Ferulic acid explained

Ferulic acid is a hydroxycinnamic acid derivative and a phenolic compound. It is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans.[1] Salts and esters derived from ferulic acid are called ferulates.

Occurrence in nature

As a building block of lignocelluloses, such as pectin and lignin, ferulic acid is ubiquitous in the plant kingdom, including a number of vegetable sources. It occurs in particularly high concentrations in popcorn and bamboo shoots.[2] [3] It is a major metabolite of chlorogenic acids in humans along with caffeic and isoferulic acid, and is absorbed in the small intestine, whereas other metabolites such as dihydroferulic acid, feruloylglycine and dihydroferulic acid sulfate are produced from chlorogenic acid in the large intestine by the action of gut flora.[4]

In cereals, ferulic acid is localized in the bran – the hard outer layer of grain. In wheat, phenolic compounds are mainly found in the form of insoluble bound ferulic acid and may be relevant to resistance to wheat fungal diseases.[5] The highest known concentration of ferulic acid glucoside has been found in flaxseed .[6] It is also found in barley grain.[7]

Asterid eudicot plants can also produce ferulic acid. The tea brewed from the leaves of yacón (Smallanthus sonchifolius), a plant traditionally grown in the northern and central Andes, contains quantities of ferulic acid. In legumes, the white bean variety navy bean is the richest source of ferulic acid among the common bean (Phaseolus vulgaris) varieties.[8] It is also found in horse grams (Macrotyloma uniflorum).

Although there are many sources of ferulic acid in nature, its bioavailability depends on the form in which it is present: free ferulic acid has limited solubility in water, and hence poor bioavailability. In wheat grain, ferulic acid is found bound to cell wall polysaccharides, allowing it to be released and absorbed in the small intestine.[9]

In herbal medicines

Ferulic acid has been identified in Chinese medicine herbs such as Angelica sinensis (female ginseng), Cimicifuga heracleifolia[10] and Ligusticum chuangxiong. It is also found in the tea brewed from the European centaury (Centaurium erythraea), a plant used as a medical herb in many parts of Europe.[11]

In processed foods

Cooked sweetcorn releases increased levels of ferulic acid.[12] As plant sterol esters, this compound is naturally found in rice bran oil, a popular cooking oil in several Asian countries.[13]

Ferulic acid glucoside can be found in commercial breads containing flaxseed.[14] Rye bread contains ferulic acid dehydrodimers.[15]

Metabolism

Biosynthesis

Ferulic acid is biosynthesized in plants from caffeic acid by the action of the enzyme caffeate O-methyltransferase.[16] [1]

In a proposed ferulic acid biosynthetic pathway for Escherichia coli, L-tyrosine is converted to 4-coumaric acid by tyrosine ammonia lyase, which is converted to caffeic acid by Sam5, which is then converted to ferulic acid by caffeic acid methyltransferase.[17]

Ferulic acid, together with dihydroferulic acid, is a component of lignocellulose, serving to crosslink the lignin and polysaccharides, thereby conferring rigidity to the cell walls.[18]

It is an intermediate in the synthesis of monolignols, the monomers of lignin, and is also used for the synthesis of lignans.

Biodegradation

Ferulic acid is converted by certain strains of yeast, notably strains used in brewing of wheat beers, such as Saccharomyces delbrueckii (Torulaspora delbrueckii), to 4-vinyl guaiacol (2-methoxy-4-vinylphenol) which gives beers such as Weissbier and Wit their distinctive clove-like flavour. Saccharomyces cerevisiae (dry baker's yeast) and Pseudomonas fluorescens are also able to convert trans-ferulic acid into 2-methoxy-4-vinylphenol.[19] In P. fluorescens, a ferulic acid decarboxylase has been isolated.[20]

Ecology

Ferulic acid is one of the compounds that initiate the vir (virulence) region of Agrobacterium tumefaciens, inducing it to infect plant cells.[21]

Extraction

It can be extracted from wheat bran and maize bran using concentrated alkali.[22]

See also

Notes and References

  1. 10.1111/pbi.12292. Ferulic acid: A Key Component in Grass Lignocellulose Recalcitrance to Hydrolysis. 2015. De Oliveira. Dyoni Matias. Finger-Teixeira. Aline. Rodrigues Mota. Thatiane. Salvador. Victor Hugo. Moreira-Vilar. Flávia Carolina. Correa Molinari. Hugo Bruno. Craig Mitchell. Rowan Andrew. Marchiosi. Rogério. Ferrarese-Filho. Osvaldo. Dantas Dos Santos. Wanderley. Plant Biotechnology Journal. 13. 9. 1224–1232. 25417596. free.
  2. Zhao. Zhaohui. Moghadasian. Mohammed H.. Chemistry, natural sources, dietary intake and pharmacokinetic properties of ferulic acid: A review. Food Chemistry. August 2008. 109. 4. 691–702. 10.1016/j.foodchem.2008.02.039. 26049981.
  3. Kumar. Naresh. Pruthi. Vikas. Potential applications of ferulic acid from natural sources. Biotechnology Reports. December 2014. 4. 86–93. 10.1016/j.btre.2014.09.002. 28626667. 5466124.
  4. Book: Bagchi. Debasis. Moriyama. Hiroyoshi. Swaroop. Anand. Green Coffee Bean Extract in Human Health. 2016. CRC Press. 9781315353982. 92. 23 September 2017. en.
  5. 10.1111/j.1365-2621.2005.01057.x . Effect of wheat variety, farming site, and bread-baking on total phenolics . 2006 . Gelinas . Pierre . McKinnon . Carole M. . International Journal of Food Science and Technology . 41 . 3 . 329–332.
  6. 10.1002/pca.973 . 17623361 . Microwave-assisted extraction of the main phenolic compounds in flaxseed . 2007 . Beejmohun . Vickram . Fliniaux . Ophélie . Phytochemical Analysis . 18 . 4 . 275–285.
  7. Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration. Zory. Quinde-Axtell. Byung-Kee. Baik. J. Agric. Food Chem.. 2006. 54. 26. 9978–84. 10.1021/jf060974w. 17177530.
  8. Luthria . Devanand L. . Pastor-Corrales . Marcial A. . 2006 . Phenolic acids content of fifteen dry edible bean (Phaseolus vulgaris L.) varieties . Journal of Food Composition and Analysis . 19 . 2–3. 205–211 . 10.1016/j.jfca.2005.09.003.
  9. 10.1016/j.jcs.2008.12.001 . Bioavailability of ferulic acid is determined by its bioaccessibility. 2009 . Anson . Nuria Mateo . van den Berg . Robin . Bast . Aalt . Haenen . Guido R. M. M. . Journal of Cereal Science . 49 . 2 . 296–300.
  10. Sakai. S.. Kawamata. H.. Kogure. T.. Mantani. N.. Terasawa. K.. Umatake. M.. Ochiai. H.. Inhibitory effect of ferulic acid and isoferulic acid on the production of macrophage inflammatory protein-2 in response to respiratory syncytial virus infection in RAW264.7 cells. Mediators of Inflammation. 1999. 8. 3. 173–175. 10704056. 10.1080/09629359990513. 1781798.
  11. 10.1021/jf001145s . Antioxidant Activity of Centaurium erythraea Infusion Evidenced by Its Superoxide Radical Scavenging and Xanthine Oxidase Inhibitory Activity . 2001 . Valentão . P. . Fernandes . E. . Carvalho . F. . Andrade . P. B. . Seabra . R. M. . Bastos . M. L. . Journal of Agricultural and Food Chemistry . 49 . 7 . 3476–3479 . 11453794.
  12. Web site: Cooking sweet corn boosts its ability to fight cancer and heart disease by freeing healthful compounds, Cornell scientists find . Cornell News . 2009-09-07.
  13. Book: Orthoefer, F. T. . Bailey's Industrial Oil and Fat Products . 6th . 2 . F. . Shahidi . 2005 . John Wiley & Sons, Inc. . 978-0-471-38552-3 . 465 . Chapter 10: Rice Bran Oil . https://books.google.com/books?id=wG-0QgAACAAJ . 2012-03-01.
  14. 10.1016/j.foodchem.2008.02.088 . 26047292 . Phenolic glucosides in bread containing flaxseed . 2008 . Strandås . C. . Kamal-Eldin . A. . Andersson . R. . Åman . P. . Food Chemistry . 110 . 4 . 997–999.
  15. Boskov Hansen. H.. Andreasen. M.. Nielsen. M.. Larsen. L.. Knudsen. Bach K.. Meyer. A.. Christensen. L.. Hansen. Å.. Changes in dietary fibre, phenolic acids and activity of endogenous enzymes during rye bread-making. European Food Research and Technology. 214. 1. 2014. 33–42. 1438-2377. 10.1007/s00217-001-0417-6. 85239461.
  16. Book: Shahadi . Fereidoon. Naczk . Marian. Phenolics in Food and Nutraceuticals. limited . CRC Press. Florida. 978-1-58716-138-4. 4 . 2004.
  17. Kang . Sun-Young . Choi . Oksik . Lee . Jae Kyung . Hwang . Bang Yeon . Uhm . Tai-Boong . Hong . Young-Soo . Artificial biosynthesis of phenylpropanoic acids in a tyrosine overproducing Escherichia coli strain . Microbial Cell Factories . December 2012 . 11 . 1 . 153 . 10.1186/1475-2859-11-153 . 23206756 . 3554431 . free .
  18. Iiyama. K.. Lam. T. B.-T.. Stone. B. A.. Covalent Cross-Links in the Cell Wall. Plant Physiology. 104. 2. 1994. 315–320. 0032-0889. 10.1104/pp.104.2.315. 12232082. 159201.
  19. Huang . Z. . Dostal . L. . Rosazza . J. P. . Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens . Applied and Environmental Microbiology . 59 . 7 . 2244–2250 . 1993 . 10.1128/AEM.59.7.2244-2250.1993 . 8395165 . 182264.
  20. Huang . Z. . Dostal . L. . Rosazza . J. P. . Purification and characterization of a ferulic acid decarboxylase from Pseudomonas fluorescens. Journal of Bacteriology . 176 . 19 . 5912–5918 . 1994 . 7928951 . 196807. 10.1128/jb.176.19.5912-5918.1994.
  21. Kalogeraki. Virginia S.. Zhu. Jun. Eberhard. Anatol. Madsen. Eugene L.. Winans. Stephen C.. The phenolic vir gene inducer ferulic acid is O-demethylated by the VirH2 protein of an Agrobacterium tumefaciens Ti plasmid. Molecular Microbiology. November 1999. 34. 3. 512–522. 10.1046/j.1365-2958.1999.01617.x. 10564493. 28658847. free.
  22. Buranov. Anvar U.. G.. Mazza. Extraction and purification of ferulic acid from flax shives, wheat and corn bran by alkaline hydrolysis and pressurised solvents. Food Chemistry. 2009. 115. 4. 1542–1548. 10.1016/j.foodchem.2009.01.059.