Sesquiterpene lactone and friedelane derivative from Drypetes molunduana

Wandji, Jean; Wansi, Jean-Duplex; Fuendjiep, Victorine; Dagne, Ermias; Mulholland, Dulcie A.; Tillequin, François; Fomum, Z. Tanee; Sondengam, B.L.; Nkeh, B.; Njamen, Dieudonné

doi:10.1016/s0031-9422(00)00040-6

Cited by 33 publications

(25 citation statements)

References 6 publications

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“…A total of 25 fractions of approximately 100 mL each were collected and combined on the basis of similar TLC. Fractions 21-30 were further chromatographed over silica gel 60 with a mixture of CH 2 Cl 2 -EtOAc (2:1) to yield oleanolic acid (9) (13.5 mg), betulinic acid (6) (20.5 mg), hederagenin (10) (10.5 mg), and bayogenin acid (11) (8.0 mg) (Wansi et al, 2007;Wandji et al, 2000). Similarly, fraction D was chromatographed over a silica gel 60 column with a CH 2 Cl 2 -EtOAc, EtOAc-MeOH gradient.…”

Section: Extraction and Isolationmentioning

confidence: 99%

Antimicrobial and antioxidant effects of phenolic constituents fromKlainedoxa gabonensis

Wansi

Chiozem

Tcho

et al. 2010

Pharmaceutical Biology

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Section: Extraction and Isolationmentioning

confidence: 99%

Antimicrobial and antioxidant effects of phenolic constituents fromKlainedoxa gabonensis

Wansi

Chiozem

Tcho

et al. 2010

Pharmaceutical Biology

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“…The known compounds were isolated in high degree of pureness and they were respectively identified as 3-oxofriedelane (1), 12,13 3β-hydroxyfriedelane (2), 14 3-oxo-12α-hydroxyfriedelane (3), 8 3,11-dioxofriedelane (4), 15 3,16-dioxofriedelane (5). 12,16 For the identification, their physical and spectral data were analyzed and the results compared with previously published data.…”

Section: Resultsmentioning

confidence: 99%

Chemical constituents from branches of Maytenus gonoclada (Celastraceae) and evaluation of antimicrobial activity

Silva¹,

Duarte²,

Silva³

et al. 2011

J. Braz. Chem. Soc.

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Seis triterpenos pentacíclicos isolados dos galhos de Maytenus gonoclada (Celastraceae), incluindo todos os dados de RMN do novo composto 3-oxo-12α,29-diidroxifriedelano são aqui relatados. A estereoquímica do novo friedelano foi estabelecida por dados de RMN bidimensional (HSQC, HMBC e NOESY), e sua massa molecular confirmada por espectrometria de massas (ESI). Testes de atividade antimicrobiana usando método de difusão em disco e de macrodiluição foram realizados contra as bactérias Escherichia coli, Citrobacter freundii e Bacillus cereus, e contra o fungo Candida albicans. O triterpeno 3-oxo-12α-hidroxifriedelano mostrou resultado positivo contra C. albicans.Six pentacyclic triterpenes were isolated from branches of Maytenus gonoclada (Celastraceae) and all NMR data of a new compound 3-oxo-12α,29-dihydroxyfriedelane are herein reported. The stereochemistry of the new friedelane was established by bidimensional NMR (HSQC, HMBC and NOESY) data, and its molecular weight confirmed by ESI mass spectrometry. Antimicrobial activity assays using the method of disk diffusion and macrodilution were carried out against the bacteria Escherichia coli, Citrobacter freundii, and Bacillus cereus, and against the fungi Candida albicans. The triterpene 3-oxo-12α-hydroxyfriedelane showed positive result against C. albicans. Celastraceae, antimicrobial activity Keywords: Maytenus gonoclada, IntroductionCelastraceae family contains many species that have been extensively studied in function of their use in traditional medicine. Some species of Maytenus genus are worldwide distributed and have been used by Africans to treat cancer, by Asian people as an insecticide, 1 and by the South American people on the treatment of gastrointestinal diseases. 2 The biological activities associated to Maytenus species have been assigned to different classes of secondary metabolites such as phenolic glucosides, 3 flavonoids 4 and triterpenes. 5 Pentacyclic triterpenes (PCTT) have been commonly isolated from species of the Celastraceae family, and some of them, like 3-oxofriedelane and 3β-hydroxyfriedelane, are considered taxonomic markers of Maytenus genus. 4 A large number of pharmacological activities has been associated to triterpenes isolated from species of the Maytenus genus, such as, 3,15-dioxo-21α-hydroxyfriedelane, isolated from Maytenus robusta, that showed antiulcerogenic activity, 6 and maytenfolic acid, isolated from Maytenus heterophylla, that showed growth inhibitory effect on Candida albicans. 7 Maytenus gonoclada Martius, popularly known as "tiuzinho", can be found in regions of "cerrado" and rupestrian fields of Southeastern and Northeastern Brazil. In our previous studies of the hexane extract from M. gonoclada leaves, the occurrence of five PCTT of the friedelane series was reported. 8 Chemical Constituents from Branches of Maytenus gonoclada (Celastraceae) J. Braz. Chem. Soc. 944 The present paper reports the phytochemical study of hexane extract from branches of M. gonoclada, which was isolated five known triterpene...

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“…To identify the active principles, bioassay-guided isolation was performed using silica gel chromatography, resulting in compounds 1-6. Four of the compounds were identified as triterpenoids, 3β-acetoxy-28-hydroxyolean-12-ene (1), 3β-acetoxyolean-12-en-28-acid (2), 3β-acetoxyolean-12-en-28-aldehyde (3), taraxerol (5) by analysis of NMR and MS data, together with comparison of their spectral data with those in the literature; a stigmasterol (6) was also identified using the same method (Kim et al, 2004;Wandji et al, 2000;Min et al, 2004a) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Triterpenoids and a sterol from the stem‐bark of Styrax japonica and their protein tyrosine phosphatase 1B inhibitory activities

Kwon

Chang

Seo

et al. 2008

Phytotherapy Research

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Five pentacyclic triterpenoids (1-5) and a sterol (6) were isolated from the stem-bark of Styrax japonica. The six compounds, 1-6, were determined to be 3beta-acetoxy-28-hydroxyolean-12-ene (1), 3beta-acetoxyolean-12-en-28-acid (2), 3beta-acetoxyolean-12-en-28-aldehyde (3), 3beta-acetoxy-17beta-hydroxy-28-norolean-12-ene (4), taraxerol (5) and stigmasterol (6), respectively, by spectroscopic means, including the 2D-NMR technique. Compound 4 is a newly discovered natural compound. The protein tyrosine phosphatase 1B (PTP1B) inhibitory activities of the isolated compounds (1-6) were determined in vitro. Among the isolated compounds, 3beta-acetoxyolean-12-en-28-acid (2) and 3beta-acetoxyolean-12-en-28-aldehyde (3) had the most potent inhibitory PTP1B activity, with IC50 values of 7.8 and 9.3 microm, respectively.

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Sesquiterpene lactone and friedelane derivative from Drypetes molunduana

Cited by 33 publications

References 6 publications

Antimicrobial and antioxidant effects of phenolic constituents fromKlainedoxa gabonensis

Antimicrobial and antioxidant effects of phenolic constituents fromKlainedoxa gabonensis

Chemical constituents from branches of Maytenus gonoclada (Celastraceae) and evaluation of antimicrobial activity

Triterpenoids and a sterol from the stem‐bark of Styrax japonica and their protein tyrosine phosphatase 1B inhibitory activities

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