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Biological synthesis and anti-inflammatory activity of arylalkylamine

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Abstract

Hydroxycinnamic acid amides (HCAAs) are natural compounds with antifungal, anticancer, and anti-inflammatory activities. Extraction from plants and chemical synthesis have been the major approaches to obtain these compounds. We used a biological method to synthesize HCAA derivatives (arylalkylamines). Two genes, SHT encoding serotonin N-hydroxycinnamoyl transferase and 4CL encoding 4-coumaroyl-CoA ligase, were introduced into Escherichia coli. Using this E. coli transformant as a biocatalyst, 24 arylalkylamines were synthesized. The anti-inflammatory activities of five synthesized compounds, including N-p-coumaroyl phenethylamine, N-caffeoyl phenethylamine, N-p-coumaroyl 3-phenylpropylamine, N-p-coumaroyl 4-phenylbutylamine, and N-p-coumaroyl 4-methoxyphenethylamine, were measured. Among them, N-p-coumaroyl 4-phenylbutylamine showed the best anti-inflammatory activity.

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References

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

    Article  CAS  Google Scholar 

  2. Facchini PJ, Hagel J, Zulak KG (2002) Hydroxycinnamic acid amide metabolism: physiology and biochemistry. Can J Bot 80:577–589

    Article  CAS  Google Scholar 

  3. Macoy DM, Kim WY, Lee SY, Kim MG (2015) Biotic stress related functions of hydroxycinnamic acid amide in plants. J Plant Biol 58:156–163

    Article  CAS  Google Scholar 

  4. Boonen J, Bronselaer A, Nielandt J, Veryser L, De Tré G, De Spiegeleer B (2012) Alkamid database: chemistry, occurrence and functionality of plant N-alkylamides. J Ethnopharmacol 142:563–590

    Article  CAS  Google Scholar 

  5. Lee DG, Park Y, Kim MR, Jung HJ, Seu YB, Hahm KS, Woo E-R (2004) Anti-fungal effects of phenolic amides isolated from the root bark of Lycium chinense. Biotech Lett 26:1125–1130

    Article  CAS  Google Scholar 

  6. Campos L, Lisón P, López-Gresa MP, Rodrigo I, Zacarés L, Conejero V, Bellés JM (2014) Transgenic tomato plants overexpressing tyramine N-hydroxycinnamoyltransferase exhibit elevated hydroxycinnamic acid amide levels and enhanced resistance to Pseudomonas syringae. Mol Plant-Microbe Interact 27:1159–1169

    Article  Google Scholar 

  7. Macoy DM, Kim WY, Lee SY, Kim MG (2015) Biosynthesis, physiology, and functions of hydroxycinnamic acid amides in plants. Plant Biotechnol Rep 9:269–278

    Article  Google Scholar 

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

    Article  Google Scholar 

  9. Back K, Jang SM, Lee BC, Schmidt A, Strack D, Kim KM (2001) Cloning and characterization of a hydroxycinnamoyl-CoA: tyramine N-(hydroxycinnamoyl)transferase induced in response to UV-C and wounding from Capsicum annuum. Plant Cell Physiol 42:475–481

    Article  CAS  Google Scholar 

  10. Jang S-M, Ishihara A, Back K (2004) Production of coumaroylserotonin and feruloylserotonin in transgenic rice expressing pepper hydroxycinnamoyl-coenzyme A:serotonin N-(hydroxycinnamoyl)transferase. Plant Physiol 135:346–356

    Article  CAS  Google Scholar 

  11. Eudes A, Benites VT, Wang G, Baidoo EEK, Lee TS, Keasling JD, Loqué D (2015) Precursor-directed combinatorial biosynthesis of cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in Saccharomyces cerevisiae. PLoS ONE 2015:10

    Google Scholar 

  12. Lee YJ, Jeon Y, Lee JS, Kim BG, Lee CH, Ahn J-H (2007) Enzymatic synthesis of phenolic CoAs using 4-coumarate:coenzyme A ligase (4CL) from rice. Bull Kor Chem Soc 28:365–366

    Article  CAS  Google Scholar 

  13. Son S, Lewis BA (2002) Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: structure–activity relationship. J Agric Food Chem 50:468–472

    Article  CAS  Google Scholar 

  14. Park JB, Schoene N (2003) N-Caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3. Cancer Lett 202:161–171

    Article  CAS  Google Scholar 

  15. Xie LW, Atanasov AG, Guo DA, Malainer C, Zhang JX, Zehl M, Guan SH, Heiss EH, Urban E, Dirsch VM, Kopp B (2014) Activity-guided isolation of NF-kappaB inhibitors and PPAR gamma agonists from the root bark of Lycium chinense Miller. J Ethnopharmacol 152:470–477

    Article  CAS  Google Scholar 

  16. Kim EO, Min KJ, Kwon TK, Um BH, Moreau RA, Choi SW (2012) Anti-inflammatory activity of hydroxycinnamic acid derivatives isolated from corn bran in lipopolysaccharide-stimulated Raw 264.7 macrophages. Food Chem Toxicol 50:1309–1316

    Article  CAS  Google Scholar 

  17. Wang S, Suh JH, Zheng X, Wang Y, Ho C-T (2017) Identification and quantification of potential anti-inflammatory hydroxycinnamic acid amides from wolfberry. J Agric Food Chem 65:364–372

    Article  CAS  Google Scholar 

  18. Lee Y-T, Hsieh Y-L, Yeh Y-H, Huang C-Y (2015) Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo. RSC Adv 5:85806–85815

    Article  CAS  Google Scholar 

  19. Sim GY, Yang SM, Kim BG, Ahn J-H (2015) Bacterial synthesis of N-hydroxycinnamoyl phenethylamines and tyramines. Microb Cell Fact 14:162

    Article  Google Scholar 

  20. Kim MJ, Kim B-G, Ahn J-H (2013) Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli. Appl Microbiol Biot 97:7195–7204

    Article  CAS  Google Scholar 

  21. Yoon J-A, Kim B-G, Lee WJ, Lim Y, Chong Y, Ahn J-H (2012) Production of a novel quercetin glycoside through metabolic engineering of Escherichia coli. Appl Environ Microbiol 78:4256–4262

    Article  CAS  Google Scholar 

  22. An DG, Yang SM, Kim BG, Ahn J-H (2016) Biosynthesis of two quercetin O-diglycosides in Escherichia coli. J Ind Microbioi Biotechnol 43:841–849

    Article  CAS  Google Scholar 

  23. Kang K, Back K (2009) Production of phenylpropanoid amides in recombinant Escherichia coli. Met Eng 11:64–68

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by a grant from the Next-Generation BioGreen 21 Program (PJ00948301), Rural Development Administration, and the Priority Research Centers Program through the National Research Foundation of Korea, funded by the Ministry of Education, Science and Technology (2009-0093824).

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Authors M. K. Song and S. J. Lee contributed equally to this work.

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Correspondence to Joong-Hoon Ahn.

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Song, M.K., Lee, S.J., Kang, Y.Y. et al. Biological synthesis and anti-inflammatory activity of arylalkylamine. Appl Biol Chem 60, 597–602 (2017). https://doi.org/10.1007/s13765-017-0315-7

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  • DOI: https://doi.org/10.1007/s13765-017-0315-7

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