Phenylpropenoids from <i>Bupleurum fruticosum</i> as Anti-Human Rhinovirus Species A Selective Capsid Binders

Fois, Benedetta; Bianco, Giulia; Sonar, Vijay P.; Distinto, Simona; Maccioni, Elias; Meleddu, Rita; Melis, Claudia; Marras, Luisa; Pompei, Raffaello; Floris, C.; Caboni, Pierluigi; Cottiglia, Filippo

doi:10.1021/acs.jnatprod.7b00648

Cited by 17 publications

(7 citation statements)

References 42 publications

(82 reference statements)

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“…Continuing our search for biologically active secondary metabolites from Sardinian higher plants 19,20 , we have found that the petroleum ether and ethyl acetate extracts of Magydaris pastinacea seeds exhibited potent inhibitory activity against hCA IX and XII. As a consequence, in order to identify the active compounds, a phytochemical investigation of the extracts was performed.…”

Section: Introductionmentioning

confidence: 99%

Coumarins fromMagydaris pastinaceaas inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation

Fois

Distinto

Meleddu

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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In an in vitro screening for human carbonic anhydrase (hCA) inhibiting agents from higher plants, the petroleum ether and ethyl acetate extracts of Magydaris pastinacea seeds selectively inhibited hCA IX and hCA XII isoforms. The phytochemical investigation of the extracts led to the isolation of ten linear furocoumarins (1-10), four simple coumarins (12-15) and a new angular dihydrofurocoumarin (11). The structures of the isolated compounds were elucidated based on 1 D and 2 D NMR, MS, and ECD data analysis. All isolated compounds were inactive towards the ubiquitous cytosolic isoform hCA I and II (K i > 10,000 nM) while they were significantly active against the tumour-associated isoforms hCA IX and XII. Umbelliprenin was the most potent coumarin inhibiting hCA XII isoform with a K i of 5.7 nM. The cytotoxicity of the most interesting compounds on HeLa cancer cells was also investigated.

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Section: Introductionmentioning

confidence: 99%

Coumarins fromMagydaris pastinaceaas inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation

Fois

Distinto

Meleddu

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…During the continuous search of secondary plant metabolites with antiviral activity [24][25][26] , we found that the ethyl acetate (EtOAc) extract from the leaves of Teucrium flavum subsp. glaucum showed a significant inhibitory activity towards this enzyme function, with an IC 50 of 28.6 lg/mL (Table 1).…”

Section: Introductionmentioning

confidence: 99%

Flavonoids and Acid-Hydrolysis derivatives ofNeo-Clerodane diterpenes fromTeucrium flavumsubsp.glaucumas inhibitors of the HIV-1 reverse transcriptase–associated RNase H function

Fois

Corona

Tramontano

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Bioassay-guided fractionation of the ethyl acetate extract from Teucrium flavum subsp. glaucum, endowed with inhibitory activity towards the HIV-1 reverse transcriptase-associated RNase H function, led to the isolation of salvigenin (1), cirsimaritin (2) and cirsiliol (3) along with the neo-clerodanes teuflavin (4) and teuflavoside (5). Acid hydrolysis of the inactive teuflavoside provided three undescribed neo-clerodanes, flavuglaucins A-C (7-9) and one known neo-clerodane (10). Among all neo-clerodanes, flavuglaucin B showed the highest inhibitory activity towards RNase H function with a IC 50 value of 9.1 lM. Molecular modelling and site-directed mutagenesis analysis suggested that flavuglaucin B binds into an allosteric pocket close to RNase H catalytic site. This is the first report of clerodane diterpenoids endowed with anti-reverse transcriptase activity. Neo-clerodanes represent a valid scaffold for the development of a new class of HIV-1 RNase H inhibitors.

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“…In the past, natural product chemists used to rely on polarimetry to draw conclusions about either enantiomeric purity or AC of isolated chiral secondary metabolites [ 27 ]. Even today, however, it is not unusual to find stereochemical assignments based on comparisons of chiroptical properties (optical rotation, sometimes measured in different conditions, and/or ECD) for structurally correlated compounds [ 28 , 29 , 30 ], or even based on biosynthetic considerations [ 31 , 32 ]. It is important to mention that herein we are not questioning the referenced assignments, but rather highlighting practices that may result in misassignments.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment

Batista

Cass

2018

Molecules

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Chiral natural product molecules are generally assumed to be biosynthesized in an enantiomerically pure or enriched fashion. Nevertheless, a significant amount of racemates or enantiomerically enriched mixtures has been reported from natural sources. This number is estimated to be even larger since the enantiomeric purity of secondary metabolites is rarely checked in the natural product isolation pipeline. This latter fact may have drastic effects on the evaluation of the biological activity of chiral natural products. A second bottleneck is the determination of their absolute configurations. Despite the widespread use of optical rotation and electronic circular dichroism, most of the stereochemical assignments are based on empirical correlations with similar compounds reported in the literature. As an alternative, the combination of vibrational circular dichroism and quantum chemical calculations has emerged as a powerful and reliable tool for both conformational and configurational analysis of natural products, even for those lacking UV-Vis chromophores. In this review, we aim to provide the reader with a critical overview of the occurrence of enantiomeric mixtures of secondary metabolites in nature as well the best practices for their detection, enantioselective separation using liquid chromatography, and determination of absolute configuration by means of vibrational circular dichroism and density functional theory calculations.

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Phenylpropenoids from Bupleurum fruticosum as Anti-Human Rhinovirus Species A Selective Capsid Binders

Cited by 17 publications

References 42 publications

Coumarins fromMagydaris pastinaceaas inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation

Coumarins fromMagydaris pastinaceaas inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation

Flavonoids and Acid-Hydrolysis derivatives ofNeo-Clerodane diterpenes fromTeucrium flavumsubsp.glaucumas inhibitors of the HIV-1 reverse transcriptase–associated RNase H function

Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment

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