N-Feruloylserotonin andN-(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] Thesepolyphenols 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]
The biosynthetic pathway ofN-feruloylserotonin andN-(p-coumaroyl)serotonin has been reported.[5] In plants, the enzymeanthranilate synthase (AS) is composed of two subunits that modulate the production or suppression oftryptophan fromchorismate.[6] Tryptophan is thendecarboxylated by tryptophan decarboxylase (TDC) intotryptamine.[5] Tryptamine 5-hydroxylase (T5H) then hydroxylates tryptamine intoserotonin.[7][8]Serotonin, the precursor toN-(p-coumaroyl) andN-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: serotoninN-(hydroxycinnamoyl)transferase (SHT).[6]
^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.
