Literature DB >> 8506367

Azamacrolides: a family of alkaloids from the pupal defensive secretion of a ladybird beetle (Epilachna varivestis).

A B Attygalle1, K D McCormick, C L Blankespoor, T Eisner, J Meinwald.   

Abstract

Defensive droplets from glandular hairs of the pupa of the Mexican bean beetle, Epilachna varivestis, contain a group of structurally novel alkaloids, the azamacrolides. The major constituent of this secretion, epilachnene, is shown to be (5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide. The secretion also contains an epilachnadiene and trace amounts of three closely related components.

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Year:  1993        PMID： 8506367      PMCID： PMC46684          DOI： 10.1073/pnas.90.11.5204

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  3 in total

1.  Gas chromatography of volatile compounds in small samples of biological materials.

Authors:  E D Morgan; L J Wadhams
Journal:  J Chromatogr Sci       Date:  1972-08       Impact factor: 1.618

2.  Hemorrhage in a Coccinellid Beetle and Its Repellent Effect on Ants.

Authors:  G M Happ; T Eisner
Journal:  Science       Date:  1961-08-04       Impact factor: 47.728

3.  Defensive alkaloid in blood of Mexican bean beetle (Epilachna varivestis).

Authors:  T Eisner; M Goetz; D Aneshansley; G Ferstandig-Arnold; J Meinwald
Journal:  Experientia       Date:  1986-02-15
  3 in total
  10 in total

1.  Miriamin, a defensive diterpene from the eggs of a land slug (Arion sp.).

Authors:  F C Schroeder; A Gonzàlez; T Eisner; J Meinwald
Journal:  Proc Natl Acad Sci U S A       Date:  1999-11-23       Impact factor: 11.205

2.  Tocopheryl acetates from the pupal exocrine secretion of the squash beetle, Epilachna borealis (Coccinellidae).

Authors:  A B Attygalle; S R Smedley; T Eisner; J Meinwald
Journal:  Experientia       Date:  1996-06-15

3.  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

4.  Mayolenes: labile defensive lipids from the glandular hairs of a caterpillar (Pieris rapae).

Authors:  Scott R Smedley; Frank C Schroeder; Douglas B Weibel; Jerrold Meinwald; Katie A Lafleur; J Alan Renwick; Ronald Rutowski; Thomas Eisner
Journal:  Proc Natl Acad Sci U S A       Date:  2002-05-07       Impact factor: 11.205

5.  Acetylation of alpha-tocopherol by the squash beetle, Epilachna borealis. Defense mechanisms of arthropods, 134 [1].

Authors:  A B Attygalle; J Meinwald; C Rossini; T Eisner
Journal:  Naturwissenschaften       Date:  1996-06

6.  Biosynthesis of a defensive insect alkaloid: epilachnene from oleic acid and serine.

Authors:  A B Attygalle; C L Blankespoor; T Eisner; J Meinwald
Journal:  Proc Natl Acad Sci U S A       Date:  1994-12-20       Impact factor: 11.205

7.  Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, ambrettolide, epothilone C, and nakadomarin A.

Authors:  Chenbo Wang; Miao Yu; Andrew F Kyle; Pavol Jakubec; Darren J Dixon; Richard R Schrock; Amir H Hoveyda
Journal:  Chemistry       Date:  2013-01-23       Impact factor: 5.236

8.  New type of Sesiidae sex pheromone identified from the hornet moth Sesia apiformis.

Authors:  W Francke; V Karalius; E Plass; L Lehmann; A Dos Santos; V Buda; A K Borg-Karlson; R Mozuraitis
Journal:  J Chem Ecol       Date:  2004-04       Impact factor: 2.626

Review 9.  The chemistry of phyletic dominance.

Authors:  J Meinwald; T Eisner
Journal:  Proc Natl Acad Sci U S A       Date:  1995-01-03       Impact factor: 11.205

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

Authors:  F C Schroeder; S R Smedley; L K Gibbons; J J Farmer; A B Attygalle; T Eisner; J Meinwald
Journal:  Proc Natl Acad Sci U S A       Date:  1998-11-10       Impact factor: 11.205
  10 in total

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