Cannabaceae

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N-Feruloylserotonin
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
  • InChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+
    Key: WGHKJYWENWLOMY-XVNBXDOJSA-N
  • COc1cc(ccc1O)/C=C/C(=O)NCCc2c[nH]c3c2cc(cc3)O
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).

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[edit]

N-Feruloylserotonin 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[edit]

The biosynthetic pathway of N-feruloylserotonin 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-feruloylserotonin, 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]

Biosynthesis of N-feruloylserotonin and N-(p-coumaroyl)serotonin

References[edit]

  1. ^ a b Takimoto T, Suzuki K, Arisaka H, Murata T, Ozaki H, Koyama N (October 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". Molecular Nutrition & Food Research. 55 (10): 1561–1571. doi:10.1002/mnfr.201000545. PMID 21648068.
  2. ^ a b Han SJ, Lim MJ, Lee KM, Oh E, Shin YS, Kim S, et al. (March 2021). "Safflower Seed Extract Attenuates the Development of Osteoarthritis by Blocking NF-κB Signaling". Pharmaceuticals. 14 (3): 258. doi:10.3390/ph14030258. PMC 7999399. PMID 33809253.
  3. ^ Kanehira T, Takekoshi S, Nagata H, Matsuzaki K, Kambayashi Y, Osamura RY, Homma T (November 2003). "A novel and potent biological antioxidant, Kinobeon A, from cell culture of safflower". Life Sciences. 74 (1): 87–97. doi:10.1016/j.lfs.2003.06.033. PMID 14575815.
  4. ^ Kang S, Kang K, Lee K, Back K (November 2007). "Characterization of tryptamine 5-hydroxylase and serotonin synthesis in rice plants". Plant Cell Reports. 26 (11): 2009–2015. doi:10.1007/s00299-007-0405-9. PMID 17639402.
  5. ^ a b Kang K, Kang S, Lee K, Park M, Back K (June 2008). "Enzymatic features of serotonin biosynthetic enzymes and serotonin biosynthesis in plants". Plant Signaling & Behavior. 3 (6): 389–390. doi:10.4161/psb.3.6.5401. PMC 2634310. PMID 19704574.
  6. ^ a b Radwanski ER, Last RL (July 1995). "Tryptophan biosynthesis and metabolism: biochemical and molecular genetics". The Plant Cell. 7 (7): 921–934. doi:10.1105/tpc.7.7.921. PMC 160888. PMID 7640526.
  7. ^ Facchini PJ, Huber-Allanach KL, Tari LW (May 2000). "Plant aromatic L-amino acid decarboxylases: evolution, biochemistry, regulation, and metabolic engineering applications". Phytochemistry. 54 (2): 121–138. doi:10.1016/s0031-9422(00)00050-9. PMID 10872203.
  8. ^ Kang S, Kang K, Lee K, Back K (December 2007). "Characterization of rice tryptophan decarboxylases and their direct involvement in serotonin biosynthesis in transgenic rice". Planta. 227 (1): 263–272. doi:10.1007/s00425-007-0614-z. PMID 17763868.
  9. ^ Bowden K, Brown BG, Batty JE (November 1954). "5-Hydroxytryptamine: its occurrence in cowhage". Nature. 174 (4437): 925–926. doi:10.1038/174925a0. PMID 13214042.
  10. ^ Kushiro T, Nambara E, McCourt P (March 2003). "Hormone evolution: The key to signalling". Nature. 422 (6928): 122. doi:10.1093/aob/mcg113. PMC 4243638.
  11. ^ Vigliante I, Mannino G, Maffei ME (March 2019). "Chemical Characterization and DNA Fingerprinting of Griffonia simplicifolia Baill". Molecules. 24 (6): E1032. doi:10.3390/molecules24061032. PMC 6472197. PMID 30875930.
source: https://en.wikipedia.org/wiki/N-Feruloylserotonin

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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