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Phenolic Phytochemicals: Sources, Biosynthesis, Extraction, and Their Isolation

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Role of Phenolic Phytochemicals in Diabetes Management

Abstract

Phenolic compounds are among the major group of phytochemicals that are extremely diverse in nature, ranging from flavonoids to polyphenolic amides. They are available in almost every plant part; however, their bioavailability differs from one plant to another. Their biosynthesis is a complex phenomena where one phenolic compound is an intermediate or precursor of another. In this chapter, classification of phenolic phytochemicals and their biosynthesis has been discussed. Various extraction and isolation techniques have been briefly discussed. Finally, a brief discussion on identification, quantification, and structural characterization of various phenolic compounds has been highlighted.

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References

  • Abascal K, Ganora L, Yarnell E (2005) The effect of freeze-drying and its implications for botanical medicine: a review. Phytother Res 19:655–660

    Article  PubMed  Google Scholar 

  • Abd El-Mawla AMA, Beerhues L (2002) Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum. Planta 214(5):727–733

    Article  CAS  PubMed  Google Scholar 

  • Aherne SA, O’Brien NM (2002) Dietary flavonols: chemistry, food content, and metabolism. Nutrition 18:75–81

    Article  CAS  PubMed  Google Scholar 

  • Amalraj A, Pius A, Gopi S, Gopi S (2017) Biological activities of curcuminoids, other biomolecules from turmeric and their derivatives – a review. J Tradit Complement Med 7:205–233

    Article  PubMed  Google Scholar 

  • Bianco A, Ramunno A (2006) The chemistry of Olea Europaea. Stud Nat Prod Chem 33(PART M):859–903

    Article  CAS  Google Scholar 

  • Bontpart T, Cheynier V, Ageorges A, Terrier N (2015) BAHD or SCPL acyltransferase? What a dilemma for acylation in the world of plant phenolic compounds. New Phytol 208:695–707

    Article  CAS  PubMed  Google Scholar 

  • Campos‐Vega R, Oomah BD (2013) Chemistry and classification of phytochemicals. In: Tiwari B, Brunton NP, Brennan CS (eds) Handbook of plant food phytochemicals. Available from: https://doi.org/10.1002/9781118464717.ch2

    Chapter  Google Scholar 

  • Chan SC, Chang YS, Kuo SC (1997) Neoflavonoids from Dalbergia odorifera. Phytochemistry 46(5):947–949

    Article  CAS  Google Scholar 

  • Chan C-H, Yusoff R, Ngoh G-C (2014) Modeling and kinetics study of conventional and assisted batch solvent extraction. Chem Eng Res Des 92(6):1169–1186

    Article  CAS  Google Scholar 

  • Cheynier V, Comte G, Davies KM, Lattanzio V, Martens S (2013) Plant phenolics: recent advances on their biosynthesis, genetics, andecophysiology. Plant Physiol Biochem 72:1–20

    Article  CAS  PubMed  Google Scholar 

  • Chitra M, Sukumar E, Suja V, Devi S (1994) Antitumor, anti-inflammatory and analgesic property of Embelin, a plant product. Chemotherapy 40(2):109–113. Available from: https://doi.org/10.1159/000239181

    Article  CAS  PubMed  Google Scholar 

  • D’Auria JC (2006) Acyltransferases in plants: a good time to be BAHD. Curr Opin Plant Biol 9:331–340

    Article  PubMed  CAS  Google Scholar 

  • Dai J, Mumper RJ (2010) Plant phenolics: extraction, analysis and their antioxidant and anticancer properties. Molecules 15:7313–7352

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Daniel EM, Krupnick AS, Heur YH, Blinzler JA, Nims RW, Stoner GD (1989) Extraction, stability, and quantitation of ellagic acid in various fruits and nuts. J Food Compos Anal 2(4):338–349

    Article  CAS  Google Scholar 

  • Dao TTH, Linthorst HJM, Verpoorte R (2011) Chalcone synthase and its functions in plant resistance. Phytochem Rev 10(3):397–412

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Del Rio D, Rodriguez-Mateos A, Spencer JPE, Tognolini M, Borges G, Crozier A (2013) Dietary (Poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases. Antioxid Redox Signal 18(14):1818–1892

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Dixon RA (2004) Phytoestrogens. Annu Rev Plant Biol 55(1):225–261

    Article  CAS  PubMed  Google Scholar 

  • Esclapez MD, García-Pérez JV, Mulet A, Cárcel JA (2011) Ultrasound-assisted extraction of natural products. Food Eng Rev 3:108–120

    Article  Google Scholar 

  • Ferreira D, Slade D (2002) Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Nat Prod Rep 19(5):517–541

    Article  CAS  PubMed  Google Scholar 

  • Figueiras TS, Neves-Petersen MT, Petersen SB (2011) Activation energy of light induced isomerization of resveratrol. J Fluoresc 21(5):1897–1906

    Article  CAS  PubMed  Google Scholar 

  • Gabetta B, Fuzzati N, Griffini A, Lolla E, Pace R, Ruffilli T et al (2000) Characterization of proanthocyanidins from grape seeds. Fitoterapia 71(2):162–175

    Article  CAS  PubMed  Google Scholar 

  • Gensheimer M (2004) Chalcone isomerase family and fold: no longer unique to plants. Protein Sci 13(2):540–544

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Gião MS, Pereira CI, Fonseca SC, Pintado ME, Malcata FX (2009) Effect of particle size upon the extent of extraction of antioxidant power from the plants Agrimonia eupatoria, Salvia sp. and Satureja montana. Food Chem 117(3):412–416

    Article  CAS  Google Scholar 

  • Gocan S (2002) Stationary phases for thin-layer chromatography. J Chromatogr Sci 40(10):538–549

    Article  CAS  PubMed  Google Scholar 

  • Gupta A, Naraniwal M, Kothari V, Education S, Gupta A, Naraniwal M et al (2012) Modern extraction methods for preparation of bioactive plant extracts. Int J Appl Nat Sci 1(1):8–26

    Google Scholar 

  • Guzik U, Wojcieszyñska D, Jaroszek P (2010) Biosynthesis of gallic acid and its application. Biotechnologia 1:119–131

    Google Scholar 

  • Hackman RM, Polagruto JA, Zhu QY, Sun B, Fujii H, Keen CL (2008) Flavanols: digestion, absorption and bioactivity. Phytochem Rev 7:195–208

    Article  CAS  Google Scholar 

  • Hauptman PJ, Kelly RA (1999) Digitalis. Circulation 99(9):1265–1270

    Article  CAS  PubMed  Google Scholar 

  • Hawryl MA, Nowak R, Waksmundzka-Hajnos M, Swieboda R, Robak M (2012) Two-dimensional thin layer chromatographic separation of phenolic compounds from Eupatorium cannabinum extracts and their antioxidant activity. Med Chem 8(1):118–131

    Article  CAS  PubMed  Google Scholar 

  • Heinonen S, Nurmi T, Liukkonen K, Poutanen K, Wähälä K, Deyama T et al (2001) In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. J Agric Food Chem 49(7):3178–3186

    Article  CAS  PubMed  Google Scholar 

  • Hendrich S (2002) Bioavailability of isoflavones. J Chromatogr B Anal Technol Biomed Life Sci 777:203–210

    Article  CAS  Google Scholar 

  • Huynh NT, Smagghe G, Gonzales GB, Van Camp J, Raes K (2014) Enzyme-assisted extraction enhancing the phenolic release from cauliflower (Brassica oleracea L. var. botrytis) outer leaves. J Agric Food Chem 62(30):7468–7476

    Article  CAS  PubMed  Google Scholar 

  • Hyun MW, Yun YH, Kim JY, Kim SH (2011) Fungal and plant phenylalanine ammonia-lyase. Mycobiology 39:257–265

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ibrahim UK, Muhammad II, Salleh RM (2011) The effect of pH on color behavior of Brassica oleracea anthocyanin. J Appl Sci 11(13):2406–2410

    Article  CAS  Google Scholar 

  • Iriti M, Faoro F (2009) Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution. Int J Mol Sci 10:3371–3399

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Junior MRM, Leite AV, Dragano NRV (2014) Supercritical fluid extraction and stabilization of phenolic compounds from natural sources – review (Supercritical extraction and stabilization of phenolic compounds). Open Chem Eng J 5(1):51–60

    Article  Google Scholar 

  • Kasiotis KM, Pratsinis H, Kletsas D, Haroutounian SA (2013) Resveratrol and related stilbenes: their anti-aging and anti-angiogenic properties. Food Chem Toxicol 61:112–120

    Article  CAS  PubMed  Google Scholar 

  • Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M (1999) Quantitation of flavonoid constituents in Citrus fruits. J Agric Food Chem 47(9):3565–3571

    Article  CAS  PubMed  Google Scholar 

  • Khadem S, Marles RJ (2010) Monocyclic phenolic acids; hydroxy- and polyhydroxybenzoic acids: occurrence and recent bioactivity studies. Molecules 15:7985–8005

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Khoddami A, Wilkes MA, Roberts TH (2013) Techniques for analysis of plant phenolic compounds. Molecules 18:2328–2375

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Knop DR, Draths KM, Chandran SS, Barker JL, Von Daeniken R, Weber W et al (2001) Hydroaromatic equilibration during biosynthesis of shikimic acid. J Am Chem Soc 123(42):10173–10182

    Article  CAS  PubMed  Google Scholar 

  • Koleckar V, Kubikova K, Rehakova Z, Kuca K, Jun D, Jahodar L et al (2008) Condensed and hydrolysable tannins as antioxidants influencing the health. Mini Rev Med Chem 8(5):436–447

    Article  CAS  PubMed  Google Scholar 

  • Kris-Etherton P, Hecker KD, Bonanome A, Coval SM, Binkoski AE, Hilpert KF et al (2002) Bioactive compounds in foods: their role in the prevention of cardiovascular disease and cancer. Am J Med 113(Suppl 01):71S–88S

    Article  CAS  PubMed  Google Scholar 

  • Lairson LL, Henrissat B, Davies GJ, Withers SG (2008) Glycosyltransferases: structures, functions, and mechanisms. Annu Rev Biochem 77(1):521–555

    Article  CAS  PubMed  Google Scholar 

  • Lewandowska H, Kalinowska M, Lewandowski W, Stepkowski TM, Brzóska K (2016) The role of natural polyphenols in cell signaling and cytoprotection against cancer development. J Nutr Biochem 32:1–19

    Article  CAS  PubMed  Google Scholar 

  • Liazid A, Palma M, Brigui J, Barroso CG (2007) Investigation on phenolic compounds stability during microwave-assisted extraction. J Chromatogr A 1140(1–2):29–34

    Article  CAS  PubMed  Google Scholar 

  • Lindon JC, Nicholson JK, Wilson ID (2000) Directly coupled HPLC-NMR and HPLC-NMR-MS in pharmaceutical research and development. J Chromatogr B Biomed Sci Appl 748(1):233–258

    Article  CAS  PubMed  Google Scholar 

  • Lu M, Ho CT, Huang Q (2017) Extraction, bioavailability, and bioefficacy of capsaicinoids. J Food Drug Anal 25:27–36

    Article  CAS  PubMed  Google Scholar 

  • Magalhães AF, Ruiz ALTG, Tozzi AMGA, Magalhães EG (1999) Dihydroflavonols and flavanones from Lonchocarpus atropurpureus roots. Phytochemistry 52(8):1681–1685

    Article  Google Scholar 

  • Mandal V, Mohan Y, Hemalatha S (2007) Microwave assisted extraction – an innovative and promising extraction tool for medicinal plant research. Pharmacogn Rev 1(1):7–18

    CAS  Google Scholar 

  • Mandal SC, Mandal V, Das AK (2015) Qualitative phytochemical screening. In: Essentials of botanical extraction. Elsevier, pp 173–185

    Google Scholar 

  • Martens S, Mithöfer A (2005) Flavones and flavone synthases. Phytochemistry 66:2399–2407

    Article  CAS  PubMed  Google Scholar 

  • Mates M, Nesher G, Zevin S (2007) Quinines--past and present. Harefuah 146(7):560–562,572

    PubMed  Google Scholar 

  • Matthews S, Mila I, Scalbert A, Pollet B, Lapierre C, Hervé Du Penhoat CLM et al (1997) Method for estimation of Proanthocyanidins based on their acid Depolymerization in the presence of nucleophiles. J Agric Food Chem 45(4):1195–1201

    Article  CAS  Google Scholar 

  • Metri K, Bhargav H, Chowdhury P, Koka PS (2013) Ayurveda for chemo-radiotherapy induced side effects in cancer patients. J Stem Cells 8(2):115–129

    PubMed  Google Scholar 

  • Meydani M (2009) Potential health benefits of avenanthramides of oats. Nutr Rev 67:731–735

    Article  PubMed  Google Scholar 

  • Milder IEJ, Arts ICW, van de Putte B, Venema DP, Hollman PCH (2005) Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutr 93(03):393

    Article  CAS  PubMed  Google Scholar 

  • Miller DJ, Hawthorne SB (2000) Solubility of liquid organic flavor and fragrance compounds in subcritical (hot/liquid) water from 298 K to 473 K. J Chem Eng Data 45(2):315–318

    Article  CAS  Google Scholar 

  • Miyazawa M (2001) Biotransformation of Lignans and Neolignans. Curr Org Chem 5(9):975–986

    Article  CAS  Google Scholar 

  • Mohanlall V, Steenkamp P, Odhav B (2011) Isolation and characterization of anthraquinone derivatives from Ceratotheca triloba (Bernh.) Hook.f. J Med Plant Res 5(14):3132–3141

    CAS  Google Scholar 

  • Mueller-Harvey I (2001) Analysis of hydrolysable tannins. Anim Feed Sci Technol 91(1–2):3–20

    Article  CAS  Google Scholar 

  • Na Y (2009) Recent cancer drug development with xanthone structures. J Pharm Pharmacol 61(6):707–712

    Article  CAS  PubMed  Google Scholar 

  • Naczk M, Shahidi F (2006) Phenolics in cereals, fruits and vegetables: occurrence, extraction and analysis. J Pharm Biomed Anal 41:1523–1542

    Article  CAS  PubMed  Google Scholar 

  • Ottaviani JI, Momma TY, Heiss C, Kwik-Uribe C, Schroeter H, Keen CL (2011) The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo. Free Radic Biol Med 50(2):237–244

    Article  CAS  PubMed  Google Scholar 

  • Palcic MM (2011) Glycosyltransferases as biocatalysts. Curr Opin Chem Biol 15:226–233

    Article  CAS  PubMed  Google Scholar 

  • Richards LA, Dyer LA, Forister ML, Smilanich AM, Dodson CD, Leonard MD et al (2015) Phytochemical diversity drives plant–insect community diversity. Proc Natl Acad Sci 112(35):10973–10978

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Rojas LF, Gallego A, Gil A, Londoño J, Atehortúa L (2015) Monitoring accumulation of bioactive compounds in seeds and cell culture of Theobroma cacao at different stages of development. In Vitro Cell Dev Biol Plant 51(2):174–184

    Article  CAS  Google Scholar 

  • Rozmer Z, Perjési P (2016) Naturally occurring chalcones and their biological activities. Phytochem Rev 15:87–120

    Article  CAS  Google Scholar 

  • Saibabu V, Fatima Z, Khan LA, Hameed S (2015) Therapeutic potential of dietary phenolic acids. Adv Pharmacol Sci 2015:Article ID 823539

    Google Scholar 

  • Sanchez S, Demain AL (2011) Secondary metabolites, comprehensive biotechnology, 2nd edn. Elsevier, pp 155–167

    Google Scholar 

  • Sankawa U, Hakamatsuka T (1997) Biosynthesis of isoflavone and related compounds in tissue cultures of Pueraria lobata. Dynamic aspects of natural products chemistry. Kodansha Scientific, Tokyo, pp 25–48

    Google Scholar 

  • Sejali SNF, Anuar MS (2011) Effect of drying methods on phenolic contents of neem ( Azadirachta indica) leaf powder. J Herbs Spices Med Plants 17(2):119–131

    Article  CAS  Google Scholar 

  • Sepúlveda L, Ascacio A, Rodríguez-Herrera R, Aguilera-Carbó A, Aguilar CN (2011) Ellagic acid: biological properties and biotechnological development for production processes. Afr J Biotechnol 10(22):4518–4523

    Google Scholar 

  • Setyaningsih W, Saputro IE, Palma M, Barroso CG (2015) Optimisation and validation of the microwave-assisted extraction of phenolic compounds from rice grains. Food Chem 169:141–149

    Article  CAS  PubMed  Google Scholar 

  • Sharma OP, Bhat TK, Singh B (1998) Thin-layer chromatography of gallic acid, methyl gallate, pyrogallol, phloroglucinol, catechol, resorcinol, hydroquinone, catechin, epicatechin, cinnamic acid, p-coumaric acid, ferulic acid and tannic acid. J Chromatogr A 822(1):167–171

    Article  CAS  Google Scholar 

  • Shouqin Z, Jim X, Changzheng W (2005) Note: effect of high hydrostatic pressure on extraction of flavonoids in propolis. Food Sci Technol Int 11(3):213–216

    Article  CAS  Google Scholar 

  • Shrivastava SRB, Shrivastava PS, Ramasamy J (2015) Mainstreaming of Ayurveda, Yoga, Naturopathy, Unani, Siddha, and homeopathy with the health care delivery system in India. J Tradit Complement Med 5(2):116–118

    Article  PubMed  PubMed Central  Google Scholar 

  • Škerget M, Kotnik P, Hadolin M, Hraš AR, Simonič M, Knez Ž (2005) Phenols, proanthocyanidins, flavones and flavonols in some plant materials and their antioxidant activities. Food Chem 89(2):191–198

    Article  CAS  Google Scholar 

  • Stalmach A, Crozier A, Clifford MN, Williamson G (2011) Phytochemicals in coffee and the bioavailability of chlorogenic acids. Teas, cocoa coffee plant second metab heal. Blackwell publishing Ltd, pp 143–168

    Google Scholar 

  • Surh Y-J (2003) Cancer chemoprevention with dietary phytochemicals. Nat Rev Cancer 3(10):768–780

    Article  CAS  PubMed  Google Scholar 

  • Tohge T, Watanabe M, Hoefgen R, Fernie AR (2013) Shikimate and phenylalanine biosynthesis in the green lineage. Front Plant Sci 4:62

    Article  PubMed  PubMed Central  Google Scholar 

  • Tripoli E, La Guardia M, Giammanco S, Di Majo D, Giammanco M (2007) Citrus flavonoids: molecular structure, biological activity and nutritional properties: a review. Food Chem 104(2):466–479

    Article  CAS  Google Scholar 

  • Tsao R (2010) Chemistry and biochemistry of dietary polyphenols. Nutrients 2:1231–1246

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tzin V, Galili G (2010) New insights into the shikimate and aromatic amino acids biosynthesis pathways in plants. Mol Plant 3:956–972

    Article  CAS  PubMed  Google Scholar 

  • Van Hoyweghen L, De Beer T, Deforce D, Heyerick A (2012) Phenolic compounds and anti-oxidant capacity of twelve morphologically heterogeneous bamboo species. Phytochem Anal 23(5):433–443

    Article  PubMed  CAS  Google Scholar 

  • Vinatoru M (2001) An overview of the ultrasonically assisted extraction of bioactive principles from herbs. Ultrason Sonochem 8(3):303–313

    Article  CAS  PubMed  Google Scholar 

  • Vogt T (2010) Phenylpropanoid biosynthesis. Mol Plant 3(1):2–20

    Article  CAS  PubMed  Google Scholar 

  • Wang L, Weller CL (2006) Recent advances in extraction of nutraceuticals from plants. Trends Food Sci Technol 17:300–312

    Article  CAS  Google Scholar 

  • Weidner S, Powałka A, Karamać M, Amarowicz R (2012) Extracts of phenolic compounds from seeds of three wild grapevines-comparison of their antioxidant activities and the content of phenolic compounds. Int J Mol Sci 13(3):3444–3457

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Williamson G (2017) The role of polyphenols in modern nutrition. Nutr Bull 42:226–235

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Winkel BSJ (2006) The biosynthesis of flavonoids. In: The science of flavonoids. Springer, New York, pp 71–95

    Chapter  Google Scholar 

  • Yu O, Jez JM (2008) Nature’s assembly line: biosynthesis of simple phenylpropanoids and polyketides. Plant J 54:750–762

    Article  CAS  PubMed  Google Scholar 

  • Zhuang C, Zhang W, Sheng C, Zhang W, Xing C, Miao Z (2017) Chalcone: a privileged structure in medicinal chemistry. Chem Rev 117:7762–7810

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Hoda, M., Hemaiswarya, S., Doble, M. (2019). Phenolic Phytochemicals: Sources, Biosynthesis, Extraction, and Their Isolation. In: Role of Phenolic Phytochemicals in Diabetes Management. Springer, Singapore. https://doi.org/10.1007/978-981-13-8997-9_2

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