Isolation and structure of pulcherrimine, a novel bitter-tasting amino acid, from the sea urchin (Hemicentrotus pulcherrimus) ovaries.
A novel sulfur-containing amino acid, pulcherrimine, has been isolated as a bitter principle from ovaries of the sea urchin Hemicentrotus pulcherrimus. The structure was elucidated as 4-(2'-carboxy-2'-hydroxy-ethylthio)-2-piperidinecarboxylic acid by spectroscopic and chemical methods. Absolute stereochemistry was determined by NOE experiments and chiral HPLC analysis. Pulcherrimine exhibited bitterness with a threshold value of 0.306 mM.
Murata
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National Research Institute of Fisheries Science, 2-12-4, Fukuura, Kanazawa-ku, Yokohama 236-8648, Japan. betty@nrifs.affrc.go.jp
Sata
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D000603:Amino Acids, Sulfur / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D005260:Female; D015394:Molecular Structure; D010053:Ovary / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry* / Q000302:isolation & purification; D012617:Sea Urchins; D017747:Seafood; D013649:Taste
D000603:Amino Acids, Sulfur; D010880:Piperidines; C417737:pulcherrimine