Advertisement

Phenylpropanoids (Phenylpropenes) in Diets

  • Sushmita NathEmail author
  • Lutfun Nahar
  • Satyajit D. Sarker
Living reference work entry

Abstract

Phenylpropanoids are a large group of phytochemicals that are biosynthesized from the amino acids, phenylalanine, and tyrosine, and they contain at least a phenyl ring linked to a three-carbon alkyl (propyl) group (C6–C3 structure). They also form one of the common groups of bioactive phytochemicals that are distributed in plant-based diets. A majority of phenylpropanoids contains an unsaturated three-carbon alkenyl chain and is commonly known as phenylpropenes, e.g., cinnamic acid and its derivatives. Thus, the main coverage of this chapter is on phenylpropene derivatives found in food plants and their bioactivities that are established from in vivo testing using either animal models or human trials. The chapter also briefly deals with bioavailability and metabolism of these bioactive dietary phytochemicals.

Keywords

Phenylpropanoids Phenylpropenes Phenolics Bioactivity Secondary metabolite Bioavailability Food source Plant Marketed products Patents 

References

  1. Alagawany M, El-Hack MEA, Farag MR, Gopi M, Karthik K, Malik YS, Dhama K (2017) Rosmarinic acid: modes of action, medicinal values and health benefits. Anim Health Res Rev 18:167–176PubMedCrossRefGoogle Scholar
  2. Al-Dhabi NA, Arasu MV, Park CH, Park SU (2014) Recent studies on rosmarinic acid and its biological and pharmacological activities. EXCLI J 13:1192PubMedPubMedCentralGoogle Scholar
  3. Alhusainy W, Williams GM, Jeffrey AM, Iatropoulos MJ, Taylor S, Adams TB, Rietjens IM (2014) The natural basil flavonoid nevadensin protects against a methyleugenol-induced marker of hepatocarcinogenicity in male F344 rat. Food Chem Toxicol 74:28–34PubMedCrossRefGoogle Scholar
  4. Ashakirin SN, Tripathy M, Patil UK, Majeed ABA (2017) Chemistry and bioactivity of cinnamaldehyde: a natural molecule of medicinal importance. Int J Pharm Sci Res 8:2333–2340Google Scholar
  5. Ashwini R, Gajalakshmi S, Mythili S, Sathiavelu A (2011) Terminalia chebula- a pharmacological review. J Pharm Res 4:2884–2887Google Scholar
  6. Atkinson RG (2016) Phenylpropenes: occurrence, distribution, and biosynthesis in fruit. J Agric Food Chem 66:2259–2272CrossRefGoogle Scholar
  7. Bachiega TF, De Sousa JPB, Bastos JK, Sforcin JM (2012) Clove and eugenol in noncytotoxic concentrations exert immunomodulatory/anti-inflammatory action on cytokine production by murine macrophages. J Pharm Pharmacol 64:610–616PubMedCrossRefGoogle Scholar
  8. Bandara T, Uluwaduge I, Jansz E (2012) Bioactivity of cinnamon with special emphasis on diabetes mellitus: a review. Int J Food Sci Nutr 63:380–386PubMedCrossRefGoogle Scholar
  9. Baser KHC, Buchbauer G (2015) Handbook of essential oils: science, technology, and applications, 2nd edn. CRC Press, Boca Raton. ISBN 9781466590465CrossRefGoogle Scholar
  10. Beevers CS, Huang S (2011) Pharmacological and clinical properties of curcumin. Bot Target Ther 1:5–18Google Scholar
  11. Benzie IF, Wachtel-Galor S (2011) Herbal medicine: biomolecular and clinical aspects, 2nd edn. CRC Press, Boca Raton. ISBN 9781439807132CrossRefGoogle Scholar
  12. Bewley JD, Black M, Halmer P (2006) The encyclopedia of seeds: science, technology and uses. CABI, Wallingford. ISBN 9780851997230Google Scholar
  13. Bilal A, Jahan N, Ahmed A, Bilal SN, Habib S, Hajra S (2012) Phytochemical and pharmacological studies on Ocimum basilicum Linn-A review. Int J Curr Res Rev 4:73–83Google Scholar
  14. Castleman M (2001) The new healing herbs: the classic guide to nature’s best medicines featuring the top 100 time-tested herbs. Rodale Books, Emmaus. ISBN 9781579543044Google Scholar
  15. Cavender A (2006) Folk medical uses of plant foods in southern Appalachia, United States. J Ethnopharmacol 108:74–84PubMedCrossRefGoogle Scholar
  16. Chan M, Rocha S, Lehman M, White S, Santana I, Nip J, Iwasaki C, Usui T, Barratt M, Potterf S (2004) Clinical and in vitro investigation of the effects of ferulic acid on human skin pigmentation. J Investig Dermatol 122:A157–A157Google Scholar
  17. Charmkar NK, Singh R (2017) Emblica officinalis Gaertn.(Amla): a wonder gift of nature to humans. Int J Curr Microbiol App Sci 6:4267–4280CrossRefGoogle Scholar
  18. Chen KI, Erh MH, Su NW, Liu WH, Chou CC, Cheng KC (2012) Soyfoods and soybean products: from traditional use to modern applications. Appl Microbiol Biotechnol 96:9–22PubMedCrossRefGoogle Scholar
  19. Chevallier A (2016) Encyclopedia of herbal medicine, 3rd edn. Penguin, New Delhi. ISBN 9780241229446Google Scholar
  20. de Cássia da Silveira e Sá R, Andrade LN, Dos Reis Barreto De Oliveira R, De Sousa DP (2014) A review on anti-inflammatory activity of phenylpropanoids found in essential oils. Molecules 19:1459–1480PubMedCrossRefGoogle Scholar
  21. Dhawan K, Dhawan S, Sharma A (2004) Passiflora: a review update. J Ethnopharmacol 94:1–23PubMedCrossRefGoogle Scholar
  22. Diao WR, Hu QP, Zhang H, Xu JG (2014) Chemical composition, antibacterial activity and mechanism of action of essential oil from seeds of fennel (Foeniculum vulgare Mill.). Food Control 35:109–116CrossRefGoogle Scholar
  23. Duke JA (2002) Handbook of medicinal herbs, 2nd edn. CRC Press, Boca Raton. ISBN 9780849312847CrossRefGoogle Scholar
  24. Fajemiroye JO, Galdino PM, De Paula JAM, Rocha FF, Akanmu MA, Vanderlinde FA, Zjawiony JK, Costa EA (2014) Anxiolytic and antidepressant like effects of natural food flavour (E)-methyl isoeugenol. Food Funct 5:1819–1828PubMedCrossRefGoogle Scholar
  25. Freire RS, Morais SM, Catunda-Junior FEA, Pinheiro DC (2005) Synthesis and antioxidant, anti-inflammatory and gastroprotector activities of anethole and related compounds. Bioorg Med Chem 13:4353–4358PubMedCrossRefGoogle Scholar
  26. Gaire BP, Subedi L (2014) Phytochemistry, pharmacology and medicinal properties of Phyllanthus emblica Linn. Chin J Integr Med 1–8.  https://doi.org/10.1007/s11655-014-1984-2
  27. Gang DR, Lavid N, Zubieta C, Chen F, Beuerle T, Lewinsohn E, Noel JP, Pichersky E (2002) Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. Plant Cell 14:505–519PubMedPubMedCentralCrossRefGoogle Scholar
  28. Gharib R, Najjar A, Auezova L, Charcosset C, Greige-Gerges H (2017) Interaction of selected phenylpropenes with dipalmitoylphosphatidylcholine membrane and their relevance to antibacterial activity. J Membr Biol 250:259–271PubMedCrossRefGoogle Scholar
  29. Gross M, Lewinsohn E, Tadmor Y, Bar E, Dudai N, Cohen Y, Friedman J (2009) The inheritance of volatile phenylpropenes in bitter fennel (Foeniculum vulgare Mill. var. vulgare, Apiaceae) chemotypes and their distribution within the plant. Biochem Syst Ecol 37:308–316CrossRefGoogle Scholar
  30. Guillén SC, Arraiza MP, Sarmiento MA (2017) Medicinal and aromatic plants sustainable assessment. In: Medicinal and aromatic plants: the basics of industrial application, vol 1. Bentham Science Publishers, Sharjah, pp 103–117CrossRefGoogle Scholar
  31. Gupta SC, Sung B, Kim JH, Prasad S, Li S, Aggarwal BB (2013) Multitargeting by turmeric, the golden spice: from kitchen to clinic. Mol Nutr Food Res 57:1510–1528PubMedCrossRefGoogle Scholar
  32. Hameed H, Aydin S, Başaran N (2016) Sinapic acid: is it safe for humans? FABAD J Pharm Sci 41:39–49Google Scholar
  33. Hechtman L (2013) Clinical naturopathic medicine-eBook. Churchill Livingstone Elsevier, Australia. eISBN 9780729582261Google Scholar
  34. Jafri M, Javed K, Singh S (2001) Evaluation of the gastric antiulcerogenic effect of large cardamom (fruits of Amomum subulatum Roxb). J Ethnopharmacol 75:89–94PubMedCrossRefGoogle Scholar
  35. Jirovetz L, Buchbauer G, Stoilova I, Stoyanova A, Krastanov A, Schmidt E (2006) Chemical composition and antioxidant properties of clove leaf essential oil. J Agric Food Chem 54:6303–6307PubMedCrossRefGoogle Scholar
  36. Kádasi A, Sirotkin AV, Maruniaková N, Kolesárová A, Bulla J, Grossmann R (2012) The effect of curcumin on secretory activity, proliferation and apoptosis of the porcine ovarian granulosa cells. J Microbiol Biotechnol Food Sci 2:349Google Scholar
  37. Kang P, Kim KY, Lee HS, Min SS, Seol GH (2013) Anti-inflammatory effects of anethole in lipopolysaccharide-induced acute lung injury in mice. Life Sci 93:955–961PubMedCrossRefPubMedCentralGoogle Scholar
  38. Kapoor LD (2017) Handbook of ayurvedic medicinal plants: herbal reference library. Routledge, New York. eBook ISBN 9781351443241CrossRefGoogle Scholar
  39. Kaur G, Sultana S (2012) Evaluation of antiarthritic activity of isoeugenol in adjuvant induced arthritis in murine model. Food Chem Toxicol 50:2689–2695PubMedCrossRefPubMedCentralGoogle Scholar
  40. Khare CP (2004) Indian herbal remedies: rational western therapy, ayurvedic, and other traditional usage, botany. Springer Science & Business Media, Berlin. ISBN 9783540010265CrossRefGoogle Scholar
  41. Kichu M, Malewska T, Akter K, Imchen I, Harrington D, Kohen J, Vemulpad SR, Jamie JF (2015) An ethnobotanical study of medicinal plants of Chungtia village, Nagaland, India. J Ethnopharmacol 166:5–17PubMedCrossRefGoogle Scholar
  42. Kim H, Song MJ, Potter D (2006) Medicinal efficacy of plants utilized as temple food in traditional Korean Buddhism. J Ethnopharmacol 104:32–46PubMedCrossRefGoogle Scholar
  43. Koeduka T (2018) Functional evolution of biosynthetic enzymes that produce plant volatiles. Biosci Biotechnol Biochem 82:192–199PubMedCrossRefGoogle Scholar
  44. Koeduka T, Sugimoto K, Watanabe B, Someya N, Kawanishi D, Gotoh T, Ozawa R, Takabayashi J, Matsui K, Hiratake J (2014) Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens. Plant Biol 16:451–456PubMedCrossRefGoogle Scholar
  45. Kooti W, Ali-Akbari S, Asadi-Samani M, Ghadery H, Ashtary-Larky D (2015) A review on medicinal plant of Apium graveolens. Adv Herb Med 1:48–59Google Scholar
  46. Kraft D (2016) The A–Z guide to food as medicine. CRC Press, Boca Raton. eBook ISBN 9780429186424CrossRefGoogle Scholar
  47. Kuete V (2017) Medicinal spices and vegetables from Africa: therapeutic potential against metabolic, inflammatory, infectious and systemic diseases. Academic, Amsterdam. ISBN 978012809286Google Scholar
  48. Kumar KS, Bhowmik D, Duraivel S, Umadevi M (2012) Traditional and medicinal uses of banana. J Pharmacogn Phytochem 1:51–63Google Scholar
  49. Lans CA (2006) Ethnomedicines used in Trinidad and Tobago for urinary problems and diabetes mellitus. J Ethnobiol Ethnomed 2:45PubMedPubMedCentralCrossRefGoogle Scholar
  50. Lim TK (2012a) Citrus x limon. In: Edible medicinal and non-medicinal plants: volume 4, fruits. Springer, Dordrecht. eBook ISBN 978940074053Google Scholar
  51. Lim TK (2012b) Cucumis melo (Reticulatus Group). In: Edible medicinal and non-medicinal plants: volume 2, fruits. Springer, Dordrecht. eBook ISBN 9789400717640Google Scholar
  52. Lim TK (2012c) Fragaria x ananassa. In: Edible medicinal and non-medicinal plants: volume 4, fruits. Springer, Dordrecht. eBook ISBN 978940074053Google Scholar
  53. Lim TK (2012d) Malus x domestica. In: Edible medicinal and non-medicinal plants: volume 4, fruits. Springer, Dordrecht. eBook ISBN 978940074053Google Scholar
  54. Lim TK (2012e) Morus alba. In: Edible medicinal and non-medicinal plants: volume 3, fruits. Springer, Dordrecht. eBook ISBN 9789400725348Google Scholar
  55. Lim TK (2012f) Musa acuminata (AA Group) ‘Sucrier’. In: Edible medicinal and non-medicinal plants: volume 3, fruits. Springer, Dordrecht. eBook ISBN 9789400725348Google Scholar
  56. Lim TK (2012g) Myristica fragrans. In: Edible medicinal and non-medicinal plants: volume 3, fruits. Springer, Dordrecht. eBook ISBN 9789400725348Google Scholar
  57. Lim TK (2012h) Myrtus communis. In: Edible medicinal and non-medicinal plants: volume 3, fruits. Springer, Dordrecht. eBook ISBN 9789400725348Google Scholar
  58. Lim TK (2012i) Passiflora edulis. In: Edible medicinal and non-medicinal plants: volume 4, fruits. Springer, Dordrecht. eBook ISBN 978940074053Google Scholar
  59. Lim TK (2013a) Elettaria cardamomum. In: Edible medicinal and non-medicinal plants: volume 5, fruits. Springer, Dordrecht. eBook ISBN 9789400756533Google Scholar
  60. Lim TK (2013b) Foeniculum vulgare. In: Edible medicinal and non-medicinal plants: volume 5, fruits. Springer, Dordrecht. eBook ISBN 9789400756533Google Scholar
  61. Lim TK (2013c) Illicium verum. In: Edible medicinal and non-medicinal plants: volume 6, fruits. Springer. eBook ISBN 9789400756281, DordrechtGoogle Scholar
  62. Lim TK (2014) Syzygium aromaticum. In: Edible medicinal and non-medicinal plants: volume 8, flowers. Springer, Dordrecht. eBook ISBN 9789401787482Google Scholar
  63. Lin FH, Lin JY, Gupta RD, Tournas JA, Burch JA, Selim MA, Monteiro-Riviere NA, Grichnik JM, Zielinski J, Pinnell SR (2005) Ferulic acid stabilizes a solution of vitamins C and E and doubles its photoprotection of skin. J Investig Dermatol 125:826–832PubMedCrossRefGoogle Scholar
  64. Long EL, Nelson A, Fitzhugh O, Hansen W (1963) Liver tumours produced in rats by feeding safrole. Arch Pathol 75:595–604Google Scholar
  65. Mantle F, Tiran D (2009) A–Z of complementary and alternative medicine E-book: a guide for health professionals. Churchill Livingstone Elsevier, New York. ISBN 9780443103292Google Scholar
  66. Marei GI, Abdelgaleil S (2018) Antifungal potential and biochemical effects of monoterpenes and phenylpropenes on plant pathogenic fungi. Plant Prot Sci 54:9–16Google Scholar
  67. Marinov V, Valcheva-Kuzmanova S (2015) Review on the pharmacological activities of anethole. Scr Sci Pharm 2:14–19Google Scholar
  68. Mckenna DJ, Jones K, Hughes K, Tyler VM (2011) Botanical medicines: the desk reference for major herbal supplements. Routledge, New York. ISBN 0789012650Google Scholar
  69. Miladi H, Chaieb K, Ammar E, Bakhrouf A (2010) Inhibitory effect of clove oil (Syzygium aromaticum) against Listeria monocytogenes cells incubated in fresh-cut salmon. J Food Saf 30:432–442CrossRefGoogle Scholar
  70. Morita T, Jinno K, Kawagishi H, Arimoto Y, Suganuma H, Inakuma T, Sugiyama K (2003) Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury. J Agric Food Chem 51:1560–1565PubMedCrossRefGoogle Scholar
  71. Nayak BS, Ramdath DD, Marshall JR, Isitor GN, Eversley M, Xue S, Shi J (2010) Wound-healing activity of the skin of the common grape (Vitis Vinifera) variant, cabernet sauvignon. Phytother Res 24:1151–1157PubMedGoogle Scholar
  72. Nazzaro F, Fratianni F, De Martino L, Coppola R, De Feo V (2013) Effect of essential oils on pathogenic bacteria. Pharmaceuticals 6:1451–1474PubMedPubMedCentralCrossRefGoogle Scholar
  73. Nićiforović N, Abramovič H (2014) Sinapic acid and its derivatives: natural sources and bioactivity. Compr Rev Food Sci Food Saf 13:34–51CrossRefGoogle Scholar
  74. Nunes S, Madureira AR, Campos D, Sarmento B, Gomes AM, Pintado M, Reis F (2017) Therapeutic and nutraceutical potential of rosmarinic acid-cytoprotective properties and pharmacokinetic profile. Crit Rev Food Sci Nutr 57:1799–1806PubMedGoogle Scholar
  75. Okonkwo C, Ogu A (2014) Nutritional evaluation of some selected spices commonly used in the south-eastern part of Nigeria. J Biol Agric Healthc 4:97–102Google Scholar
  76. Olajide OA, Makinde JM, Awe SO (2000) Evaluation of the pharmacological properties of nutmeg oil in rats and mice. Pharm Biol 38:385–390CrossRefGoogle Scholar
  77. Ou S, Kwok KC (2004) Ferulic acid: pharmaceutical functions, preparation and applications in foods. J Sci Food Agric 84:1261–1269CrossRefGoogle Scholar
  78. Özcan MM, Chalchat JC (2006) Chemical composition and antifungal effect of anise (Pimpinella anisum L.) fruit oil at ripening stage. Ann Microbiol 56:353–358CrossRefGoogle Scholar
  79. Paiva LBD, Goldbeck R, Santos WDD, Squina FM (2013) Ferulic acid and derivatives: molecules with potential application in the pharmaceutical field. Braz J Pharm Sci 49:395–411CrossRefGoogle Scholar
  80. Parthasarathy VA, Chempakam B, Zachariah TJ (2008) Chemistry of spices. CABI, Wallingford. ISBN 9781845934057CrossRefGoogle Scholar
  81. Pasay C, Mounsey K, Stevenson G, Davis R, Arlian L, Morgan M, Vyszenski-Moher D, Andrews K, Mccarthy J (2010) Acaricidal activity of eugenol based compounds against scabies mites. PLoS One 5:e12079PubMedPubMedCentralCrossRefGoogle Scholar
  82. Preedy VR (2015) Essential oils in food preservation, flavour and safety. Academic, Amsterdam. ISBN 9780124166417Google Scholar
  83. Preedy VR, Watson RR, Patel VB (2011) Nuts and seeds in health and disease prevention. Academic, San Diego. ISBN 9780123756886Google Scholar
  84. Price L, Price S (2012) Aromatherapy for health professionals. Churchill Livingstone Elsevier, Amsterdam. ISBN 9780702035647Google Scholar
  85. Rahimi R, Ardekani MRS (2013) Medicinal properties of Foeniculum vulgare Mill. in traditional Iranian medicine and modern phytotherapy. Chin J Integr Med 19:73–79PubMedCrossRefGoogle Scholar
  86. Rahman A, Khanom A (2013) Taxonomic and ethno-medicinal study of species from Moraceae (Mulberry) Family in Bangladesh Flora. Res Plant Sci 1:53–57Google Scholar
  87. Rahmatullah M, Ferdausi D, Mollik A, Jahan R, Chowdhury MH, Haque WM (2010) A survey of medicinal plants used by Kavirajes of Chalna area, Khulna district, Bangladesh. Afr J Tradit Complement Altern Med 7:91–97Google Scholar
  88. Ravindran PN (2000) Black pepper: Piper nigrum. CRC Press, The Netherlands. ISBN 9057024535Google Scholar
  89. Ravindran PN (2017) The encyclopedia of herbs and spices. CABI, Boston. ISBN 9781786391148CrossRefGoogle Scholar
  90. Ravindran PN, Madhusoodanan KJ (2002) Cardamom: the Genus Elettaria, 1st edn. CRC Press, London. eBook ISBN 9780429218637Google Scholar
  91. Ross I (2005) Medicinal plants of the world: volume 3, chemical constituents, traditional and modern uses. Humana Press Inc, Totowa. ISBN 9781588291295Google Scholar
  92. Saija A, Tomaino A, Cascio RL, Trombetta D, Proteggente A, De Pasquale A, Uccella N, Bonina F (1999) Ferulic and caffeic acids as potential protective agents against photooxidative skin damage. J Sci Food Agric 79:476–480CrossRefGoogle Scholar
  93. Sarker S, Nahar L (2007) Chemistry for pharmacy students: general, organic and natural product chemistry. Wiley, Hoboken. eBook ISBN 9781118687536CrossRefGoogle Scholar
  94. Sarker, S. D., Latif, Z., Stewart, M. & Nahar, L. 2002. Phytochemistry of the genus Magnolia, medicinal and aromatic plants–industrial profiles. Taylor & Francis, London. eBook ISBN 0203216652Google Scholar
  95. Shojaii A, Abdollahi Fard M (2012) Review of pharmacological properties and chemical constituents of Pimpinella anisum. Int Sch Res Netw Pharm 2012:1–8Google Scholar
  96. Świzdor A, Panek A, Milecka-Tronina N, Kołek T (2012) Biotransformations utilizing β-oxidation cycle reactions in the synthesis of natural compounds and medicines. Int J Mol Sci 13:16514–16543PubMedCrossRefGoogle Scholar
  97. Tisserand R, Young R (2014) Essential oil safety: a guide for health care professionals. Churchill Livingstone Elsevier, Edinburgh. ISBN 9780443062414Google Scholar
  98. Variya BC, Bakrania AK, Patel SS (2016) Emblica officinalis (Amla): a review for its phytochemistry, ethnomedicinal uses and medicinal potentials with respect to molecular mechanisms. Pharmacol Res 111:180–200PubMedCrossRefGoogle Scholar
  99. Verma S, Rajeevan V, Bordia A, Jain V (2010) Greater cardamom (Amomum subulatum Roxb.)–a cardio-adaptogen against physical stress. J Herb Med Toxicol 4:55–58Google Scholar
  100. Wang GW, Hu WT, Huang BK, Qin LP (2011) Illicium verum: a review on its botany, traditional use, chemistry and pharmacology. J Ethnopharmacol 136:10–20PubMedCrossRefGoogle Scholar
  101. Yogalakshmi B, Viswanathan P, Anuradha CV (2010) Investigation of antioxidant, anti-inflammatory and DNA-protective properties of eugenol in thioacetamide-induced liver injury in rats. Toxicology 268:204–212PubMedCrossRefGoogle Scholar
  102. Zhang P, Tang Y, Li NG, Zhu Y, Duan JA (2014) Bioactivity and chemical synthesis of caffeic acid phenethyl ester and its derivatives. Molecules 19:16458–16476PubMedPubMedCentralCrossRefGoogle Scholar
  103. Zhao Z, Moghadasian MH (2008) Chemistry, natural sources, dietary intake and pharmacokinetic properties of ferulic acid: a review. Food Chem 109:691–702PubMedCrossRefGoogle Scholar

Copyright information

© Springer Nature Singapore Pte Ltd. 2020

Authors and Affiliations

  • Sushmita Nath
    • 1
    Email author
  • Lutfun Nahar
    • 1
  • Satyajit D. Sarker
    • 1
  1. 1.Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular SciencesLiverpool John Moores UniversityLiverpoolUK

Personalised recommendations