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Home , Flavanone, Isoflavonoid, Phenolic acid, Phenylpropanoid, Phloroglucinol, Tangeretin

Turkish Journal of Agricultural and Natural Sciences Special Issue: 1, 2014

TÜRK TURKISH TARIM ve DOĞA JOURNAL of AGRICULTURAL

BİLİMLERİ DERGİSİ and NATURAL SCIENCES

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Phenolic Compounds and Uses in Fruit Growing a,b Melekber SULUSOGLU * aKocaeli University, Arslanbey Agricultural Vocational School, TR-41285, Kocaeli/Turkey. bKocaeli University, Graduate School of Natural and Applied Sciences, Department of Horticulture, TR-41380, Kocaeli/Turkey *Corresponding author: [email protected]

Abstract Phenolic compounds are a class of chemical compounds in organic chemistry which consist of a hydroxyl group directly bonded to an aromatic hydrocarbon group. Phenolic compounds find in cell wall structures and play a major role in the growth regulation of plant as an internal physiological regulators or chemical messengers. They are used in the fruit growing field. They are related with defending system against pathogens and stress. They increase the success of tissue culture; can be helpful to identification of fruit cultivars, to determination of graft compatibility and identification of vigor of trees. They are also important because of their contribution to the sensory quality of fruits during the technological processes. In this review, the simple classification was given for these compounds and uses in the agricultural field were described.

Key words: Phenolic compounds, fruit quality, fruit growing, cultivar identification, grafting, tree vigor

Fenolik Bileşikler ve Meyve Yetiştiriciliğinde Kullanımı

Özet Aromatik hidrokarbon grubuna bağlı bir hidroksil grubu içeren fenolik bileşikler organik kimyanın bir sınıfıdır. Fenolik bileşikler hücre duvarı yapısında bulunmakta ve içsel bir fizyolojik düzenleyici veya kimyasal haberci olarak bitki büyümesinin organizasyonunda önemli rol oynamaktadır. Meyve yetiştiriciliği alanında kullanılmaktadır. Bu bileşikler patojenlere ve stres koşullarına karşı savunma sistemi ile doğrudan bağlantılıdır. Doku kültürü çalışmalarında başarıyı artırmaktadır; çeşitlerin tanımlanmasında, aşı uyuşmazlığının belirlenmesinde ve ağaçların büyüme kuvvetinin saptanmasında kullanılabilmektedir. Meyve kalitesine etkilerinden dolayı, fenolik bileşikler ürün işleme sırasında da önem taşımaktadır. Bu derleme makalede fenolik bileşikler basitçe sınıflandırılmış ve meyve yetiştiriciliği alanında kullanımlarına yer verilmiştir.

Anahtar Kelimeler: Fenolik bileşikler, meyve kalitesi, meyve yetiştiriciliği, çeşit tanılama, aşılama, bodurluk

Introduction and stilbenes (Ralston et al., 2005; are among the most Lacikova et al., 2009; Pereira et al., 2009). is widespread class of metabolites in nature, and the simple structure form of these compounds. their distribution is almost ubiquitous. It is Chemically, they are compounds with an aromatic estimated that 100,000 to 200,000 secondary ring link to one or more hydroxyl groups and metabolites exist and some 20% of the carbon hydroxyl group of phenol determines its acidity fixed by photosynthesis is channeled into the whereas the benzene ring characterizes its basicity. pathway, thus generating the Phenol is moderately soluble in water (Nguyen et majority of the natural-occurring phenolics, such as al., 2003). Polyphenolic compounds are widely

947 Turkish Journal of Agricultural and Natural Sciences Special Issue: 1, 2014 distributed in the vegetable and fruits and are The most important flavonoids are , essential for the growth of plants and affect flavanols, , , various physiological events. They find in cell wall and (Scalbert and Williamson, 2000). structures, features of woods and barks, flower They are among the most potent antioxidants from color and they actively inhibited or stimulate some plants. can be classified into two major physiological process, such as defending system groups, hydrolysable and condensed tannins against pathogens and stress, some of the quality (Chung et al., 1998). The and phloridzin properties of fruits quality (aroma, flavors, color, are characteristics of apples, while arbutin of pears and astringency), structure, pollination, and . Chalcones is the main pigments germination process of seed after harvesting and of yellow flowers (Karakaya, 2004). are growth as well as development and reproduction. more common in nature in the form of They are considered as bioactive non-nutritional and are mainly found in (Sanchez-Moreno, compounds, due to their antioxidant functions 2002). (Yordi et al., 2012; Reis Gaida, 2013). Phenolic acids can be divided into two groups: This article, after a simple classification benzoic acids and cinnamic acids. In the group of and biosynthesis of plant phenolic compounds, benzoic acids there are protocatechuic acids, some affects as internal physiological regulators or vanillic acids, , , salicylic chemical messengers and uses in the fruit growing acid, p-hydroxybenzoic acid and field were investigated. (Sanchez-Moreno, 2002).

Biosynthesis of phenolic compounds Uses of phenolics compounds in the fruit growing Although a large variety of plant exists, most of these compounds arise from a Role of phenolics as pigments and aromatic common origin: the amino acids or compounds . The plant phenolic compounds are Many phenolic compounds are responsible primarily derived from the for coloring of the plant flowers, fruits and are (Castellano et al., 2012). Precursors of important for their quality. Factors affecting fruit phenylpropanoids are synthesized from two basic color are primarily genetically determined. In pathway: the shikimic acid pathway and the addition, environmental factors such as nutrients, malonic pathway. The shikimic acid pathway temperature and light conditions can have an produces most plant phenolics, whereas the effect on composition and on the final malonic pathway, which is an important source of hue of the fruit. The other important role of phenolics in fungi and bacteria, is less significant in flavonoids is to serve as visual signals for animals in higher plants (Seabra et al., 2009; Pereira et al., attracting pollinators in flowers and help to 2009; Saltveit, 2010). Phenolic compounds have pollination and of course fruit set (Lattanzio et al., three main characteristics. First one is the 2006). range from hues to pink presence of at least one aromatic ring hydroxyl- through deep red to purple in plants (Ryugo, 1988). substituted (Morton et al., 2000). Another Chalcones and are two classes of characteristic of these substances is that they are flavonoids that contribute to yellow flower colour presented commonly bound to other molecules, in plants (Karakaya, 2004; Lattanzio et al., 2006). frequently to sugars and proteins. However, it is Among the polyphenols, flavonols are responsible less common, phenolic compounds occur in free for cream-yellowish hue, which are found form in the plants (Reis Giada, 2013). principally in the outer parts of fruits (Tomas-

Barberan et al., 2000). is a flavonoid

present in green-yellow apples, cherries and Simple classification of phenolic compounds grapes (Yordi et al., 2012). Phenolic compounds divided in two groups Many phenolic compounds are responsible for mainly as simple phenols and polyphenols. Main some of the sensorial properties of fruit and classes of phenolic compounds are flavonoids, related with the quality. There are bitter tannins, chalcones, coumarins and phenolic acids.

948 Turkish Journal of Agricultural and Natural Sciences Special Issue: 1, 2014 polyphenols, such as certain citrus flavanones such as , gallic acid or flavonoids, have ( from grapefruit and neohesperidine from been found to either stimulate or inhibit spore the bitter oranges) or present in olives. germination and hyphal growth of saprophytic (condensed tannins) and fungi (Weir et al., 2004; Lattanzio et al., 2006). hydrolysable tannins confer astringency to fruits, Phenolic acids strongly influence cell membrane and some simple phenols are important for the potentials and supports the hypothesis that their aroma of certain fruits, such as in influence on ion uptake (Glass and Dunlop, 1974). bananas. derivatives such as effects on bud dormancy too. Several caffeic, ferulic and sinapic acids are present in a phenolics, e.g. , , , number of fruits. Tannins are not pigments but , 0- and p-coumaric acid, ferulic acid, when plant tissues are injured, these chemicals are salicyclic acid, , quercetin and oxidized to brownish-black pigments. When a fruit , have been identified as occurring in is bruised, cells rupture and these substances come buds of woody species (Szember and Wocior, into contact with the polyphenoloxidase 1976; Altree-Williams et al., 1975). A correlation and peroxidases and this cause to browning between the seasonal growth activity and reaction. Tannis obtain the astringent taste endogenous levels of specific phenolics has been because they are reacting with the proteins on the found in buds of sour cherry (Szember and Wocior, surface of tongue. Persimmon is a good example to 1976). However, exogenously applied naringenin this property of tannins (Ryugo, 1988). did not delay bud burst in peach Dennis and Edgerton (1961). It appears, that naringenin's role in peach bud dormancy is not one of causation or Role of phenolic compounds on the growth and regulation. development physiology of fruit trees Plant phenolics are internal physiological regulators or chemical messengers within the Characterization of fruit cultivars with phenolic intact plants. They found in the hydroxycinnamic compounds acids, particularly p-coumaric acid and ferulic acid, Varieties are often morphologically very are found in the insoluble or cell wall fraction. similar and chemical analysis of plants is helpful for Phenolic compounds have been shown to have the distinction of closely related cultivars. both stimulatory and inhibitory effects on plant Secondary compounds can play an important role development. They play a significant role in cell in distinguishing cultivars. Whereas the wall development act in biosynthesis (Fry, conventional pomologist normally uses the fruit to 1983; Hatfield et al., 1999). Some phenolic distinguish cultivars, these techniques are lack of compounds have a role as natural auxin transport clear and are only semi quantitative (Martelock et regulators in plants. Mono-and dihydroxy al., 1994). Therefore, the phenolic “fingerprints” flavonoids are implicated as inhibitors of IAA can be helpful to prove identification of cherry transport (Jacobs and Rubery, 1988). There was a cultivars in an early stage of tree development relationship between the metabolism (Geibel et al., 1990; Mısırlı, 2000a). Phenolic and seasonal development of plant tissues compounds occur in almost all higher plants; they (Treutter et al., 1987). They can influence plant show a high structural diversity within different growth by promoting leaf expansion (Hegedus and tissues and therefore best suited as taxonomical Phan, 1982), stimulating callus growth (Gould and markers (Geibel et al., 1990). The mean level of Murashige, 1985), and increasing rooting of phenolic compounds in the apple cortex was cuttings (Jones, 1979; Gould and Murashige, 1985). different greatly among the cultivars and Allelopathy refers to the chemical inhibition quantitative analysis of the phenolic compounds in of one species by another and describes the the fruit with correspondence analysis of chemical interaction between two plants. polyphenol profile has been found useful in Phenolics as a signal for growing and can directly taxonomic studies of apple cultivars for affect the composition and activity of decomposer classification and identification (McRae et al., communities. Different types of soluble phenolics, 1990). In order to identify cultivars of cherry cultivars, phenolic extracts of the inner bark layer

949 Turkish Journal of Agricultural and Natural Sciences Special Issue: 1, 2014

(phloem) used to characterize a few cherry 1992). Phenols escape from the vacuole into the cultivars (Treutter and Feucht, 1985). Again, for cytoplasmic matrix where they are oxidized by characterization of cherry cultivars and seedlings peroxidases and phenoloxidases. These irreversible HPLC method was used and unknown cultivars unions can also lead to protein precipitation identified as a results (Geibel at al., 1990). Phenolic resulting in cellular necrosis. These precipitations compounds of 23 sweet cherry varieties, including might be the cause of the necrotic line observed in some local selections of the same variety, were the xylem of certain incompatible combinations. analyzed to check their identity or distinctness. The The field testing of newest graft combinations is of high discriminatory potential of phenolic long duration and expensive. Phenol analysis is an compounds for variety identification has been applicable early sign for the prediction of graft shown and different origins of the same variety incompatibility especially when new cultivars were have been identified (Martelock et al., 1994). used for different new cultivar/rootstock Mısırlı (2000a) investigated the leaf phenolic combinations. Phloem of Prunus spp. contains compounds of apricot cultivars with thin layer considerable amounts of polyphenols which are chromatography and found different spot easily determined (Treutter et al., 1987; Usenik et characteristics among parents and suggested that al., 2006) and they can translocate around the it was important from the point of parent-hybrid graft union area. The accumulated polyphenols relations. content and other phenolic was above the union were , proanthocyanidins, determined as different in the mature and chlorogenix acids. An increase of polyphenols as a immature leaves of apricot cultivars (Mısırlı et al., symptom of incompatibility was frequently 1993 a). Phenolic compounds and isoenzyme accompanied by more or less localized browning of patterns of 12 cultivars of PRUNUS DOMESTICA phloem and is a symptom of graft compatibility. In were extracted from the inner bark (phloem) of 1- Prunus avium , qualitative and quantitative amount year-old shoots. The genetic relationship among of flavonoids changed and increased in the these cultivars was studied by biochemical markers senescing interspecific graftings as compared to and compared with the systematical classification, healthy homospecific ones, especially in the as described by Hegi and Röder, based on growing season (Treutter et al., 1987). Karadeniz morphological characters. As a result, a revised and Kazankaya (1997) found a negative systematic, according to isoenzyme and phenolic relationship between the graft success and the marker is described (Groh et al., 1994). phenolic contents of the scions. Phenolic Comparision of peach cultivars for flavonoid and compounds are suggested as markers of graft other phenolic compounds by high performance incompatibility determination in the graft callusing liquid chromatography (HPLC) procedures stage in vitis spp . On the other hand, as a indicated that the cultivars were of 3 phylogenic contribution to the investigation of the graft types (LianSen et al., 1994) incompatibility of P. avium /P. cerasus combinations, the wall bound phenols of the Relationship between graft incompatibility and phloem were determined and were found very uses to detection incompatible graft slight quantitative differences due to the genotype. Graft incompatibility is an important It has been assumed that wall bound phenols criterion that should be considered during the might not be responsible for bad union formation selection process of new cultivars and rootstocks. during the initial stage (Treutter et al., 1990). It is suggested that biochemical causes, rather than anatomical ones, are responsible for the Role of phenolic compounds in the resistance alterations at the cambial continuity. Phenolic mechanism of fruit trees against pathogens and compounds have been implicated in process of disease division, development and differentiation into new There are numerous pests and pathogens in tissues (Errea, 1998; Mısırlı, 2000b). The the natural environment of plants. The plant cell concentration of phenolic compounds, the wall is a defensive system against external threats, flavanols ( and proanthocyanidins) including pollutants, mechanical wounding, and increase as a result of grafting stress (Feucht et al., intrusion by pathogenic microorganisms and

950 Turkish Journal of Agricultural and Natural Sciences Special Issue: 1, 2014 insects pests (Lagrimini et al., 1993). Plants and Overeem, 1968). Coumarin compounds have produce secondary metabolites, many of which been reported to have some important have antifungal activity. Some of these compounds physiological properties such as pathogen are constitutive, existing in healthy plants in their inhibition (Kim et al., 1991; Ortuno et al., 1997). biologically active forms. Some phenolics are stored in plant cells as inactive bound forms and Effects of phenolic compounds on seed are activated in response to tissue damage or germination pathogen attack (Osbourn, 1996). Well-known It has been suggested that the inhibition of examples include phenols and phenolic glycosides, seed germination in fruit was generally not due to unsaturated lactones, sulphur compounds, a single compound but was due to the synergistic , cyanogenic glycosides, and action of several compounds. Some of phenolic glucosinolates. Phenolic compounds which play a compounds found in both seed coats and embryos major role in the growth regulation of living plant and affect seed germination and dormancy. are known to be related with resistance. Naturally, Hydroxycinnamic acids, coumarins, tannins and resistant plants or specific tissues may have ferulic acid have been some of the common seed inherently higher phenolic contents. Activation of germination inhibitors (Bewley and Black, 1994). It phenolic radicals with oxygen species obtains has been suggested that phenolics may be active barriers (Southerland, 1991) such as lignin as germination inhibitors by inhibiting the cellulose, callose, and (DeLeeuw, 1985). transport of amino acids and the formation of Pecan and persimmon, which show resistance to proteins in the seeds (Lattanzio et al., 2006). the fungus Dematophora necatrix , the causal agent Another possible function of the phenolic acids in of white root rot disease, contain phenolic seed germination may be their role in the synthesis compounds which inhibit its growth. Roots of and degradation of indole-3-acetic acid (lAA) resistant crops contain higher concentrations of (Rabin and Klein, 1957). In the peach seeds, phenolic compounds than those of susceptible fruit products of amygdalin degradation species apple, almond and peach. Catechol, (mandelonitrile, benzaldehyde and cyanide) do not methylcatechol, hydroquinone and 8- seem directly related to the breaking of peach seed hydroxyquinoline significantly inhibited the growth dormancy (Aitken, 1967). According to Bewley and of the fungus (Sztejnberg et al., 1983). On the Black (1994), testa of the seed protects the other hand, tannin content may increase after the embryo, and contains some phenolics. There are infection as observed in Citrus cultivars that some external applications of phenolic compounds phenolic content in the leaves of the tolerant for seed germination too. Peach juice is injurious to cultivars increased while remained same in the peach seed germination (Scot et al., 1942) while susceptible ones. Similarly, peach trees phenolics the flavonoid, naringenin, which has been isolated increase when attached by fungus (Wisniewski et from peach buds by Hendershott and Walker al., 1984). It seems that differences in tannin (1959), has inhibited effect on lettuce seeds content of apricot varieties strengthen them germination. against to disease (Mısırlı et al., 1993b). Two constitutive secondary metabolites of the bitter Dwarfing mechanism and phenolic compounds orange Citrus aurantium , the -naringin, interactions and the polymethoxyflavone-tangeretin showed The use of small trees in orchard systems antifungal activity against Penicillium digitatum reduces manual labor thus provides economically (Arcas et al., 2000). , catechin, and advantageous. The most important issue in oleuropein showed a greatest accumulation in the breeding studies is the determination of tree vigor. cortex of stem tissue and showed antifungal Phenolic compounds are thought to be related to activity in vitro studies of olive ( Olea europaea L.) the growth vigor of trees, however, there were not thus affecting plant resistance against Phytophtora a causal link between phenolics compound content sp. (Del Rio et al., 2003). Phloridzin oxidation and dwarfism (Usenik and Stampar, 2002; Usenik products has been found defensive in apple leaves et al., 2005). In the dwarfing mechanism, against the scab fungus Venturia inaequalis (Raa relationship of auxin with the bark stem is not clear

951 Turkish Journal of Agricultural and Natural Sciences Special Issue: 1, 2014 but authors think that phenols are related to this like substances for defensing system. Thus, mechanism, so mono-phenols has an antagonist oxidized phenolics in resistant varieties of apple effects with IAA while has an co-factor effects on play an important role in the restricted lesion peroxidase. Interaction of IAA and phenolic formation associated with the brown rot disease of compounds in the bark tissue has a reducing effect fruits caused by Sclerotinia fructigena Aderh (Byrde on size of the scion. The presence of thick bark in et al., 1960) or with rotting of stored Golden apples has been associated with the dwarfing Delicious apples caused by Phlyctaena vagabunda response and interested with the phenolic (Lattanzio et al., 2001). Green mould caused by compounds (Lockard and Schneider, 1981; Weibel, Penicillium digitatum is a big problem for stored 2008). The total phenolic content and some citrus fruit and cause huge losses. Usually synthetic mineral nutrition of Mahaleb genotypes were fungicides are employed to control this disease but found to different according to vigor capacity and they have adverse effects on human and suggested that total phenolic content and mineral environmental health. Some phenolic compounds, nutrition can be used as a criterion for prediction quercetin, scopoletin and scoporone, tested in vigor (Moghadam et al., 2007). vitro and in vivo against P. digitatum . These compounds present in several agricultural crops Uses of phenolic compounds in tissue culture and associated with response to stress. As a result, In vitro propagation of fruit species are very phenolics significantly reduced disease symptoms common and commercially use. The success of and represent an interesting alternative to plant tissue culture as a means of plant synthetic fungicides (Sanzani et al., 2014). propagation is greatly influenced by the nature of the culture medium used. The effects of adding Phenolic compounds and effects on fruit phenols to culture media are mainly an processing enhancement of callus growth, more effective Phenolics are also important because of adventitious shoot formation, the improved their effects during the technological processes rooting of shoots, and a greater rate of shoot used for obtaining the juices and other proliferation in certain shoot cultures (George et transformation products (Raynal et al., 1986, al., 2008). The addition of phloroglucinol into Spanos et al., 1990). It was showed that some culture media containing growth substances was phenolic compounds could be useful in able to enhance growth and the rate of axillary characterization and differentiation of fruit juice shoot production from shoot cultures in Malus and too (Simon et al., 1992; Abad-Garcia et al., 2012). Prunus (Jones, 1976; Jones, 1979). Vitrification is prevented by phloroglucinol in most of plants Conclusion (George et al., 2008). Rooting may be stimulated Phenolic compounds are widely distributed by phloroglucinol when added to rooting media in plant and play significant roles in their life-cycle. together with auxin. This effect has been especially Different uses and advantages have been noted in apple (Zimmerman, 1984), in Prunus described in fruit growing. They are a part of the (Hammerschlag et al., 1987; Hammatt, 1994), plant nature and need to deep research on these and Rubus genotypes (James, 1979), compounds. and Prunus cerasifera (Hammerschlag 1982). has been stimulating callus References growth of Prunus avium stem segments (Feucht Abad-Garcia, B., Berrueta, L.A., Garmon-Lobato S., and Johal, 1977). Urkaregi, A., Gallo, B., Vicente, F., 2012. Chemometric characterization of fruit juices Importance of phenolic compounds during the from Spanish cultivars according to their storage of fruits phenolic compound contents: I. Citrus Phenolic compounds affect the strength of fruits. J. Agric. Food Chem 60 (14):3635- fruits during storage (Lattanzio et al., 2006). Many 3644. simple low molecular phenolic compounds are polymerized by oxidation to yield brown tannin-

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