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Bioavailability of Phenolic Compounds Critical Reviews in Food Science and Nutrition ISSN: 1040-8398 (Print) 1549-7852 (Online) Journal homepage: http://www.tandfonline.com/loi/bfsn20 Bioavailability of Phenolic Compounds SIBEL KARAKAYA To cite this article: SIBEL KARAKAYA (2004) Bioavailability of Phenolic Compounds, Critical Reviews in Food Science and Nutrition, 44:6, 453-464, DOI: 10.1080/10408690490886683 To link to this article: http://dx.doi.org/10.1080/10408690490886683 Published online: 10 Aug 2010. Submit your article to this journal Article views: 907 View related articles Citing articles: 85 View citing articles Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=bfsn20 Download by: [Chinese Academy of Agricultural Sciences] Date: 19 January 2017, At: 01:10 Critical Reviews in Food Science and Nutrition, 44:453–464 (2004) Copyright C Taylor and Francis Inc. ISSN: 1040-8398 DOI: 10.1080/10408690490886683 Bioavailability of Phenolic Compounds SIBEL KARAKAYA Department of Food Engineering, Faculty of Engineering, Ege University, Izmir, Turkey Phenolic compounds in foods originate from one of the main classes of secondary metabolites in plants. They are essential for the growth and reproduction of plants, and are produced as a response for defending injured plants against pathogens. In recent years, there is a growing interest in phenolic compounds and their presumed role in the prevention of various degenerative diseases, such as cancer and cardiovascular diseases. The importance of antioxidant activities of phenolic compounds and their possible usage in processed foods as a natural antioxidant have reached a new high in recent years. The absorption and bioavailability of phenolics in humans are also controversial. Data on these aspects of phenolics are scarce and merely highlight the need for extensive investigations of the handling of phenolics by the gastrointestinal tract and their subsequent absorption and metabolism. In this article, absorption, metabolism, and the bioavailability of phenolic compounds are reviewed. Keywords absorption, bioavailability, flavonoids, phenolic acids, phenolic compounds INTRODUCTION of phenolic compounds extracted from, especially, tea (Vinson et al., 1995a; Cao et al., 1996; Karakaya et al., 2000), fruits The term phenolic compounds refers to the main classes of and vegetables (Vinson et al., 1995b; Wang et al., 1996; Miller secondary metabolites in plants. Several thousand molecules and Rice-Evans, 1997; Prior et al., 1998; Karakaya et al., 2000), have been identified in various plant species. They are closely and red and white wines (Kanner et al., 1994; Vinson and Hontz, related to the sensory and nutritional quality of foods derived 1995; Hurtado et al., 1997; Soleas et al., 1997; Ghiselli et al., from plant sources. Phenolic compounds, at low concentration, 1998; G¨und¨u¸c and El, 2001) have been intensively studied using may act as an antioxidant and protect foods from oxidative de- in vitro methods. The results of these studies showed that pheno- terioration. However, at high concentrations, they or their oxi- lic compounds are powerful antioxidants. However, there is still dation products may interact with proteins, carbohydrates, and a controversy whether in vitro similar effects can be obtained minerals. Phenols are important compounds because of their in vivo, because the lack of knowledge concerning whether phe- contribution to human health and their multiple biological ef- nolic compounds can stay at sufficient time with efficient chem- fects, such as antioxidant activity, antimutagenic and/or anti- ical forms in human body. Phenolic molecule is characteristic of carcinogenic activities, and antiinflammatory action (Grimmer a plant species or even of a particular organ or tissue of that plant. et al., 1992; Xie et al., 1993; Stavric, 1994; Shahidi and Naczk, Therefore, to know all of the phenolic compounds we ingest is 1995; Hollman and Katan, 1997; Ek¸si, 1998; Acar, 1998; Parr impossible. Scalbert and Williamson, (2000) suggested that it and Bolwell, 2000). would be desirable to know the nature of main phenolic com- The results of epidemiologic studies showed the inverse re- pounds consumed. The main classes of phenolic compounds lationship between coronary heart diseases and flavonoid con- according to the nature of their carbon skeleton are mostly sumption (Hertog et al., 1993; Hertog et al., 1995; Knekt et al., phenolic acids, flavonoids and the less common stilbenes and 1996; Rimm et al., 1996). In recent years, the number of stud- lignans. Therefore studies in the field of phenolic compounds ies that are conducted to the determine antioxidant activity of bioavailability are discussed in two parts, phenolic acids and phenolic compounds has increased due to the possible role of flavonoids. reactive oxygen species in the pathogenesis of degenerative dis- eases, such as atherosclerosis, cancer, and chronic inflamma- tion (Halliwell, 1994). In this respect, the antoxidant activities PHENOLIC ACIDS Address correspondence to Sibel Karakaya, Ph.D. Department of Food Engineering, Faculty of Engineering, Ege University, Izmir 35100, Turkey. Hydroxycinnamic acids, such as ferulic, sinapic, caffeic, and E-mail: [email protected] p-coumaric acid, are among the most widely distrubuted in plants 453 454 S. KARAKAYA and grains. They occur in most tissues in a variety of conjugated enriched with ferulic acid at a dose of 5.15 mgkg−1 body weight. forms, but seldom as the free acids. Esters and amides are the However, ferulic acid and conjugated forms were not detected most frequently reported types of conjugates, whereas glyco- in plasmas of the control group. The main forms in plasma were sides rarely occur. These include low molecular weight, water- sulfated metabolites (58% of the total ferulic acid), followed by soluble compounds present in cytasol, lipid-soluble forms asso- free ferulic acid (24%) and glucuronidated metabolites (18%). ciated with waxes at the plant surface, and bound forms esterified The maximum ferulic acid concentration in the urine obtained or etherified to cell wall polymers. The most abundant member 1.5 h after ingestion was 38.8–48% of total ferulic acid. The of dietary hydroxycinnamates are ferulic acid and caffeic acid. recovered ferulic acid was mainly in the conjugated form (84% Ferulic acid is covalently linked to plant cell walls and is es- of total excreted ferulic acid). This result suggested that ferulic pecially abundant in an insoluble form in cereal brans. Caffeic acid rapidly metabolized and excreted after ingestion. The dif- acid is ester linked to quinic acid (chlorogenic acid) and found ference between the proportion of conjugated forms detected in at high levels in coffee (Kroon and Williamson, 1999; Chesson urine (84%) and plasma (76%) was explained by the possible et al., 1999; Faulds and Williamson, 1999). conjugation in kidney. According to the researchers the renal In a study, when rats were fed with 14C-labeled hydroxycinna- pathway could be an efficient way in the metabolism of ferulic mates obtained from cultured spinach cell walls, approximately acid. Rondini et al. (2002) concluded that the correlation be- 25% label was found in body tissues after 2 h. Since no label was tween the decrease of glucuronidated conjugates with time, and found in hindgut within this period, researchers concluded that the increase of sulfoglucuronidated or sulfated forms in bladder hydroxycinnamates were absorbed from the foregut (Chesson urine could be accepted as an indicator of the conjugation in the et al., 1999). An in situ model of intestinal perfusion was used kidney by the action of phase II enzymes, such as sulfatese or to determine the bioavaiability of ferulic acid, which was given to β-glucuronidase. However, in the study of Bourne and Rice Wistar rats. Adam et al. (2002) reported that the directly propor- Evans (1998), the excretion of ferulic acid in humans was found tional absorption of ferulic acid to the perfusion concentration to be slower (7–9 h after ingestion) than those of rats. Cereal suggests that ferulic acid could be absorbed by passive diffu- brans contain significant amounts of the ferulic acid, and of its sion or by facilitated transport that appears not to be saturated, oxidatively coupled products, the diferulic acids are ester-linked even at a luminal concentration of 50 µmol L−1.Itwas found to the cell wall polymers. The analysis of plasma samples of male that absorption of ferulic acid and free cinnamic acid were con- Wistar rats showed that diferulic acids were present in the plas- trolled by the Na+/dependent carrier-mediated transport process mas of rats. Researchers concluded that these results provide the in rat jejunal segments (Wolffram et al., 1995; Chesson et al., first evidence for the absorption of diferulic acids through the 1999). When Wistar rats were fed a diet enriched with ferulic gastrointestinal barrier into the vascular system of mammals. acid (10–50 µmol l−1), 56% of the perfused ferulic acid was In this study, it was shown that human small intestinal mucosal found to be absorbed through the small intestine, and 5–7% cells and nonfecal extracts were able to convert diferulic acids of perfused dose was determined in bile conjugated with glu- to monoesters, and fecal extract was able to hydrolyze diferulic curonic acid or sulfate. The level of ferulic acid in feces was acids to monoesters and free acids. This result was supported the reported to be negligible, regardless of the dose of ferulic acid claim that the colon was the most effective area in the degrada- ingested. The estimated conjugated form of ferulic acid in pe- tion of diferulic acids (Andreasen et al., 2001). Chlorogenic acid ripheral tissues showed that 45–53% of the perfused dose was is formed by the esterification of caffeic acid with quinic acid. available for peripheral tissues. Since there was a proportion be- It is found in a wide range of fruits and vegetables, but partic- tween ferulic acid urinary excretion and ingested dose of ferulic ularly in high concentration in coffee.
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