Aryl Ketones fromAcronychia pedunculata with Cyclooxygenase-2 Inhibitory Effects

Pathmasiri, Wimal; El‐Seedi, Hesham R.; Han, Xiao; Janson, Jan‐Christer; Huss, Ulrika; Bohlin, Lars

doi:10.1002/cbdv.200590026

Cited by 20 publications

(16 citation statements)

References 14 publications

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“…Acronychia ‐type acetophenones (AtA) are considered as a characteristic chemical group of natural products found in the genus Acronychia of Rutaceae family . Their biological interest is focused mainly on their significant cytotoxicity against several human tumor cell lines and anti‐inflammatory activities . Up to date, a small number of derivatives have been reported exhibiting high potential as anticancer agents against human melanoma and prostate tumor cell lines .…”

Section: Introductionmentioning

confidence: 99%

“…This particular nature of AtA renders their identification challenging, and until now, limited data have been reported for the structure elucidation thereof. A previous study presenting the X‐ray crystallography of acrovestone ( 1 ), a model AtA compound, is available, but mainly, the structure elucidation of these compounds has been performed using nuclear magnetic resonance techniques . However, high temperature nuclear magnetic resonance (47 °C) acquisitions and nuclear Overhauser effect experiments are highly required for the elucidation of isomers .…”

Section: Introductionmentioning

confidence: 99%

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Ion tree-based structure elucidation of acetophenone dimers (AtA) fromAcronychia pedunculataand their identification in extracts by liquid chromatography electrospray ionization LTQ-Orbitrap mass spectrometry

et al. 2015

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Acronychia-type acetophenones (AtA) is a chemical group of compounds of important structural and biological interest, abundant in Acronychia species. However, there are no data available for their characterization using mass spectrometry. In the current work, AtA have been investigated by multistage high resolution mass spectrometry and both electrospray ionization and atmospheric pressure chemical ionization, in positive and negative mode, were utilized for their structure elucidation and identification. The analysis of AtA using a linear ion trap-Orbitrap analyzer enabled the structural determination of key fragment ions and cleavages, which can be used for the structural characterization thereof. A systematic nomenclature based on protonated and deprotonated fragment ions under collision-induced dissociation conditions and decision trees for the structural determination of AtA are proposed. Furthermore, taking advantage of the characteristic fragmentation patterns, a selective Ultra High Performance Liquid Chromatography Electrospray Ionization multistage Mass Spectrometry (UHPLC-ESI(-)-MS(n)) method was developed and successfully applied for the dereplication of known AtA and the identification of potentially new ones in Acronychia extracts. Despite the structure similarity and the presence of isomers, accurate characterization of known and unknown AtA derivatives was possible.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ion tree-based structure elucidation of acetophenone dimers (AtA) fromAcronychia pedunculataand their identification in extracts by liquid chromatography electrospray ionization LTQ-Orbitrap mass spectrometry

et al. 2015

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“…The 1 H NMR spectrum (Table 1) of 2 was closely related to that of known acrofolione B, previously isolated as a racemate from A. trifoliolata. 7 Some signals were broadened in the 1 H and 13 C NMR spectra because of freely rotatable aryl moieties in 2, making the structural elucidation difficult. Although the connectivities could not be determined from the spectra in (CD 3 ) 2 SO, confirmation was provided by measuring the spectra in several deuterated solvents, such as C 6 D 6 and (CD 3 ) 2 CO (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis

et al. 2019

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The isolation of 12 secondary metabolites, including seven new acetophenone monomers, from the 50% CH 3 OH/CH 2 Cl 2 extract (N089419-L/6) of Acronychia trifoliolata was reported previously. In the present work, three new prenylated acetophenone dimers (1-3) and five known dimers (4-8) were isolated, and their structures were elucidated by using various NMR spectroscopic techniques and HRMS. Among the new dimers, an unprecedented 4-isobutyl-3 isopropyltetrahydro-2H-pyran ring was observed in the structure of 1. This study is the first to report the formation of a 2H-pyran ring between two prenylated acetophloroglucinols. Only four related dimers have been reported before, and they were formylated phloroglucinol dimers from the family Eucalypteae. Compounds 2 and 3 are acrovestone-like dimers, and the structure of 3 was confirmed by total synthesis. The evaluation of the antiproliferative activity of isolated and synthesized acrovestone-like dimers indicated that a double bond in the prenyl-like moiety as *

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“…This is the most commonly used way of determining bioactives. Despite significant increase in the number of studies reporting bioactives [29][30][31][32] through this process, a large number of botanicals and their preparations are still in use without any knowledge of their bioactives [33][34][35][36]. The synergy directed fractionation method uses bioactivity-guided fractionation combined with bioactivity testing in order to understand synergistic connections between the compounds present in a mixture.…”

Section: Isolation and Characterization Of Bioactive Compoundsmentioning

confidence: 99%

Plant-Based Phytochemicals as Possible Alternative to Antibiotics in Combating Bacterial Drug Resistance

et al. 2020

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The unprecedented use of antibiotics that led to development of resistance affect human health worldwide. Prescription of antibiotics imprudently and irrationally in different diseases progressed with the acquisition and as such development of antibiotic resistant microbes that led to the resurgence of pathogenic strains harboring enhanced armors against existing therapeutics. Compromised the treatment regime of a broad range of antibiotics, rise in resistance has threatened human health and increased the treatment cost of diseases. Diverse on metabolic, genetic and physiological fronts, rapid progression of resistant microbes and the lack of a strategic management plan have led researchers to consider plant-derived substances (PDS) as alternative or in complementing antibiotics against the diseases. Considering the quantitative characteristics of plant constituents that attribute health beneficial effects, analytical procedures for their isolation, characterization and phytochemical testing for elucidating ethnopharmacological effects has being worked out for employment in the treatment of different diseases. With an immense potential to combat bacterial infections, PDSs such as polyphenols, alkaloids and tannins, present a great potential for use, either as antimicrobials or as antibiotic resistance modifiers. The present study focuses on the mechanisms by which PDSs help overcome the surge in resistance, approaches for screening different phytochemicals, methods employed in the identification of bioactive components and their testing and strategies that could be adopted for counteracting the lethal consequences of multidrug resistance.

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Aryl Ketones fromAcronychia pedunculata with Cyclooxygenase-2 Inhibitory Effects

Cited by 20 publications

References 14 publications

Ion tree-based structure elucidation of acetophenone dimers (AtA) fromAcronychia pedunculataand their identification in extracts by liquid chromatography electrospray ionization LTQ-Orbitrap mass spectrometry

Ion tree-based structure elucidation of acetophenone dimers (AtA) fromAcronychia pedunculataand their identification in extracts by liquid chromatography electrospray ionization LTQ-Orbitrap mass spectrometry

Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis

Plant-Based Phytochemicals as Possible Alternative to Antibiotics in Combating Bacterial Drug Resistance

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