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. 2024 Aug 2:15:1446283.
doi: 10.3389/fmicb.2024.1446283. eCollection 2024.

Anti- Agrobacterium tumefactions sesquiterpene derivatives from the marine-derived fungus Trichoderma effusum

Yunfeng Liu  1   2 , Lu Qi  3 , Minghui Xu  2 , Wanyun Li  2 , Na Liu  1 , Xueli He  2 , Yuxing Zhang  1
Affiliations

Anti- Agrobacterium tumefactions sesquiterpene derivatives from the marine-derived fungus Trichoderma effusum

Yunfeng Liu et al. Front Microbiol. .

Abstract

Agrobacterium tumefaciens can harm various fruit trees, leading to significant economic losses in agricultural production. It is urgent to develop new pesticides to effectively treat this bacterial disease. In this study, four new sesquiterpene derivatives, trichoderenes A-D (1-4), along with six known compounds (5-10), were obtained from the marine-derived fungus Trichoderma effusum. The structures of 1-4 were elucidated by extensive spectroscopic analyses, and the calculated ECD, ORD, and NMR methods. Structurally, the hydrogen bond formed between the 1-OH group and the methoxy group enabled 1 to adopt a structure resembling that of resorcylic acid lactones, thereby producing the ECD cotton effect. Compound 3 represents the first example of C12 nor-sesquiterpene skeleton. Compounds 1-10 were tested for their antimicrobial activity against A. tumefactions. Among them, compounds 1-3 and 8-10 exhibited inhibitory activity against A. tumefactions with MIC values of 3.1, 12.5, 12.5, 6.2, 25.0, and 12.5 μg/mL, respectively.

Keywords: Agrobacterium tumefaciens; Trichoderma effusum; bioactivity; marine-derived fungus; sesquiterpene.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

Figure 1
Figure 1
Structures of the compounds 1–10.
Figure 2
Figure 2
Key HMBC and COSY of compounds 1–4.
Figure 3
Figure 3
Experimental and calculated ECD curves for 1.
Figure 4
Figure 4
Experimental and calculated ORD curves for 2.
Figure 5
Figure 5
Regression analysis and individual deviations of experimental vs. calculated 13C NMR chemical shifts of 3.
Figure 6
Figure 6
Experimental and calculated ECD curves for 4.
Figure 7
Figure 7
(A) Anti-Agrobacterium tumefactions activity of 1 using plate spread inhibition assay. (B) Time-kill curves of 1 against A. tumefactions. (C) Biofilm inhibition activity of 1 against A. tumefactions.
See this image and copyright information in PMC

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