The chemistry of the West and Central African Penianthus zenkeri Diels (Menispermaceae)

Tabekoueng, Georges Bellier; Akak, Carine Mvot; Happi, Gervais Mouthé; Langat, Moses K.; Frese, Marcel; Stammler, Hans‐Georg; Neumann, Beate; Azebaze, Anatole Guy Blaise; Waffo, Alain François Kamdem; Wansi, Jean Duplex; Lenta, Bruno Ndjakou; Sewald, Norbert; Vardamides, Juliette Cathérine; Nkengfack, Augustin E.

doi:10.1016/j.phytol.2020.04.017

Cited by 4 publications

(4 citation statements)

References 40 publications

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“…The total alkaloid extract of the stem bark of A. soyauxii (TAE), fractions obtained from TAE (FTAE1-FTAE3), natural compounds 1 – 7 and 9 , and semi-synthetic derivatives 3a–c, 4b, 5a, 6a were evaluated for their anticancer properties against the cervix carcinoma cell line (KB-3-1) as described in previous reports [ 13 , 14 , 15 , 16 ]. Extracts and fractions were inactive.…”

Section: Resultsmentioning

confidence: 99%

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

et al. 2022

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The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2-10. In addition, six semi-synthetic derivatives 3a-c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2-4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1-7 and 9, and semi-synthetic derivatives 3a-c, 4b, 5a and 6a were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

et al. 2022

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“…The chemical investigations of the stem bark and roots of the medicinal plant Ficus sycomorus led to the isolation and identification of twenty-four distinct compounds (Figure 3) including ten triterpenoids belonging to five different classes including one taraxastane-type triterpenoid named epi-ψ-taraxastanonol or 3-oxo-20R-hydroxytaraxastane (1) (Anjaneyulu et al, 1999), two ursane-type triterpenoids α-amyrin acetate (2) and ursolic acid (3) (Tabekoueng et al, 2020;Wouamba et al, 2020), three oleanane-type triterpenoids β-amyrin acetate (4), oleanolic acid (5) and 2-O-trans-p-coumaroyl maslinic acid (6) (Yan et al, 2014), one friedelane-type triterpenoid named canophyllol (7) (Ngouamegne et al, 2008), as well as three lupanetype triterpenoids lupeol (8), betulinic acid (9) and lupeol acetate (10) (Javed et al, 2021;Mbougnia et al, 2021). Additionally to the ten triterpenoids, we isolated one diterpenoid called ent-kauran-2β,3α,16α-triol (11) (Dongmo et al, 2019); five steroids including stigmasterol (12), stigmast-22-ene-3,6-dione (13) (Lima et al, 2013), stigmast-7-en-3-one (14) (Wu et al, 1990), β-sitosterol (15) and β-sitosterol-3-O-β-D-glucopyranoside ( 16) (Mbougnia et al, 2021); four flavonoids among which three isoflavones namely alpinumisoflavone (17) (Kuete et al, 2008), derrone (18) (Chibber & Sharma, 1980) and 3'-(3-methylbut-2enyl)-biochanin A (19) (Abiy et al, 1998), as well as one flavone named atalantoflavone (20) (Nsangou et al, 2021).…”

Section: Phytochemical Studymentioning

confidence: 99%

“…Infectious diseases commonly spread among humans are caused by the production of toxins by microbes in the human host also called dysbiosis of the human microbiota which will have a significant incidence on the immune system, leading to antibiotic resistance or causing the new emerging infectious or microbial diseases like HIV, hepatitis and many others (Brenchley & Douek, 2012;Cohen, 2016;Hand et al, 2012;Hu et al, 2016). Moreover, the resistance of infectious pathogens to existing drugs has been the major cause of the increasing rate of microbial diseases and the emergence of new ones around the world (Kemayou et al, 2021;Tabekoueng et al, 2020). The medicinal plants including those of the genus Ficus have been long used as the first line of treatment in folk medicine to manage several microbial illnesses and might represent a good source of new antimicrobial lead compounds to address the need for new potent drugs to face that resistance (Happi et al, 2021;Mbobda et al, 2021;Mbougnia et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and cytotoxic extractives from Ficus sycomorus L. (Moraceae)

Mandou¹,

Tsopgni²,

Nsangou³

et al. 2022

NRFHH

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Our search for antimicrobial and cytotoxic leads from Ficus sycomorus led to the isolation of twenty-four known compounds (1‒24) from its methanolic stem bark and root extracts. The structures of all the isolated compounds were established using their 1D- and 2D-NMR spectroscopic data while the crude extracts, some fractions and compounds were tested for their antibacterial, antifungal and cytotoxicity activities. In the antimicrobial assay, compound 18 displayed good to moderate activity with MIC values of 31.25 µg/ml against Escherichia coli, 125 µg/ml against Salmonella typhimurium cpc and Pseudomonas aeruginosa, while compounds 10, 13 and 14 demonstrated moderate activities on almost all the tested strains, with the highest potency observed for compound 13 on E. coli (MIC = 125 µg/ml). However, although compounds 18 and 19 gave a significant inhibition of the VERO cell line ATCC CRT-1586 with CC50 values of 52.60 µg/ml and 69.10 µg/ml, respectively, all the extract samples and other tested compounds did not show distinguishable cytotoxicity. Finally, the chemophenetic significance of the isolated compounds is discussed.

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“…Inhibiting urease activity has been proposed as a viable strategy for eradicating Helicobacter pylori from the human body (Amin et al, 2013). Our recent research on Cameroonian medicinal plants and their endophytes contributed to identifying lead bioactive compounds with antimicrobial, antiparasitic, antioxidant and cytotoxic potencies (Happi et al, 2015;Jouwa et al, 2020;Makong et al, 2019;Tabekoueng et al, 2020). As a continuity of our research works on Cameroonian medicinal plants, the plant Guibourtia ehie has been investigated for its antioxidant compounds and urease and α-glucosidase inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Phytochemical compounds of Guibourtia ehie and their antioxidant, urease and α-glucosidase inhibitory activities

Bongmo¹,

Happi²,

Tabekoueng³

et al. 2022

NRFHH

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Thirteen compounds (1‒13) were isolated and identified during phytochemical analysis of the leaves and stem bark of Guibourtia ehie (A. Chev) J. Leonard. Spectroscopic and spectrometric methods and the comparison of their results with those given in the literature were used to ascertain their structures. Furthermore, the acetylation of 3,3′-di-O-methylellagic acid 4′-O-β-D-xylopyranoside (2) afforded a new derivative 3,3′-di-O-methylellagic acid 4′-O-β-D-(4,2′′,4′′-triacetyl)-xylopyranoside (2a). Extracts, fractions, and isolated compounds were assessed for their antioxidant, urease, and α-glucosidase inhibitory activities. Compound 1 demonstrated potent antioxidant activity in the DPPH with an IC50 value of 36.4 ± 0.2 µM, while rhaponticin (3), 2,6-dimethoxybenzoquinone (4), and taraxerol (6) exhibited a strong α-glucosidase inhibitory activity with the IC50 values of 35.5 ± 0.1, 25.5 ± 0.2 and 43.4 ± 0.3 µM, respectively. The present study enriches the chemistry of Guiboutia ehie and provides further evidence on its bioactive constituents, which might help in the development of hypoglycaemic drugs.

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The chemistry of the West and Central African Penianthus zenkeri Diels (Menispermaceae)

Cited by 4 publications

References 40 publications

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

Antimicrobial and cytotoxic extractives from <i>Ficus sycomorus</i> L. (Moraceae)

Phytochemical compounds of <i>Guibourtia ehie</i> and their antioxidant, urease and α-glucosidase inhibitory activities

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