Characterization of a New Insecticidal Anthraquinone Derivative from an Endophyte of Acremonium vitellinum against Helicoverpa armigera

Abstract

Endophytic fungi have proven to be prolific producers of bioactive secondary metabolites with agricultural applications. In this study, bioassay-guided isolation of the endophytic fungus Acremonium vitellinum yielded four anthraquinone derivatives (compounds 1−4), including a previously undescribed dimethylated derivative of bipolarin, 6,8-di-O-methylbipolarin (1). Their structures were determined by 1D and 2D nuclear magnetic resonance analysis as well as high-resolution electrospray ionization mass spectrometry data, and the absolute configuration of 1 was established by comparing the calculated and experimental electronic circular dichroism spectra. The insecticidal activity of the isolated compounds against the cotton bollworm Helicoverpa armigera was evaluated. The new compound 1 showed the strongest larvicidal activity against the 3rd instar larvae of H. armigera with an LC 50 value of 0.72 mg/mL. In addition, transcriptome sequencing was performed to evaluate the molecular mechanism of the insecticidal activity. In total, 5732 differentially expressed genes were found, among which 2904 downregulated genes and 2828 upregulated genes were mainly involved in cell autophagy, apoptosis, and DNA mismatch repair and replication. The results presented in this study reveal how 1 exerts its insecticidal effects against H. armigera via genome-wide differential gene expression analyses. Our findings suggest that anthraquinone derivatives are potential biopesticides for cotton bollworm control.

The Chemical Ecology Approach to Reveal Fungal Metabolites for Arthropod Pest Management

“…Colonization of plants with endophytic fungi was found to decrease a number of some phytophagous insects on the common host [157]. Therefore, endophytes, which are a rich source of bioactive natural compounds, recently attracted renewal interest as producers of insecticidal metabolites [243][244][245]. Phytopathogenic fungi (for example, pathogens of cereals and weeds) can also produce anti-insectan compounds [194,200,246,247].…”

Biotransformation ability of endophytic fungi: from species evolution to industrial applications

“…NRRL 3052 Munumbicins E-4, Munumbicins E-5 Broad-spectrum antibiotics Castillo et al ( 2006 ) 36 Helianthus annuus Nigrospora sphaerica TISTR3654 5-Pentyldihydrofuran-2(3 H )-one Activity of anti- Staphylococcus aureus and methicillin–resistant S. aureus , the activity of anti-fungi Talaromyces marneffei and the significant cytotoxic effect on A549 human cancer cell Supaphon and Preedanon ( 2019 ) 37 ( Z )-Methyl 4-(isobutyryloxy)but-3-enoate 38 2-Phenylacetic acid 39 Cephalotaxus fortunei Xylaria sp . KU645984.1 Xylariasins A Cytotoxic activity Ma et al ( 2021 ) 40 Marine red alga Acremonium vitellinum MH726097 6,8-di- O -Methylbipolarin Insecticidal activity Yuan et al ( 2020 ) 41 Achyranthes bidentata Phomopsis sp. CGMCC 5416 Chermesinone B Anti-HIV-1 virus, cytotoxic activity Yang et al ( 2020b ) 42 Phomopsone C 43 Cyclosorus parasiticus Diaporthe sp.…”

Promising approaches to the search for fungal metabolites for management of arthropod pests

“…Как малоизученые продуценты низкомолекулярных инсектицидных молекул интерес представляют эндофитные грибы (Gange et al, 2019). В последнее время интерес к ним существенно повышен (Zhang et al, 2019;Mao et al, 2020;Yuan et al, 2020). Наши собственные исследования показывают, что и фитопатогенные грибы (на примере патогенов злаков и сорных растений) могут образовывать инсектицидные метаболиты (Берестецкий и др., 2018б, 2020Dalinova et al, 2019Dalinova et al, , 2020.…”