2D NMR-spectroscopic screening reveals polyketides in ladybugs.

Abstract:

:Small molecules of biological origin continue to yield the most promising leads for drug design, but systematic approaches for exploring nature's cache of structural diversity are lacking. Here, we demonstrate the use of 2D NMR spectroscopy to screen a library of biorationally selected insect metabolite samples for partial structures indicating the presence of new chemical entities. This NMR-spectroscopic survey enabled detection of novel compounds in complex metabolite mixtures without prior fractionation or isolation. Our screen led to discovery and subsequent isolation of two families of tricyclic pyrones in Delphastus catalinae, a tiny ladybird beetle that is employed commercially as a biological pest control agent. The D. catalinae pyrones are based on 23-carbon polyketide chains forming 1,11-dioxo-2,6,10-trioxaanthracene and 4,8-dioxo-1,9,13-trioxaanthracene derivatives, representing ring systems not previously found in nature. This study highlights the utility of 2D NMR-spectroscopic screening for exploring nature's structure space and suggests that insect metabolomes remain vastly underexplored.

authors

Deyrup ST,Eckman LE,McCarthy PH,Smedley SR,Meinwald J,Schroeder FC

doi

10.1073/pnas.1107020108

subject

Has Abstract

pub_date

2011-06-14 00:00:00

pages

9753-8

issue

24

eissn

0027-8424

issn

1091-6490

pii

1107020108

journal_volume

108

pub_type

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