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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
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
^ abTakimoto 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. PMID21648068.
^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. PMID14575815.
^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. PMID17639402.
^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. PMID17763868.
^Bowden K, Brown BG, Batty JE (November 1954). "5-Hydroxytryptamine: its occurrence in cowhage". Nature. 174 (4437): 925–926. doi:10.1038/174925a0. PMID13214042.
This page was last edited on 27 March 2024, at 18:32