Kurzilactone from Cryptocarya kurzii

Fu, Tse-Kai; Sévenet, A.; Hamid, Abdulkareem; Hadi,; Remy, F.; Païs, M.

doi:10.1016/0031-9422(93)85065-y

Cited by 43 publications

(34 citation statements)

References 4 publications

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“…2). This is in accordance with our observation of no NOESY correlations between HÀC(5) and HÀC (7). c) The correlations HÀC(2)/HÀC(2'), HÀC(2)/HÀC(3), HÀC(5)/HÀC(6), HÀC(5)/HÀC(11), HÀC(6)/HÀC(7), and HÀC(7)/HÀC(8) were also observed in the NOESY experiments (Fig.…”

supporting

confidence: 93%

“…Previous chemical studies of the genus Cryptocarya have indicated the isolation of several components, including flavonoids [2 -5], pyranones [6 -8], pavines [9 -11], aporphines [10 -12], benzylisoquinolines [12] [13], and lignans [14]. Cytotoxic [2 -5] [7] [8] [13] [14] and antioxidant [6] activities have been demonstrated for some of those compounds, but antituberculosis activity of this genus has seldom been studied [15]. In our continuing studies on the antitubercular constituents of Formosan plants, over 1300 species have been screened for in vitro antituberculosis activity to date [16 -31], and C. chinensis has been found to be one of the active species.…”

mentioning

confidence: 99%

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New Flavanones from the Leaves of Cryptocarya chinensis and Their Antituberculosis Activity

Chou

Chen

et al. 2011

Chemistry & Biodiversity

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Four new flavanones, cryptoflavanones A-D (1-4, resp.), together with eight known compounds, were isolated from the leaves of Cryptocarya chinensis. The structures of these new compounds were determined by spectral analyses. Among the isolated compounds, pinocembrin (5) and cryptocaryone (6) exhibited antituberculosis activity against Mycobacterium tuberculosis H(37) Rv strain in vitro with MIC values of 3.5 and 25.0 μg/ml, respectively.

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supporting

confidence: 93%

mentioning

confidence: 99%

New Flavanones from the Leaves of Cryptocarya chinensis and Their Antituberculosis Activity

Chou

Chen

et al. 2011

Chemistry & Biodiversity

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“…98:2) and repeated purification by centrifugal planar chromatography (hexane/CHCl 3 , 9:1) to provide infectocaryone (3) (6 mg) [10], cryptocaryone (4) (390 mg) [14] and pinocembrin (6) (33 mg) [15]. After a series of separation and purification procedures using centrifugal planar chromatography (eluents CHCl 3 ), fraction E (17.8 g) afforded desmethylinfectocaryone (2) (23 mg) and kurzichalcolactone A (5) (45 mg) [16]. Using a similar procedure, trans-N-feruloyltyramine (7) (25 mg) [17] was obtained from fraction F (8.6 g).…”

Section: Extraction and Isolationmentioning

confidence: 99%

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

et al. 2009

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Two chalcone derivatives, 2'-hydroxychalcone (1) and desmethylinfectocaryone (2), together with five known phenolic compounds infectocaryone (3), cryptocaryone (4), kurzichalcolactone A (5), pinocembrin (6) and trans-N-feruloyltyramine (7), were isolated from the methanol extract of the wood of Cryptocarya konishii. The structures of the new compounds were determined based on the analysis of spectroscopic data, including UV, IR, 1D and 2D NMR, and mass spectra. Evaluation of the cytotoxic and tyrosine kinase inhibitory activities of compounds 1-7 showed that compounds 2-4 strongly inhibited the growth of murine leukemia P-388 cells, whereas compound 4 significantly inhibited the enzyme.

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“…[16] Apart from these rather complex structures, structurally simpler natural products exist which also have biological activity, such as kurzilactone (3), which is cytotoxic to KB cells. [17] Many of these small molecules feature a carbon chain functionalized with at least one 1,3-diol unit.…”

Section: Introductionmentioning

confidence: 99%

Biology‐Oriented Synthesis of Stereochemically Diverse Natural‐Product‐Derived Compound Collections by Iterative Allylations on a Solid Support

Umarye

Leßmann

García

et al. 2007

Chemistry A European J

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A strategy aiming at the introduction of stereocenters into polymer-bound natural-product-derived and -inspired compound collections is presented. Treatment of immobilized aldehydes with Brown's pinene-derived allylboranes results in the stereoselective formation of homoallylic alcohols with up to 89 % ee (ee=enantiomeric excess). Subsequent iterative ozonolysis-allylation sequences with up to three allylations on a solid support give access to 1,3-polyols with different relative configurations. Esterification with acryloyl chloride and final ring-closing metathesis yields alpha,beta-unsaturated delta-lactones with multiply oxygenated side chains, a substructure found in a group of natural products with a broad range of biological activity. The flexibility of the approach is exemplified by the parallel synthesis of all eight diastereomers of cryptocarya diacetate on a solid support. The individual isomers are obtained in overall yields of 40-60 % over 10 steps and with 63-85 % diastereoselectivity for the major isomer.

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Kurzilactone from Cryptocarya kurzii

Cited by 43 publications

References 4 publications

New Flavanones from the Leaves of Cryptocarya chinensis and Their Antituberculosis Activity

New Flavanones from the Leaves of Cryptocarya chinensis and Their Antituberculosis Activity

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

Biology‐Oriented Synthesis of Stereochemically Diverse Natural‐Product‐Derived Compound Collections by Iterative Allylations on a Solid Support

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