THE OCCURRENCE OF CAFESTOL AND KAHWEOL DITERPENES IN DIFFERENT COFFEE BREWS
DOI:
https://doi.org/10.25186/cs.v14i2.1571Keywords:
Brew preparations, diterpene content, hypercholesterolemiaAbstract
Coffee is the second most consumed brew in the world, after water. Cafestol and kahweol are two diterpenes that have been identified, until now, exclusively in the coffee tree. They are co-extracted from the coffee beans that are roasted and ground for the beverage preparation. Their pharmacological properties are related to anticancer and anti-inflammatory activities, although they also increase the serum cholesterol. Several researches reported that coffee brew preparation methods influence directly the levels of the diterpenes. This paper describes a compilation of the main results published for different coffee brews and all variables related to their preparation. Major differences in the reported concentrations have been noted.References
ABIC (2018a). História. Disponível em: <http://abic.com.br/cafe-com/historia/>. Acesso em: 12 dec. 2018.
ABIC (2018b). Métodos de preparo. Disponível em: <http://abic.com.br/o-cafe/dicas-do-cafe/metodos-de-preparo/>. Acesso em: 12 dec. 2018.
ALVES, R. C.; CASAL, S.; OLIVEIRA, B. Benefícios do café na saúde: mito ou realidade? Química Nova, São Paulo, v. 32, n. 8, p. 2169-2180, 2009.
ARO, A.; TUOMILEHTO, J.; KOSTIAINEM, E.; et al. Boiled coffee increases serum low density lipoprotein concentration. Metabolism, v. 26, n. 11, p. 1027-1030, 1987.
BENGIS, R. O.; ANDERSON, R. J. The chemistry of the coffee-bean. I. Concerning the unsaponifiable matter of the coffee-bean oil. Preparation and properties of kahweol. Journal of Bilogical Chemistry, v. 97, n. 1, p. 99-113, jul. 1932
BERTHOLET, R. Preparation of Cafestol. U.S. Pat. 4,692,534. 31 May 1988.
BUTT, M. S.; SULTAN, M. T. Coffee and its consumption: Benefits and risks. Critical Reviews in Food Science and Nutrition, v. 51, n. 4, p. 363-373, mar. 2011.
CARDENAS, C.; QUESADA, A. R.; MEDINA, M. A. Anti-angiogenic and anti-inflamatory properties of kahweol a coffee diterpene. Journal Plos One, v. 6, n. 8, p. e23407, aug. 2011.
CARDENAS, C.; QUESADA, A. R.; MEDINA, M. A. Kahweol, a coffee diterpene with anti-inflammatory properties. In: PREEDY, V. R. (Ed.). Coffee in Health and Disease Prevention. London: Academic Press, 2015. chap. 70, p. 627-633.
CAVIN, C.; HOLZHAUSER, D.; CONSTABLE, A.; et al. The coffee-specific diterpenes cafestol and kahweol protect against Aflatoxin B1-induced genotoxicity through a dual mechanism. Carcinogenesis, v. 19, n. 8, p. 1369-1375, aug. 1998.
CHENG, B.; FURTADO, A.; SMYTH, H. E.; et al. Influence of genotype and environment on coffee quality. Trends in Food Science & Technology, v. 57, p. 20-30, sep. 2016.
DEL CASTILLO, M. L. R.; HERRAIZ, M.; BLACH, G. P. Rapid analysis of cholesterol-elevating compounds in coffee brews by off-Line High-Performance Liquid Chromatography/High-Resolution Gas Chromatography. Journal of Agricultural and Food Chemistry, Easton, v. 47, n. 4, p. 1525-1529, mar. 1999.
ERNY, G. L.; MOEENFARD, M.; ALVES, A. Liquid chromatography with diode array detection combined with spectral deconvolution for the analysis of some diterpene esters in Arabica coffee brew. Journal of Separation Science, v. 38, n. 4, p. 612-620, jan. 2015.
FARAH, A. Coffee constituents. In Y.-F. Chu (Ed.), Coffee: Emerging health effects and disease prevention. Iowa: John Wiley & Sons Inc, 2012. Chap. 2, p. 21-58.
FINOTELLO, C.; FORZATO, C.; GASPARINI, A.; et al. NMR quantification of 16-O-methylcafestol and kahweol in Coffea canephora var. robusta beans from different geographical origins. Food Control, Oxford, v. 75, p. 62-69, may 2017.
FOLSTAR, P. Lipids. In: CLARKE, R. J. (Ed.). Coffee Volume 1: Chemistry. London: Springer Netherlands, 1985. Chap. 6, p. 203-222.
FUMMIOTO, R.; SAKAI, E.; YAMAGUCHI, Y.; et al. The coffee diterpene kahweol prevents osteoclastogenesis via impairment of NFATc1 expression and blocking of Erk phosphorylation. Journal of Pharmacological Sciences, v. 118, n. 4, p. 479-486, mar. 2012.
GARRETT, R.; SCHMIDT, E. M.; PEREIRA, L. F. P, et al. Discrimination of arabica coffee cultivars by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry and chemometrics. LWT – Food Science and Technology, v. 50, n. 2, p. 496-502, mar. 2013.
GOVERNO DO BRASIL. Cresce consumo de café entre os jovens, revela pesquisa. Disponível em: <http://www.brasil.gov.br/governo/2011/05/cresce-consumo-de-cafe-entre-os-jovens-revela-pesquisa>. Acesso em: 12 dec. 2018.
GUZZO, L. S.; ROMERO, T. R. L.; QUEIROZ-JUNIOR, C. M.; et al. Involvement of endogenous opioid peptides in the peripheral antinociceptive effect induced by the coffee specific diterpene kahweol. Pharmacological Reports, v. 67, n. 5, p. 1010-1015, mar. 2015.
ICO (2018a). World coffee consumption. Disponível em: <http://www.ico.org/prices/new-consumption-table.pdf>. Acesso em: 12 dec. 2018.
ICO (2018b). Total production by all exporting countries. Disponível em: <http://www.ico.org/prices/po-production.pdf>. Acesso em: 12 dec. 2018.
KITZBERGER, C. S. G.; SCHOLZ, M. B. S.; PEREIRA, L. F. P.; et al. Diterpenes in green and roasted coffee of Coffea arabica cultivars growing in the same edapho-climatic conditions. Journal of Food Composition and Analysis, v. 30, n. 1, p. 52-57, feb. 2013.
KÖLLING-SPEER, I.; STROHSCHNEIDER, S.; SPEER, K. Determination of free diterpenes in green and roasted coffees. Journal of High Resolution Chromatography, v. 22, n. 1, p. 43-46, jan. 1999.
LAM, L. K. T.; SPARNINS, V. L.; WATTENBERG, W. Isolation and identification of kahweol palmitate and cafestol palmitate as active constituents of green coffee beans that enhance Glutathione S-Transferase activity in the mouse. Cancer Research, v. 42, n. 4, p. 1193-1198, apr. 1982.
LEE, K. J.; JEONG, H. G. Protective effects of kahweol and cafestol against hydrogen peroxide-induced oxidative stress and DNA damage. Toxicology Letters, n. 173, n. 2, p. 80-87, sep. 2007.
LITMAN, I.; NUMRYCH, S. The role lipids play in the positive and negative flavors of food. In: SUPRAN, M. K. (Ed.). Lipids as a Source of Flavor, New Jersey: Englewood Cliffs, 1978. Chap. 1, p. 1-17.
MASTEN, S.; TICE, R. Cafestol and kahweol: review of toxicological literature. North Corolina: Integ Lab Syst, 1999. p. 2-39.
MILLER, E. G.; FORMBY, W. A.; RIVERA-HIDALGO, F.; et al. Inhibition of hamster buccal pouch carcinogenesis by green coffee beans. Oral Surgery, v. 65, n. 6, p. 745-479, mar. 1988.
MOEENFARD, M.; ERNY, G. L.; ALVES, A. Variability of some diterpene esters in coffee beverages as influenced by brewing procedures. Journal Food Science and Technology, v. 53, n. 11, p. 3916-3927, nov. 2016.
MOEENFARD, M.; SILVA, J. A.; BORGES, N.; et al. Diterpenes in espresso coffee: impact of preparation parameters. European Food Research and Technology, v. 240, n. 4, p. 763-773, apr. 2015a.
MOEENFARD, M.; SILVA, J. A.; BORGES, N.; et al. Quantification of diterpenes and their palmitate esters in coffee brews by HPLC-DAD. International Journal of Food Properties, v. 18, n. 10, p. 2284-2299, jan. 2015b.
NACKUNSTZ, B.; MAIER, H. G. Diterpenoids in coffee. III. Cafestol and Kahweol. Zeitschrift für Lebensmittel-Untersuchung und Forschung, Berlin, v. 184, n. 6, p. 494-499, jun. 1987.
NAVARINI, L.; NOBILE, E.; PINTO, F.; et al. Experimental investigation of steam pressure coffee extraction in a stove-top coffee maker. Applied Thermal Engineering, v. 29, p. 998–1004, 2009.
NESPRESSO. Nespresso. Disponível em: <https://www.nespresso.com/br/pt/home> Acesso em: 16 fev. 2017.
PETRACCO, M. Our everyday cup of coffee: the chemistry behind its magic. Journal of Chemical Education, v. 82, n. 8, p. 1161-1167, aug. 2005.
PREEDY, V. R. Coffee in Health and Disease Prevention. 1. ed. London: Academic Press, 2015. 437 p.
RATNAYAKE, W. M. N.; HOLLYWOOD, R.; O’GRADY, E.; et al. Lipid content and composition of coffee brews prepared by different methods. Food and Chemistry Toxicology, v. 31, n. 4, p. 263-269, apr. 1993.
RENDÓN, M. Y.; SCHOLZ, M. B. S.; BRAGAGNOLO, N.; Is cafestol retained on the paper filter in the preparation of filter coffee? Food Research International, v. 100, p. 798–803, aug. 2017.
RENDÓN, M. Y.; SCHOLZ, M. B. S.; BRAGAGNOLO, N.; Physical characteristics of the paper filter and low cafestol content filter coffee brews. Food Research International, v. 108, p. 280-285, mar. 2018.
RICKETTS, M.-L. Does coffee raise cholesterol? Future Lipidology, v. 2, n 4, p. 373-377, 2007
SAKAI, E.; TSUKUBA, T. Coffee and bone metabolism: Kahweol and osteoclastogenesis. In: Preedy, V. R. (Ed.). Coffee in Health and Disease Prevention. London: Academic Press, 2015. Chap. 96, p. 869-875.
SILVA, J. A.; BORGES, N.; SANTOS, A.; et al. Method validation for
cafestol and kahweol quantification in coffee brews by HPLC-DAD. Food Analytical Methods, v. 5, n. 6, p. 1404-1410, dec. 2012.
SPEER, K.; KÖLLING-SPEER, I. The lipid fraction of the coffee bean. Brazilian Journal of Plant Physiology, Campos dos Goytacazes, v. 18, n. 1, p. 201-216, mar. 2006.
SRIDEVI, V.; GIRIDHAR, P.; RAVISHANKAR, G. A. Evaluation of roasting and brewing effect on antinutriotional diterpenes – cafestol and kahweol in coffee. Global Journal of Medical Reaserch, v. 11, n. 5, p. 11-22, dec. 2011.
TISCORNIA, E.; CENTI-GROSSI, M.; TASSI-MICCO, C.; et al. Sterol fractions of coffee seeds oil (Coffea arabica L.). Rivista Italiana Delle Sostanze Grasse, Milano, v. 56, p. 283-292, 1979.
TOLEDO, P. R. A. B.; PEZZA, L.; PEZZA, H. R.; et al. Relationship between the different aspects related to coffee quality and their volatile compounds. Comprehensive Reviews in Food Science and Food Safety, v. 15, n. 4, p. 705-719, april 2016.
URGERT, R.; VAN DER WEG, G.; KOSMEIJER-SCHUIL, T. G.; et al. Level of the cholesterol-elevating diterpenes cafestol and kahweol in various coffee brews. Journal of Agricultural and Food Chemistry, Easton, v. 43, n. 8, p. 2167-2172, aug. 1995.
WANG, S.; YOON, Y. C.; SUNG, M.; et al. Antiangiogenic properties of cafestol, a coffee diterpene, in human umbilical vein endothelial cells. Biochemical and Biophysical Research Communications, v. 421, n. 3, p. 567-571, may 2012.
WOUW, M. P. M. E. W-V.; KATAN, M. B.; VIANAI, R.; et al. Identity of the cholesterol-raising factor from boiled coffee and its effects on liver function enzymes. Journal of Lipid Research, v. 35, p. 721-733, apr. 1994.
WUERGES, K. L.; SANTOS, A. C. F.; MORI, A. L. B.; et al. Contents of diterpenes in espresso coffee brews prepared from commercial capsules. Coffee Science, Lavras, v. 11, n. 2, p. 276-284, jun. 2016.
YILMAZ, B.; ACAR-TEK, N; SÖZLÜ, S. Turkish cultural heritage: a cup of coffee. Journal of Ethnic Foods, Wanju-gun, v. 4, p. 213-220, nov. 2017.
ZHANG, C.; LINFORTH, R.; FISK, I. Cafestol extraction yield from different coffee brew mechanisms. Food Research International, v. 49, n. 1, p. 27-31, nov. 2012.
ZOCK, P. L.; KATAN, M. B.; MERKUS, M. P.; et al. Effect of a lipid-rich fraction from boiled coffee on serum cholesterol. The Lancet, v. 335, n. 8700, p. 1235-1237, may 1990.
Published
How to Cite
Issue
Section
Os direitos autorais dos artigos publicados nesta revista pertencem aos autores, com os primeiros direitos de publicação pertencentes à revista. Como os artigos aparecem nesta revista com acesso aberto, eles podem ser usados livremente, com as devidas atribuições, em aplicativos educacionais e não comerciais.
