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. 2021 Nov 18;13(11):812.
doi: 10.3390/toxins13110812.

Phytotoxins Produced by Two Biscogniauxia rosacearum Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran

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Phytotoxins Produced by Two Biscogniauxia rosacearum Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran

Marco Masi et al. Toxins (Basel). .

Abstract

Biscogniauxia rosacearum, recognized for the first time as a pathogen involved in grapevine trunk diseases in Paveh (west of Iran) vineyards, produced meso-2,3-butanediol (1) as the only phytotoxin. Nectriapyrone (2), (3R)-5-methylmellein (3), (3R)-5-methyl-6-methoxymellein (4), and tyrosol (5) were instead produced as phytotoxins from a strain of the same fungus isolated from oak trees in Zagros forests of Gilan-e Gharb, Kermanshah Province. They were identified comparing their 1H and 13C NMR, ESIMS, and specific optical rotation data with those already reported in the literature. The phytotoxicity of metabolites (1-5) was estimated by leaf puncture assay on Quercus ilex L. and Hedera helix L., and by leaf absorption assay on grapevine (Vitis vinifera L.) at a concentration of 5 × 10-3 and 10-3 M. Tested on grapevine, meso-2,3-butanediol (1) and (3R)-5-methyl-6-methoxymellein (4) resulted to be the most phytotoxic compounds. On Q. ilex, nectriapyrone (2) and tyrosol (5) showed severe necrosis at the highest concentration while none of the compounds (1-5) was active on H. helix. Furthermore, the phytotoxicity of compounds 3 and 4 was also compared with that of some related natural melleins to perform a structure-activity relationship (SAR) study. The results of this study were also discussed.

Keywords: Biscogniauxia rosacearum; SAR studies; grapevine; isocoumarines; oak trees; phytotoxins.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of: meso-2,3-butanediol (1) isolated from B. rosacearum IRAN 4194C; nectriapyrone (2), (3R)-5-methylmellein (3), (3R)-5-methyl-6-methoxymellein (4), and tyrosol (5) isolated from B. rosacearum IRAN 4287C; and (3R)-mellein (6), (3R,4R)-4-hydroxymellein (7), (3R,4S)-4-hydroxymellein (8), (3R)-6-hydroxymellein (9), and (3R)-4-methoxymellein (10).
Figure 2
Figure 2
Phytotoxic activity induced by meso-2,3-butanediol (1) (A), nectriapyrone (2) (B), (3R)-5-methylmellein (3) (C), (3R)-5-methyl-6-methoxymellein (4) (D), and tyrosol (5) (E) at 10−3 M by leaf absorption assay on grapevine. Negative control is 4% MeOH in MilliQ H2O (F).
Figure 3
Figure 3
Phytotoxic activity observed by testing by meso-2,3-butanediol (1) (A), nectriapyrone (2) (B), (3R)-5-methylmellein (3) (C), (3R)-5-methyl-6-methoxymellein (4) (D), and tyrosol (5) (E) at 10−3 M using leaf puncture assay on Q. ilex L. (left leaves) and H. helix L. (right leaves). Negative control is 4% MeOH in MilliQ H2O (F).

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