Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae)

Mbaze, Luc Meva’a; Lado, Jean Alexandre; Wansi, Jean Duplex; Shiao, Tze Chieh; Chiozem, David Dako; Mesaik, M. Ahmed; Choudhary, M. Iqbal; Lacaille‐Dubois, Marie‐Aleth; Wandji, Jean; Roy, René; Sewald, Norbert

doi:10.1016/j.phytochem.2009.08.007

Cited by 45 publications

(31 citation statements)

References 19 publications

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“…While pellitorine also shows inhibitory properties against leukemia cell lines, capsaicinoids induce the apoptosis of prostate cancer cell lines and autography in colon cancer cell lines. 1,3-benzodioxol-acid IBAs like fagaramide (188) and derivatives (187, 188), however, possess no cytotoxicity against prostate tumor cell lines (Mbaze et al, 2009). (2E/Z)-N-(4-amino-2,3-dihydroxybutyl)-3-(4-hydroxyphenyl)prop-2-enamide (pharnilatin A (252) and B (342)) show in-vitro cytotoxicity against skin melanoma and lung, ovary and colon carcinoma (Kim et al, 2010a).…”

Section: Othersmentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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Section: Othersmentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

109

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“…It is also used as medicinal plant in central Africa for the treatment of many diseases such as cancer, syphilis, malaria, cardiac palpitations, uro-genital affections [13,14]. Several molecules were isolated from the stem bark of Z. heitzii among them, two amides: heitziamide A and heitziamide B and two phenylethanoids: heitziethanoid A and heitziethanoid B and s trans-fagaramide, arnottianamide, iso-c fagarine, iso-skimmianine, arctigenin methyl ether, savinin, (+)-eudesmin, (+)-sesamin, lupeol, lupeone, b-sitosterol, stigmasterol and stigmasterol-3-O-β-D-glucopyranoside [15]. The bark of Z. heitzii is used as insecticides and revealed some activities against cadiac affections [16].…”

Section: Introductionmentioning

confidence: 99%

The in vitro antisickling and antioxidant effects of aqueous extracts Zanthoxyllum heitzii on sickle cell disorder

Pauline

Cabral

Pieme

et al. 2013

BMC Complement Altern Med

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BackgroundSeveral plant extracts from Rutaceae family are currently used to the management of sickle cell disorder (SCD) in the African. Few reports have shown that extracts from Zanthoxyllum or Fagara genus demonstrated anti-sickling property. This study investigates the in vitro antisickling and antioxidant properties of extracts from Zanthoxyllum heitzii.MethodsThe sickling of red blood cells (RBCs) was induced using sodium metabisulfite (2%) followed by treatment with extracts at different concentrations. The osmotic fragility tests permits to explore the effect of Z. heitzii extracts on haemoglobin S solubility and sickle cells membrane stability. For each extract, qualitative phytochemical tests were used to identify the presence of alkaloids, tannins, saponins, flavonoids, glycosides and phenols, while some quantitative methods such as Folin, Ferric Reducing Antioxidant Power (FRAP) and diphenyl 1, 2 picryl hydrazyl (DPPH) were used to determine the antioxidant potential of these extracts.ResultsSodium metabisulphite increased the sickling of RBCs from 29.62 to 55.46% during 2 h. Treatment of sickling cells with extracts at different concentrations showed that a decrease of the percentage of sickling cells was found in both induced and non induced sickling cells. The fruits extract of Z. heitzii demonstrated the best anti-sickling property. The same extract at 250 μg/mL showed the best membrane cell stability compared to others. All the extracts revealed an antioxidant and anti-radical activities although lesser compared to the standard.ConclusionThe fruit extract of Z. Heitzii demonstrated the most significant antisickling effect with a potential for use in the clinical management of SCD.

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“…14 Given this analysis, we became intrigued by the structure of heitziamide A ( 31 ), an amide natural product isolated as a racemate from the medicinal shrub Fagara heitzii . 15 This compound almost certainly arises from a Diels–Alder cycloaddi-tion between trans -fagaramide ( 33 ), another amide endogenous to F. heitzii , 15 and the monoterpene myrcene ( 34 ). However, the polarization of the diene and dienophile π bonds suggests that the regiochemistry expected from the thermal Diels–Alder reaction would afford the isomeric cycloadduct 32 .…”

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confidence: 99%

Radical Cation Diels–Alder Cycloadditions by Visible Light Photocatalysis

et al. 2011

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Ruthenium(II) polypyridyl complexes promote the efficient radical cation Diels–Alder cycloaddition of electron-rich dienophiles upon irradiation with visible light. These reactions enable facile [4+2] cycloadditions that would be electronically mismatched under thermal conditions. Key to the success of this methodology is the availability of ligand-modified ruthenium complexes that enable the rational tuning of electrochemical properties of the catalyst without significantly perturbing the overall photophysical properties of the system.

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Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae)

Cited by 45 publications

References 19 publications

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

The in vitro antisickling and antioxidant effects of aqueous extracts Zanthoxyllum heitzii on sickle cell disorder

Radical Cation Diels–Alder Cycloadditions by Visible Light Photocatalysis

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