Journal of Food Bioactives, ISSN 2637-8752 print, 2637-8779 online
Journal website www.isnff-jfb.com

Review

Volume 5, March 2019, pages 57-119

Phenolic compounds in agri-food by-products, their bioavailability and health effects

Figures

Figure 1.
Figure 1. General breakdown of non-nutritive plant-base natural products.
Figure 2.
Figure 2. Major classes of flavonoids and its some individual compounds.
Figure 3.
Figure 3. Generic structures of major classes of flavonoids.
Figure 4.
Figure 4. Structures of common benzoic acid derivatives.
Figure 5.
Figure 5. Structure of ellagic acid (dimeric derivative of gallic acid).
Figure 6.
Figure 6. Structures of common cinnamic acid derivatives.
Figure 7.
Figure 7. Structure of chlorogenic acid.
Figure 8.
Figure 8. General structures for theaflavins and their specific compounds and thearubigin. Source: Adapted from Beecher, (2003).
Figure 9.
Figure 9. Parent structure of lignan [coupling (B) of two C6-C3 molecule (A)].
Figure 10.
Figure 10. Structure of major dietary lignans.
Figure 11.
Figure 11. Structure of trans-resveratrol (trans-3,5,4-trihydroxystilbene).
Figure 12.
Figure 12. Structure of hydroxytyrosol.
Figure 13.
Figure 13. Major bioactive compounds in Apple seed. Source: Adapted from Lu and Foo, (1998).
Figure 14.
Figure 14. Structure of quercetin-3-glycoside and phloretin identified in apple pomace. Source: Adapted from Lommen et al., (2000).
Figure 15.
Figure 15. Structures of flavanone aglycones and glycosides identified in citrus peel. Source: Adapted from Harborne et al., (1999).
Figure 16.
Figure 16. Structures of flavan-3-ol monomer and dimer in grape seed. Source: Adapted from Nawaz et al., (2006).
Figure 17.
Figure 17. Structures of the xanthone C-glycosides mangiferin and isomangiferin. Source: Adapted from Schieber et al., (2003b).
Figure 18.
Figure 18. General structure of flavonol glycosides detected in mango peels. Source: Adapted from Schieber et al., (2003b).
Figure 19.
Figure 19. Total phenolic contents of seed of mango, tamarind, longan, avocado and jackfruit. Source: Adapted from Soong and Barlow, (2004).
Figure 20.
Figure 20. Schematic illustration of pomegranate fruit parts and their terminology.
Figure 21.
Figure 21. Major phenolic compounds identified in pomegranate peel. Source: Adapted from Seeram et al., (2005).
Figure 22.
Figure 22. Chemical structure of dopamine.
Figure 23.
Figure 23. Basic structure of anthocyanidins and most common anthocyanidins of banana bracts. Source: Adapted from Pazmino-Duran et al., (2001).
Figure 24.
Figure 24. A molecular structure of quercetin and glucosides.
Figure 25.
Figure 25. Chlorogenic acid isomers in potato peel. Source: Adapted from Friedman, (1997).
Figure 26.
Figure 26. Phenolic compounds in almond hulls. Source: Adapted from Sang et al., (2002a).
Figure 27.
Figure 27. Chemical structure of flavonols, flavonol glycosides and flavonone glycoside identified in almond skin (Sang et al., 2002). 1. Quercetin; 2. Kaempferol; 3. Isorhamnetin; 4. 3-O-methylquercetin 3-O-β-d-glucopyranoside; 5. 3-O-methylquercetin 3-O-β-d-galactopyranoside; 6. 3-O-methylquercetin 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside; 7 Kaempferol 3-O-α-l-rhamnopyranosyl- (1→6)-β-d-glucopyranoside; 8. Naringenin 7-O-β-d-glucopyranoside (prunin).
Figure 28.
Figure 28. Structures of flavan-3-ols, phenolic acids and flavanones identified in almond skin. Source: Adapted from Shahidi et al., (2009).
Figure 29.
Figure 29. Hazelnut kernel and hazelnut by-products (Shahidi et al., 2007).
Figure 30.
Figure 30. Chemical structures of some of the phenolic compounds contained in CNSL. Source: Adapted from Kubo et al., (1993a).
Figure 31.
Figure 31. Structure of major polyphenols identified in walnut. Source: Adapted from Alasalvar and Shahidi, (2009).
Figure 32.
Figure 32. Structure of major flavonoid in peanut hull.
Figure 33.
Figure 33. Isovitexin (C-glycosyl flavonoid) in rice hull. Source: Adapted from Ramarathnam et al., (1989).
Figure 34.
Figure 34. Structure of flavonol, C-glycosyl flavone isolated from buckwheat hulls. Source: Adapted from Watanabe et al., (1997).
Figure 35.
Figure 35. Some monophenolic compounds identified in oat hull.
Figure 36.
Figure 36. Structure of demethyloleuropein.
Figure 37.
Figure 37. Structure of soy isoflavones identified in soybean cake.
Figure 38.
Figure 38. Structure of soy isoflavone glucosides.
Figure 39.
Figure 39. Cleavage of lignin/phenolics-carbohydrate complexes in flax shives with alkali. Source: Adapted from Buranov and Mazza, (2008).
Figure 40.
Figure 40. Structure of (−)-epigallocatechin-3-O-gallate tea catechins.

Table

Table 1. Phenolic compounds in agri-food by-products
 
By-productsMajor phenolic compoundsTotal Phenolic contentaReference
Abbbreviations: GAE: gallic acid equivalents; CE: catechin equivalents; TAE: tannic acid equivalents; SE: sinapic acid equivalents; CGE: chlorogenic acid equivalents. aExpressed as dry weight.
Apple peelQuercetin glycosides, phloretin glycosides, catechins, procyanidins, phloridzin, caffeic acid, chlorogenic acid, cyanidin glycosides33.42 mg/g (GAE)Wijngaard et al. (2009), Wolfe and Liu (2003)
Apple seedAmygdalin, phloridzin2.17 mg/gSchieber et al. (2003a), Lu and Foo (1998)
Apple pomacePhloridzin, chlorogenic acid, quercetin glycosides4.22–8.67 (CGE)Schieber et al. (2003a), Ćetković et al. (2008)
Berry pomaceCyanidin-3-O-glucoside, quercetin-3-O-glucoside, gallic acid, protocatechuic acid21.7–47.4 mg/g (GAE)Zhou et al. (2009)
Grape skinCatechin, epicatechin, epicatechin gallate, epigallocatechinSouquet et al. (1996)
Grape seedCatechin, epicatechin, epicatechin-3-O-gallate, dimeric procyanidins B2 and B3325.37–811.95 mg/g (GAE)Anastasiadi et al. (2009)
Grape stemtrans-Resveratrol, e-viniferin367.1–494.2 mg/g (GAE)Anastasiadi et al. (2009), Püssa et al. (2006)
Grape pomaceAnthocyanins, catechins, flavonol glycosides, phenolic acids, trans-resveratrol107.12–376.71 mg/g (GAE)Anastasiadi et al. (2009), Yi et al. (2009)
Citrus by products (peel)Hesperidin, narirutin, naringin eriocitrin and their glycosides, hydroxycinnamic acid24 mg/g (GAE)Manthey and Grohmann (2001), Peterson et al. (2006), Sultana et al. (2008)
Mango peelFlavonol-O-glycosides, xanthone-C-glycosides55–110 mg/g (GAE)Ajila et al. (2007), Schieber et al. (2003b)
Mango seedGallic acid, ellagic acid, gallates117 mg/g (GAE)Puravankara et al. (2000), Soong and Barlow (2004)
Pomegranate peelPunicalagin, punicalin, ellagic acid, gallagic acid, quercetin, kaemferol, myricetin364 mg/g (GAE)Sultana et al. (2008)
Banana peelDopamine, flavonone glycoside, naringin, rutin11 mg/g (GAE)Kanazawa and Sakakibara (2000), Sultana et al. (2008)
Banana bractsAnthocyaninPazmino-Duran et al. (2001)
Longan seedsGallic acid, ellagic acidSoong and Barlow (2005, 2006)
Almond hullCatechin, procatechuic acid, chlorogenic acid, cryptochlorogenic acid, prenylated benzoic acid35.9–166.7 mg/g (GAE)Sang et al. (2002a), Sfahlan et al. (2009)
Almond green shell coverCaffeic acid, p-coumaric acid, ferulic acid, sinapic acid18.5–62.7 mg/g (GAE), 71 mg/g (CE)Sfahlan et al. (2009), Wijeratne et al. (2006), Siriwardhana and Shahidi (2002)
Almond skinFlavan-3-ols, flavonol glycosides, dihydroflavonols, flavonones, phenolic acid88 mg/g (CE)Siriwardhana and Shahidi (2002)
Hazelnut skinPhenolic acids577.7 mg/g (CE)Shahidi et al. (2007)
Hazelnut shell214.1 mg/g (CE)Shahidi et al. (2007)
Hazelnut green leafy cover127.3 mg/g (CE)Shahidi et al. (2007)
Hazelnut leaf134.7 mg/g (CE)Shahidi et al. (2007)
Cashew nut shell liquidAnacardic acids, cardols, cardanols353.6 mg/gTrevisan et al. (2006)
Cashew fibreAlkyl phenols6.1 mg/gTrevisan et al. (2006).
Cashew skinEpicatechin, catechin243 mg/gKamath and Rajini (2007)
Pistachio hullGallic acid32.8–34.7 mg/g (TAE)Goli et al. (2005), Vahabzadeh et al. (2004)
Walnut skin (pellicle)Juglone, syringic acid, ellagic acid, hydrolysable tannins, condensed tannins230–490 mg/g (GAE)Colaric et al. (2005), Labuckas et al. (2008)
Red onion dry peelQuercetin, quercetin glycoside384.7 mg/g (GAE)Singh et al. (2009)
Tomato skinQuercetin, kaempferol, rutin, phenolic acids, naringenin0.29 mg/g (GAE)Toor and Savage (2005)
Potato peelChlorogenic acid, gallic acid, protocatechuic acid, caffeic acid2.9–4.2 mg/gSingh and Rajini (2008)
Red Beet pomacel-Tryptophan, p-coumaric acid, ferulic acid87–151 mg/g (GAE)Peschel et al. (2006)
Carrot peelChlorogenic acid, caffeic acid13.8 mg/g (GAE), 9.79 mg/g (GAE)Chantaro et al. (2008), Zhang and Hamauzu (2004)
Pumpkin peelsVanillic acid, p-coumaric acid, sinapic acidSchmidtlein and Herrmann (1975)
Pumpkin seed hullp-Hydroxybenzoic acid, protocatechuic acid, vanillic acid, trans-p-coumaric acid, ferulic acid, trans-sinapic acids, syringic acid, p-hydroxybenzaldehydePeričin et al. (2009)
Pumpkin oil cakep-Hydroxybenzoic acid, protocatechuic acid, vanillic acid, trans-p-Coumaric acid, ferulic acid, trans-sinapic acids, caffeic acid, p-hydroxybenzaldehydePeričin et al. (2009)
Artichoke by-productsCaffeoylquinic acid derivatives, luteolin and apigenin glycosides, cynarosideLiorach et al. (2002), Zhu et al. (2004)
Peanut skinCaffeic acid, chlorogenic acid, ferulic acid and coumaric acid, catechins, procyanidins, resveratrol90–125 mg/g, 144.1–158.6 mg/gNepote et al. (2002), Yu et al. (2005)
Peanut hullLuteolin7.3–41.8 mg/gDuh et al. (1992)
Bean seed coatCondensed tannins, anthocyanins, quercetin, kaempferol glycosides6.7–270 mg/g (CE)Madhujith and Shahidi (2005a)
Corn branFerulic acid p-coumeric acid and vannilin50 mg/g (GAE)Ou and Kwok (2004)
Corn tassel0.74–1.57 mg/g (GAE)Mohsen and Ammar (2009)
Corn cob12–42 mg/g (GAE)Sultana et al. (2007)
Wheat branFerulic, syringic, p-hydroxybenzoic, vanillic, coumaric, caffeic, salicylic, trans-cinnamic acids4 mg/g (GAE)Kim et al. (2006), Ou and Kwok (2004), Sultana et al. (2008)
Rice bran4 mg/g (GAE)Sultana et al. (2008)
Rice hullPhytic acid, vannillic acid, syringic acid, ferulic acid, iosvitexin2 mg/g (GAE)Sultana et al. (2008)
Oat hullFerulic, p-coumaric, p-hydroxybenzoic, vanillic, o-coumaric, sinapic, 4-hydroxyphenylacetic, salicylic acids, vanillin, catechol0.56 mg/gXing and White (1997)
Buckwheat hullQuercetin, rutin, hyperin, vitexin, isovitexin, protocatechuic acid, 3,4-dihydroxybenzaldehyde, proanthocyanidins39 mg/gWatanabe et al. (1997)
Canola HullPhenolic acids, condensed tannin94.3–296 mg/g (SE)Amarowicz et al. (2000a), Naczk et al. (2005)
Olive leavesOleuropein, hydroxytyrosol, luteolin-7-glucoside, apigenin-7-glucoside, verbascosideBenavente-Garcia et al. (2000)
Olive mill waste waterHydroxytyrosol, tyrosol, oleuropein, dimethyloleuropein, verbascoside, catechol, hydroxycinnamic acids, 4-hydroxybenzoic acidBianco et al. (2003), Casa et al. (2003), Feki et al. (2006), Lesage-Meesen et al. (2001), Ramos-Cormenzana et al. (1996)
Sunflower seed shellChlorogenicacid, o-cinnamic acid, protocatechuic acid, caffeic acid, ferulic acid, syringic acid0.4–0.86 mg/gLeonardis et al. (2005), Weisz et al. (2009),
Sesame seed coatSesamin, sesamolin146.6–29.7 mg/g (CE)Chang et al. (2002), Shahidi et al. (2006)
Soybean cakeDaidzein, genistein and glycitein and their glucosides, acetylglucoside, malonylglucosideKao et al. (2008)
Flax shivep-Coumaric acid, ferulic acid, p-hydroxybenzaldehyde, vanillic acid, syringic acid, vanillin, acetovanilloneBuranov and Mazza (2009)
Cocoa leavesEpicatechin, epigallocatechin gallate, epigallocatechin, gallic acid, epicatechin gallate284 mg/gOsman et al. (2004)