Accepted Manuscript

Estimated dietary intake and major food sources of polyphenols in the Polish arm of the HAPIEE study

Giuseppe Grosso, Urszula Stepaniak, Roman Topor-Mądry, Krystyna Szafraniec, Andrzej Pająk

PII: S0899-9007(14)00204-4 DOI: 10.1016/j.nut.2014.04.012 Reference: NUT 9290

To appear in: Nutrition

Received Date: 7 February 2014 Revised Date: 8 April 2014 Accepted Date: 8 April 2014

Please cite this article as: Grosso G, Stepaniak U, Topor-Mądry R, Szafraniec K, Pająk A, Estimated dietary intake and major food sources of polyphenols in the Polish arm of the HAPIEE study, Nutrition (2014), doi: 10.1016/j.nut.2014.04.012.

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. ACCEPTED MANUSCRIPT Title: Estimated dietary intake and major food sources of polyphenols in the Polish arm of the HAPIEE study

Running title: Dietary polyphenol intake in Polish adults

Authors: Giuseppe Grosso1,2, Urszula Stepaniak2, Roman Topor-Mądry2, Krystyna Szafraniec2, Andrzej Pająk2

1Department of Clinical and Molecular Biomedicine, Section of Pharmacology and Biochemistry, University of Catania, Catania, Italy, 2Department of Epidemiology and Population Studies, Jagiellonian University Medical College, Krakow, Poland

Corresponding author:

Giuseppe Grosso

Department of Clinical and Molecular Biomedicine

Section of Pharmacology and Biochemistry

University of Catania

V.le A. Doria 6, 95125, Catania, Italy

Phone: +39.095.7384278

Fax: +39.095.7384220 Email: [email protected] MANUSCRIPT Authorship:

Giuseppe Grosso and Urszula Stepaniak equally contributed to the paper. Giuseppe Grosso and Urszula Stepaniak designed the study, performed analysis and drafted the manuscript. Roman Topor-Mądry and Urszula Stepaniak contributed in collecting data. Roman Topor-Mądry and Krystyna Szafraniec provided critical revision for data analysis methods. Andrzej Pająk designed the study and provided critical revision. All authors provided final approval for the manuscript.

Acknowledgments

The study has been funded by the Wellcome Trust (grants 064947/Z/01/Z and 081081/Z/06/Z), US National Institute on Ageing (grant 1R01 AG23522-01) and the MacArthur Foundation Initiative on Social Upheaval and Health (award 71208). Giuseppe Grosso was supported by the International Ph.D. Program in Neuropharmacology,ACCEPTED University Medical School of Catania, Catania, Italy.

Words count: 5574

ACCEPTED MANUSCRIPT Abstract

Objective: to estimate the intake of known individual polyphenols and their major dietary sources in the Polish arm of the HAPIEE study.

Research Methods and Procedures: a total of 10,477 random sample (45–69 y) of urban population of Krakow, Poland, completed a validated 148-item food frequency questionnaire (FFQ). Polyphenol intake was calculated by matching food consumption data with the recently developed Phenol-Explorer database.

Results: the mean intake of polyphenols was 1756.5 ± 695.8 mg/d (median = 1662.5 mg/d). The main polyphenol groups were flavonoids (897 mg/d) and phenolic acids (800 mg/d). A total of 347 polyphenols from 19 polyphenol subclasses were found. The individual compounds with the highest intakes were isomers of chlorogenic acid (i.e., 5-Caffeoylquinic acid and 4-Caffeoylquinic acid) among hydroxycinnamic acids (average intake 150 mg/d), that largely originated from coffee, and compounds belonging to the catechin chemical family [i.e., (+)-Gallocatechin, (-)-Epigallocatechin 3-O-gallate, and (-)-Epicatechin] among flavanols (average intake 50 mg/d), that mostly originated from tea and cocoa products.

Conclusions: the current study provides the most updated data for individual polyphenols intake in the diet of a well-established nutritional cohort. These findings will be useful to assess potential beneficial role on health of specific foods with high polyphenol content and characterize the effects of individual phenolic compounds.

Keywords: polyphenols; intake; general population; MANUSCRIPTfood sources; Polish adults

ACCEPTED ACCEPTED MANUSCRIPT Introduction

Fruits and vegetables consumption has been showed to have a protective effect against cardiovascular disease (CVD) [1-4]. In the last ten years, a rise in interest also on tea, cocoa, coffee and wine consumption has been motivated by their content of polyphenols [5, 6]. These compounds constitute a heterogeneous group of molecules divided into five main classes according to their chemical structure: flavonoids, phenolic acids, stilbenes, lignans and others [7]. The considerable diversity of their structures makes polyphenols different from other antioxidants. Their bioavailability and biological properties vary to a great extent and are affected by their chemical structure [8]. Further, the conjugation reactions with methyl, sulfate or glucuronide groups and the nature and amounts of metabolites formed by the gut microflora, may influence their absorption and their bioavailability [8-11].

Despite the promising evidence on the possible role of polyphenols in disease prevention, data regarding their consumption at the population level is still inadequate to suggest optimal intake levels and dietary recommendations [12]. Some recent European investigations pointed out on the importance of using a similar methodology in order to allow comparisons and reduce the variability of estimated dietary intake of compounds among studies [13, 14]. The most recently used tool was the Phenol-Explorer database (www.phenol-explorer.eu), a comprehensive database containing food-composition data on a total of 502 polyphenols in 452 foods [15]. A reasonable comparison of the polyphenols intake is possible due to the similar methodology reported in both the French SU.VI.MAX and the Spanish PREDIMED cohorts [13, 14]. However, despite the emerging interest on polyphenol consumption among population, information about the Central and Eastern European countries is poor. A Polish study assessed the total polyphenol intake of the population investigated [16] but the analysis did not included information regardingMANUSCRIPT specific polyphenol classes and individual polyphenols. The aim of this study was (i) to estimate the dietary polyphenol intake in a well-established nutritional cohort, (ii) to describe the intake of individual polyphenols, and (iii) to document the contribution of specific foods to total and individual polyphenol intake.

Materials and Methods

Study population

Study sample constituted of participants of the Polish arm of the Health, Alcohol and Psychosocial factors In Eastern Europe (HAPIEE) study, which is a prospective cohort study aimed to investigate the determinants of CVDs and other chronic conditions in Central and Eastern Europe. The study protocol with the rationale, design, and methods have been described in detail elsewhere [17]. Briefly, 10,728 subjects (aged 45–69 y) were randomly selected in Krakow at the baseline survey conducted in 2002–2005 (response ratio of 59%). The participants provided written informed consent and the studyACCEPTED protocol was approved by the ethics committee at University College London, UK and by the bioethics committee of the Jagiellonian University (no. KE/99/03/B/284 2).

Data regarding demographic (i.e., age, gender, educational and occupational level) and lifestyle characteristics (i.e., physical activity, smoking and drinking habits) were collected. Educational level was categorized as (i) low (primary/secondary), (ii) medium (high school), and (ii) high (university). Occupational level was categorized as (i) low (unskilled/unemployed workers), (ii) medium (partially skilled workers), and (iii) high (skilled workers). Physical activity level was categorized as daily (i) low active [expended energy <16.7kJ (<4 kcal)/min], (ii) moderately active ACCEPTED MANUSCRIPT [expended energy 16.7–29.3 kJ (4–7 kcal)/min], and (iii) highly active [expended energy >29.3 kJ (7 kcal)/min]. Smoking status was categorized as (i) non-smoker and (ii) current smoker. Alcohol consumption was categorized as (i) none or moderate drinker (<12 g/d) and (ii) alcohol drinker (>12 g/d).

Dietary assessment

Dietary data were collected by using a food frequency questionnaire (FFQ) based on the tool developed by Willett et al. [18] and subsequently adapted in the Whitehall II Study [19]. The FFQs consisted of 148 food and drink items representative of the diet during the preceding 3 months. A country-specific instruction manual that included photographs to facilitate the estimation of portion sizes was used. Participants were asked how often, on average, they had consumed that amount of the item during the last three months, with nine responses ranging from "never or less than once per month" to "six or more times per day". Moreover, participants were asked to include additional foods and frequency of consumption by manual entry. We excluded 251 questionnaires with extreme energy intakes (<500/>4000 kcal/d for females and <800/>5000 kcal/d for males).

Estimation of polyphenol intake

Data on the polyphenol content in foods were obtained from the Phenol-Explorer database (www.phenol-explorer.eu) [15]. All foods that contained no polyphenols were excluded from the FFQ. The items of the FFQ containing more food components were separated according to their ingredients and weight loss or gain during cooking was corrected using yield factors [20]. Several products that contained refined wheat flour were included in the list of foods (i.e., pizza, biscuits) and polyphenol content in these foods was estimated from their wheat-flour contents. The average food consumption was calculated (in g or ml) by followingMANUSCRIPT the standard portion sizes used in the study and then converted in 24-hour intake. Finally, an advanced search was carried out in the Phenol-Explorer database to retrieve mean content values for all polyphenols contained in the foods obtained and individual polyphenol intake from each food was calculated by multiplying the content of each polyphenol by the daily consumption of each food. Accordingly, the database also allows calculating the aglycones. Total polyphenol intake was calculated as the sum of all individual polyphenol intakes from all food sources encountered according to this process. As described in previous studies with similar methodology [13, 14], the polyphenol content of foods included in the FFQ that could correspond to several entries in the Phenol-Explorer database (i.e., “wine”, “fruit juice”, “nuts”, and “seeds” could have corresponded to a number of foods in Phenol- Explorer database) was weighted according to their consumptions in the Polish population.

Statistical analysis

Data are presented ACCEPTEDas medians, means and standard deviations for continuous variables and frequencies and percentages for categorical variables. Total polyphenols in the Polish HAPIEE cohort were determined for the whole study sample as well as according to the socio-demographic and lifestyle characteristics. Polyphenol intake distribution was controlled by Kolmogorov-Smirnov test and it roughly followed a normal distribution, partially asymmetric due to extreme values in the upper side. Thus, we also reported median values to compare differences in intakes between groups by using Mann-Whitney U-test and Kruskall-Wallis test, as appropriate. Since polyphenols may be associated with total energy intake either because they contribute directly to energy intake or because individuals who consume more total energy also eat, on average, more of all specific ACCEPTED MANUSCRIPT nutrients, polyphenol intake was also calculated in energy-adjusted terms (mg of nutrient per 1000 kcal/d of total energy consumed).

Mean intakes of all individual polyphenols, polyphenol groups (phenolic acids, anthocyanidins, flavones, flavonols, flavanones, proanthocyanidins, ellagitannins, isoflavonoids, and lignans) and major food contributors were determined. All reported P values were based on two-sided tests and compared to a significance level of 5%. SPSS 17 (SPSS Inc., Chicago, IL, USA) software was used for all the statistical calculations.

Results

Total polyphenols intake

A total of 10,477 subjects were available for the final analyses. Among 148 food items considered in the HAPIEE questionnaire, 80 contained relevant polyphenols according to the Phenol-Explorer database. A total of 347 polyphenols from 19 polyphenol subclasses were found in these foods. The mean intake of polyphenols was 1756.5 ± 695.8 mg/d (median = 1662.5 mg/d). These intake values included intakes of sugars and polyols linked to aglycones, thus the total intake of aglycones was determined, resulting in 1192.3 ± 412 mg/d (median = 912 mg/d). Nutrient density by energy intake was also calculated, with a mean intake of 854.3 ± 331.3 mg/d per 1000 kcal (Table 1).

Polyphenol intake is presented according to demographic characteristics (Table 1). Intakes were slightly higher in men than in women (1771.2 ± 729.5 compared with 1742.3 ± 661.5 mg/d, respectively; P = 0.034), but when the energy-adjusted amount was calculated, women had a higher intake of polyphenols than men. Age, within the limited range tested, had significant influence on total and energy-adjusted polyphenols intakes, being MANUSCRIPThigher among younger subjects. Subjects with a university education level showed higher total and energy-adjusted polyphenols intake than subjects with lower educational categories whereas different groups of occupational level had significant different polyphenols intake only by energy intake. Increased means and medians of polyphenols intake were also found among higher physical activity groups, smokers, and alcohol non-drinker, but when comparing energy-adjusted polyphenol intake, alcohol drinkers had higher intakes (860.4 ± 332.6 vs. 736.6 ± 277.9 mg/d per 1000 kcal, P <0.001).

Groups of polyphenols intake and main food contributors

The main polyphenol groups were flavonoids (897 mg/d, 572 mg/d as aglycone equivalents, 52% of total intake of polyphenols), phenolic acids (800 mg/d, 521 mg/d as aglycone equivalents, 46% of total intake of polyphenols), whereas alkylphenols (1.5%) and other polyphenols, such as lignans, stilbenes, and tyrosols accounted for lower proportions (1%) (Table 2). The mean daily intakes of flavanols (637 mg/d)ACCEPTED in the flavonoids and hydroxycinnamic acids (705 mg/d) in the phenolic acids were high compared with others groups. Comparable mean intakes were found for flavonols, flavanones, and hydroxybenzoic acids (an average of 100 mg/d), whereas intake of anthocyanins, flavones, and dihydrocalcones was lower. When expressed as aglycone equivalents, the relative contribution of flavanols (412 mg/d) increased from about 30% to 35% and that of hydroxycinnamic acids (401 mg/d) was reduced from about 40% to 35%, whereas the relative contributions of the other polyphenol subclasses remained similar. ACCEPTED MANUSCRIPT The main dietary sources for the total polyphenols were coffee, tea, and chocolate, whereas fruits and vegetables accounted to a lower percentage of the total amount of polyphenols in the diet of our cohort (Table 2). Within each food group, the main beverages contributors were identified as coffee and tea for nonalcoholic and wine and beer for alcoholic beverages. For other food groups, chocolate and vegetable oils were the second most important contributors of total polyphenols intake. Among fruit, polyphenols were mostly coming from apples, oranges, and several berry-fruit, whereas among vegetables, spinach and potatoes were the main contributors.

Coffee was the primary food item contributing to phenolic acid intake (66%) and also to the total intake of polyphenols (40%). Tea was identified as the most important source, especially for flavanols and flavonols, contributing almost 300 mg of daily flavonoid intake. Other important contributors to the intake of flavonols, flavanones, and flavones were fruits (especially apple and orange juices); flour products were the major source for flavones; black currant for anthocyanidins; apples for dihydrochalcones; and soy meat for isoflavones. Major contributors for intake of phenolic acids were coffee (75% of hydroxycinnamic acids), tea (89% of hydroxybenzoic acids), and vegetable oils (8% of hydroxycinnamic acids). Among other minor contributors, apples and raspberries contributed to 2-3% of total phenolic acids. Lignans were derived from seeds, tea, and bread, whereas stilbenes, tyrosols, hydroxycoumarins, and hydroxybenzaldehydes came mostly from alcoholic beverages (especially wine and beer).

Intake of individual polyphenols

The intake of all individual polyphenols consumed in the Polish HAPIEE cohort was determined (see supplemental data in the online issue). A total of 108 compounds out of the 347 consumed polyphenols had mean intake values higher than 1 mg/d.MANUSCRIPT The numbers of more commonly consumed polyphenols are shown in Table 3. The 25 first compounds in the list were all consumed in amounts greater than 20 mg/d and all together accounted for 74% of the total polyphenol intake. As expected, most of them were phenolic acids and flavonoids, mostly among the hydroxycinnamic acids (7 compounds) and flavanols (14 compounds) classes. The individual compounds with the highest intakes were isomers of chlorogenic acid (i.e., 5-Caffeoylquinic acid and 4-Caffeoylquinic acid) among hydroxycinnamic acids (average intake 150 mg/d), that largely originated from coffee, and compounds belonging to the catechin chemical family [i.e., (+)-Gallocatechin, (-)- Epigallocatechin 3-O-gallate, and (-)-Epicatechin] among flavanols (average intake 50 mg/d) that mostly originated from tea and cocoa products (Table 3). The remaining compounds among these 25 polyphenols were two antocyanins (namely Hesperidin and Hesperetin) uniquely coming from citrus fruits (and juices).

Discussion

This study is the firstACCEPTED to report a detailed description of the classes and individual polyphenols intake in a large nutritional cohort in Poland, and the largest among those studied. The mean polyphenols intake of this study (1756.5 mg/d, 1092.3 mg/d as aglycones) was higher than in the previous reports for the Polish population (1172 ± 354 mg/d for men and 1031 ± 320 mg/d for women) [16], as well as than in other studies reported in the French (1193 ± 510 mg/d) [13], Spanish (820 ± 323 mg/d) [14] and Finnish (863 ± 415 mg/d) [21] populations. The flavonoids intake (897 mg/d) was higher than those reported for US [22], Denmark [23], Finland [24, 25], the Netherlands [26], Japan [27] and similar to that reported for tea consumers in the US population ACCEPTED MANUSCRIPT [28]. Smaller differences regarded the intakes of phenolic acids (800 mg/d), compared with those reported in the France [13], Spanish [14] and Finnish populations [21]. Flavanols (proanthocyanidins) were the second most abundant flavonoid consumed in all cohorts, whereas other polyphenol classes were less consumed, accounting for about 1 mg/d per person, due to their low contents in foods (lignans and stilbenes) or to the low consumption of their main dietary sources (isoflavones).

The aforementioned differences in polyphenol intakes may depend on country-specific food preferences and, consequently, on preferences for their main dietary sources. Indeed, the main food contributors to polyphenol intakes were mostly represented by non-alcoholic beverages (such as tea and coffee) that accounted all together for 67% of the total polyphenol intake (about 1000 mg/d), followed by chocolate, apples, and vegetable oils (which accounted for 9%, 6%, and 3%, respectively, of the total polyphenol intake). Specifically, coffee was the main food source of hydroxycinnamic acids, thus enhancing the total phenolic acid intake, whereas tea was the main dietary source of flavonoids. Compared with other cohorts studied, the Polish HAPPIEE cohort accounted a higher intake of coffee and tea. The 83% and 97% of the Polish cohort were consumers of coffee and tea (namely at least one cup/d), respectively: the mean intake of coffee and tea was 237 ml/d and 525 ml/d, respectively, and the 79% of population consumed >300 ml/d of tea (more than 2 cups per day). Mediterranean populations account for a very low consumption of tea and relatively low also of coffee. The French SU.VI.MAX cohort reported that 40% of females and 64% of male did not consume tea, with an average tea intake of 200 ml/d and only 34% having >300 ml/d [29]. As well, the Spanish PREDIMED cohort reported an average intake of about 50 ml/week (0.4 ± 1.6 cups/week) of tea and nearly one cup per day of coffee (6.5 ± 5.2 cups/week, about 100 ml/d) [30]. Compared with our study, both aforementioned cohorts reported similar or slightly higher contribution to polyphenol intake from fruit and MANUSCRIPT vegetables, and a significant higher intake from alcohol beverages, due to the higher consumption of red wine [29, 30]. Another noteworthy difference between Mediterranean countries’ polyphenol intake and the Polish HAPIEE cohort was the relevant contribution of seeds, vegetable oils, and cocoa products over the total amount of polyphenols (especially hydroxycinnamic acids). The Mediterranean cohorts (i.e., the SU.VI.MAX and the PREDIMED cohorts) reported that seeds and oils contributed to about 12 [13] and 32 mg/d [14] of polyphenols per person, whereas the Polish arm of the HAPIEE study accounted for a total of about 72 mg/d, mostly depending on the vegetable oil consumption. As well, the cocoa products accounted for about 90 mg/d of polyphenols in the French cohort, about 16 mg/d in the Spanish cohort, and 166 mg/d in our HAPIEE Polish cohort. These differences emphasize how the total and specific classes of polyphenols may vary according to country-specific food preferences. Despite non-Mediterranean countries share some common nutritional habits, such as high coffee and tea intake, also the amount reported for the Finnish FINDIET 2002 cohort was much lower than that observed in the PolishACCEPTED cohort, showing a pooled coffee and tea intake of 409 ± 11 ml/d [21] (vs. 762 ml/d accounted in our study). Major contributors to polyphenols intakes in the Finnish diet were tea, apples, and berries, similar to the Polish cohort, despite the average pooled intake of coffee and tea in the latter was nearly twice times higher than the former. No information was given about vegetable oils intake in the Finnish cohort, whereas total mean of cocoa products amounted to 667 mg/100g. Thus, the differences in amounts of coffee, tea, vegetable oils, and seeds between Mediterranean and non-Mediterranean countries may justify the higher total amount of polyphenols consumed in the Polish cohort compared with the others, whereas type of fruits and vegetables may ACCEPTED MANUSCRIPT have influenced not only differences concerning polyphenols related to the aforementioned foods (i.e., flavanols, and hydroxycinnamic acids), but also regarding the other polyphenol classes.

Previous studies reported that polyphenol intake was influenced by gender, with men having higher absolute intakes of total polyphenols [13, 21], and specifically flavonoids [22, 31], than women due to higher consumption of coffee and wine. Despite we also reported a slightly higher intake of polyphenols in men, the energy-adjusted intake revealed a higher energy-density of polyphenols in women, suggesting that polyphenol intake in men is influenced by quantity of food whereas in women by quality (i.e., higher consumption of tea). Significant differences of polyphenol intake were also due to age (higher intakes in younger participants), by education and physical activity. It may be speculated that a high education (especially among younger participants) may mediate healthier lifestyle and eating behaviors, such as increased physical activity and consumption of fruit and vegetables, which are rich in polyphenols. On the contrary, this was not valid for drinking and smoking, both associated with higher intake of energy-adjusted polyphenols intake. It may be explained that alcoholic beverages (especially wine and beer) are contributors of polyphenols, and smokers were more likely to drink coffee, which was as well one of the main contributors of polyphenol intake.

A recent research adopting the methodology of our study reported that polyphenol intake was significantly associated with 46% reduction in risk of CVD when comparing the highest (1235 mg/d) vs. the lowest (483 mg/d) quintile of intake [32]. The polyphenols with the strongest inverse associations were flavanols (263 mg/d), lignans (0.94 mg/d), and hydroxybenzoic acids (36.1 mg/d). Compared with our study, we reported a similar intake of lignans but a general higher intake of both flavonoids and phenolic acids due to the higher consumption of tea and coffee, respectively. This data suggests that a significant part of our sampleMANUSCRIPT may benefit of the daily intake of polyphenols we reported. Further research would clarify whether the high consumption of such drinks and, consequently, increased intake of polyphenols in the Polish population could be translated with a better health or protection against CVD.

Results of this study should be interpreted based on some limitations. First, differences in absolute intakes of polyphenols with the other studies are no doubt due to methodological differences. Despite the source of data regarding polyphenols is the same among studies, the use of a FFQ may overestimate or rather give a more complete estimation of food consumption compared with 24-h recall. However, as discussed above, the authors consider this issue is marginal, since the most of the differences in polyphenols intake depended on coffee and tea consumption (which was actually much higher than in other countries), whereas the contribution of other foods rich in polyphenols (i.e., fruits and vegetables) was quite similar. Second, the FFQ used to collect dietary data referred to a limited amount of items and some foods rich in polyphenols were lacking (i.e., spices) or grouped (i.e., wine)ACCEPTED leading to possible bias in the assessment of the total polyphenols intake. Third, due to the nature of the instrument, data may have been affected by recall bias and the low response rate (59%) may suggest that information could be representative of subjects with better health status [33].

Conclusions

This study gives a complete description of the total polyphenol intake and main food contributors of dietary polyphenols in a Polish urban population. Together with the protective effects of vegetables ACCEPTED MANUSCRIPT and fruits against chronic diseases, the effects on health of other polyphenol-rich foods, such as tea, coffee, and cocoa products should be further investigated.

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MANUSCRIPT

ACCEPTED ACCEPTED MANUSCRIPT Table 1. Total and energy-adjusted polyphenol intake according to demographic characteristics and distribution of Polish participants of the HAPIEE study (n = 10,477).

Polyphenol intake Energy-adjusted1 polyphenol

intake N (%) Median Mean ± SD P2 Median Mean ± SD P2 Total population 10477 1662·5 1740·7 ± 630·2 801·1 854·3 ± 331·3 Gender 0·034 <0·001 Male 5137 1665·7 1755·4 ± 729·5 781·9 840·1 ± 317·9 Female 5340 1659·1 1726·5 ± 661·5 817·1 869·6 ± 343·3 Age class <0·001 <0·001 <50 1933 1745·9 1817·1 ± 710·5 835·9 884·8 ± 353·3 50-54 2161 1688·1 1763·5 ± 671·4 797·9 850·7 ± 313·7 55-59 2194 1675·4 1758·7 ± 740·0 801·3 862·6 ± 367·4 60-64 2084 1616·4 1693·3 ± 689·0 783·9 840·2 ± 315·5 ≥65 2105 1606·7 1675·4 ± 656·5 789·7 839·9 ± 301·9 Educational level <0·001 <0·001 Low 1210 1618·6 1688·1 ± 652·9 773·1 825·5 ± 309·2 Medium 6269 1659·1 1729·5 ± 680·3 793·3 844·8 ± 326·4 High 2987 1694·6 1787·1 ± 741·5 828·6 888·7 ± 347·7 Occupational level 0·049 <0·001 Low 5550 1653·6 1727·8 ± 695·6 MANUSCRIPT 785·5 839·3 ± 317·8 Medium 3499 1686·1 1764·7 ± 707·0 823·7 879·1 ± 354·7 High 1126 1663·5 1744·1 ± 671·6 802·4 858·0 ± 317·8 Physical activity <0·001 0·041 Low 2944 1629·1 1710·3 ± 685·7 790·4 849·9 ± 336·6 Medium 3585 1660·4 1738·0 ± 690·8 812·8 866·9 ± 333·2 High 3365 1699·7 1776·8 ± 710·0 798·9 847·1 ± 324·6 Smoking status <0·001 0·033 Yes 3194 1697·6 1782·1 ± 709·5 809·3 866·2 ± 328·5 Not 6700 1649·5 1724·3 ± 689·3 832·7 849·9 ± 332·7 Alcohol driking 0·017 <0·001 Yes 9477 1661·0 1739·0 ± 694·7 805·1 860·4 ± 332·6 Not ACCEPTED417 1780·9 1832·8 ± 727·6 701·9 736·6 ± 277·9 1 per 1000 kcal 2 evaluated by Mann-Whitney U-test or Kruskall-Wallis test

ACCEPTED MANUSCRIPT

Table 2. Total, classes and subclasses of polyphenol intake according to food groups sources and main food contribution.

Food group Non- Main food contributors (% contribution Total Alcoholic Seeds and alcoholic Fruits Vegetables Cereals Others to polyphenol class) foods beverages oils Polyphenol class beverages mg/d per person (mean ± SD) Total polyphenolsa 1740·7 ± 1150·2 ± 38·9 ± 167·8 ± Coffee (40) Tea (27) Chocolate 9 ± 10·3 213·9 ± 88·8 ± 53·2 72 ± 65·1 630·2 501·3 29·8 112·3 (8) Flavonoidsb 897·6 ± 500·6 ± 164·6 ± 13·5 ± 165·5 ± Tea (48) Chocolate Apples (8) 6·4 ± 11·3 46·9 ± 47·3 7·9 ± 8·2 423·4 131·3 106·5 44·7 294·9 (18) Flavanols 637·3 ± 69·6 ± 13·5 ± 161·7 ± Tea (60) Chocolate Apples (7) 388·8 ± 91·3 2·4 ± 12·5 1·2 ± 15·5 - 311 17·7 44·7 290·5 (25) Flavonols 106·1 ± 15·2 ± Tea (47) Onion Spinach 51·1 ± 21·5 0·2 ± 1·5 37·2 ± 33·5 - <0·01 2·36 ± 4·2 89·2 40·8 (13) (13) Flavanones 103·8 ± 45·8 ± Orange Squash Oranges 54·7 ± 64·9 2·9 ± 9 0·3 ± 0·5 MANUSCRIPT - <0·01 - 70·4 58·2 juice (29) (24) (23) Flavones Flour (51) Orange Squash 15·5 ± 11 5·2 ± 6·1 <0·1 0·7 ± 0·6 1·62 ± 1·81 7·93± 8·23 <0·01 - juice (23) (10) Anthocyanins 29·7 ± 22·7 ± Black Beans (19) Strawberri <0·1 0·6 ± 3·5 6·4 ± 5·4 - - - 93·3 92·4 currant (21) es (16) 11·3 ± Apple Dihydrochalcones 0·8 ± 1·1 - 10·6 ± 9·5 - - - - Apples (93) 10·7 juice (7) Isoflavonoids Soy meat Beans (12) Soy milk 1·6 ± 0·2 - <0·1 - 0·2 ± 0·2 - - 1·4 ± 8·4 (85) (3) Phenolic acidsc 800·2 ± 641·8 ± 58·15 ± Coffee (66) Tea (12) Vegetable 2·1 ± 7·4ACCEPTED 49·2 ± 6 41·8 ± 23·9 4·78 ± 4·9 2·2 ± 4·1 345·8 403·6 76·5 oils (7) Hydroxybenzoic acids 94·6 ± Tea (89) Apples (3) Raspberri 85·4 ± 42·3 1 ± 3·6 6·8 ± 24·3 1·3 ± 2·6 0·10 ± 0·2 0·1 ± 1·7 - 72·9 es (2) ACCEPTED MANUSCRIPT

Hydroxycinnamic acids 705·5 ± 556·4 ± 58·1 ± 2·27 ± Coffee (75) Vegetable Apples (5) 1·1 ± 3·6 42·5 ± 5 40·4 ± 21·8 4·7 ± 1·7 419·4 307·2 76·5 4·07 oil (8) Alkylphenols 26·1 ± 26·1 ± Cereals (51) Dark Pasta (3) ------32·1 32·1 bread (45) Alkylmethoxyphenols 3·7 ± 3·1 3·6 ± 3·1 - - - - <0·01 - Coffee (98) Beer (2) Lignans Seeds (51) Tea (27) Dark 0·6 ± 11·9 0·17 ± 0·1 <0·1 <0·1 <0·1 0·1 ± 0·1 0·3 ± 11·8 <0·01 bread (8) Stilbenes Red wine Strawberri White 0·2 ± 0·6 - 0·1 ± 0·6 <0·1 <0·01 - - <0·01 (56) es (14) wine (12) Tyrosols Beer (33) Red wine Olives (20) 0·4 ± 3·3 - 0·3 ± 1·2 - 0·1 ± 3·2 - <0·01 - (26) a do not include hydroxybenzoketones, hydroxyphenilpropenes, methoxyphenols, naphtoquinones, furanocoumarins, hydroxycinnamaldehydes, hydroxycoumarins, and hydroxybenzaldehydes in traces b do not include dihydroflavonols and chalcones in traces c do not include hydroxyphenylpropanoic acids and hydroxyphenylacetic acid in traces MANUSCRIPT

ACCEPTED ACCEPTED MANUSCRIPT Table 3. Intake of most-consumed individual polyphenols and their main food sources

Polyphenol Main food contributors (% contribution to polyphenol Polyphenol subclass intake, mg/day class) Polyphenol (mean ± SD)

5-Caffeoylquinic acid Hydroxycinnamic acids 224·6 ± 112·7 Coffee (73) Apples (11) Potatoes (9)

4-Caffeoylquinic acid Hydroxycinnamic acids 149·1 ± 124·8 Coffee (94) Tea (4) Apples (1) 3-Caffeoylquinic acid Hydroxycinnamic acids 128·2 ± 111·6 Coffee (96) Plums (2) Tea (1)

(+)-Gallocatechin Flavanols 73·6 ± 64·8 Tea (100)

5-O-Galloylquinic acid Hydroxybenzoic acids 60·8 ± 45·4 Tea (100) Polymers (>10 mers) Flavanols 58·3 ± 43·8 Chocolate (68) Nuts (15) Strawberries (8) (-)-Epigallocatechin 3- O-gallate Flavanols 48·1 ± 39·5 Tea (100)

Procyanidin dimer B2 Flavanols 46·3 ± 34·7 Apples (61) Tea (28) Chocolate (7) (-)-Epicatechin Flavanols 45·9 ± 34·2 Tea (45) Apples (35) Chocolate (14)

Ferulic acid Hydroxycinnamic acids 43·9 ± 33·7 Coffee (68) Flour (7) Beans (6)

04-06 mers Flavanols 43·4 ± 31·4 Chocolate (85) Nuts (4) Strawberries (4) (-)-Epicatechin 3-O-

gallate Flavanols 38·6 ± 22 Tea (100) (-)-Epigallocatechin Flavanols 38·0 ± 21·2 Tea (100)

Hesperidin Anthocyanins 37·5 ± 21·4 Squash (56) Orange juice (44) Stigmastanol ferulate Hydroxycinnamic acids 37·5 ± 22·6 MANUSCRIPT Vegetable oils (100) Hesperetin Anthocyanins 28·1 ± 12·3 Oranges (63) Orange juice (20) Lemons (15)

5-Feruloylquinic acid Hydroxycinnamic acids 27·9 ± 14·3 Coffee (99) Carrots (1) 03 mers Flavanols 27·4 ± 12·2 Chocolate (93) Plums (2) Strawberries (2)

02 mers Flavanols 26·7 ± 12·3 Chocolate (90) Beans (3) Plums (2)

Gallic acid Hydroxybenzoic acids 25·0 ± 11·2 Tea (97) Bananas (1) Cauliflowers (1) (+)-Catechin 3-O-

gallate Flavanols 24·9 ± 12·3 Tea (100) Theaflavin 3'-O-gallate Flavanols 21·4 ± 12·8 Tea (100)

07-10 mers Flavanols 20·5 ± 14·5 Chocolate (75) Nuts (10) Strawberries (7) 4-Feruloylquinic acid Hydroxycinnamic acids 20·4 ± 12 Coffee (100) Procyanidin dimer B1 ACCEPTED Flavanols 20·0 ± 12 Tea (97) Plums (1) Apple juice (1)

ACCEPTED MANUSCRIPT broccoli potatoes Protocatechuic acid 0 0 Gallic acid 0 0 Vanillic acid 0 0 Ellagic acid 0 0 Valoneic acid dilactone 0 0 Gentisic acid 0 0 Syringic acid 0 0 2-Hydroxybenzoic acid 0 0 3-Hydroxybenzoic acid 0 0 2,3-Dihydroxybenzoic acid 0 0 3,5-Dihydroxybenzoic acid 0 0 2,6-Dihydroxybenzoic acid 0 0 Gallic acid 3-O-gallate 0 0 Gallic acid 4-O-glucoside 0 0 4-Hydroxybenzoic acid 0 0 5-O-Galloylquinic acid 0 0 4-Hydroxybenzoic acid 4-O-glucoside 0 0 Protocatechuic acid 4-O-glucoside 0 0 Ellagic acid glucoside 0 0 Ellagic acid arabinoside 0 0 Ellagic acid acetyl-xyloside 0 0 Ellagic acid acetyl-arabinoside 0 0 Lambertianin C 0 0 Sanguiin H-6 0 0 Galloyl glucose 0 0 Hydroxybenzoic acids MANUSCRIPT0 0 5-p-Coumaroylquinic acid 0 0 4-p-Coumaroylquinic acid 0 0 3-p-Coumaroylquinic acid 0 0 3-Caffeoylquinic acid 0.79706 0 4-Caffeoylquinic acid 0 0 5-Caffeoylquinic acid 0.2417 20.54174 1,2-Disinapoylgentiobiose 0.17245 0 1-Sinapoyl-2-feruloylgentiobiose 0.17924 0 1,2-Diferuloylgentiobiose 0.35983 0 1,2,2'-Trisinapoylgentiobiose 0.18738 0 1,2'-Disinapoyl-2-feruloylgentiobiose 0.2417 0 1-Sinapoyl-2,2'-diferuloylgentiobiose 0.1643 0 1,2,2'-Triferuloylgentiobiose 0.03666 0 5-Feruloylquinic acid ACCEPTED 0 0 4-Feruloylquinic acid 0 0 3-Feruloylquinic acid 0 0 3,5-Dicaffeoylquinic acid 0 0 3,4-Dicaffeoylquinic acid 0 0 3,4-Diferuloylquinic acid 0 0 3,5-Diferuloylquinic acid 0 0 Caffeoyl tartaric acid 0 0 Feruloyl glucose 0 0 Caffeoyl glucose 0 0 Feruloyl tartaric acid ACCEPTED MANUSCRIPT 0 0 Chicoric acid 0 0 p-Coumaric acid 0 0 p-Coumaroyl glucose 0 0 Caffeic acid 0 1.244954 Ferulic acid 0 0 Sinapic acid 0 0 Cinnamic acid 0 0 o-Coumaric acid 0 0 m-Coumaric acid 0 0 Hydroxycaffeic acid 0 0 Verbascoside 0 0 2,5-di-S-Glutathionyl caftaric acid 0 0 p-Coumaroyl malic acid 0 0 p-Coumaroyl glycolic acid 0 0 p-Coumaroyl tartaric acid 0 0 2-S-Glutathionyl caftaric acid 0 0 p-Coumaric acid 4-O-glucoside 0 0 p-Coumaroylquinic acid 0 0 24-Methylcholestanol ferulate 0 0 24-Methylcholesterol ferulate 0 0 24-Methyllathosterol ferulate 0 0 Stigmastanol ferulate 0 0 Sitosterol ferulate 0 0 Schottenol ferulate 0 0 24-Methylenecholestanol ferulate 0 0 Caffeic acid 4-O-glucoside MANUSCRIPT0 0 Ferulic acid 4-O-glucoside 0 0 Hydroxycinnamic acids 2.38031 21.78669 3,4-Dihydroxyphenylacetic acid 0 0 4-Hydroxyphenylacetic acid 0 0 Homovanillic acid 0 0 Hydroxyphenylacetic acids 0 0 Dihydro-p-coumaric acid 0 0 Dihydrocaffeic acid 0 0 Hydroxyphenylpropanoic acids 0 0 PHENOLIC ACIDS 2.38031 21.78669 Luteolin 0 0 Luteolin 7-O-glucuronide 0 0 Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside 0 0 Apigenin ACCEPTED 0 0.001537 Apigenin 7-O-glucoside 0 0 Apigenin 7-O-apiosyl-glucoside 0 0 Sinensetin 0 0 Nobiletin 0 0 Tangeretin 0 0 Tetramethylscutellarein 0 0 Apigenin arabinoside-glucoside 0 0 Apigenin galactoside-arabinoside 0 0 Apigenin 6-C-glucoside 0 0 Apigenin 6,8-di-C-glucoside ACCEPTED MANUSCRIPT 0 0 Flavones 0 0.001537 (+)-Catechin 0 0 (-)-Epicatechin 0 0 (+)-Gallocatechin 0 0 (-)-Epigallocatechin 0 0 (-)-Epicatechin 3-O-gallate 0 0 (-)-Epigallocatechin 3-O-gallate 0 0 (+)-Catechin 3-O-gallate 0 0 (+)-Gallocatechin 3-O-gallate 0 0 Procyanidin dimer B1 0 0 Procyanidin dimer B2 0 0 Procyanidin dimer B3 0 0 Procyanidin dimer B4 0 0 Procyanidin dimer B5 0 0 Procyanidin dimer B7 0 0 Prodelphinidin dimer B3 0 0 Procyanidin trimer C1 0 0 Procyanidin trimer C2 0 0 Procyanidin trimer EEC 0 0 Theaflavin 0 0 Theaflavin 3-O-gallate 0 0 Theaflavin 3'-O-gallate 0 0 Theaflavin 3,3'-O-digallate 0 0 Prodelphinidin trimer GC-GC-C 0 0 Prodelphinidin trimer GC-C-C 0 0 Prodelphinidin trimer C-GC-C MANUSCRIPT0 0 Procyanidin trimer T2 0 0 02 mers 0 0 Polymers (>10 mers) 0 0 03 mers 0 0 04-06 mers 0 0 07-10 mers 0 0 (-)-Epicatechin-(2a-7)(4a-8)-epicatechin 3-O-galactoside 0 0 Cinnamtannin A2 0 0 (+)-Catechin 3-O-glucose 0 0 Flavanols 0 0 Quercetin 3,4'-O-diglucoside 0 0 Isorhamnetin 0 0 Quercetin 7,4'-O-diglucoside 0 0 Quercetin 4'-O-glucosideACCEPTED 0 0 Isorhamnetin 3-O-glucoside 0 0 Isorhamnetin 4'-O-glucoside 0 0 Quercetin 3-O-arabinoside 0 0 Quercetin 3-O-sophoroside 0.8826 0 Quercetin 3-O-galactoside 0 0 Quercetin 3-O-glucoside 0.24441 0 Quercetin 3-O-rhamnoside 0 0 Quercetin 3-O-rutinoside 0 0 Quercetin 3-O-xyloside 0 0 Quercetin 3-O-glucuronide ACCEPTED MANUSCRIPT 0 0 Quercetin 3-O-xylosyl-glucuronide 0 0 Quercetin 3-O-(6"-malonyl-glucoside) 0 0 Quercetin 3-O-(6"-malonyl-glucoside) 7-O-glucoside 0 0 Quercetin 3-O-glucosyl-rhamnosyl-galactoside 0 0 Quercetin 3-O-glucosyl-rhamnosyl-glucoside 0 0 Quercetin 3-O-rhamnosyl-galactoside 0 0 Patuletin 3-O-glucosyl-(1->6)-[apiosyl(1->2)]-glucoside 0 0 Spinacetin 3-O-glucosyl-(1->6)-[apiosyl(1->2)]-glucoside 0 0 Patuletin 3-O-(2''-feruloylglucosyl)(1->6)-[apiosyl(1->2)]-glucoside 0 0 Spinacetin 3-O-(2"-p-coumaroylglucosyl)(1->6)-[apiosyl(1->2)]-glucoside 0 0 Spinacetin 3-O-(2"-feruloylglucosyl)(1->6)-[apiosyl(1->2)]-glucoside 0 0 Spinacetin 3-O-glucosyl-(1->6)-glucoside 0 0 Jaceidin 4'-O-glucuronide 0 0 5,3',4'-Trihydroxy-3-methoxy-6:7-methylenedioxyflavone 4'-O-glucuronide 0 0 5,4'-Dihydroxy-3,3'-dimethoxy-6:7-methylenedioxyflavone 4'-O-glucuronide 0 0 3,7-Dimethylquercetin 0 0 Kaempferol 3-O-glucuronide 0 0 Kaempferol 3-O-glucoside 0.1901 0 Kaempferol 3-O-galactoside 0 0 Kaempferol 3-O-rutinoside 0 0 Kaempferol 3-O-glucosyl-rhamnosyl-galactoside 0 0 Kaempferol 3-O-glucosyl-rhamnosyl-glucoside 0 0 Kaempferol 3-O-sophoroside 2.25403 0 Kaempferol 3,7-O-diglucoside 0.20368 0 Kaempferol 3-O-acetyl-glucoside 0 0 Kaempferol MANUSCRIPT0.76718 0.038424 Quercetin 0.57708 0.003842 Myricetin 0 0.000768 Myricetin 3-O-glucoside 0 0 Myricetin 3-O-rutinoside 0 0 3-Methoxysinensetin 0 0 3-Methoxynobiletin 0 0 Morin 0 0 Flavonols 5.11908 0.043035 Cyanidin 3-O-galactoside 0 0 Cyanidin 3-O-arabinoside 0 0 Cyanidin 3-O-xyloside 0 0 Cyanidin 3-O-glucoside 0 0 Cyanidin 3-O-rutinoside 0 0 Cyanidin 3-O-sophorosideACCEPTED 0 0 Cyanidin 3-O-sambubioside 0 0 Malvidin 3-O-(6''-p-coumaroyl-glucoside) 0 0 Cyanidin 3-O-glucosyl-rutinoside 0 0 Delphinidin 3-O-sambubioside 0 0 Cyanidin 3-O-xylosyl-rutinoside 0 0 Pelargonidin 3-O-glucoside 0 0 Pelargonidin 3-O-rutinoside 0 0 Peonidin 0 0 Pelargonidin 0 0 Cyanidin ACCEPTED MANUSCRIPT 0 0 Peonidin 3-O-glucoside 0 0 Peonidin 3-O-rutinoside 0 0 Delphinidin 3-O-glucoside 0 0 Delphinidin 3-O-rutinoside 0 0 Petunidin 3-O-glucoside 0 0 Petunidin 3-O-rutinoside 0 0 Malvidin 3-O-glucoside 0 0 Cyanidin 3,5-O-diglucoside 0 0 Pelargonidin 3,5-O-diglucoside 0 0 Delphinidin 3-O-feruloyl-glucoside 0 0 Cyanidin 3-O-(6''-malonyl-glucoside) 0 0 Delphinidin 3-O-glucosyl-glucoside 0 0 Cyanidin 3-O-(6''-malonyl-3''-glucosyl-glucoside) 0 0 Delphinidin 3-O-(6''-acetyl-glucoside) 0 0 Cyanidin 3-O-(6''-acetyl-glucoside) 0 0 Petunidin 3-O-(6''-acetyl-glucoside) 0 0 Malvidin 3-O-(6''-acetyl-glucoside) 0 0 Peonidin 3-O-(6''-acetyl-glucoside) 0 0 Peonidin 3-O-(6''-p-coumaroyl-glucoside) 0 0 Petunidin 3-O-(6''-p-coumaroyl-glucoside) 0 0 Cyanidin 3-O-(6''-p-coumaroyl-glucoside) 0 0 Vitisin A 0 0 Delphinidin 3-O-(6''-p-coumaroyl-glucoside) 0 0 Pigment A 0 0 Pinotin A 0 0 Malvidin 3-O-(6''-caffeoyl-glucoside) MANUSCRIPT0 0 Cyanidin 3-O-(6''-succinyl-glucoside) 0 0 Pelargonidin 3-O-(6''-succinyl-glucoside) 0 0 Pelargonidin 3-O-arabinoside 0 0 Pelargonidin 3-O-(6''-malonyl-glucoside) 0 0 Pelargonidin 3-O-sophoroside 0 0 Pelargonidin 3-O-glucosyl-rutinoside 0 0 Anthocyanins 0 0 Daidzein 0 0 Glycitin 0 0 6''-O-Malonylgenistin 0 0 Daidzin 0 0 Genistin 0 0 6''-O-Acetylgenistin 0 0 Glycitein ACCEPTED 0 0 6''-O-Acetyldaidzin 0 0 6''-O-Acetylglycitin 0 0 6''-O-Malonyldaidzin 0 0 6''-O-Malonylglycitin 0 0 Formononetin 0 0 Coumestrol 0 0 Biochanin A 0 0 Genistein 0 0 Isoflavonoids 0 0 Naringenin 7-O-glucoside ACCEPTED MANUSCRIPT 0 0 Naringenin 0 0 8-Prenylnaringenin 0 0 6-Prenylnaringenin 0 0 6-Geranylnaringenin 0 0 Hesperidin 0 0 Hesperetin 0 0 Eriodictyol 0 0 Naringin 0 0 Eriocitrin 0 0 Narirutin 0 0 Neohesperidin 0 0 Neoeriocitrin 0 0 Didymin 0 0 Poncirin 0 0 Isoxanthohumol 0 0 Flavanones 0 0 Xanthohumol 0 0 Chalcones 0 0 Phloridzin 0 0 Phloretin 2'-O-xylosyl-glucoside 0 0 3-Hydroxyphloretin 2'-O-glucoside 0 0 Dihydrochalcones 0 0 Dihydroquercetin 3-O-rhamnoside 0 0 Dihydromyricetin 3-O-rhamnoside 0 0 Dihydroflavonols 0 0 FLAVONOIDS MANUSCRIPT5.11908 0.044572 Secoisolariciresinol 0 0 1-Acetoxypinoresinol 0 0 Matairesinol 0 0 Lariciresinol 0 0 Pinoresinol 0 0 Syringaresinol 0 0 Isolariciresinol 0 0 Sesamin 0 0 Sesamolin 0 0 Sesaminol 0 0 Sesamolinol 0 0 Sesamol 0 0 Episesamin 0 0 Episesaminol ACCEPTED 0 0 Isohydroxymatairesinol 0 0 Arctigenin 0 0 7-Hydroxymatairesinol 0 0 Secoisolariciresinol-sesquilignan 0 0 Cyclolariciresinol 0 0 7-Oxomatairesinol 0 0 Todolactol A 0 0 Conidendrin 0 0 7-Hydroxysecoisolariciresinol 0 0 Nortrachelogenin ACCEPTED MANUSCRIPT 0 0 Lariciresinol-sesquilignan 0 0 Dimethylmatairesinol 0 0 Medioresinol 0 0 Lignans 0 0 Piceatannol 0 0 e-Viniferin 0 0 d-Viniferin 0 0 Pallidol 0 0 Piceatannol 3-O-glucoside 0 0 Resveratrol 0 0 Resveratrol 3-O-glucoside 0 0 Stilbenes 0 0 Bergapten 0 0 Psoralen 0 0 Xanthotoxin 0 0 Isopimpinellin 0 0 Furanocoumarins 0 0 Tyrosol 0 0 Hydroxytyrosol 0 0 Oleuropein 0 0 Demethyloleuropein 0 0 3,4-DHPEA-EA 0 0 Ligstroside 0 0 3,4-DHPEA-EDA 0 0 p-HPEA-EDA 0 0 p-HPEA-EA MANUSCRIPT0 0 Ligstroside-aglycone 0 0 Oleoside 11-methylester 0 0 Oleuropein-aglycone 0 0 Tyrosols 0 0 3,4-Dihydroxyphenylglycol 0 0 Catechol 0 0 Pyrogallol 0 0 Phenol 0 0 Phlorin 0 0 3-Methoxyacetophenone 0 0 2-Methoxy-5-prop-1-enylphenol 0 0 Arbutin 0 0 Others 0 0 4-Ethylguaiacol ACCEPTED 0 0 3-Methylcatechol 0 0 4-Methylcatechol 0 0 4-Ethylcatechol 0 0 Guaiacol 0 0 4-Vinylguaiacol 0 0 Alkylmethoxyphenols 0 0 4-Vinylphenol 0 0 5-Heneicosenylresorcinol 0 0 5-Heneicosylresorcinol 0 0 5-Heptadecylresorcinol ACCEPTED MANUSCRIPT 0 0 5-Nonadecylresorcinol 0 0 5-Nonadecenylresorcinol 0 0 5-Pentacosenylresorcinol 0 0 5-Pentacosylresorcinol 0 0 5-Tricosenylresorcinol 0 0 5-Tricosylresorcinol 0 0 Alkylphenols 0 0 Syringaldehyde 0 0 Protocatechuic aldehyde 0 0 Vanillin 0 0 Hydroxybenzaldehydes 0 0 2,3-Dihydroxy-1-guaiacylpropanone 0 0 Hydroxybenzoketones 0 0 Ferulaldehyde 0 0 Sinapaldehyde 0 0 Hydroxycinnamaldehydes 0 0 Scopoletin 0 0 Esculetin 0 0 Umbelliferone 0 0 4-Hydroxycoumarin 0 0 Hydroxycoumarins 0 0 Juglone 0 0 1,4-Naphtoquinone 0 0 Naphtoquinones 0 0 MANUSCRIPT

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ACCEPTED