- Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells
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A cycloartane-type triterpenoid (1), an aliphatic alcohol glycoside (2), an eudesmane-type sesquiterpenoid (3), and a guaiane-type sesquiterpenoid (4) were isolated from the resinous exudates of Commiphora opobalsamum along with six known sesquiterpenoids (5-10). Their structures were established by extensive analysis of their 1D and 2D NMR spectroscopic data and chemical methods. The isolated compounds 1-3 and 5-9 were tested against human prostate cancer cell PC 3 and LNCaP. Among them, 1 and 2 showed moderate antiproliferative effects on human prostate cancer cell lines with IC50 values ranging from 5.7 to 23.6 μM; they were also able to inhibit the expression of androgen receptor (AR) in LNCaP cells. The six sesquiterpenoids were inactive in the bioassays.
- Shen, Tao,Wan, Wenzhu,Yuan, Huiqing,Kong, Feng,Guo, Huaifang,Fan, Peihong,Lou, Hongxiang
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- Convenient synthesis of D- and L-xylo-1,2,3,4-alkane tetrols from a D-gluco-configured common building block
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D-gluco-Configured building block derived from d-(+)-gluconolactone has served as a common chiral template for the synthesis of enantiopure d- and l-xylo-configured 1,2,3,4-alkane tetrols. This has enabled synthesis of medicinally important guggultetrols and their enantiomers from a common starting point. Wittig and Grignard reactions are the key steps used for the incorporation of lipophilic chain.
- Borkar, Santosh Ramdas,Manjunath, Beedimane Narayana,Balasubramaniam, Sivaraman,Aidhen, Indrapal Singh
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- A short enantioselective synthesis of guggultetrol, a naturally occurring lipid
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An enantioselective synthesis of the naturally occurring lipid, guggultetrol, is described with an overall yield of 24% starting from commercially available l-pentadecanol in ten linear steps. The key chiral-inducing steps include a Sharpless asymmetric epoxidation of allylic alcohol and a dihydroxylation of an α,β-unsaturated ester.
- George, Shyla,Suryavanshi, Gurunath,Sudalai, Arumugam
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experimental part
p. 558 - 561
(2010/08/06)
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- Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol
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γ-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol.
- Prasad, Kavirayani R.,Chandrakumar, Appayee
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p. 1798 - 1805
(2007/10/03)
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- SYNTHESIS AND PROPERTIES OF SOME STEREOISOMERIC LONG-CHAIN 1,2,3,4-TETROLS
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Syntheses of 1,2S,3R,4R, 1,2S,3R,4S, 1,2R,3S,4R, and 1,2S,3S,4R-icosanetetrol, as well as of 1,2S,3S,4R-octadecanetetrol, are described, all based upon Wittig reactions of 1,2,3-protected pentodialdo-1,4-furanoses, serving as "chiral templates", with pentadecyl (or tridecyl) triphenylphosphorane, followed by catalytic hydrogenation, hydrolysis, and reduction.The tetrols, all forming liquid crystals on heating, are characterized spectroscopically and as their O-tetraacetates.The latter serve admirably for GLC-separation and -characterization of all non-enantiomeric tetrols.From the sign of rotation and GLC-comparison with the synthetic O-tetraacetates it follows that the 1,2,3,4-octadecanetetrol and 1,2,3,4-icosanetetrol, reported several years ago as the predominant members of a homologous series of tetrols derived from the gum-resin of Commiphora mukul, possess the 2S,3S,4R-configuration ("D-xylo").
- Kjaer, Anders,Kjaer, Dana,Skrydstrup, Troels
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p. 1439 - 1448
(2007/10/02)
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