Some biochemical effects of hypoglycin

Renzo, E.C. De; McKerns, Kenneth W.; Bird, Harris H.; Cekleniak, Walter P.; Coulomb, B.S.; Kaleita, E.

doi:10.1016/0006-2952(59)90106-6

Cited by 21 publications

(7 citation statements)

References 6 publications

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“…In another study, a single dose of pentenoic acid did result in an apparent elevation of FFA's in rats fasted only 4 hr (22). Elevated FFA's have been reported in hypoglycin-treated hypoglycemic rats (7). In the chronically treated rats in this study there was a suggestion that FFA's rise in response to stress.…”

Section: T E S T Control T E S T Control T E S T Controlsupporting

confidence: 57%

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Production of the Features of Reye's Syndrome in Rats with 4-Pentenoic Acid

1975

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IN VIVO D-GLUCOSE(1 l), in perfusion studies of the proximal intestine, found rate of absorption of glucose to be about 10 mg/hr/lO cm. In the present study, rate of absorption from a solution with a similar mean glucose concentration was 8 mg/hr/lO cm of the perfused jejunum + ileum. SUMMARYIn vivo study of D-glucose absorption in small intestine of rats between 7 and 73 days of age suggested that rate of absorption normalized for intestinal weight incre'ased twofold at the time of weaning (21-23 days of age) with no further increase thereafter. REFERENCES AND NOTES

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Section: T E S T Control T E S T Control T E S T Controlsupporting

confidence: 57%

“…The numbers refer to the pair number. Rats [7][8][9][10][11][12] were given purified pentenoic acid. Twelve pairs of rats were studied.…”

Section: Chronic Studiesmentioning

confidence: 99%

Production of the Features of Reye's Syndrome in Rats with 4-Pentenoic Acid

1975

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“…Pent-4-enoic acid is the simplest hypoglycaemic fatty acid structurally related to methylenecyclopropylacetic acid, the active metabolite of hypoglycin from the fruit of the ackee, Blighia sapida. Ingestion of unripe ackee fruits may cause vomiting sickness, a disease characterized by severe hypoglycaemia (Anderson et al, 1958;De Renzo et al, 1958;von Holt, 1966;Senior & Sherratt, 1968a,b;Sherratt et al, 1971) and probably by isovaleric-acidaemia (Tanaka et al, 1972). Both pent-4-enoic acid and hypoglycin are thought to cause hypoglycaemia by impairing gluconeogenesis secondarily to inhibiting fatty acid oxidation (Senior, 1967;Sherratt et al, 1971) and pent-4-enoic acid has been used to demonstrate the dependence of gluconeogenesis on fatty acid oxidation in perfused rat liver (Ruderman et al, 1968;Toews et al, 1970;Williamson et al, 1970;Menahan & Williams, 1971).…”

mentioning

confidence: 99%

Biochemical effects of the hypoglycaemic compound pent-4-enoic acid and related non-hypoglycaemic fatty acids. Effects of the free acids and their carnitine esters on coenzyme A-dependent oxidations in rat liver mitochondria

Holland

Sherratt

1973

Biochemical Journal

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1. The synthesis of pent-4-enoyl-l-carnitine, cyclopropanecarbonyl-l-carnitine and cyclobutanecarbonyl-l-carnitine is described. 2. Pent-4-enoate strongly inhibits palmitoyl-l-carnitine oxidation in coupled but not in uncoupled mitochondria. Pent-4-enoyl-l-carnitine strongly inhibits palmitoyl-l-carnitine oxidation in uncoupled mitochondria. Prior intramitochondrial formation of pent-4-enoyl-CoA is therefore necessary for inhibition. 3. There was a small self-limiting pulse of oxidation of pent-4-enoyl-l-carnitine during which the ability to inhibit the oxidation of subsequently added palmitoyl-l-carnitine developed. 4. Pent-4-enoate and pent-4-enoyl-l-carnitine are equally effective inhibitors of the oxidation of all even-chain acylcarnitines of chain length C(4)-C(16). Pent-4-enoyl-l-carnitine also inhibits the oxidation of pyruvate and of 2-oxoglutarate. 5. Pent-4-enoate strongly inhibits the oxidation of palmitate but not that of octanoate. This is presumably due to competition between octanoate and pent-4-enoate for medium-chain acyl-CoA ligase. 6. There was less inhibition of the oxidation of pyruvate by pent-4-enoyl-l-carnitine, and of palmitoyl-l-carnitine by cyclopropanecarbonyl-l-carnitine, after pre-incubation with 10mm-arsenate. This suggests that these inhibitions were caused either by depletion of free CoA or by increase of acyl-CoA concentrations, since arsenate deacylates intramitochondrial acyl-CoA. There was little effect on the inhibition of palmitoyl-l-carnitine oxidation by pent-4-enoyl-l-carnitine. 7. Penta-2,4-dienoate strongly inhibited palmitoyl-l-carnitine oxidation in coupled mitochondria; acrylate only inhibited slightly. 8. Pent-4-enoate (0.1mm) caused a rapid and almost complete decrease in free CoA and a large increase in acid-soluble acyl-CoA when incubated with coupled mitochondria. Cyclopropanecarboxylate caused a similar decrease in CoA, with an equivalent rise in acid-soluble acyl-CoA concentrations. n-Pentanoate caused extensive lowering of CoA and a large increase in acid-soluble acyl-CoA and acetyl-CoA concentrations. Octanoate caused a 50% lowering of CoA and an increase in acid-soluble acyl-CoA and acetyl-CoA concentrations. 9. Cyclopropanecarboxylate and n-pentanoate were less potent inhibitors of palmitate oxidation than was pent-4-enoate. 10. It is concluded that pent-4-enoate causes a specific inhibition of beta-oxidation after the formation intramitochondrially of its metabolites.

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“…2 Each of these compounds, methylenecyclopropylacetic acid (I), 3-methylenecyclobutane-1-carboxylic acid (II), and 4-pentenoic acid (III) has a vinyl group separated by two carbon atoms from the carboxyl group. CH2 CH2 = C CHCH2COOH (I)…”

mentioning

confidence: 99%