epifano Francesco, Genovese Salvatore, Menghini Luigi, Curini Massimo (2007): Chemistry and pharmacology of oxyprenylated secondary plant metabolites. Phytochemistry, 68, 939-953  https://doi.org/10.1016/j.phytochem.2007.01.019
 
Epifano Francesco, Sosa Silvio, Tubaro Aurelia, Marcotullio M. Carla, Curini Massimo, Genovese Salvatore (2011): Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives. Bioorganic & Medicinal Chemistry Letters, 21, 769-772  https://doi.org/10.1016/j.bmcl.2010.11.107
 
Epifano F., Genovese S. (2013): Recent acquisitions on naturally occurring oxyprenylated secondary plant metabolites. In: Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds. London, CRC Press: 239–258.
 
Genovese Salvatore, Epifano Francesco (2012): Recent Developments in the Pharmacological Properties of 4'-Geranyloxyferulic Acid, a Colon Cancer Chemopreventive Agent of Natural Origin. Current Drug Targets, 13, 1083-1088  https://doi.org/10.2174/138945012802009008
 
Genovese S., Epifano F., Carlucci G., Marcotullio M.C., Curini M., Locatelli M. (2010): Quantification of 4'-geranyloxyferulic acid, a new natural colon cancer chemopreventive agent, by HPLC-DAD in grapefruit skin extract, Journal of Pharmaceutical and Biomedical Analysis, 53: 212–214.
 
Genovese Salvatore, Fiorito Serena, Locatelli Marcello, Carlucci Giuseppe, Epifano Francesco (2014): Analysis of Biologically Active Oxyprenylated Ferulic Acid Derivatives in Citrus Fruits. Plant Foods for Human Nutrition, 69, 255-260  https://doi.org/10.1007/s11130-014-0427-8
 
Locatelli M., Carlucci G., Genovese S., Epifano F. (2012): Analytical methods and phytochemistry of the typical italian liquor limoncello: a review. In: Rao V. (ed.): Phytochemicals – A Global Perspective of their Role in Nutrition and Health. Rjieka, InTech: 93–106.
 
MUNAKATA Ryosuke, INOUE Tsuyoshi, KOEDUKA Takao, SASAKI Kanako, TSURUMARU Yusuke, SUGIYAMA Akifumi, UTO Yoshihiro, HORI Hitoshi, AZUMA Jun-ichi, YAZAKI Kazufumi (): Characterization of Coumarin-Specific Prenyltransferase Activities in Citrus limon Peel. Bioscience, Biotechnology and Biochemistry, 76, 1389-1393  https://doi.org/10.1271/bbb.120192
 
Prager RH, Thredgold HM (1966): Some neutral constituents of Acronychia baueri. Australian Journal of Chemistry, 19, 451-  https://doi.org/10.1071/CH9660451
 
Schipilliti Luisa, Bonaccorsi Ivana, Cotroneo Antonella, Dugo Paola, Mondello Luigi (2013): Evaluation of Gas Chromatography–Combustion–Isotope Ratio Mass Spectrometry (GC-C-IRMS) for the Quality Assessment of Citrus Liqueurs. Journal of Agricultural and Food Chemistry, 61, 1661-1670  https://doi.org/10.1021/jf3028073
 
Shimizu M., Kochi T., Shirakamiì Y., Genovese S., Epifano F., Fiorito, S., Mori T., Tanaka T., Moriwaki H. (2014): A newly synthesized compound, 4’-geranyloxyferulic acid–N(omega)-nitro-l-arginine methyl ester suppresses inflammation-associated colorectal carcinogenesis in male mice, International Journal of Cancer, 135: 774–785.
 
Taddeo Vito Alessandro, Epifano Francesco, Fiorito Serena, Genovese Salvatore (2015): A novel oxyprenylated metabolite in Citrus paradisi Macfad. seeds extract. Biochemical Systematics and Ecology, 58, 72-74  https://doi.org/10.1016/j.bse.2014.11.006
 
Andrea Versari, Nadia Natali, Teresa Russo Maria, Andrea Antonelli (2003): Analysis of Some Italian Lemon Liquors (Limoncello). Journal of Agricultural and Food Chemistry, 51, 4978-4983  https://doi.org/10.1021/jf030083d
 
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