Isolation and identification of tentoxin from Alternaria porri (Ellis) Ciferri.

Agricultural and Biological Chemistry
1990.0

Abstract

In the course of investigation on the bioactive products of Alternaria porri (Ellis) Ciferri (the causal fungus of black spot disease in stone-leek and onion), previous studies reported three reduced anthraquinone derivatives (altersolanol A, B and dactylariol) and anthraquinone dimers (alterporriol A, B and C). This communication describes the isolation and identification of another bioactive compound, tentoxin, from A. porri. The fungus was cultured using stone-leek decoction medium for thirty days. Active substances were extracted with ethyl acetate from the culture liquid, concentrated, and subjected to preparative TLC (Merck Kieselgel 60PF254) with a solvent system of chloroform-acetone-formic acid (200:100:1). Repeated preparative TLC (Rf: 0.37) followed by recrystallization from benzene gave colorless needles (mp 173-174°C). Structural identification was based on spectral data: SIMS mass spectrum showed a peak at m/z 415 (MH+), molecular formula C22H30N4O4 (from El-high-resolution mass spectral data), IR spectrum (amide group at 1670, 1630 cm⁻¹; monosubstituted phenyl at 1520, 760, 700 cm⁻¹), and ¹H-NMR (400 MHz in CDCl₃) and ¹³C-NMR (INEPT method) spectra. Comparison with IR, NMR and mass spectra of an authentic sample confirmed the compound as tentoxin, a phytotoxin known to be produced by some Alternaria species (e.g., A. tenuis, A. mali, A. citri) causing chlorosis in dicotyledonous plants. From a chemotaxonomical perspective, it is of interest that tentoxin was identified as a metabolite of A. porri.

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