LC–MS/MS-Guided Molecular Networking for Targeted Discovery of Undescribed and Bioactive Ophiobolins from <i>Bipolaris eleusines</i>

Wang, Yanduo; Yang, Jian; Hu, Ling; Bai, Ruibin; Wang, Tielin; Xing, Xiaoke; Chen, Lin; Ding, Gang

doi:10.1021/acs.jafc.3c03352

Cited by 10 publications

(5 citation statements)

References 24 publications

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“…We tested the anticancer activity of bipoladiens A–E ( 1–5 ) and bipolaricin R ( 6 ) against A549, MCF-7, HepG2, and RKO by a CCK-8 kit. Compounds 1–5 had no significant anticancer activity (IC 50 > 40 μM), whereas 6 showed excellent antiproliferation effects against A549 and MCF-7 with IC 50 values of 4.14 and 4.09 μM, respectively, which also exhibited moderate antiproliferation effects against HepG2 and RKO with IC 50 values of 17.84 and 24.65 μM, respectively (Figure A).…”

Section: Resultsmentioning

confidence: 99%

Bipoladien A, a Sesterterpenoid Containing an Undescribed 5/8/5/7 Carbon Skeleton from Bipolaris maydis

Shen,

Chen,

Zhao

et al. 2024

J. Agric. Food Chem.

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Bipoladiens A−E (1−5), five new ophiobolin-derived sesterterpenoids, and a known compound 6 (bipolaricin R) were isolated from the cultures of the phytopathogenic fungus Bipolaris maydis. Their structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, HRESIMS, electronic circular dichroism (ECD) calculations, and singlecrystal X-ray diffraction analyses. Notably, compound 1 has an undescribed tetracyclic 5/8/5/7 fused carbon skeleton, and compound 2 possesses a rare multicyclic caged ring system. The biosynthetic pathway of 1 was proposed starting from 6 via a series of oxidation and cyclization reactions. Compound 6 showed excellent antiproliferation and apoptosis induction effects against A549 cell line. Additionally, compounds 5 and 6 exhibited noticeable antimicrobial ability against Bacillus cereus, Staphylococcus aureus, and Staphylococcus epidermidis. These findings not only developed the chemical and bioactivities diversities of ophiobolin-sesterterpenoid but also provided an idea to boost the application of natural products in the control of food pathogens.

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Section: Resultsmentioning

confidence: 99%

Bipoladien A, a Sesterterpenoid Containing an Undescribed 5/8/5/7 Carbon Skeleton from Bipolaris maydis

Shen,

Chen,

Zhao

et al. 2024

J. Agric. Food Chem.

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“…In summary, three new aminated fusaric acid derivatives, hepialiamides A-C (1-3), and one novel hybrid polyketide, hepialide (4), together with 18 known miscellaneous compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22), were isolated from the cultures of the deep-sea-derived fungus Samsoniella hepiali W7 with the aid of GNPS molecular networking. Hepialiamides A-C feature a glycine/alanine unit embedded in the fusaric acid backbone, representing the third examples of naturally occurring fusaric amides, while hepialide features an uncommon isopropenylated pyrrolidone moiety.…”

Section: Discussionmentioning

confidence: 99%

“…These fragment ions (nodes) are then organized into relational networks depending on their similarity [9][10][11]. GNPS has been widely used to identify known compounds and potential new analogs, greatly speeding up the dereplication and structure-based discovery of natural products [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Hepialiamides A–C: Aminated Fusaric Acid Derivatives and Related Metabolites with Anti-Inflammatory Activity from the Deep-Sea-Derived Fungus Samsoniella hepiali W7

Zou,

Wu,

Yang

et al. 2023

Marine Drugs

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A systematic investigation combined with a Global Natural Products Social (GNPS) molecular networking approach, was conducted on the metabolites of the deep-sea-derived fungus Samsoniella hepiali W7, leading to the isolation of three new fusaric acid derivatives, hepialiamides A–C (1–3) and one novel hybrid polyketide hepialide (4), together with 18 known miscellaneous compounds (5–22). The structures of the new compounds were elucidated through detailed spectroscopic analysis. as well as TD-DFT-based ECD calculation. All isolates were tested for anti-inflammatory activity in vitro. Under a concentration of 1 µM, compounds 8, 11, 13, 21, and 22 showed potent inhibitory activity against nitric oxide production in lipopolysaccharide (LPS)-activated BV-2 microglia cells, with inhibition rates of 34.2%, 30.7%, 32.9%, 38.6%, and 58.2%, respectively. Of particularly note is compound 22, which exhibited the most remarkable inhibitory activity, with an IC50 value of 426.2 nM.

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“…The Network Topk was set at 10 and 10 minimum matched peaks, which should be met in the design formulas. Finally, molecular networking data were visualized in Cytoscape version 3.9.0 …”

Section: Methodsmentioning

confidence: 99%

Anti-Inflammatory Sesquiterpenes from Fruiting Bodies of Schizophyllum commune

Chen,

Liu,

et al. 2024

J. Agric. Food Chem.

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Schizophyllum commune, a fleshy fungus, is an important medicinal and food-homologous mushroom in China. In this work, eight undescribed sesquiterpenes schizomycins A−H (1−8) and one new meroterpenoid schizomycin I (9) together with three known analogues (10−12) were isolated from fruiting bodies of S. commune. Their planar structures were established by extensive spectroscopic and mass spectrometric data. The absolute configurations of compounds 1, 2, and 4 were determined by single crystal X-ray diffraction, and compounds 3 and 5−9 were confirmed by electronic circular dichroism calculations. Antiinflammatory activities of all isolated compounds were evaluated for their inhibitory effects on IL-6 and IL-1β production in RAW 264.7 cells. Among them, compound 7 exhibited significant IL-6 inhibitory activity with an IC 50 value of 3.6 μM. The results of molecular docking showed that compound 7 interacts with amino acid residues (Gly117, Lys118, Asp120, Thr166, and Try168) of the IL-6 receptor protein through hydrogen bonding.

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LC–MS/MS-Guided Molecular Networking for Targeted Discovery of Undescribed and Bioactive Ophiobolins from Bipolaris eleusines

Cited by 10 publications

References 24 publications

Bipoladien A, a Sesterterpenoid Containing an Undescribed 5/8/5/7 Carbon Skeleton from Bipolaris maydis

Bipoladien A, a Sesterterpenoid Containing an Undescribed 5/8/5/7 Carbon Skeleton from Bipolaris maydis

Hepialiamides A–C: Aminated Fusaric Acid Derivatives and Related Metabolites with Anti-Inflammatory Activity from the Deep-Sea-Derived Fungus Samsoniella hepiali W7

Anti-Inflammatory Sesquiterpenes from Fruiting Bodies of Schizophyllum commune

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