Abstract
Phenolic acids are plant metabolites widely spread throughout the plant kingdom. Recent interest in phenolic acids stems from the potential protection they offer against oxidative damage diseases (e.g., coronary heart disease, stroke, and cancers) when consumed in fruits and vegetables. This chapter discusses the function of plant phenolic acids associated with diverse roles, including nutrient uptake, protein synthesis, photosynthesis, and allelopathy. It also provides an update of the health-promoting benefits of their important biological and pharmacological properties, especially anti-inflammatory, antioxidant, and antimutagenic and anticarcinogenic activities. The main methodologies currently being used for the extraction and quantification of these important phenolic compounds are also discussed.
Keywords
- Biosynthesis
- food
- health
- phenolic acids
- plant cell culture
This is a preview of subscription content, access via your institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsAbbreviations
- 4CL4:
-
Coumarate:coenzyme A ligase
- CA:
-
Caffeic acid
- CA4H:
-
Cinnamic acid 4-hydroxylase
- CO:
-
p-coumaric acid BA-Benzoic acid
- DAD:
-
Diode array detection
- E:
-
Ellagic
- FA:
-
Ferulic
- G:
-
Gentisic
- GA:
-
Gallic acid
- GC-MS:
-
Gas chromatography–mass spectrometry
- HCA:
-
Hydrocinnamic acid
- HPLC:
-
High-performance liquid chromatography
- JA:
-
Jasmonic acid
- LC-MS:
-
Liquid chromatography–mass spectrometry
- MS:
-
Mass spectrometry
- NADPH:
-
Nicotinamide adenine dinucleotide phosphate (reduced form)
- PAL:
-
Phenylalanine ammonia lyase
- PDAD:
-
Photodiode array detection
- RA:
-
Rosmarinic acid
- RP:
-
Reversed phase
- SA:
-
Salicylic acid
- SIA:
-
Sinapic acid
- TLC:
-
Thin-layer chromatography
- UV:
-
Ultraviolet
References
Verpoorte R, Contin A, Memelink J (2002) Biotechnology for the production of plant secondary metabolites. Phytochem Rev 1:13
Croteau R, Kutchan TM, Lewis NG (2000) Natural products (secondary metabolites). In: Buchanan B, Gruissem W, Jones R (eds) Biochemistry & molecular biology of plants. American Society of Plant Physiologists, Rockville, p 1250
Herrmann KM, Weaver LM (1999) The shikimate pathway. Annu Rev Plant Physiol Plant Mol Biol 50:473–503
Clifford MN (1999) Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden. J Sci Food Agric 79:362
Dixon R, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7:1085
Maas JL, Galletta GJ, Stoner GD (1991) Ellagic acid, an anticarcinogen in fruits, especially in strawberries: a review. HortScience 26:10
Strube M, Dragsted LO, Larsen JC (1993) Naturally occurring antitumourigens. I. Plant phenols. Nordiske Seminar- og Arbejdsrapporter 605. Nordic Council of Ministers, Copenhagen
Strack D (1997) Phenolic metabolism. In: Dey PM, Harborne JB (eds) Plant biochemistry. Academic, London, p 387
Shahidi F, Nacsk M (1995) Food phenolics: sources, chemistry, effects and application. Technomic Publ, Lancaster
Andreasen MF, Christensen LP, Meyer AS, Hansen A (2000) Content of phenolic acids and ferulic acid dehydrodimers in rye (Secale cereale L.) varieties. J Agric Food Chem 48:2837
Hartley RD, Jones EC (1978) Carbohydrates and carbohydrate esters of ferulic acid released from cell walls of lolium multiflorum by treatment with cellulotyic enzymes. Phytochemistry 15:3052
Brett C, Waldron K (1996) Cell wall architecture and the skeletal role of the cell wall. In: Brett C, Waldron K (eds) Physiology and biochemistry of plant cell walls. Chapman and Hall, London, pp 4–57
Lam TBT, Kadoya K, Liyama K (2001) Bonding of hydroxycinnamic acids to lignin: ferulic and p-coumaric acids are predominantly linked at the benzyl position of lignin, not the â-position, in grass cell walls. Phytochemistry 57:987
Klick S, Herrmann K (1998) Glucosides and glucose esters of hydroxybenzoic acids in plants. Phytochemistry 27:2177
Shahidi F, Naczk M (2004) Phenolics in food and nutraceuticals: sources, applications and health effects. CRC Press, Boca Raton, FL
Macheix JJ, Fleuriet A, Billot J (1990) Fruit phenolics. CRC Press, Boca Raton
Luy JF, Jiang H, Wu K, Zheng X, Cai Y, Katakowski M, Chopp M (2010) Effects of mixtures of phenolic acids on phosphorus uptake by cucumber seedlings. Eur J Pharmacol 641:102
Mersie W, Singh M (1993) Phenolic acids affect photosynthesis and protein synthesis by isolated leaf cells of velvet-leaf. J Chem Ecol 19:1293
Blum U, Shafer SR, Lehman ME (1999) Soils: concepts vs. an experimental model. Crit Rev Plant Sci 18:673
Moreno PRH (1995) Influence of stress factors on the secondary metabolism in suspension cultured Catharanthus roseus cells. Ph.D., Leiden University
Mandal SM, Chakraborty D, Dey S (2010) Phenolic acids act as signaling molecules in plant-microbe symbioses. Plant Signal Behav 5(4):359–368
Mirjalili MJ, Moyano E, Bonfill M, Cusido RM, Palazón J (2009) Steroidal lactones from Withania somnifera, an ancient plant for novel medicine. Molecules 14:2373
Palacio L, Baeza MC, Cantero JJ, Cusidó R, Goleniowski ME (2008) In vitro propagation of “jarilla” (Larrea divaricata cav.) and secondary metabolites production. Biol Pharm Bull 31:2321
Palacio L, Cantero JJ, Cusidó R, Goleniowski ME (2010) Effect of inoculum age on kinetic of biomass formation and phenolic accumulations in Larrea divaricata Cav. cell suspension culture. Mol Med Chem 21:64
Zhong JJ (2001) Biochemical engineering of the production of plant-specific secondary metabolites by cell suspension cultures. Adv Biochem Eng Biotechnol 72:1–26
Park MD, Uddin R, Xu H, Lee SY, Kim YK (2008) Biotechnological applications for rosmarinic acid production in plant African. J Biotechnol 7:4959
Tada H, Murakami Y, Omoto T, Shimomura K, Ishimaru K (1996) Rosmarinic acid and related phenolics in hairy root cultures of Ocimum basilicum. Phytochemistry 42:431
Chen H, Chen F, Zhang YL, Song JY (1999) Production of lithospermic acid B and rosmarinic acid in hairy root cultures of Salvia miltiorrhiza. J Ind Microbiol Biotechnol 22:133
Li W, Koike K, Asada Y, Yoshikawa T, Nikaido T (2005) Rosmarinic acid production by Coleus forskohlii hairy root cultures. Plant Cell Tissue Organ Cult 80:151
Grzegorczyk I, Krolicka A, Wysokinska H (2006) Establishment of Salvia officinalis L. hairy root cultures for the production of rosmarinic acid. Z Naturforsch 61:351
Tan SC (2000) Determinants of eating quality in fruits and vegetables. Proc Nutr Soc Aust 24:183
Fernandez de Simon B, Perez-Ilzarbe J, Hernandez T, Gomez-Cordoves CEI (1992) Importance of phenolic compounds for the characterization of fruit juices. J Agric Food Chem 40:1531
Katalinic V, Milos M, Kulisic T, Jukic M (2006) Screening of 70 medicinal plant extracts for antioxidant capacity and total phenols. Food Chem 94:550
Kim DO, Lee CY (2004) Antimelanogenic and antioxidant properties of gallic acid. Food Sci Nutr 44:253
Koshihara Y, Neichi T, Murota SI, Fujimoto AN, Tatsuno T (1984) Caffeic acid is a selective inhibitor for leukotriene biosynthesis. Biochim Biophys Acta 792:92
Lamaison JL, Petitjeanfreytet C (1996) Medicinal Lamiaceae with antioxidant activity, potential sources of rosmarinic acid. Pharm Acta Helvetiae 66:185
Yanishlieva N, Gordon M (2001) Antioxidants in food. J Agric Food Chem 52:2391
De la Rosa LA, Alvarez-Parrilla E, Gonzalez-Aguilar GA (2010) Fruit and vegetable phytochemicals- chemistry, nutritional value, and stability, 1st edn. Wiley-Blackwell, Ames
Harris CS, Mo F, Migahed L, Chepelev L, Haddad PS, Wright JS, Willmore WG, Arnason JT, Bennett SAL (2007) Plant phenolics regulate neoplastic cell growth and survival: a quantitative structure-activity and biochemical analysis. Can J Physiol Pharmacol 85:1124
Jacob RA, Burri BJ (1996) Oxidative damage and defense. Am J Clin Nutr 63:985
Huang MT, Ferraro T (1992) Phenolic compounds in food and cancer prevention. In: Phenolic compounds in food and their effects on health. II. Antioxidants and cancer prevention. American Chemical Society, Washington, DC, p 8
Block G, Patterson B, Subar A (1992) Fruit, vegetables, and cancer prevention: a review of the epidemiological evidence. Nutr Cancer 18:1–29
Olthof MR, Hollman PCH, Katan MB (2001) Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr 131:66
Falsaperlaa M, Morgiab G, Tartaronec A, Arditoc R, Romano G (2005) Support ellagic acid therapy in patients with hormone refractory prostate cancer (HRPC) on standard chemotherapy using vinorelbine and estramustine. Phosphate. Eur Urol 47:449
Kampa M, Hatzoglou A, Notas G, Damianaki A, Bakogeorgou E, Gemetzi C, Kouroumalis E, Martin PM, Castanas E (2000) Wine antioxidant polyphenols inhibit the proliferation of human prostate cancer cell lines. Nutr Cancer 37:105
Rice-Evans CA, Miller NJ, Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Rad Biol Med 20:933
Trichopoulou A, Bamia C, Trichopoulos D (2005) Mediterranean diet and survival among patients with coronary heart disease in Greece. Arch Intern Med 165:929
Fujisawa S, Atsumi T, Kadoma Y, Sakagami H (2002) Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology 177:39
Hosoda A, Ozaki Y, Kashiwada A, Mutoh M, Wakabayashi K, Mizuno K, Nomura E, Taniguchi H (2002) Syntheses of ferulic acid derivatives and their suppressive effects on cyclooxygenase-2 promoter activity. Bioorg Med Chem 10:1189
Lee SK, Mbwambo ZH, Chung HS, Luyengi L, Gamez EJC, Mehta RG, Kinghorn AD, Pezzuto JM (1998) Evaluation of the antioxidant potential of natural products. Comb Chem HighThroughput Screen 1:1
Gruz J, Ayaz FA, Torun H, Strand M (2011) Phenolic acid content and radical scavenging activity of extracts from medlar (Mespilus germanica L.) fruit at different stages of ripening. Food Chem 124:271
Stuart AE, Brooks CJW, Prescott RJ, Blackwell A (2000) 6-Methylsalicylic acid is a phytotoxin. It has antibacterial and antifeeding repellent and antifeedant activity of salicylic acid and related compounds against the biting midge, Culicoides impunctatus (Diptera: Ceratopogonidae). J Med Entomol 37:222
Heil M, Bostock RM (2002) Systemic resistance (ISR) against pathogens in the context of induced plant defences. Ann Bot 89(5):503
Verberne MC, Budi Muljono RA, Verpoorte R (1999) Salicylicacid biosynthesis. In: Hooykaas PPJ, Hall MA, Libbenga KR (eds) Biochemistry and molecular biology of plant hormones. Elsevier Science B.V, Amsterdam
Natella F, Nardini M, Di Felice M, Scaccini C (1999) Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation. Free radical research group, national institute of nutrition, Roma, Italy. J Agric Food Chem 47:1453–2323
Sircar D, Mitra A (2009) Accumulation of p-hydroxybenzoic acid in hairy roots of Daucus carota: confirming biosynthetic steps through feeding of inhibitors and precursors. J Plant Physiol 166:1370
Pugazhendhi D, Pope GS, Darbre PD (2005) Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines. J Appl Toxicol 25:301
Chong KP, Rossall S, Atong M (2009) Oestrogenic activity of p-hydroxybenzoic acid(common metabolite of paraben esters) and methylparaben in human breast cancer cell lines. J Agric Sci 1:15–20
Ashidate K, Kawamura M, Mimura D, Tohda H, Miyazaki S, Teramoto T, Hirata Y, Yamamoto Y (2005) Gentisic acid, an aspirin metabolite, inhibits oxidation of low-density lipoprotein and the formation of cholesterol ester hydroperoxides in human plasma. Eur J Pharmacol 513:173
Sharma S, Khan N, Sultana S (2004) Modulatory effect of gentisic acid on the augmentation of biochemical events of tumor promotion stage by benzoyl peroxide and ultraviolet radiation in Swiss albino mice. Toxicol Lett 28:293
Fernandez IS, Cuevas P, Angulo J, Lopez-Navajas P, Canales-Mayordomo A, Gonzalez-Corrochano R, Lozano RM, Valverde S, Jimenez-Barbero J, Romero A, Gimenez-Gallego G (2010) Gentisic acid, a compound associated with plant defense and a metabolite of aspirin, heads a new class of in vivo fibroblast growth factor inhibitors. J Biol Chem 285:11714
Wang HF, Provan GJ, Helliwell K (2003) Determination of hamamelitannin, catechins and gallic acid in witch hazel bark, twig and leaf by HPLC. J Pharm Biomed Anal 33:539
Wu JM, Jan PS, Yu HC, Haung HY, Fang HJ, Chang YI, Cheng JW, Chen HM (2009) Structure and function of a custom anticancer peptide, CB1a. Peptides 30:839
King PJ, Ma G, Miao W, Jia Q, McDougall BR, Reinecke MG, Cornell C, Kuan J, Kim TR, Robinson WE Jr (1999) Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. Med Chem 42:497
Kratz JM, Andrighetti-Frohner CR, Leal PC, Nunes RJ, Yunes RA, Trybala E, Bergstrom T, Barardi CRM, Simoes CMO (2008) Evaluation of anti-HSV-2 activity of gallic acid and pentyl gallate. Biol Pharm Bull 31:903
Itoh A, Isoda K, Kondoh M, Kawase M, Kobayashi M, Tamesada M, Yagi K (2009) Hepatoprotective effect of syringic acid and vanillic acid on concanavalin A-induced liver injury. Biol Pharm Bull 32:1215
Dhananjaya BL, Nataraju A, Gowda CDR, Sharath BK, D'Souza CJM (2009) Vanillic acid as a novel specific inhibitor of snake venom 5′-nucleotidase: a pharmacological tool in evaluating the role of the enzyme in snake envenomation. Biochemistry 74:1315
Pari L, Mohamed Jalaludeen A (2011) Protective role of sinapic acid against arsenic: induced toxicity in rats. Chem Biol Interact 194:40
Kanchana G, Shyni WJ, Rajadurai M, Periasamy R (2011) Evaluation of antihyperglycemic effect of sinapic acid in normal and streptozotocin-induced diabetes in albino rats. J Pharm 5:3338
Njoku OV, Obi C (2009) Phytochemical constituents of some selected medicinal plants. Afr J Pure Appl Chem 3:228
Ralph J, Grabber JH, Hatfield RD (1995) Lignin-ferulate crosslinks in grasses: active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr Res 275:167
Parker ML, Waldron KW (1995) Texture of Chinese water chestnut: involvement of cell wall phenolics. J Sci Food Agric 68:337
Dewick PM (2002) Medicinal natural products: a biosynthetic approach, 2nd edn. Wiley, Chichester, pp 112–129
Geissmann T, Neukom H (1971) Vernetzung von Phenolcarbonsäureestern von Polysacchariden durch oxydative phenolische Kupplung Helv. Chim Acta 54:1108
Grabber JJH, Hatfield RD, Wende G (1996) New discoveries relating to diferulates. USDFRC Research Summary
Han EH, Choi JH, Hwang YP, Park HJ, Choi CY, Chung YC, Seo JK, Jeong HG (2009) Immunostimulatory activity of aqueous extract isolated from Prunella vulgaris. Food Chem Toxicol 47:62
Hraš AR, Hadolin M, Knez Z, Bauman D (2000) Comparison of antioxidative and synergistic effects of rosemary extract with α-tocopherol, ascorbyl palmitate and citric acid in sunflower oil. Food Chem 71:229
Rimando AM, Inoshiri S, Otsuka H, Kohda H, Yamazaki K, Padolina WG, Torres L, Quintana EG, Cantoria MC (1987) Screening for mast cell histamine release inhibitory activity of Philippine medicinal plants: active constituent of Ehretia microphylla. Shoyakugaku Zasshi 41:242
Kariya K, Fukumoto Y, Tsuda T, Yamamoto T, Fukuzaki H, Takai Y (1987) Antiproliferative action of protein kinase C in cultured rabbit aortic smooth muscle cells. Exp Cell Res 173:504
Sanbongi C, Takano H, Osakabe N, Sasa N, Natsume M, Yanagisawa R, Inoue KI, Sadakane K, Ichinose T, Yoshikawa T (2004) Rosmarinic acid in perilla extract inhibits allergic inflammation induced by mite allergen, in a mouse model. Clin Exp Allergy 34:971
Lee HS, Widmer BW (1996) Phenolic compounds. In: Nollet LML (ed) Handbook of food analysis. Physical characterization and nutriet analysis. Marcel Dekker, New York, p 821
Ahmet C, Saban K, Hamdullah K, Ercan K (2005) Antifungal properties of essential oil and crude extracts of Hypericum linarioides Bosse. Biochem Syst Ecol 33:245
Marko-Varga G, Barcelo D (1992) Liquid chromatographic retention and separation of phenols and related aromatic compounds on reversed phase columns. Chromatogrphy 34:146
Hertog MGL, Hollman PCH, Katan MB (1992) Content of potentially anticarcinogenic flavonoids of vegetables and fruits commonly consumed in The Netherlands. J Agric Food Chem 40:1598
Riedel H, Cai Z, Kütük O, Smetanska I (2010) Obtaining phenolic acids from cell cultures of various Artemisia species. Afr J Biotechnol 9:8805
Konczak-Islam I, Okuno S, Yoshimoto M, Yamakawa O (2003) Composition of phenolics and anthocyanins in a sweet potato cell suspension culture. Biochem J 14:155
Kang SM, Jung HY, Kang YM, Min JY, Karigar CS, Yang JK, Kim SW, Ha YR, Lee SH, Choi MS (2004) Biotransformation and impact of ferulic acid on phenylpropanoid and capsaicin levels in Capsicum annuum L. cv. P1482 cell suspension cultures. J Agric Food Chem 53:3449
Godoy-Hernandez GC, Vazquez-Flota FA, Loyola-Vargas VM (2000) he exposure to trans-cinnamic acid of osmotically stressed Catharanthus roseus cells cultured in a 14-L bioreactor increases alkaloid accumulation. Biotechnol Lett 22:921
Budi Muljono RA, Looman AMG, Verpoorte R, Scheffer JJC (1998) Assay of salicylic acid and related compounds in plant cell cultures by capillary GC. Phytochem Anal 9:3
Budi Muljono RA (2001) The isochorismate pathway as a route to 2, 3-dihydroxybenzoic acid in Catharanthus roseus cell cultures. Ph.D. thesis, University of Leiden.
Palacio L, Cantero JJ, Cusidó R, Goleniowski ME (2011) Phenolic compound production by Larrea divaricata Cav. plant cell cultures and effect of precursor feeding. Process Biochem 46:418
Chakraborty M, Karun A, Mitra A (2009) Accumulation of phenylpropanoid derivatives in chitosan-induced cell suspension culture of Cocos nucifera. J Plant Physiol 166:63
Loescher R, Heide L (1994) Biosynthesis of p-hydroxybenzoate from p-coumarate and p-coumaroylcoenzyme A in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol 106:271
Yang JG, Uchiyama T (2000) Hydroxycinnamic acids and their dimers involved in the cessation of cell elongation in Mentha suspension culture. Biosci Biotechnol Biochem 64:862
Yoshida-Shimokawa T, Yoshida S, Kakegawa K, Ishii T (2001) Enzymic feruloylation of arabinoxylan-trisaccharide by feruloyl-CoA: arabinoxylan-trisaccharide O-hydroxycinnamoyl transferase from Oryza sativa. Planta 212:470
Zhao J, Lou J, Mou Y, Li P, Wu J, Zhou L (2011) Diterpenoids Tanshinones and phenolic acids from cultured hairy roots of Salvia milthiorrhiza. Molecules 16:2259
Morimoto S, Goto Y, Shoyama Y (1994) Production of lithospermic acid B and rosmarinic acid in callus tissue and regenerated plantlets of Salvia miltiorrhiza. J Nat Prod 57:817
Chong J, Pierrel MA, Atanassova R, Werck-Reichhart D, Fritig B, Saindrenan P (2001) Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors. Plant Physiol 125:318
Sommer J, Schroeder C, Stoeckigt J (1997) In vivo formation of vanillin glucoside. Plant Cell Tiss Org Cult 50:119
Maggi-Capeyron MF, Ceballos P, Cristol JP, Delbosc S, Le Doucen C, Pons M, Leger CL, Descomps B (2001) Wine phenolic antioxidants inhibit ap-1 transcriptional activity. J Agric Food Chem 49:5646
Makino T, Ono T, Nakamura T, Muso E, Honda G, Sasayama S (1999) Suppressive effect of rosmarinic acid on mesangioproliferative glomerulonephritis in rats. J Am Soc Nephrol 10:552
Rommel A, Wrolstad RE (1993) Ellagic acid content of red raspberry juice as influenced by cultivar, processing, and environmental factors. J Agric Food Chem 41:1951
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this entry
Cite this entry
Goleniowski, M., Bonfill, M., Cusido, R., Palazón, J. (2013). Phenolic Acids. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_64
Download citation
DOI: https://doi.org/10.1007/978-3-642-22144-6_64
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-22143-9
Online ISBN: 978-3-642-22144-6
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics