The antifeedant and antifungal cryptic metabolites isolated from tobacco endophytes induced by host medium and coculture

Chen, Jingxin; Xia, Dan-Dan; Yang, Xue‐Qiong; Yang, Ya‐Bin; Ding, Zhong‐Tao

doi:10.1016/j.fitote.2022.105335

Cited by 12 publications

(13 citation statements)

References 22 publications

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“…The antifeedant activities against silkworm larvae were conducted according to the literature . The compounds 1 , 4 , 5 , 7 , and 8 were diluted to 5 mg/mL with acetone.…”

Section: Methodsmentioning

confidence: 99%

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Antibiotic Guanacastane Diterpenoids with Two New Skeletons from Psathyrella candolleana Uncovered by Semisolid and Liquid Media

Zhao

Yang

Zhou

et al. 2023

J. Agric. Food Chem.

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The culture of Psathyrella candolleana in host Dioscorea opposite medium produced seven new guanacastane diterpenoids, psayamin (1) as an unprecedented 5/7/6/6/6/6/7/5-fused octacyclic spiro scaffold both under liquid and semisolid conditions, psathins A−C (4−6) with a 5/7/6 tricyclic backbone by liquid medium, psathins D−E (7−8) as the same unprecedented skeletons of 5/6/7/6-fused tetracyclic or 6/7/6 tricyclic structures, and psathin F (9) with a 5/7/5/6 tetracyclic backbone by semisolid medium. The structures were elucidated by detailed spectroscopic analyses and those of 1 and 7 were determined by single-crystal X-ray crystallography. The semisolid culture led to four structure types of the guanacastane diterpenoid. Compound 5 showed antifungal activity against phytopathogen Fusarium incarnatum with a minimum inhibitory concentration (MIC) of 8 μg/mL, while compound 4 showed significant antifungal activity against Alternaria sp. with an MIC of 2 μg/mL. Compounds 1 and 8 also showed antifeedant activities against the silkworms with the feeding deterrence indices of 50%, at the concentrations of 50 μg/cm 2 . Compound 1 showed significant cytotoxicity with IC 50 at 10.87 ± 0.24−15.96 ± 0.30 μM and antiacetylcholinesterase activity with IC 50 at 37.3 μM. Also, compound 1 remarkably induced apoptosis of HL-60 at 10, 20 μM in a concentration-dependent manner. The spiral ring of 1 was vital in cytotoxicity and anti-acetylcholinesterase activity. The different media fermented by P. candolleana resulted in the chemical diversity of bioactive guanacastane diterpenoids and potential applications in the agricultural and food functions.

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“…The antifeedant activities against silkworm larvae were conducted according to the literature . The compounds 1 , 4 , 5 , 7 , and 8 were diluted to 5 mg/mL with acetone.…”

Section: Methodsmentioning

confidence: 99%

“…The test fungi and compounds in PDB medium were cultured for 18 h at 28 °C. The experiments were performed three times …”

Section: Methodsmentioning

confidence: 99%

Antibiotic Guanacastane Diterpenoids with Two New Skeletons from Psathyrella candolleana Uncovered by Semisolid and Liquid Media

Zhao

Yang

Zhou

et al. 2023

J. Agric. Food Chem.

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“…Nystatin was used as the positive control. The wells containing test strains and diluted compounds were incubated at 28 °C (16–18 h) [7] …”

Section: Methodsmentioning

confidence: 99%

“…FDI (%) = [(CÀ T)/(C + T)] × 100, where T and C represent the leaf areas consumed after adding the sample and the blank control, respectively. [7]…”

Section: Antifeedant Bioassay Against Silkworm Larvaementioning

confidence: 99%

“…The production of metabolites from Aspergillus fumigatus may be regulated by specific ecological factors, such as the microbial rivals, and symbionts [3] . The co‐culture and host medium were proven to be an effective strategy to produce rare metabolites from fungi [4–7] . The metabolites from cocultures of P. chrysogenum ‐ N. primolutea and P. chrysogenum ‐ A. fumigatus isolated from plant Ziziphus jujuba by supplementing with host Z. jujuba extract showed differences by comparing with those of monocultures.…”

Section: Introductionmentioning

confidence: 99%

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Novel Antifungal and Antifeedant Metabolites from Penicillium chrysogenum Co‐Cultured with Nemania primolutea and Aspergillus fumigatus

Yang

Cen

et al. 2023

Chemistry & Biodiversity

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The endophyte Nemania primolutea, inhibited the growth of Penicillium chrysogenum in the coculture system. Four new compounds, nemmolutines A -B (1 -2), and penigenumin (3) from N. primolutea, penemin (4) from P. chrysogenum were isolated from the coculture. On the other hand, P. chrysogenum inhibited the Aspergillus fumigatus in the coculture. Induced metabolites (13-16) with monasone naphthoquinone scaffolds including a new one from P. chrysogenum were produced by the coculture of P. chrysogenum, and A. fumigatus. Interesting, cryptic metabolites penicichrins A -B isolated from wild P. chrysogenum induced by host Ziziphus jujuba medium were also found in induced P. chrysogenum cultured in PDB ordinary medium. So the induction of penicichrin production by supplementing with host extract occurred in the fungus P. chrysogenum not the host medium. The productions of penicichrins were the spontaneous metabolism, and the metabolites (13 -16) were the culture driven. Compounds 4, 6, 8, 10, 11, 14, and 15 showed significant antifungal activities against the phytopathogen Alternaria alternata with MIC S of 1 -8 μg/mL, and compounds 7, 9, and 12 indicated significant antifeedant activities against silkworms with feeding deterrence indexes (FDIs) of 92 %, 66 %, and 64 %. The carboxy group in 4-(2-hydroxybutynoxy)benzoic acid derivatives, and xylabisboeins; the hydroxy group in mellein derivatives; and the quinoid in monasone naphthoquinone increased the antifungal activities.

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The cryptic metabolites and anti-phytopathogenic activities from Nigrospora lacticolonia and Penicillium rubens uncovered by the synergism with host Paris polyphylla, monoculture, and co-culture

Shi,

Chen,

Liao

et al. 2024

Bioorganic Chemistry

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The antifeedant and antifungal cryptic metabolites isolated from tobacco endophytes induced by host medium and coculture

Cited by 12 publications

References 22 publications

Antibiotic Guanacastane Diterpenoids with Two New Skeletons from Psathyrella candolleana Uncovered by Semisolid and Liquid Media

Antibiotic Guanacastane Diterpenoids with Two New Skeletons from Psathyrella candolleana Uncovered by Semisolid and Liquid Media

Novel Antifungal and Antifeedant Metabolites from Penicillium chrysogenum Co‐Cultured with Nemania primolutea and Aspergillus fumigatus

The cryptic metabolites and anti-phytopathogenic activities from Nigrospora lacticolonia and Penicillium rubens uncovered by the synergism with host Paris polyphylla, monoculture, and co-culture

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