New alkaloids from the diversity-enhanced extracts of an endophytic fungus Aspergillus flavus GZWMJZ-288

He, Wenwen; Xu, Ya‐Qiong; Wu, Dan; Wang, Dongyang; Gao, Hai; Wang, Liping; Zhu, Weiming

doi:10.1016/j.bioorg.2020.104623

Cited by 15 publications

(16 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 1 H and 13 C NMR data of 1 (Table ) showed the presence of two sets of signals in a ratio of about 7:10 ( E - 1 : Z - 1 ). This phenomenon indicted that this compound has cis – trans isomers arising from the E - and Z -geometries of 19-NH in solutions . In this paper, the structure analysis was based on the NMR data of E - 1 .…”

Section: Resultsmentioning

confidence: 99%

Cyclopiazonic Acid and Okaramine Analogues, Including Chlorinated Compounds, from Chrysosporium undulatum YT-1

et al. 2022

View full text Add to dashboard Cite

Eight new cyclopiazonic acid (1−8) and five new okaramine (9−13) alkaloids together with 13 known compounds were isolated from the fungus Chrysosporium undulatum YT-1. Compounds 2, 4, 5, 7, 10, 11, and 13 were chlorinated indole alkaloids. The structures of compounds 1−13 were elucidated by HRESIMS and NMR spectroscopic data. Their relative and absolute configurations were established by J-based configuration analysis, NOESY, NOEDIFF experiments, ECD spectroscopic data, and biogenetic considerations. Compound 4 inhibited the growth of Bacillus subtilis with an MIC value of 6.3 μg/mL. Compounds 9−11 exhibited strong insecticidal capacity against the third instar larvae of silkworm and cotton bollworm (LD 50 : ≤7.56 μg/g). At 40 μM, compound 1 showed obvious neuroprotection to the PC12 cells with 6-OHDA treatment.

show abstract

Section: Resultsmentioning

confidence: 99%

Cyclopiazonic Acid and Okaramine Analogues, Including Chlorinated Compounds, from Chrysosporium undulatum YT-1

et al. 2022

View full text Add to dashboard Cite

show abstract

“…The bisindolylmaleimide aglycone (12) was synthesized from 2,3-dibromomaleimide with 76% total yield by four step reactions including N-benzyloxymethyl (BOM) protection of the imide group, the indole Grignard reaction, tert-butoxycarbonyl (Boc) protection of the amino group of the indole nucleus and the second Grignard reaction with another indole (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…The next work was to apply the Mitsunobu reaction to the N-glycosylation of asymmetric bisindolylmaleimide aglycone (12) with the 2-deoxyglycosyl donor (17) (Scheme 4), which afforded a 1 : 1 isolable mixture of N-β-D-glucopyranoside (18a) and N-α-D-glucopyranoside (18b).…”

Section: Resultsmentioning

confidence: 99%

“…The docking studies of compounds 1 and 7 in the active site of PKC αand PKC β II were carried out by AutoDock Vina on the PyRx version 0.8. 11,12 The 3D structures of the compounds were obtained using ChemBioDraw 15.0 and ChemBio3D 15.0 software. The AutoDockTools 1.5.6 package was employed to generate the docking input files.…”

Section: Bioassay Protocolsmentioning

confidence: 99%

“…Apart from ZHD-0501, its seven isomers, ent-ZHD-0501 (2), 5-deoxo-7-oxo-ent-ZHD-0501 (3), 3′,4′-diepi-ZHD-0501 (4), 3′,4′-diepi-5-deoxo-7-oxo-ZHD-0501 (5), 1′,5′-diepi-ZHD-0501 (6), 1′,5′-diepi-5-deoxo-7-oxo-ZHD-0501 (7) and 5-deoxo-7-oxo-ZHD-0501 (8) (Fig. 1), as well as 37 new ICZ intermediates (12,(18)(19)(20)(21)(22)(23)(24)(25)(26)(32)(33)(34)(35)(36)(37)(38)(39)(40) were also synthesized in this process. The antiproliferative activities of compounds 1-8 and their key synthetic precursors 26a, 26b, 40a and 40b against four tumor cell lines and protein kinase C alpha/beta (PKC α/ β) were evaluated.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Total synthesis of the indolocarbazole alkaloid ZHD-0501 and its seven isomers

Wang

Zhang

et al. 2022

Org. Chem. Front.

Self Cite

View full text Add to dashboard Cite

show abstract

Expanding Chemical Frontiers: Approaches for Generating Diverse and Bioactive Natural Product‐Like Compounds Libraries from Extracts

Beato,

Haudecoeur,

Boucherle

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

The realms of natural products and synthetic compounds exhibit distinct chemical spaces that not only differ but also complement each other. While the convergence of these two domains has been explored through hemisynthesis and conventional pharmacomodulation endeavours applied to natural frameworks, a recent and innovative approach has recently emerged that involves the combinatorial generation of libraries of ‘natural product‐like compounds’ (NPLCs) through the direct synthetic derivatization of natural extracts. This has led to the production of numerous NPLCs that incorporate structural elements from both their natural (multiple saturated rings, oxygen content, chiral centres) and synthetic (aromatic rings, nitrogen and halogen content, drug‐like properties) precursors. Through careful selection of extracts and reagents, specific bioactivities have been achieved, and this strategy has been deployed in various ways, showing great promise without reaching its full potential to date. This review seeks to provide an overview of reported examples involving the chemical engineering of extracts, showcasing a spectrum of natural product alterations spanning from simple substitutions to complete scaffold remodelling. It also includes an analysis of the accomplishments, perspectives and technical challenges within this field.

show abstract

New alkaloids from the diversity-enhanced extracts of an endophytic fungus Aspergillus flavus GZWMJZ-288

Cited by 15 publications

References 35 publications

Cyclopiazonic Acid and Okaramine Analogues, Including Chlorinated Compounds, from Chrysosporium undulatum YT-1

Cyclopiazonic Acid and Okaramine Analogues, Including Chlorinated Compounds, from Chrysosporium undulatum YT-1

Total synthesis of the indolocarbazole alkaloid ZHD-0501 and its seven isomers

Expanding Chemical Frontiers: Approaches for Generating Diverse and Bioactive Natural Product‐Like Compounds Libraries from Extracts

Contact Info

Product

Resources

About