Biological activities of synthetic analogues of Alternaria alternata toxin (AAL-toxin) and fumonisin in plant and mammalian cell cultures

H. K. Abbas; T. Tanaka; W. T. Shier

doi:10.1016/0031-9422(95)00470-R

Biological activities of synthetic analogues of Alternaria alternata toxin (AAL-toxin) and fumonisin in plant and mammalian cell cultures

H. K. Abbas, T. Tanaka, W. T. Shier

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

In a search for an analogue of AAL-toxin with high phytotoxicity and low mammalian toxicity, aminopentols [(AP₁), hexacetyl AP₁ and N-acetyl AP₁], and nine analogues (1-9), were tested for toxicity to duckweed (Lemna pausicostata), susceptible tomato (asc/asc) leaf discs, black nightshade leaf discs and mammalian cell lines, including dog kidney (MDCK), rat liver hepatoma (H4TG) and mouse fibroblasts (NIH3T3). These were compared with AAL-toxin and fumonisin B₁ (FB₁). Analogue 9 at 10 μM increased cellular leakage and chlorophyll loss from both tomato and black nightshade leaf discs. The diester 9 was the most active in the duckweed bioassay, but it was much less toxic to MDCK and H4TG cells with an IC₅₀ of 200 μM compared to 10 μM for FB₁. Analogue 9 and FB₁ showed similar low toxicities (IC₅₀ = 150 μM) to NIH3T3 cells. Among the substances tested, only analogue 9 had significant phytotoxicity and low mammalian toxicity, indicating some potential for development of safe and effective natural herbicides.

Original language	English (US)
Pages (from-to)	1681-1689
Number of pages	9
Journal	Phytochemistry
Volume	40
Issue number	6
DOIs	https://doi.org/10.1016/0031-9422(95)00470-R
State	Published - Dec 1995

Bibliographical note

Funding Information:
Acknowledgements-We thank Bobbie J. Johnson for technical assistance; Dr C. M. Ricks (Tomato Genetics Resource Center, University of California, Davis) for providing tomato seeds; and Dr G. A. Kraus, Dr J. M. Applegate and Q. Su, Department of Chemistry, Iowa State University, Ames. This research was supported in part by grant 93-37201-9561 awarded by NRICGP/ USDA.

Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.

Keywords

AAL-toxin
cytotoxicity
fumonisins
phytotoxicity
phytotoxins

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title = "Biological activities of synthetic analogues of Alternaria alternata toxin (AAL-toxin) and fumonisin in plant and mammalian cell cultures",

abstract = "In a search for an analogue of AAL-toxin with high phytotoxicity and low mammalian toxicity, aminopentols [(AP1), hexacetyl AP1 and N-acetyl AP1], and nine analogues (1-9), were tested for toxicity to duckweed (Lemna pausicostata), susceptible tomato (asc/asc) leaf discs, black nightshade leaf discs and mammalian cell lines, including dog kidney (MDCK), rat liver hepatoma (H4TG) and mouse fibroblasts (NIH3T3). These were compared with AAL-toxin and fumonisin B1 (FB1). Analogue 9 at 10 μM increased cellular leakage and chlorophyll loss from both tomato and black nightshade leaf discs. The diester 9 was the most active in the duckweed bioassay, but it was much less toxic to MDCK and H4TG cells with an IC50 of 200 μM compared to 10 μM for FB1. Analogue 9 and FB1 showed similar low toxicities (IC50 = 150 μM) to NIH3T3 cells. Among the substances tested, only analogue 9 had significant phytotoxicity and low mammalian toxicity, indicating some potential for development of safe and effective natural herbicides.",

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Biological activities of synthetic analogues of Alternaria alternata toxin (AAL-toxin) and fumonisin in plant and mammalian cell cultures

Abstract

Bibliographical note

Keywords

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