Biosynthesis of N-(alpha-hydroxyethyl) lysergamide, a metabolite of Claviceps paspali Stevens and Hall.
1. The biosynthetic origin of the amide substituent of N-(alpha-hydroxyethyl)lysergamide has been studied. 2. [1-(14)C]Acetate, [(14)C]formate, [2-(14)C]mevalonic acid lactone, [2-(14)C]indole, dl-[3-(14)C]tryptophan, dl-[3-(14)C]serine, dl-[2-(14)C]alanine and [2-(14)C]pyruvate were efficiently incorporated into the alkaloid, but not dl-[1-(14)C]alanine or [1-(14)C]pyruvate. 3. Only the dl-[2-(14)C]alanine- and [2-(14)C]pyruvate-derived alkaloid contained appreciable radioactivity in the amide substituent. 4. l-[(15)N]Alanine-derived alkaloid was shown to be specifically labelled in the amide nitrogen. However, l-[(14)C,(15)N]alanine was found to be incorporated into the methylcarbinolamide substituent with an appreciable increase in the (15)N/(14)C ratio, suggesting that alanine is not the direct precursor of this moiety.
D000085:Acetates / Q000378:metabolism; D000409:Alanine / Q000378:metabolism; D000470:Alkaloids / Q000096:biosynthesis*; D000577:Amides / Q000096:biosynthesis*; D001203:Ascomycota / Q000378:metabolism*; D002247:Carbon Isotopes; D005561:Formates / Q000378:metabolism; D007211:Indoles / Q000378:metabolism; D007783:Lactones / Q000378:metabolism; D008798:Mevalonic Acid / Q000378:metabolism; D011773:Pyruvates / Q000378:metabolism; D012694:Serine / Q000378:metabolism; D014364:Tryptophan / Q000378:metabolism
D000085:Acetates; D000470:Alkaloids; D000577:Amides; D002247:Carbon Isotopes; D005561:Formates; D007211:Indoles; D007783:Lactones; D011773:Pyruvates; D012694:Serine; D014364:Tryptophan; D000409:Alanine; D008798:Mevalonic Acid