Biosynthesis of Quinoline by a Stick Insect

Athula B. Attygalle, Kithsiri B. Hearth, Vikram K. Iyengar, Randy C. Morgan

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)527-530
Number of pages4
JournalJournal of Natural Products
Volume84
Issue number2
DOIs
StatePublished - 26 Feb 2021

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