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. 2024 Jan 2;14(4):381-392.
doi: 10.1080/21501203.2023.2265662. eCollection 2023.

Mycotoxins from Alternaria Panax, the specific plant pathogen of Panax ginseng

Huiqing Chen  1 , Jianzi Liu  1 , Ling Hu  2 , Jian Yang  3 , Yanduo Wang  1 , Wensong Sun  4 , Rong Wang  1 , Gang Ding  1 , Yong Li  1
Affiliations

Mycotoxins from Alternaria Panax, the specific plant pathogen of Panax ginseng

Huiqing Chen et al. Mycology. .

Abstract

Ginseng black spot, caused by Alternaria panax, is one of the most common diseases of Panax ginseng, which usually causes serious yield loss of ginseng plants. However, the pathogenic mechanism of A. panax has not been clarified clearly. Mycotoxins produced by phytopathogens play an important role in the process of infection. Previous study reported that dibutyl phthalate (DBP) identified from the metabolites of A. panax is a potent mycotoxin against P. ginseng. However, more evidence suggests that DBP is one of the constituents of plasticisers. To identify mycotoxins from A. panax and evaluate their phytotoxicity on the leaves of P. ginseng, different chromatographic, spectral and bioassay-guided methods were used together in this report. As a result, tyrosol (1), 3-hydroxy-3-(4-methoxyphenyl) propanoic acid (2), and 3-benzylpiperazine-2,5-dione (3) were isolated and characterised from the extract of A. panax, in which compounds 1 and 2 showed phytotoxic activity on ginseng leaves. Furthermore, DBP was confirmed to come from the residue of ethyl acetate through UPLC-MS/MS analysis, and displayed no phytotoxicity on ginseng leaves based on biological experiments. The results in this report first revealed that tyrosol (1), and 3-hydroxy-3-(4-methoxyphenyl) propanoic acid (2) not DBP were the potent mycotoxins of A. panax.

Keywords: Alternaria panax; Panax ginseng; dibutyl phthalate; mycotoxin; phytotoxic activities.

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Conflict of interest statement

No potential conflict of interest was reported by the authors.

Figures

Figure 1.
Figure 1.
Phytotoxic activities of EtOAc crude extract against leaves of panax ginseng. 75% ethanol (control) (a), the EtOAc crude extract (b).
Figure 2.
Figure 2.
Structures of tyrosol (1), 3-hydroxy-3-(4-methoxyphenyl) propanoic acid (2), and 3-benzylpiperazine-2, 5-dione (3).
Figure 3.
Figure 3.
1H, 13C-NMR of compound 1.
Figure 4.
Figure 4.
1H-NMR of compound 2.
Figure 5.
Figure 5.
1H, 13C-NMR of compound 3.
Figure 6.
Figure 6.
Phytotoxic activity of tyrosol (1) (a), 3-hydroxy-3-(4-methoxyphenyl) propanoic acid (2) (b), and 3-benzylpiperazine-2, 5-dione (3) (c) at 5 × 10−3 mol. 75% ethanol was used as the control (d).
Figure 7.
Figure 7.
UPLC-ESI-TOF/MS/MS profiles of standard sample of DBP.
Figure 8.
Figure 8.
UPLC-MS/MS profiles of chemical pure EtOAc solvent (a); UPLC-MS/MS profiles of the EtOAc extract from liquid culture of Alternaria panax (b).
Scheme 1.
Scheme 1.
Possible fragmentation pathway of DBP.
Figure 9.
Figure 9.
Leaf infiltration assay; 75% ethanol (control) (a), DBP (b).
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