Penaloidines A and B: two unprecedented pyridine alkaloids from <i>Penicillium</i> sp. KYJ-6

Gan, Dong; Zhu, Li; Zhang, Xiaoran; Li, Chen-Zhe; Wang, Chen-yao; Cai, Le; Ding, Zhong‐Tao

doi:10.1039/d1qo01879e

Cited by 11 publications

(4 citation statements)

References 33 publications

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“…Water molecules were deleted and the polar hydrogen atoms, charge, and magnetic field were added before docking. AutoDock Tools 1.5.6 ( https://autodock.scripps.edu ) was used for molecular docking and processing of ligands and receptors ( Zheng et al, 2021 ; Gan et al, 2022 ). Active pockets were built and saved as protein data bank (PDB), partial charge (Q), and atom type (T) (PDBQT) files.…”

Section: Methodsmentioning

confidence: 99%

“…It can overcome water retention, promote circulation of Qi ( Chen and Xu, 2003 ), remove blood stasis, staunch bleeding, expel sores and carbuncles, dispel pathogenic wind, remove edema, and stop itching ( Editorial Committee of Flora Reipublicae Popularis Sinicae, 1997 ). It can be used as a hemostatic agent for bleeding due to external injury, and as a treatment for tumors, ulcers, edema, abdominal mass, abdominal distension, ascites due to liver cirrhosis, and skin itching ( Wu et al, 1992 ; Chen et al, 2014 ; Gan et al, 2022 ). E. nematocypha is also used to treat bruises, stiffness, indigestion, toothache, and diabetes mellitus ( Roy et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity and molecular-docking approach of a new rosane-type diterpenoid from the roots of Euphorbia nematocypha

et al. 2022

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A new rosane-type diterpenoid (1) along with nine known diterpenoids (2–10), were isolated from the dried roots of Euphorbia nematocypha. The absolute configuration was elucidated from spectroscopic (nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, and electronic circular dichroism) and optical-rotation analyses. Cytotoxicity and the ability to scavenge 2,2-diphenyl-1-picrylhydrazyl radicals were determined. Compound 1 showed remarkable cytotoxicity against human cancer cell lines (HeLa, CT26, and HCC 1806) in vitro. The interaction between compound 1 and proteins of ribosomal S6 kinase was revealed using molecular docking and provided valuable insights into the cytotoxic mechanism of action of compound 1. The latter could be developed as a pharmaceutical agent in the future.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cytotoxicity and molecular-docking approach of a new rosane-type diterpenoid from the roots of Euphorbia nematocypha

et al. 2022

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“…Likewise, the methyl group on the cycloesadienone of penicitrinone H is essential for inhibitory activity when compared with its B analogue [ 141 ], while palitantin was reported to be significantly more potent than its analogue 13-hydroxypalitantin [ 142 ]. Some quantitative differences have also been found among stereoisomers, such as (+)- and (-)-penicilliumine [ 143 ], quinolactacins A1–A2 [ 144 ], and penaloidines A–B, which are unprecedented pyridine alkaloids possessing a tetrahydrofuro[3,2-c][2,7]naphthyridinyl scaffold [ 145 ].…”

Section: Effects On the Nervous Systemmentioning

confidence: 99%

Anti-Insect Properties of Penicillium Secondary Metabolites

et al. 2023

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In connection with their widespread occurrence in diverse environments and ecosystems, fungi in the genus Penicillium are commonly found in association with insects. In addition to some cases possibly implying a mutualistic relationship, this symbiotic interaction has mainly been investigated to verify the entomopathogenic potential in light of its possible exploitation in ecofriendly strategies for pest control. This perspective relies on the assumption that entomopathogenicity is often mediated by fungal products and that Penicillium species are renowned producers of bioactive secondary metabolites. Indeed, a remarkable number of new compounds have been identified and characterized from these fungi in past decades, the properties and possible applications of which in insect pest management are reviewed in this paper.

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“…Reassignment of the structures of pestalopyrones A-D was reported by Wang et al 101 Polychlorinated cyclopentenes from a marine derived Periconia sp. were studied by Oberlies et al 102 Ding et al 103 reported on penaloidines A and B: two unprecedented pyridine alkaloids from Penicillium sp. Hamann et al 104 reported on structure and antimicrobial activity of rare lactone lipids from the sooty mold.…”

Section: Nuclear Shielding Calculation In Natural Productsmentioning

confidence: 99%

Theory and computation of nuclear shielding

2023

Nuclear Magnetic Resonance

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This chapter continues earlier reviews of essential works on theoretical issues of nuclear magnetic shieldings published from 1 January to 31 December 2022. As previously, the chapter concentrates on theoretical calculations of nuclear shielding parameters and/or chemical shifts in case of free molecules in the gas phase and solution, and in some cases in the solid state using a periodic formulation. The nuclear shieldings in solution are mainly calculated using inexpensive polarizable continuum model of solvent (PCM). The use of discrete solvent molecules (in particular water and other polar solvents), which is essential for correct description of hydrogen bonding, is often omitted by numerous authors. Most calculations use a relatively simple and fast, but reliable density functional theory (DFT) combined with gauge-including atomic orbital (GIAO) approach. On the other hand, reports on prediction of nuclear magnetic shielding parameters using high level theoretical methods combined with large and flexible basis sets are not so common due to the enormous computational cost. In addition, correction of raw theoretical nuclear magnetic shieldings due to ro-vibration (zero-point vibration correction, ZPVC) and temperature corrections (TC), as well as implicit and explicit solvent effects and relativistic corrections are not often reported.

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Penaloidines A and B: two unprecedented pyridine alkaloids from Penicillium sp. KYJ-6

Abstract: Penaloidines A (1) and B (2), a pair of epimers, unprecedented meroterpenoid pyridine alkaloids possessing a tetrahydrofuro[3,2-c][2,7]naphthyridinyl scaffold, were characterized from Penicillium sp. KYJ-6. Their structures were elucidated by spectroscopic...

Cited by 11 publications

References 33 publications

Cytotoxicity and molecular-docking approach of a new rosane-type diterpenoid from the roots of Euphorbia nematocypha

Cytotoxicity and molecular-docking approach of a new rosane-type diterpenoid from the roots of Euphorbia nematocypha

Anti-Insect Properties of Penicillium Secondary Metabolites

Theory and computation of nuclear shielding

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