Literature DB >> 12199498

(R)-(+)-palasonin, a cantharidin-related plant toxin, also occurs in insect hemolymph and tissues.

Oliver Fietz1, Konrad Dettner, Helmar Görls, Kerstin Klemm, Wilhelm Boland.   

Abstract

Gas chromatographic and mass spectroscopic analyses of extracts of cantharidin-containing meloid, clerid, and staphylinid beetles revealed the presence of minor to significant amounts of palasonin, previously only known from seeds and fruits of the Indian shrub Buteafrondosa (Leguminaceae). Unlike (S)-(-)-palasonin (> 99% ee) from B. frondosa, the insects produce palasonin of low ee with the (R)-(+)-enantiomer (0-50% ee) prevailing. The ee of palasonin from individual specimens of predatory insects (Trichodes apiarius), which acquire their chemical protection from cantharidin-producing insects, may vary considerably. The absolute configuration of (S)-(-)-palasonin, previously deduced from indirect chemical and spectroscopic methods, was confirmed by X-ray crystal structure analysis of a cyclic imide derived from (S)-(-)-palasonin and (S)-(-)- 1 -(4-nitrophenyl)-ethylamine.

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Year:  2002        PMID: 12199498     DOI: 10.1023/a:1019561517040

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN: 0098-0331            Impact factor:   2.626


  8 in total

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Journal:  Proc Natl Acad Sci U S A       Date:  1996-06-25       Impact factor: 11.205

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Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600

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Authors:  J E Carrel; T Eisner
Journal:  Science       Date:  1974-02-22       Impact factor: 47.728

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Journal:  Chem Ind       Date:  1970-10-24       Impact factor: 0.161

5.  Effect of Butea frondosa, Vernonia anthelmintica and Carica papaya against oxyurids in mice.

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Journal:  Indian Vet J       Date:  1966-08

Review 6.  The structure and regulation of protein phosphatases.

Authors:  P Cohen
Journal:  Annu Rev Biochem       Date:  1989       Impact factor: 23.643

7.  Effects of norcantharidin, a protein phosphatase type-2A inhibitor, on the growth of normal and malignant haemopoietic cells.

Authors:  X H Liu; I Blazsek; M Comisso; S Legras; S Marion; P Quittet; A Anjo; G S Wang; J L Misset
Journal:  Eur J Cancer       Date:  1995-06       Impact factor: 9.162

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Authors:  J E Carrel; J P Doom; J P McCormick
Journal:  J Chem Ecol       Date:  1986-03       Impact factor: 2.626

  8 in total
  4 in total

1.  First record of a Mermithidae (Nematoda) from the meloid beetle Meloe violaceus Marsham, 1802 (Coleoptera: Meloidae).

Authors:  Johannes Lückmann; George O Poinar
Journal:  Parasitol Res       Date:  2003-02-12       Impact factor: 2.289

2.  New Evidence of Canthariphily: Tilloidea transversalis (Coleoptera: Cleridae) Sequestering Cantharidin From Lydus trimaculatus (Coleoptera: Meloidae).

Authors:  Marco Molfini; Luca Stefanuto; Silvia Gisondi; Tecla Gasperi; Andrea Di Giulio; Emiliano Mancini; Marco A Bologna
Journal:  J Insect Sci       Date:  2022-05-01       Impact factor: 2.066

Review 3.  Antitumor potential of the protein phosphatase inhibitor, cantharidin, and selected derivatives.

Authors:  Yulin Ren; A Douglas Kinghorn
Journal:  Bioorg Med Chem       Date:  2021-01-09       Impact factor: 3.641

Review 4.  Drug Discovery Insights from Medicinal Beetles in Traditional Chinese Medicine.

Authors:  Stephen T Deyrup; Natalie C Stagnitti; Mackenzie J Perpetua; Siu Wah Wong-Deyrup
Journal:  Biomol Ther (Seoul)       Date:  2021-03-01       Impact factor: 4.634

  4 in total

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