TY - JOUR
T1 - Biosynthesis of epilachnene, a macrocyclic defensive alkaloid of the Mexican bean beetle
AU - Attygalle, Athula B.
AU - Svatoš, Aleš
AU - Veith, Martin
AU - Farmer, Jay J.
AU - Meinwald, Jerrold
AU - Smedley, Scott
AU - González, Andrés
AU - Eisner, Thomas
PY - 1999/1/22
Y1 - 1999/1/22
N2 - The carbon skeleton of the azamacrolide epilachnene, the principal defensive alkaloid of Epilachna varivestis pupae, can be derived from oleic acid and serine. Analytical evidence from three experiments in which insects were fed (2H35)octadecanoic acid, (Z)-9- [11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-2H17]octadecenoic acid and (Z)-9-[11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-2H15]octadecenoic acid, indicates that only the C-15 methylene group of oleic acid is involved in the mechanism leading to carbon-nitrogen bond formation in epilachnene. Support for this scheme is provided by the observation of an unusual ion at m/z 170 in the electron-ionization mass spectrum of epilachnene, rationalized as CH2=CH-COO-CH2-CH2-NH+=CH-CH2-CH2-CH3.
AB - The carbon skeleton of the azamacrolide epilachnene, the principal defensive alkaloid of Epilachna varivestis pupae, can be derived from oleic acid and serine. Analytical evidence from three experiments in which insects were fed (2H35)octadecanoic acid, (Z)-9- [11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-2H17]octadecenoic acid and (Z)-9-[11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-2H15]octadecenoic acid, indicates that only the C-15 methylene group of oleic acid is involved in the mechanism leading to carbon-nitrogen bond formation in epilachnene. Support for this scheme is provided by the observation of an unusual ion at m/z 170 in the electron-ionization mass spectrum of epilachnene, rationalized as CH2=CH-COO-CH2-CH2-NH+=CH-CH2-CH2-CH3.
KW - Biosynthesis
KW - Insects
KW - Labelling
KW - Mass spectrometry
KW - Natural products
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U2 - 10.1016/S0040-4020(98)01102-8
DO - 10.1016/S0040-4020(98)01102-8
M3 - Article
AN - SCOPUS:0033593526
SN - 0040-4020
VL - 55
SP - 955
EP - 966
JO - Tetrahedron
JF - Tetrahedron
IS - 4
ER -