Octadec‐6‐ynoic acid (tariric acid) fed to rats as triglyceride is incorporated both into depot fat and liver lipids. As a metabolite the so far undesdribed dec‐4‐ene‐6‐ynedioic acid, HOOC(CH2)2CHCHCGC(CH2)2COOH, was isolated from the urine.
Szimmary. Crepenynic acid (9-octadeccn-12-ynoic acid) fcd t o rats as naturally occurring triglyceride is not incorporated into brain and livcr lipids, and into the dcpot f a t only t o a small amount. As a metabolite the prcviously unknown 4-clecynedioic acid W A S isolated from t h e urine.In fruheren Arbeiten I 1 1 wurde gezeigt, dass Fettsauren mit Dreifachbindung naturliclie Komponenten von Fetten und Olen aus zahlreichen pflanzlichen Samenim tierisclien Organismus nicht vollig abgebaut werden, vielmehr zu zur Ausscheidung gelangenden Metaboliten fiihren.Die 9-Octadecen-12-insaure CH,-(CH,),-C=C-CH,-CH-CH-(CH,),-COOH wurde 1964 von MIKOLAJCZAK und Mit. 1 2 1 aus dem Samenol von Crepis foetida (ComjJositae) isoliert und 1967 von BKADSHAW und Mit. 131 synthetisch hergestellt. Kurzlich bewiesen HAIGH und Mit. [4j ihre Biosyntliese aus l-l4C-0lsaure in Crepis rubra. Die Frage nach dem Verhalten der Crepissaure irn Stoffwechsel schien uns unter verschiedenen Aspekten interessant. Diese Saure ist strukturell verwandt rnit der Linolsaure (c~s-cis-9,12-Octadecadiensaure), von der BERNHARD 8. ScH6xmInim [51 zeigten, dass sie in1 Tierkorper nicht aufgebaut werden kann.Wir haben dalier an Ratten Samen von Crepis rubra und daraus erhaltenes 01 verfiittert. Nachdem es keine weitere Acetylenfettsaure enthalt, konnte auf eine Isolierung der Crepissaure verzichtet und ilire leiclit mogliclie Autoxydation vermieden werden.
SummaryFeeding of acetylenic monoacids with chain length of 11 to 18 C-atoms to rats led to excretion of dicarboxylic acids with retained triple bonds. 10-Octadecynoic acid led to the formation of metabolites with even and odd number of C-atoms, suggesting in addition to established o-and P-oxidation an a-oxidative pathway. Dass die o-Oxydation im Falle der 10,12-Pentadecadiinsaure auf der Stufe der Hydroxylverbindung zum Stillstand kommt, beweist die Schwierigkeit der Bildung
SummaryOctadec-9-ynoic acid (stearolic acid) fed to rats leads to the metabolic excretion of six dicarboxylic acids with retained triple bond. The main metabolic steps are m-, p-, and presumably a-oxidation. Feeding of ''C-stearolic acid proves that the a-oxidative step involves the methyl end of the original acid. It could further be shown that this acid is incorporated partially in the body lipids. To a substantial degree it is totally oxidized and expired as l4C-CO,.
Summary. 10,12-Hencicosadiynoic acid (I), 5,7-hexadecadiynoic acid (IV), and 10,12-docosadiynedioic acid (VI) were fed to rats. As metabolites 4,6-undecadiynedioic acid (11), 5,7-dodecadiynedioic acid (V), and 4,6-decadiynedioic acid (VII) respectively were isolated from the urine. 10,12-Heptadecadiynoic acid (111) also yielded metabolite 11. Furthermore 9,ll-eicosadiyne (X) and for comparison purposes eicosane (XI), hexadecanedioic acid (VIII), and docosanedioic acid (IX) were fed. X and X I were incorporated into depot fat and liver lipids to a certain degree. The diynes I, 11, IV, and X are new compounds.
Untersuchungen iiber das Schicksal von Fettsauren mit Dreifachbindungen imTierkorper, z. B. der Stearol-, Behenol-, Taririn
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