αβ-Dehydrocurvularin and Curvularin from Alternaria cinerariae

Abstract

Secondary metabolite production by the phytopathogen Alternaria cinerariae has been investigated resulting in the isolation and identification of αβ-dehydrocurvularin and curvularin as products of this fungus. The phytotoxicity of these compounds is demonstrated.

Unique Spindle Poisons, Curvularin and Its Derivatives, Isolated fromPenicilliumSpecies

“…290.1153) indicated that 2 was 8-dehydrocurvularin. 7 ,S) This identification was confirmed by hydrogenation of 2 over Adams platinum quantitatively giving 1. The trans configuration proposed for the double bond was based on the coupling constant (J = 16 Hz) betweeen the two olefinic protons.…”

Isolation and Difference in Anti-Staphylococcus aureus Bioactivity of Curvularin Derivates from Fungus Eupenicillium sp.

“…The compound curvularin (1) is a macrolide, which shows antibiotic activity towards some fungi as a non-specific phytotoxin [1]. Curvularin and its derivatives could be potential nematicides against the root-lesion nematode, Pratylenchus penetrans [2].…”

βγ-Dehydrocurvularin and Related Compounds as Nematicides ofPratylenchus penetransfrom the FungusAspergillussp.

“…1). [7][8][9][10][11][12][13][14][15] The physicochemical properties of bg-dehydrocurvularin (1) The HREIMS data (Jeol JMS-SX 102 mass spectrometer) of 1 gave (M ＋ ) at 290.1160, consistent with the molecular formula C16H18O5 which is identical with that of 2. The 1 H-and 13 C-NMR spectra (Jeol JNM-ESP 500 NMR spectrometer) indicated the presence of one methyl, four methylene, one O-substituted aliphatic methine, two oleˆnic methine, one tetra-substituted phenyl, one carboxyl and one carbonyl groups.…”

“…[3][4][5][6] In a continuation of our search for novel naturally occurring nematicides that could be suitable as new lead compounds, we investigated the metabolites of Aspergillus sp. Bioassay-guided fractionation led to the isolation of four active compounds, bg-dehydrocurvularin (1), ab-dehydrocurvularin (2), [7][8][9][10][11][12][13][14][15] 8-b-hydroxy-7-oxocurvularin (3) 8,11,14,15) and 7-oxocurvularin (4) 14,15) In this report, we describe the isolation, structural elucidation, and biological activities of 1-4.…”

“…[11][12][13][14][15] ab-Dehydrocurvularin (2), 8-b-hydroxy-7-oxocurvularin (3) and 7-oxocurvularin (4) are produced by a number of phytopathogenic fungal species such as Curvularia, Penicillium, Cochliobolus, and Alternaria. [7][8][9][10][11][12][13][14][15] Compound 2 has shown phytotoxic, antifungal and cytotoxic activities. [7][8][9][10][11][12][13][14][15] The biological activi- ties of 1-4 were examined by the nematode, lettuce and rice bioassay methods, 2) although 3 was not examined with the rice bioassay due to its low yield.…”