Very-long-chain fatty acid biosynthesis is inhibited by cafenstrole, N,N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide and its analogs.
The rice herbicide cafenstrole and its analogs inhibited the incorporation of [1-(14)C]-oleate and (2-(14)C]-malonate into very-long-chain fatty acids (VLCFAs), using Scenedesmus cells and leek microsomes from Allium porrum. Although the precise mode of interaction of cafenstrole at the molecular level is not completely clarified by the present study, it is concluded that cafenstrole acts as a specific inhibitor of the microsomal elongase enzyme involved in the biosynthesis of fatty acids with alkyl chains longer than C18. For a strong VLCFA biosynthesis inhibition an -SO2- linkage of the 1,2,4-triazole-1-carboxamides was required. Furthermore, N,N-dialkyl substitution of the carbamoyl nitrogen and electron-donating groups such as methyl at the benzene ring of 1,2,4-triazole-1-carboxamides produced a strong inhibition of VLCFA formation. A correlation was found between the phytotoxic effect against barnyardgrass (Echinochloa oryzicola) and impaired VLCFA formation.
Takahashi
H
H
Graduate School of Agricultural Science, Tamagawa University, Machida-shi, Tokyo, Japan.
Ohki
A
A
Kanzaki
M
M
Tanaka
A
A
Sato
Y
Y
Matthes
B
B
Böger
P
P
Wakabayashi
K
K
D000081:Acetamides / Q000633:toxicity; D000490:Allium / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism; D000460:Chlorophyta / Q000378:metabolism*; D003066:Coenzyme A Ligases / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000633:toxicity; D005230:Fatty Acids, Nonesterified / Q000096:biosynthesis*; D006540:Herbicides / Q000633:toxicity*; D007700:Kinetics; D008314:Malonates / Q000378:metabolism*; D008861:Microsomes / Q000187:drug effects / Q000378:metabolism*; D015394:Molecular Structure; D019301:Oleic Acid / Q000378:metabolism*; D012275:Oryza / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism*; D010088:Oxidoreductases / Q000037:antagonists & inhibitors; D044925:Oxidoreductases Acting on CH-CH Group Donors; D050768:Protoporphyrinogen Oxidase; D012097:Repressor Proteins; D029701:Saccharomyces cerevisiae Proteins; D013450:Sulfones / Q000633:toxicity*; D014230:Triazoles / Q000633:toxicity*; D000098859:Long-Chain-Fatty-Acid-CoA Ligase
D000081:Acetamides; D004791:Enzyme Inhibitors; D005230:Fatty Acids, Nonesterified; D006540:Herbicides; D008314:Malonates; D012097:Repressor Proteins; D029701:Saccharomyces cerevisiae Proteins; D013450:Sulfones; D014230:Triazoles; C444649:cafenstrole; C000188:alachlor; D019301:Oleic Acid; C030290:malonic acid; D010088:Oxidoreductases; D044925:Oxidoreductases Acting on CH-CH Group Donors; D050768:Protoporphyrinogen Oxidase; D003066:Coenzyme A Ligases; C090799:FAA2 protein, S cerevisiae; D000098859:Long-Chain-Fatty-Acid-CoA Ligase