TY - JOUR
T1 - Biosynthesis of Quinoline by a Stick Insect
AU - Attygalle, Athula B.
AU - Hearth, Kithsiri B.
AU - Iyengar, Vikram K.
AU - Morgan, Randy C.
N1 - Publisher Copyright:
© 2021 American Chemical Society and American Society of Pharmacognosy.
PY - 2021/2/26
Y1 - 2021/2/26
N2 - The Peruvian stick insect Oreophoetes peruana is the only known animal source for unsubstituted quinoline in nature. When disturbed, these insects discharge a defensive secretion containing quinoline. Analysis of samples obtained from l-[2′,4′,5′,6,′7′-2H5]tryptophan-fed stick insects demonstrated that the insects convert it to [5,6,7,8-2H4]quinoline by removing the 2′-CH moiety in the indole ring of tryptophan. Analogous experiments using l-[1′-15N]tryptophan and l-[1′-15N,15NH2]tryptophan showed that the indole-N atom is retained while the α-amino group is eliminated during the biosynthesis. Mass spectra recorded from quinoline derived from [2-13C1]tryptophan-fed insects indicated that the α-carbon atom of tryptophan is incorporated as the C-2 atom of the quinoline ring.
AB - The Peruvian stick insect Oreophoetes peruana is the only known animal source for unsubstituted quinoline in nature. When disturbed, these insects discharge a defensive secretion containing quinoline. Analysis of samples obtained from l-[2′,4′,5′,6,′7′-2H5]tryptophan-fed stick insects demonstrated that the insects convert it to [5,6,7,8-2H4]quinoline by removing the 2′-CH moiety in the indole ring of tryptophan. Analogous experiments using l-[1′-15N]tryptophan and l-[1′-15N,15NH2]tryptophan showed that the indole-N atom is retained while the α-amino group is eliminated during the biosynthesis. Mass spectra recorded from quinoline derived from [2-13C1]tryptophan-fed insects indicated that the α-carbon atom of tryptophan is incorporated as the C-2 atom of the quinoline ring.
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U2 - 10.1021/acs.jnatprod.0c00945
DO - 10.1021/acs.jnatprod.0c00945
M3 - Article
C2 - 33497223
AN - SCOPUS:85100838640
SN - 0163-3864
VL - 84
SP - 527
EP - 530
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 2
ER -