Chemistry:N-Feruloylserotonin

From HandWiki
N-Feruloylserotonin
Feruloylserotonin.svg
Names
Preferred IUPAC name
(2E)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Other names
Moschamine
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
C20H20N2O4
Molar mass 352.390 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

File:Biosynthetic Pathway.tif N-Feruloylserotonin an alkaloid and polyphenol found in safflower seed. Chemically, it is an amide formed between serotonin and ferulic acid. It has in vitro anti-atherogenic activity.[1]

Serotonin Derivatives Found in Safflower Seeds

N-feruloyl serotonin and N-(p-coumaroyl)serotonin are natural products that can be found in the extract of safflower seeds (Carthamus tinctorius ).[2] These natural products have been isolated and studied to investigate their antioxidant effects.[3] These polyphenols have been utilized in traditional Chinese medicine and other eastern medicine practices to have strong antioxidant effects, chemotherapeutic effects, and atherosclerosis attenuation.[1][4] It has been found that N-(p-coumaroyl) and N- feruloyl serotonin can suppress the expression of matrix metalloproteinases MMP3/13 and a disintegrin and metalloproteinase with thrombospondin motifs (ADAMTS), thus attenuating cartilage degradation.[2]

Biosynthesis

The biosynthetic pathway of N- feruloyl serotonin and N-(p-coumaroyl) serotonin has been reported.[5] In plants, the enzyme anthranilate synthase (AS) is composed of two subunits that modulate the production or suppression of tryptophan from chorismate.[6] Tryptophan is then decarboxylated by tryptophan decarboxylase (TDC) into tryptamine.[5] Tryptamine 5-hydroxylase (T5H) then hydroxylates tryptamine into serotonin.[7][8] Serotonin, the precursor to N-(p-coumaroyl) and N- feruloyl serotonin, is found in the seeds of the safflower plant.[9][10][11] Hydroxycinnamic acids are then transferred to serotonin from hydroxycinnamoyl-CoA esters by hydroxycinnamoyl-CoA: serotonin N-(hydroxycinnamoyl)transferase (SHT).[6]

References

  1. ↑ 1.0 1.1 "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". Molecular Nutrition & Food Research 55 (10): 1561–1571. October 2011. doi:10.1002/mnfr.201000545. PMID 21648068. 
  2. ↑ 2.0 2.1 "Safflower Seed Extract Attenuates the Development of Osteoarthritis by Blocking NF-κB Signaling". Pharmaceuticals 14 (3): 258. March 2021. doi:10.3390/ph14030258. PMID 33809253. 
  3. ↑ "A novel and potent biological antioxidant, Kinobeon A, from cell culture of safflower". Life Sciences 74 (1): 87–97. November 2003. doi:10.1016/j.lfs.2003.06.033. PMID 14575815. 
  4. ↑ "Characterization of tryptamine 5-hydroxylase and serotonin synthesis in rice plants". Plant Cell Reports 26 (11): 2009–2015. November 2007. doi:10.1007/s00299-007-0405-9. PMID 17639402. 
  5. ↑ 5.0 5.1 "Enzymatic features of serotonin biosynthetic enzymes and serotonin biosynthesis in plants". Plant Signaling & Behavior 3 (6): 389–390. June 2008. doi:10.4161/psb.3.6.5401. PMID 19704574. 
  6. ↑ 6.0 6.1 "Tryptophan biosynthesis and metabolism: biochemical and molecular genetics". The Plant Cell 7 (7): 921–934. July 1995. doi:10.1105/tpc.7.7.921. PMID 7640526. 
  7. ↑ "Plant aromatic L-amino acid decarboxylases: evolution, biochemistry, regulation, and metabolic engineering applications". Phytochemistry 54 (2): 121–138. May 2000. doi:10.1016/s0031-9422(00)00050-9. PMID 10872203. 
  8. ↑ "Characterization of rice tryptophan decarboxylases and their direct involvement in serotonin biosynthesis in transgenic rice". Planta 227 (1): 263–272. December 2007. doi:10.1007/s00425-007-0614-z. PMID 17763868. 
  9. ↑ "5-Hydroxytryptamine: its occurrence in cowhage". Nature 174 (4437): 925–926. November 1954. doi:10.1038/174925a0. PMID 13214042. 
  10. ↑ "Hormone evolution: The key to signalling". Nature 422 (6928): 122. March 2003. doi:10.1093/aob/mcg113. 
  11. ↑ "Chemical Characterization and DNA Fingerprinting of Griffonia simplicifolia Baill". Molecules 24 (6): E1032. March 2019. doi:10.3390/molecules24061032. PMID 30875930. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:N-Feruloylserotonin&oldid=3331315"