Preussianone, a New Flavanone-Chromone Biflavonoid from Garcinia preussii Engl.

Messi, Bernadette Biloa; Ndjoko-Ioset, Karine; Hertlein-Amslinger, Barbara; Lannang, Alain Méli; Nkengfack, Augustin E.; Wolfender, Jean‐Luc; Hostettmann, Kurt; Bringmann, Gerhard

doi:10.3390/molecules17056114

Cited by 29 publications

(12 citation statements)

References 33 publications

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“…Biflavonoids are a group of natural products that have limited occurrence in plant kingdom; but besides restricted distribution, they are one of the most significant secondary metabolites [1]. Biflavonoids are flavonoid dimers that have been attached to each other by either C-C or C-O-C bonds representing a variety of chemical structures [2].…”

Section: Introductionmentioning

confidence: 99%

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

et al. 2014

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Beta-site amyloid precursor protein cleaving enzyme (BACE-1) is a well-known therapeutic target for Alzheimer disease (AD) due to its characteristic role in the pathogenesis of AD. Numerous researches have been focused on the design and development of potent peptidic and nonpeptidic BACE-1 inhibitors. In the present contribution, a series of experimentally validated biflavonoid BACE-1 inhibitors (1-21) were subjected to our structure-based molecular modeling studies. Binding modes were elucidated through molecular docking in the active site of the enzyme. Relatively good correlations between the theoretical and experimental binding affinities could be achieved (R 2 = 0.61). Analysis of intermolecular binding energy components was performed via functional B3LYP in association with splitvalence basis set using polarization functions (Def2-SVP), and structure-binding relationships were further elucidated through ligand-residue binding energies. Since little studies have been performed on the modeling and structure activity/binding relationships of biflavonoid structures as BACE-1 inhibitors, the results of this study may be useful in further extending the scope of biflavonoid structures as potential anti-Alzheimer scaffolds.

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Section: Introductionmentioning

confidence: 99%

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

et al. 2014

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“…Furthermore, compound 1 was heated at reflux in TFA for 30 min. The resulting product, bispyranoxanthone (16) allowed additional confirmation of the proposed structure for 1. (Table 4).…”

Section: Resultsmentioning

confidence: 66%

“…Compounds with similar spectral data have been previously reported from the plants of the genus Garcinia of the Guttiferae family. [15][16][17][18] Therefore, comparison of the spectroscopic data of compound 3 with those described in the literature enabled us to deduce that it was a monoglycosylated biflavonoid derivative presenting doubled NMR signals. It is noteworthy that the doubled signals in the NMR spectra of biflavonoids at room temperature may be due to the fact that the molecules adopt different conformations 16 which arise from the restricted free rotation of the 3→8 interflavanyl bond.…”

Section: Resultsmentioning

confidence: 99%

“…[15][16][17][18] Therefore, comparison of the spectroscopic data of compound 3 with those described in the literature enabled us to deduce that it was a monoglycosylated biflavonoid derivative presenting doubled NMR signals. It is noteworthy that the doubled signals in the NMR spectra of biflavonoids at room temperature may be due to the fact that the molecules adopt different conformations 16 which arise from the restricted free rotation of the 3→8 interflavanyl bond. 17 Nevertheless, these NMR signals can be merged into a single set of signals at higher temperatures because under these conditions, the molecules do not exist in a preferred stable conformation.…”

Section: Resultsmentioning

confidence: 99%

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Two xanthones and two rotameric (3⟶8) biflavonoids from the Cameroonian medicinal plant Allanblackia floribunda Oliv. (Guttiferae)

Mountessou

Tchamgoue

Dzoyem

et al. 2018

Tetrahedron Letters

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Two xanthones, 2-(3-hydroxy-3,3-dimethyldihydroallyl)-dihydro-6-deoxyisojacareubin (1) and dihydro-6-deoxyjacareubin (2), and two 3⟶8 rotameric biflavonoids, (2R,3S)volkensiflavone-7-O--acetylglucopyranoside (3) and (2S,3S)-morelloflavone-7-O-acetylglucopyranoside (4), together with fifteen known compounds, were isolated from a dichloromethane/methanol (1/1, v/v) extract of the bark of the plant Allanblackia floribunda. The structures of the new compounds were elucidated by NMR spectroscopy and mass spectroscopic techniques and those of the known ones were deduced by comparison with data reported in the literature. The isolated biflavonoids were obtained as mixtures of conformers exhibiting duplicate NMR signals in solution at 25 °C and their respective absolute configurations were assigned using circular dichroism spectroscopy. Some of the isolated compounds were assessed for their antibacterial and antioxidant properties.

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“…The literature review shows that G. ovalifolia contains several molecules among which, isoxanthochimol [ 12 , 14 ], endodesmiadol, canophyllol, canophyllal [ 12 , 15 ], gallic acid, garcinane [ 16 ], 3-methylcheffouxanthone, two new friedelane triterpene derivatives ovalifolone A and B [ 12 ]. Epi-garcinol, iso-garcinol and manniflavanone isolated from our plant ( G. ovalifolia) have also been discovered in other plants extract such as Garcinia preussii [ 17 ] Hypericum lanceolatum [ 18 ] Moronobea coccinea [ 19 ] Symphonia globulifera [ 20 ] and Garcinia bancana [ 21 ]. Several biological properties of epi-garcinol, iso-garcinol and manniflavanone have been investigated which included antiplasmodial [ 20 – 23 ], antibacterial [ 17 , 18 ] and immunosuppressant effects [ 24 ].Several biological properties of these molecules have been investigated such as antibacterial, cytotoxicity activity on Artemia salina [ 13 ] and anti-HIV [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Epigarcinol and isogarcinol isolated from the root of Garcinia ovalifolia induce apoptosis of human promyelocytic leukemia (HL-60 cells)

et al. 2015

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BackgroundPlants from garcinia genus have been used for centuries against several diseases.ObjectiveThis study aimed to investigate the mechanism of apoptosis induced by epigarcinol and isogarcinol isolated from the root of Garcinia ovalifolia (Clusiaceae) on human promyelocytic leukemia (HL-60 cells).MethodsEpigarcinol and isogarcinol were isolated from the root of G. ovalifolia by using column chromatography method. The antiproliferative property of these molecules and fractions were assessed with 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. The light fluorescence microscope was utilized to observe the morphological changes of HL-60 cells after 24 h treatment. Early apoptosis and cell cycle distribution were analyzed by using flow cytometry (FCM).ResultsThe results showed that epigarcinol and isogarcinol inhibited the proliferation of HL-60 and PC-3 cells in a concentration-dependent manner with IC50 varying between 4 and 76 µg/mL depending on the cell line and the molecule. The apoptosis rate and the number of apoptotic cells significantly increased with the augmentation of the concentration of the molecules. The results of flow cytometry (FCM) indicated that epigarcinol and isogarcinol induced significant G2/S arrest of HL-60 cells, the disruption of mitochondrial membrane potential and reactive oxygen species (ROS) generation.ConclusionThese results indicated that epigarcinol and isogarcinol demonstrated in vitro antiproliferative properties and induce apoptosis of HL-60 cells which is related to the G2/S arrest, and it exerts its apoptotic effect through the loosing of mitochondrial membrane potential.

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Preussianone, a New Flavanone-Chromone Biflavonoid from Garcinia preussii Engl.

Cited by 29 publications

References 33 publications

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

Two xanthones and two rotameric (3⟶8) biflavonoids from the Cameroonian medicinal plant Allanblackia floribunda Oliv. (Guttiferae)

Epigarcinol and isogarcinol isolated from the root of Garcinia ovalifolia induce apoptosis of human promyelocytic leukemia (HL-60 cells)

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