Structure Elucidation of a Dihydropyranone from <i>Tapinanthus dodoneifolius</i>

Ouédraogo, Maurice; Carreyre, Hélène; Vandebrouck, Clarisse; Bescond, Jocelyn; Raymond, Guy; Guissou, Innocent-Pierre; Cognard, Christian; Becq, Frédéric; Potreau, Daniel; Cousson, A.; Marrot, Jérôme; Coustard, Jean‐Marie

doi:10.1021/np070355x

Cited by 35 publications

(47 citation statements)

References 12 publications

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“…Agelanthus dodoneifolius (DC) Polhill & Wiens Danser (Loranthaceae), commonly named Tapinanthus dodoneifolius, is a ubiquitous plant which parasitizes on several plants, including Vitellaria paradoxa (Sapotaceae). This hemi plant parasite has been reported to possess a wide range of medicinal properties (10,11). In the folk medicine of Burkina Faso it is used alone and in association with other traditional remedies for the treatment of various ailments including cardiovascular and respiratory diseases, stomach-ache and wounds.…”

Section: Introductionmentioning

confidence: 99%

Modulatory activities of Agelanthus dodoneifolius (Loranthaceae) extracts on stimulated equine neutrophils and myeloperoxidase activity

Boly¹,

Dessy²,

Kohnen³

et al. 2011

Int J Mol Med

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Abstract. Agelanthus dodoneifolius DC Danser (Loranthaceae)is used for the treatment of various diseases including asthma. The aqueous and hydroalcoholic extracts have been reported to have anti-inflammatory, spasmolytic and bronchorelaxant activities. The present study investigates the effects of the aqueous decoction and the diethyl ether, ethyl acetate and butanolic fractions of Agelanthus dodoneifolius DC Danser (Loranthaceae) on reactive oxygen species (ROS) production and myeloperoxidase (MPO) release by phorbol 12-myristate 13-acetate (PMA)-stimulated equine neutrophils and on purified equine MPO activity. ROS production and MPO release by the PMA-stimulated neutrophils were measured by the lucigenin-enhanced chemiluminescence and ELISA assays, respectively. Specific immunological extraction followed by enzymatic detection (SIEFED) was used to specifically measure the equine MPO activity. Identification and quantification of the individual and total phenolic and flavonoid compounds were performed using UPLC-MS/MS equipment and colorimetric methods involving Folin-Ciocalteu and AlCl 3 , respectively. All the tested extracts displayed dose-dependent inhibitory effects on the oxidant activities of neutrophils; a stronger effect was observed with the organic fractions than the aqueous decoction. These findings could be correlated with a high content of phenolic and flavonoid compounds. The results confirm the previously shown anti-inflammatory effect of Agelanthus dodoneifolius and its potential use for the treatment of neutrophil-dependent inflammatory diseases. IntroductionPolymorphonuclear neutrophils (PMNs) are the primary effector cells in host responses to injury and infection (1-4). The antimicrobial function of stimulated PMNs is based on their phagocytic capacity and their ability to release oxidant and proteolytic enzymes as well as reactive oxygen species (ROS) involved in the destruction of microorganisms. ROS play important roles in the pathogenesis of various serious diseases, such as neurodegenerative disorders, aging, cancer, cataracts, inflammation and cardiovascular diseases including atherosclerosis (5,6).Myeloperoxidase (MPO), a heme peroxidase enzyme stored in the azurophilic granules of neutrophils, plays a crucial role in the destruction of bacteria inside PMNs. The bacterial killing process mainly uses hydrogen peroxide (H 2 O 2 ) and the chloride anion (Cl -) to produce hypochlorous

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Section: Introductionmentioning

confidence: 99%

Modulatory activities of Agelanthus dodoneifolius (Loranthaceae) extracts on stimulated equine neutrophils and myeloperoxidase activity

Boly¹,

Dessy²,

Kohnen³

et al. 2011

Int J Mol Med

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“…The 3-(4-(tert-butyldimethylsilyloxy)phenyl)propanal thus obtained after flash column chromatography (2.79 g, 94%) was used directly for further reaction. 1 5, 153.8, 148.1, 133.4, 129.1, 121.6, 119.9, 60.0, 34.0, 33.4, 25.4, 18.1, 14.1, -4.5 …”

Section: -(4-(tert-butyldimethylsilyloxy)phenyl)propanalmentioning

confidence: 99%

“…1 The structure of 1 was determined from spectroscopic and X-ray crystallographic analysis of the camphorsulphonate derivative of dodoneine.…”

Section: Introductionmentioning

confidence: 99%

A formal enantioselective synthesis of (+)-dodoneine via cyclic sulfate methodology

Kantevari¹,

Vuppalapati²,

Putapatri³

2010

Arkivoc

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“…Agelanthus dodoneifolius Polhill & Wiens Danser (Loranthaceae), previously named Tapinanthus dodoneifolius (African mistletoe), is a common plant that both parasitizes plants such as Mimosaceae and Sapotaceae and displays a wide range of medicinal properties (3,4). Phytochemical screenings of the plant have revealed the presence of tannins, anthracenosides, anthraquinones, flavonoids, anthocyanosides, sterols, triterpenes and saponosides (3,4).…”

Section: Introductionmentioning

confidence: 99%

“…Phytochemical screenings of the plant have revealed the presence of tannins, anthracenosides, anthraquinones, flavonoids, anthocyanosides, sterols, triterpenes and saponosides (3,4). In this study, we focused primarily on the flavonoid component of Agelanthus dodoneifolius and more closely on quercetin.…”

Section: Introductionmentioning

confidence: 99%

Quercetin inhibits a large panel of kinases implicated in cancer cell biology

Kiss

2011

Int J Oncol

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Abstract. Flavonoids are polyphenolic secondary metabolites from plants that possess a common phenylbenzopyrone structure (C6-C3-C6). Depending upon variations in their heterocyclic C-ring, flavonoids are categorised into one of the following groups: flavones, flavonols, flavanones, flavanols, anthocyanidins, isoflavones or chalcones. Flavonols include, among others, the molecules quercetin, myricetin and kaempferol. The anticancer activity of flavonols was first attributed to their electron-donating ability, which comes from the presence of phenolic hydroxyl groups. However, an emerging view is that flavonoids, including quercetin, may also exert modulatory actions in cells by acting through the protein kinase and lipid kinase signalling pathways. Data from the current study showed that 2 μM quercetin, a low concentration that represents less than 10% of its IC 50 growthinhibitory concentration as calculated from the average of eight distinct cancer cell lines, decreased the activity of 16 kinases by more than 80%, including ABL1, Aurora-A, -B, -C, CLK1, FLT3, JAK3, MET, NEK4, NEK9, PAK3, PIM1, RET, FGF-R2, PDGF-R· and -Rß. Many of these kinases are involved in the control of mitotic processes. Quantitative video microscopy analyses revealed that quercetin displayed strong anti-mitotic activity, leading to cell death. In conclusion, quercetin partly exerts its anticancer activity through the inhibition of the activity of a large set of kinases. Quercetin could be an interesting chemical scaffold from which to generate novel derivatives possessing various types of antikinase activities.

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Structure Elucidation of a Dihydropyranone from Tapinanthus dodoneifolius

Cited by 35 publications

References 12 publications

Modulatory activities of Agelanthus dodoneifolius (Loranthaceae) extracts on stimulated equine neutrophils and myeloperoxidase activity

Modulatory activities of Agelanthus dodoneifolius (Loranthaceae) extracts on stimulated equine neutrophils and myeloperoxidase activity

A formal enantioselective synthesis of (+)-dodoneine via cyclic sulfate methodology

Quercetin inhibits a large panel of kinases implicated in cancer cell biology

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