II. MÉTODO
2.3. Población y Muestra
Özlem Tokus¸og˘lu
Introduction
A phytochemical is a natural bioactive compound found in plant foods such as fruits, vegetables, and nuts that works with nutrients and dietary fiber to protect against diseases. Fruit phytochemicals are of significant interest for public health for their protective and preventive effects in several chronic diseases and the pathogenesis of a definite class of cancers (Meskin et al. 2003; Omaye et al. 2000).
As the name suggests, phytochemicals work together with chemical nutrients found in fruits to help slow the aging process and reduce the risk of many diseases, including cancer, heart disease, stroke, high blood pressure, cataracts, osteoporosis, and urinary tract infections (Meskin et al. 2003; Omaye et al. 2000).
Flowering plants disseminate seeds through fruit and the presence of seeds indicates that a structure is most likely a fruit, though not all seeds come from fruits (Lewis 2002).
The major types of edible fruits include the following: fleshy simple fruits, fleshy aggregate fruits, fleshy multiple fruits, and dry fruits (Anonymous 2009a; Janick and Paull 2008). A classification of com-mon edible fruits is shown in Figure 4.1.
A drupe is a fruit in which an outer fleshy part (exocarp, or skin; and mesocarp, or flesh) surrounds a shell (the pit or stone) of hardened endocarp with a seed inside. Drupe fruits develop from a single carpel.
A drupe has the definitive characteristic that the hard, lignified stone (or pit) is derived from the ovary wall of the flower (Armstrong 2008).
CONTENTS
Introduction ... 83 Cherries ... 84 Sweet Cherries ... 84 Tart Cherries ... 85 Apricot ... 87 Bioactives in Apricot Fruits ... 87 Plum and Prune ... 89 Bioactives in Plum ... 89 Chlorogenic Acid and Its Derivatives in Plums and Prunes ... 90 Other Phenolic Acids, Flavonols and Flavan-3-ols in Plums and Prunes ... 90 Anthocyanins in Plums and Prunes ... 93 Total Phenolics in Plum and Prunes... 95 Antioxidant Activity of Plums and Prunes... 96 Peach and Nectarine ... 97 Bioactives in Peach and Nectarine ... 97 Date Fruit ... 98 Bioactives in Date Fruits ... 99 References ... 100
The most common drupe fruits are sweet/sour cherry, apricot, plum, peach, nectarine, almond, and date. Oily drupes are olive, coffee, and coconut.
Cherries
The word “cherry” refers to a fleshy fruit (drupe) that contains a single stony seed. Cherries are a member of the Rosaceae family, subfamily Prunoideae as taxonomical. They occupy the Cerasus subgenus within Prunus, being fairly distinct from their stone fruit relatives: the plums, apricots, peaches, and almonds.
The subgenus is native to the temperate regions of the Northern Hemisphere, with two species in America, three in Europe, and the remainder in Asia. Cherries are typically classified as either sweet or tart. Sweet cherries Bing, Lambert, and Rainier are grown mainly in Washington State, Oregon, and Idaho. Tart cherries including Montmorency and Balaton varieties are produced prin-cipally in the Michigan area. Prunus avium L. is the sweet cherry, to which most cherry cultivars belong and Prunus cerasus L. the sour or tart cherry that is used mainly for cooking or baking.
The decrease in the proliferation of human colon cancer cells (Kang et al. 2003) has been specifically associated with cherry consumption (Serrano et al. 2005). It is stated that sweet and sour cherry pheno-lics have protective effects on neuronal cells (Kim et al. 2005). It is also reported that the consumption of sweet cherries alleviates arthritis and gout-related pain (Wang et al. 1999).
Sweet Cherries
The sweet cherry is a vigorous tree with strong apical control with an erect-pyrimidal canopy shape;
grows to about 10–15 m (12–35 feet tall). In cultivation, sweet cherries are maintained <4 m in height.
They are harvested at a firm-mature stage to reduce bruising (Anonymous 2009a). Turkey is the big-gest sweet cherry producer in the world. There are 7,450,000 sweet cherry trees yielding approximately 230,000 tons per year in Turkey. The other countries producing sweet cherries are the United States with 175,000 tons and Iran with 115,000 tons (Vursavuş, Kelebek, and Selli 2006).
Common aggregate Classification of common edible fruits
1. Drupe fruits
Figure 4.1 Possible classification of common edible fruits. (This scheme compiled by Tokuşoğlu.)
Phenolic and Beneficial Bioactives in Drupe Fruits 85
Sweet cherries are one of the most popular spring-summer fruit species and mainly consumed as a fresh table fruit. It is known that sweet cherry have various antioxidants and its major phenolic antioxi-dants are anthocyanins, phenolic acids, flavonols, and flavan-3-ols (catechins). The major phenolic acids of sweet cherries are hydroxycinnamic acids (HCA; Bernalte et al. 1999; Gao and Mazza 1995; Jakobek et al. 2007a, 2007b; Usenik, Fabčič, and Štampar 2008).
The main hydroxycinnamates of sweet cherries are neochlorogenic acid and p-coumarylquinic acid while sweet cherries contain a little amount of chlorogenic acid (Kim et al. 2005) and ferulic acid (Matilla, Hellström, and Törrönen 2006).
Sweet cherries contain approximately 1500 mg total phenols kg–1fresh weight (FW; Gao and Mazza 1995). Usenik, Fabčič, and Štampar (2008) reported that total phenolic content ranged from 443 to 879 mg gallic acid equivalents/kg–1 FW and antioxidant activity ranged from 8.0 to 17.2 mg ascor-bic acid equivalent antioxidant capacity mg/100 g FW in fruits of 13 Slovene sweet cherry cultivars:
Badascony, Burlat, Early Van Compact, Fercer, Fernier, Ferprime, Lala Star, Lapins, Noire de Meched, Sylvia, Vesseaux, Vigred (red-colored), and Ferrador (bi-colored). Gonçalves et al. (2004a) reported that Portugal cultivar Saco contained the highest amounts of phenolics [2270 mg/ kg–1 FW].
It is known that phenolics contribute to the total antioxidant activity (AA) of sweet cherries. Figure 4.2 shows that the main polyphenolic compounds present in sweet cherry cultivars are derived from shiki-mic acid via a different metabolic route.
It is stated that antioxidant activity and phenolic profiles of sweet cherries depend on the genotype (Usenik, Fabčič, and Štampar 2008; Gonçalves et al. 2004a), maturity, and are affected by climatic con-ditions and storage (Gonçalves et al. 2004b).
The 3-glucoside and 3-rutinoside of cyanidin were found as the major anthocyanins whereas peonidin and pelargonidin 3-rutinosides were the minor anthocyanins, and peonidin 3-glucoside were also present in Portugal varieties cvs Burlat and Van by Gonçalves and coworkers (2004a). Epicatechin was found as the main monomeric flavan-3-ol with catechin present in smaller amounts in sweet cherry cultivars studied by Gonçalves et al. (2004a).
It is stated that the phenolic acid contents generally decreased with storage at 1–2°C and increased with storage at 15 + /–5°C, whereas anthocyanin levels increased at both storage temperatures. The anthocyanins increased up to fivefold during storage at 15 + /–5°C in cv Van (from 47 to 230 mg/100 g of FW; Gonçalves et al. 2004b).
Tart Cherries
Tart cherries (Prunus cerasus) are also called sour cherries. Tart cherries are the smallest members of the stone fruit family. Tart cherries are very juicy and pleasantly acid, making them superior for cooking compared to their sweet cherry relative. They are best known as a key ingredient in desserts; most impor-tantly, the cherry pie and it is also used in preserved foods, salads, side dishes, and beverages.
Cyanidin-3-glucosylrutinoside and pelargonidin-3-glucoside are the major anthocyanins in tart cher-ries. It is found that a high amount of total anthocyanin content is present (6.44 and 4.02 g/kg of dry mat-ter; Pedisic et al. 2008), whereas there are a significantly lower quantity of flavonols, hydroxycinnamates, flavan-3-ols, and procyanidins in tart cherries (Pedisic et al. 2008).
Recently, Wang et al. (1999) characterized eight polyphenolic compounds in Montmorency and Balaton tart cherries from Michigan by 1H and 13C NMR experiments. These compounds are:
(1) 5,7,4′-trihydroxyflavanone, (2) 5,7,4′-trihydroxyisoflavone, (3) chlorogenic acid, (4) 5,7,3′4 ′-tetrahyd-roxyflavonol-3-rhamnoside, (5) ′-trihydroxyflavonol-3-rutinoside, (6) 5,7,4′trihydroxy 3′methoxyflavonol-3-rutinoside, (7) 5,7,4′-trihydroxyisoflavone-7-glucoside, and (8) 6,7-dimethoxy-5,8,4′-trihydroxyflavone (Figure 4.3). The antioxidant assays revealed that 7-dimethoxy-5,8,4′-trihydroxyflavone is the most active, followed by quercetin 3-rhamnoside, genistein, chlorogenic acid, naringenin, and genistin, at 10 µM concentrations (Wang et al. 1999).
Tart cherries contain powerful antioxidants called anthocyanins—which provide the distinctive red color and may hold the key to the benefits locked inside (Chandra 1992; Wang 1996, 1999). Studies suggest that these disease-fighting pigments possess antioxidant, inflammatory, antiaging, and anti-carcinogenic properties (Blando 2004). Tart cherries are one of the richest sources of anthocyanins. The
unique health benefits of cherries first came to light in the 1990s, when numerous studies were published describing the antioxidant content of this fruit. Spurred by what was then anecdotal evidence that cher-ries alleviated the pain of arthritis and gout, researchers discovered that chercher-ries had high antioxidant activity. Additional studies identified the active antioxidants as eight polyphenolic compounds, including anthocyanins, chlorogenic acid, gallic acid, p-coumaric acid, and quercetin (Wang et al. 1999).
It was reported that during ripening, anthocyanins did not change uniformly, but in most ecotypes they were determined in higher concentrations at the last stage of maturity (3.18–19.75 g per kg of dry matter;
Pedisic et al. 2010).
Pedisic et al. (2010) stated that the growing region and ripening significantly influenced the accumu-lation of individual anthocyanins and L-value of tart cherries. Individual anthocyanins from cherry cv Balaton to its jam showed that processing caused a 90% decrease in anthocyanins. In this context, more
HO
COO NH3
COO–
COOH
Benzoic acid derivatives Cinnamic acid derivatives
Flavonols derivatives
Figure 4.2 Main polyphenolic compounds present in sweet-cherry cultivars derived from shikimic acid via different metabolic routes. (Adapted from González-Gómez, D., Lozano, M., Fernández-León, M. F., Bernalte, M. J., Ayuso, M. C., and Rodríguez, A. B., J. Food Comp. Anal., 2009, JFCA-D-08-00550DOI: doi:10.1016/j.jfca.2009.02.008.)
Phenolic and Beneficial Bioactives in Drupe Fruits 87
than 73% total phenolics and more than 65% antioxidant capacity were retained after processing fruits into jams (Kim and Padilla-Zakour 2004).
Currently, tart cherries are incorporated into meat products for improved nutritional qualities of meats.
Meat products containing tart cherries have become available to consumers. It has been found that cooled low-fat ground beef that includes 12% tart cherries had less rancidity development (Crackel et al. 1988). It is also reported that the addition of cherry tissue to ground beef prior to frying significantly inhibited hete-rocyclic aromatic amine formation (Britt et al. 1998). Wang et al. (1999) stated that these protective mec-hanisms of the cherries may be involved in the potential antioxidant polyphenolics present in cherries.
Apricot
Apricot (Prunus armeniaca L.) is a species of Prunus, classified with the plum in the subgenus Prunus.
The apricot shows fleshy drupe containing a hard, stony endocarp. The endocarp contains a single seed that is toxic because of high levels of cyanogenetic glucosides (Armstrong 2008; Huxley 1992).
bioactives in apricot Fruits
Apricot fruits may be considered as a rich source of the bioactives, mainly polyphenols (Akın, Karabulut, and Topçu 2008; Bureau et al. 2009; Dragovic-Uzelac et al. 2005a, 2005b, 2007; Macheix, Fleuriet, and ve Billot 1990; Madrau et al. 2009; Radi et al. 1997; Rashid et al. 2007; Sass-Kiss et al. 2005; Stratil, Klejdus, and Kuban 2007; Sultana and Anwar 2008; Veberic and Stampar 2005; ) and carotenoids (Akın, Karabulut, and Topçu 2008; Dragovic-Uzelac et al. 2007; Kurz, Carle, and Schieber 2008; Radi et al.
1997; Ruiz et al. 2005; Sass-Kiss et al. 2005), which contribute significantly to their taste, color, and nutritive values (Figure 4.4). There is a noticeable interest in polyphenols and carotenoids owing to their antioxidant properties and ability to alleviate chronic diseases (Gardner et al. 2000; Rice-Evans, Miller, and Paganga 1997; Vinson 1998).
The alterations of the bioactives in apricots have been studied during ripening, in relation to the geo-graphical region (Bureau et al. 2009; Dragovic-Uzelac et al. 2007; Garcia-Viguera, Zafrilla, and Tomas-Barberan 1997; Radi et al. 1997), in relation to apricot genotype (cultivar) and seasonal differences (Dragovic-Uzelac et al. 2007; Radi et al. 1997; Ruiz et al. 2005; Sass-Kiss et al. 2005; Scalzo et al. 2005;
HO O
Figure 4.3 Tart cherry polyphenols. (Adapted from Wang, H., Nair, M. G., Strasburg, G. M., Booren, A. M., and Gray, J. I., J. Agric. Food Chem., 47, 840–4, 1999.)
Veberic and Stampar 2005), after puree preparation (Dragovic-Uzelac et al. 2005a, 2005b), in relation to the drying temperature (Madrau et al. 2009), and after industrial processing and storage (Durmaz and Alpaslan 2007; Jiménez et al. 2008).
The apricot varieties include different levels of polyphenols, which have been abbreviated by Macheix, Fleuriet, and ve Billot (1990). Chlorogenic acid (5-O-caffeoylquinic acid) is the dominant phenolic compound in apricots (Garcia-Viguera et al. 1994; Radi et al. 1997). The HCA (neochlorogenic acid, caffeic acid, p-coumaric acid ferulic acid, and their esters) are the most common phenolic acid bioac-tives (Herrmann 1973; Henning and Herrmann 1980a; Radi et al. 1997; Figure 4.4). (+)-Catechin and (–)-epicatechin are other important groups of flavanols in apricot fruits and apricot-based products (Arts, van de Putte, and Hollman 2000; Dragovic-Uzelac et al. 2005a, 2005b; Garcia-Viguera, Zafrilla, and Tomas-Barberan 1997; Herrmann, 1973; Radi et al. 1997; Rish & Herrmann, 1988; Figure 4.4). It is also reported that procyanidin B1, procyanidin B2, and procyanidin B3 were found in apricot fruits (Dragovic-Uzelac et al. 2007).
Flavonols in apricots occur mostly as glucosides and rutinosides of quercetin and of kaempferol, how-ever, quercetin 3-rutinoside (rutin) predominates (Dragovic-Uzelac et al. 2005a, 2005b, 2007; Garcia-Viguera et al. 1994; Henning & Herrmann 1980). Aesculetin and scopoletin have also been determined in lower amounts in some apricot cultivars (Fernandez de Simon, Perez-Ilzabre, and Hernandez 1992;
Macheix, Fleuriet, and ve Billot 1990; Resche and Herrmann 1981).
In a study given by Sultana and Anwar (2008), total flavonol levels of apricots were 784.8 ± 32.6 mg kg–1 dry matter whereas individual flavonols myricetin, quercetin, and kaempferol of apricots were 406.9 ± 16.3; 322.1 ± 6.4; 5.8 ± 0.2 mg kg–1 dry matter, respectively (Sultana and Anwar 2008).
The alterations in HCA levels in apricot fruits from all genotypes showed the same trend during ripening, with the highest values at the first ripening stage (immature) and the lowest values at the com-mercial mature stage. The decrease in HCA levels is a well-known fact during maturation (Macheix, Fleuriet, and ve Billot 1990).
Only a few reports described the biochemical changes in apricot fruits at different ripening stages. Soluble and insoluble proteins were decreased during ripening apricot fruits, free amino acids varied according to the stages of maturity, while total and soluble carbohydrates increased (Sharaf, Ahmed, and El-Saadany 1989). Differences in amounts of chlorogenic acid, kaempferol-3-rutinoside, and quercetin-3-rutinoside were observed in 11 apricot fruit varieties in three stages of maturity (Garcia-Viguera et al. 1994).
Apricot fruits are regarded as a rich source of carotenoids, especially b-carotene, which represents more than 50% of total carotenoid content (Radi et al. 1997; Sass-Kiss et al. 2005). Besides b-caro-tene, apricot fruit and its products contain smaller amounts of a-carob-caro-tene, c-carob-caro-tene, zeaxantin, and lutein (Fraser and Bramley 2004). The data about carotenoid changes during apricot fruits ripening are not fully reported. In apricot fruits, ripening is accompanied by enhanced biosynthesis of carotenoids (Katayama et al. 1971). The beta-carotene level was determined to be significantly different among varieties and among different regions within the same variety (Munzuroglu, Karatas, and Geckil 2003).
Chlorogenic acid & their glucosides
and rutinosides
Figure 4.4 Major bioactive compounds in apricots (Prunus armeniaca L.) (Compiled by Tokuşoğlu Ö.)
Phenolic and Beneficial Bioactives in Drupe Fruits 89
Research on other plant species indicated that significant changes in carotenoid amounts occur according to the stage of maturity.
Plum and Prune
A plum (Prunus domesticus L.) is a stone fruit tree in the genus Prunus, subgenus Prunus. The subgenus is different from other subgenera that belong to the peach, cherry, and so on. Plums have a plump, round shape with a stem at the top. Their skin is very smooth, shiny and can be red, purple, or yellow color. The dried plum is called a prune. Plums are the most numerous and diverse group of fruit tree species (Figure 4.5) and mostly contain fruits of Prunus domestica, Prunus salicina, Prunus spinosa whereas the dried fruit prune is of some genotypes of Prunus domestica (Armstrong 2008; Blažek 2007; Huxley 1992).
It is indicated that the European plums (P. domestica L.) are dried, for the table, and some canning while the Japanese plums are for the table (P. Salinica Lindl.), fresh, and canning (P. institia L.). P. cera-sifera Ehrh. included in Japanese plums are commonly used as rootstock and it is consumed as fresh and canning plums (Ozcagiran 1976).
bioactives in Plum
Plums are considered a fruit class with high amounts of bioactive compounds or phytochemicals such as vitamins (A, C, and E), anthocyanins and other phenolics, and carotenoids (Stacewicz-Sapuntzakis et al. 2001), which contribute to the antioxidant capacity. Plums have been known to contain various kinds of phenolics, containing HCA, flavonols, and anthocyanins (Figure 4.6).
var. formosa
var. angelina var. giant
var. papaz var. stanley
Figure 4.5 (See color insert) Various plum cultivars. (Adapted from Asli Fidancilik, İzmir, Turkey, Various plum cultivars Asli Fidancilik, İzmir, Turkey, 2009.)
Phenolic acids Flavonoids
Phenolics
Major plum & prune bioactives
Carotenoids
Figure 4.6 Major bioactives in plum and prune fruits. (Compiled by Tokuşoğlu.)
Characteristically, plums are predominant with neochlorogenic acid (73% of total phenolics) and chlorogenic acid (13%). Together, hydroxycinnamates (caffeoylquinic acids) constituted 86% of total phenolics. Minor phenolic compounds in fresh prune plums are anthocyanins (7%), flavan-3-ol cate-chin (5%), and flavonol rutin (2%; Macheix and Fleuriet 1998; Möller and Hermann 1983; Stacewicz-Sapuntzakis et al. 2001).
Chlorogenic Acid and Its Derivatives in Plums and Prunes
It was reported that chlorogenic acid and its isomers are major phenolic compounds in plums and prunes (Figure 4.7). Neochlorogenic acid (3-O-caffeoylquinic acid, 3-CQA) is a predominant polyphenol in the fresh fruit plum or dried fruit prune (Fang, Yu, and Prior 2002) and chlorogenic acid (5-O-caffeoylqui-nic acid, 5-CQA), cryptochloroge(5-O-caffeoylqui-nic acid (4-O-caffeoylqui(5-O-caffeoylqui-nic acid, 4-CQA) are often found as phenolic acids in plum varieties (Fang, Yu, and Prior 2002; Donovan, Meyer, and Waterhouse 1998; Herrmann, 1989; Nakatani et al. 2000; Tomàs-Barberàn et al. 2001; Figure 4.7).
It is reported that 88–731 mg/kg of neochlorogenic acid (3-O-caffeoylquinic acid, 3-CQA), 15–129 mg/
kg of chlorogenic acid (5-O-caffeoylquinic acid, 5-CQA), and 56 mg/kg of cryptochlorogenic acid (4-O-caffeoylquinic acid, 4-CQA) are found in fresh plums in the study described by Möller and Hermann (1983). It is indicated that 807–1306 mg/kg of neochlorogenic acid (3-O-caffeoylquinic acid, 3-CQA) is in fresh prune-making plums and 144–436 mg/kg of chlorogenic acid (5-O-caffeoylquinic acid, 5-CQA) is in pitted prunes (Donovan, Meyer, and Waterhouse 1998). It is determined that the 3-CQA ranged from 1228 to 1485 mg/kg whereas cryptochloro-genic acid (4-O-caffeoylquinic acid, 4-CQA) ranged from 288 to 351 mg/kg, and 5-CQA varied from 53 to 77 mg/kg in prunes (Prunus domestica L.) given by Nakatani et al. (2000) in a study in Osaka, Japan.
Other Phenolic Acids, Flavonols and Flavan-3-ols in Plums and Prunes
It is indicated that the HCA derivatives are mostly present in the peel of a plum (Tomàs-Barberàn et al.
2001). The total HCA level is 115–375 mg/kg in the peel part of a plum whereas 16.3–194 mg/kg is in the flesh part of a plum.
Dried prunes contain higher amounts of phenolic compounds (184 mg/100 g of fruit) than prune-ma-king plums (Donovan, Meyer, and Waterhouse 1998) owing to the dehydration process concentrates of the constituents despite partial degradation. Dried plums lead to HCA degradation related to the fruit polyphenoloxidase activity; most of the HCA compounds are degraded when plums are dried at a lower temperature (Raynal, Moutounet, and Souquet 1989, Raynal and Moutounet 1989).
O OH
OH HOOC
OR3 OR5
R5 = H;
R3 = H;
Neochlorogenic acid
Chlorogenic acid R5 =
R3 = OH
OH O
OH
OH Figure 4.7 Neochlorogenic and chlorogenic acids in plums.
Phenolic and Beneficial Bioactives in Drupe Fruits 91
Small amounts of caffeic and coumaric acids (1% of phenolics) appear in dried prunes, probably as a result of cinnamate hydrolysis during processing (Stacewicz-Sapuntzakis et al. 2001). The concen-trations of HCAs increase with fruit development, showing a loss when reaching maturity but show a remarkable loss when examined after removal of the harder seeds (Stöhr, Mosel, and Herrmann 1975).
Neochlorogenic acid represents 71% of the total phenolics and chlorogenic acid 24%, raising the content of hydroxycinnamates to 95% of all phenolic compounds (Stacewicz-Sapuntzakis et al. 2001).
It is reported that there is 1.5 mg/100 g of quercetin in the Denmark plum blue (as fresh weight;
Justesen, Knuthsen, and Leth 1998) and that 564.1 mg/kg of myricetin, 0.7 mg/kg of kaempferol, and 564.8 mg/kg of total flavonols has been detected in plums at Faisalabad, Pakistan (as dry matter; Sultana and Anwar 2008). It is reported that fresh plums from Holland and Denmark include 0.9–1.5 mg/100 g of quercetin as an edible portion (Hertog, Hollman, and Katan 1992; Justesen, Knuthsen, and Leth 1998).
Rutin (quercetin 3-rutinoside; Figure 4.8.) is present as 2% of all phenolics and is found in the exocarp of plums (Raynal, Moutounet, and Souquet 1989; Stacewicz-Sapuntzakis et al. 2001). Rutin is the predo-minant flavonol glycoside in fresh and dried plums (Fang, Yu, and Prior 2002; Raynal, Moutounet, and Souquet 1989; Stacewicz-Sapuntzakis et al. 2001).
Macheix et al. (1989) reported that Prunus domestica and Prunus salicina genotypes of plums inc-lude 3-glycosides, 3-galactosides, 3-rutinosides, and 3-arabinoside-7-rhamnosides of quercetin and kaempferol (Macheix, 1990). Henning and Herrmann (1980b) determined that six examined cultivars of Prunus domestica plums contain mainly 3-rutinosides (Figure 4.9) and smaller concentrations of
HO
OH O
O
O O
O
O
OH OH OH OH
OH
HO
HO H3C HO
Figure 4.8 Rutin (Quercetin 3-rutinoside) in plum.
HO O
OH OH
O R = galactoside
Quercetin-3-galactoside Quercetin-3-glucoside Quercetin-3-rutinoside R = glucoside
R = rutinoside
OR OH
Figure 4.9 Quercetin glycosides in plum and prunes. (Adapted from Tomas Barberàn, F. A., Gil, M. I., Cremin, P., Waterhouse, A. L., Hess-Pierce, B., and Kader, A. A., J. Agr. Food Chem., 49, 4748–60, 2001.)
the 3-glycosides and 3-galactosides of kaempferol and quercetin and quercetin-3-rhamnoside. It is also been detected that the main flavonols are kaempferol-3,7-bisrhamnoside and kaempferol-3-arabinosyl-7-rhamnoside in two examined cultivars of Prunus salicina plums in the study given by Henning and
the 3-glycosides and 3-galactosides of kaempferol and quercetin and quercetin-3-rhamnoside. It is also been detected that the main flavonols are kaempferol-3,7-bisrhamnoside and kaempferol-3-arabinosyl-7-rhamnoside in two examined cultivars of Prunus salicina plums in the study given by Henning and