Engineering of Escherichia coli for the synthesis of N-hydroxycinnamoyl tryptamine and serotonin
- 373 Downloads
Plants synthesize various phenol amides. Among them, hydroxycinnamoyl (HC) tryptamines and serotonins exhibit antioxidant, anti-inflammatory, and anti-atherogenic activities. We synthesized HC–tryptamines and HC–serotonin from several HCs and either tryptamine or serotonin using Escherichia coli harboring the 4CL (4-coumaroyl CoA ligase) and CaHCTT [hydroxycinnamoyl-coenzyme A:serotonin N-(hydroxycinnamoyl)transferase] genes. E. coli was engineered to synthesize N-cinnamoyl tryptamine from glucose. TDC (tryptophan decarboxylase) and PAL (phenylalanine ammonia lyase) along with 4CL and CaHCTT were introduced into E. coli and the phenylalanine biosynthetic pathway of E. coli was engineered. Using this strategy, approximately 110.6 mg/L of N-cinnamoyl tryptamine was synthesized. By feeding 100 μM serotonin into the E. coli culture, which could induce the synthesis of cinnamic acid or p-coumaric acid, more than 99 μM of N-cinnamoyl serotonin and N-(p-coumaroyl) serotonin were synthesized.
KeywordsN-Hydroxycinnamoyl serotonin N-Hydroxycinnamoyl tryptamine
This work was supported by a grant from the Next-Generation BioGreen 21 Program (PJ00948301), Rural Development Administration, the Priority Research Centers Program through the National Research Foundation of Korea, funded by the Ministry of Education, Science and Technology (2009-0093824), and Korea Institute of Planning and Evaluation for Technology (IPET) in Food, Agriculture, Forestry and Fisheries (115013-02).
- 4.Campos L, Lisón P, López-Gresa MP et al (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. doi: 10.1094/MPMI-04-14-0104-R CrossRefPubMedGoogle Scholar
- 6.Clifford MN (1999) Chlorogenic acids and other cinnamates-nature, occurrence and dietary burden. J Sci Food Agric 79:362–372. doi: 10.1002/(SICI)1097-0010(19990301)79:3<362:AID-JSFA256>3.0.CO;2-D CrossRefGoogle Scholar
- 11.Jendresen CB, Stahlhut SG, Li M et al (2015) Highly active and specific tyrosine ammonia-lyases from diverse origins enable enhanced production of aromatic compounds in bacteria and Saccharomyces cerevisiae. Appl Environ Microbiol 81:4458–4476. doi: 10.1128/AEM.00405-15 CrossRefPubMedPubMedCentralGoogle Scholar
- 27.Revial G, Jabin I, Lim S, Pfau M (2002) Aromatization of 1,6,7,7a-tetrahydro-2H-indol-2-ones by a novel process. Preparation of key-intermediate methyl 1-benzyl-5-methoxy-1H-indole-3-acetate and the syntheses of serotonin, melatonin, and bufotenin. J Org Chem 67:2252–2256. doi: 10.1021/jo0110597 CrossRefPubMedGoogle Scholar
- 34.Takimoto T, Suzuki K, Arisaka H et al (2011) Effect of N-(p-coumaroyl)serotonin and N-feruloylserotonin, major anti-atherogenic polyphenols in safflower seed, on vasodilation, proliferation and migration of vascular smooth muscle cells. Mol Nutr Food Res 55:1561–1571. doi: 10.1002/mnfr.201000545 CrossRefPubMedGoogle Scholar