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Literature DB >> 9665888

Combinatorial chemistry in insects: a library of defensive macrocyclic polyamines.

F C Schröder¹, J J Farmer, A B Attygalle, S R Smedley, T Eisner, J Meinwald.

Abstract

The pupal defensive secretion of the coccinellid beetle Epilachna borealis is composed principally of a combinatorial library of macrocyclic polyamines. These compounds constitute a previously unrecognized family of natural products, characterized by extremely large-ring lactonic structures derived from a small set of (2-hydroxyethylamino)alkanoic acids. The combinatorial assembly of these simple building blocks generates a high degree of structural diversity, which is further increased by slow, spontaneous intramolecular rearrangement of the macrocycles.

Entities: Chemical Species

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Year: 1998 PMID： 9665888 DOI： 10.1126/science.281.5375.428

Source DB: PubMed Journal: Science ISSN： 0036-8075 Impact factor: 47.728

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Cited

11 in total

Review 1. Unknown identification using reference mass spectra. Quality evaluation of databases.

Authors: F W McLafferty; D A Stauffer; S Y Loh; C Wesdemiotis
Journal: J Am Soc Mass Spectrom Date: 1999-12 Impact factor: 3.109

2. Understanding the chemistry of chemical communication: are we there yet?

Authors: Jerrold Meinwald
Journal: Proc Natl Acad Sci U S A Date: 2003-11-10 Impact factor: 11.205

3. An endogenous bile acid and dietary sucrose from skin secretions of alkaloid-sequestering poison frogs.

Authors: Valerie C Clark; Liva Harinantenaina; Martin Zeller; William Ronto; James Rocca; Aaron T Dossey; Daniel Rakotondravony; David G I Kingston; Chris Shaw
Journal: J Nat Prod Date: 2012-01-30 Impact factor: 4.050

4. Identification of xanthurenic acid 8-O-beta-D-glucoside and xanthurenic acid 8-O-sulfate as human natriuretic hormones.

Authors: Christopher D Cain; Frank C Schroeder; Stewart W Shankel; Mark Mitchnick; Michael Schmertzler; Neal S Bricker
Journal: Proc Natl Acad Sci U S A Date: 2007-10-31 Impact factor: 11.205

5. Biparental endowment of endogenous defensive alkaloids in Epilachna paenulata.

Authors: Soledad Camarano; Andrés González; Carmen Rossini
Journal: J Chem Ecol Date: 2008-12-04 Impact factor: 2.626

6. Sites and regulation of polyamine catabolism in the tobacco plant. Correlations with cell division/expansion, cell cycle progression, and vascular development.

Authors: Konstantinos A Paschalidis; Kalliopi A Roubelakis-Angelakis
Journal: Plant Physiol Date: 2005-07-22 Impact factor: 8.340

Combinatorial chemistry in insects: a library of defensive macrocyclic polyamines.

Review 1. Unknown identification using reference mass spectra. Quality evaluation of databases.

2. Understanding the chemistry of chemical communication: are we there yet?

3. An endogenous bile acid and dietary sucrose from skin secretions of alkaloid-sequestering poison frogs.

4. Identification of xanthurenic acid 8-O-beta-D-glucoside and xanthurenic acid 8-O-sulfate as human natriuretic hormones.

5. Biparental endowment of endogenous defensive alkaloids in Epilachna paenulata.

6. Sites and regulation of polyamine catabolism in the tobacco plant. Correlations with cell division/expansion, cell cycle progression, and vascular development.

Review 7. Integrating '-omics' and natural product discovery platforms to investigate metabolic exchange in microbiomes.

8. Natural Products as a Foundation for Drug Discovery.

9. Polyazamacrolides from ladybird beetles: ring-size selective oligomerization.

10. Defensive abdominal rotation patterns of tenebrionid beetle, Zophobas atratus, pupae.