Synthesis of (−)- and (+)-hyrtiosal and their C-16 epimers

Lunardi, Inês; Santiago, Gilvandete Maria Pinheiro; Imamura, Paulo M.

doi:10.1016/s0040-4039(02)00576-2

Cited by 15 publications

(7 citation statements)

References 5 publications

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“…Lunardi et al also completed the total synthesis of (-)-233 along with its enantiomer (+)-233 and their C-16 epimers starting from 30% ee copalic acid [156] . Bioassay-directed separation of the extract from the sponge Thorectandra (unknown species) collected in Papua New Guinea led to the isolation of luffariellolide-type sesterterpenoids, luffariellolide 234 and dehydroluffariellolide diacid 235 [157] .…”

Section: Sesterterpenesmentioning

confidence: 99%

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

2012

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This article provides an overview of approximately 300 secondary metabolites with inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), which were isolated from various natural sources or derived from synthetic process in the last decades. The structure-activity relationship and the selectivity of some compounds against other protein phosphatases were also discussed. Potential pharmaceutical applications of several PTP1B inhibitors were presented.

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Section: Sesterterpenesmentioning

confidence: 99%

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

2012

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“…Epoxide 3 was considered as the precursor for the subsequent steps, as shown in Scheme 3. The ring contraction reaction that has been reported to occur with different reagents [5][6][7] was in this case performed by using a complex Lewis acid, tris-(p-bromo-phenyl)-aminiumhexachloro-antimonate, which has efficiently promoted this kind of isomerization in related epoxides. 8 Treatment of epoxide 3 with a catalytic amount of tris-(p-bromo-phenyl)-aminium-hexachloro-antimonate in DCM at room temperature provided a mixture of isomerization products that was subjected to chromatography on a silica-gel column.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid

Kulciţki

Ungur

Gavagnin

et al. 2004

Tetrahedron: Asymmetry

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“…a characteristic diterpene of copaiba oil-resin, led to a patent describing its selective cytotoxic activity against melanoma and leukemic cell lines. [ 39 ]…”

Section: Discussionmentioning

confidence: 99%

Biological activities and cytotoxicity of Eperua oleifera Ducke oil-resin

et al. 2017

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Background:The oil-resin of Eperua oleifera Ducke has been used in popular medicine similarly to the copaiba oil (Copaifera spp.).Objective:This study aimed to investigate the effects of the acid fraction of E. oleifera oil-resin (AFEOR) on cell proliferation, collagen production in human fibroblasts, inhibition of metalloproteinases, and cytotoxicity against tumor cell lines.Materials and Methods:Acid fraction of E. oleifera was fractionated in the ion exchange column chromatography. Cytotoxicity and genotoxicity were evaluated by Alamar Blue® and Cometa assay. The inhibition of metalloproteinases was performed by zymography and Western blotting.Results:The predominant acidic diterpenes in the AFEOR were copalic and hardwickiic acids. AFEOR caused morphology alteration and decrease of proliferation at concentrations higher than 5 μg/mL. It also caused significant collagen proliferation in fibroblasts. It showed cytotoxicity against tumoral and nontumoral cell lines, with IC50 values ranging from 13 to 50 μg/mL, and a hemolytic activity with an IC50 value of 38.29 μg/mL. AFEOR inhibited collagenase activity, with an IC50 value of 46.64 μg/mL, and matrix metalloproteinase-2 (MMP)-2 and MMP-9 in HaCaT cells or MMP-1 expression in MRC-5 cells. AFEOR induced genotoxicity in MRC-5 cells with a DNA damage index between 40% and 60% when compared to the negative controls (0%–20%).Conclusion:For the first time, biological activities from oil-resin E. oleifera demonstrated ratifying somehow its popular use.SUMMARY Analysis of crude oil-resin and fractionation of diterpenic fraction was performance using selective ion-exchange column chromatographyCytotoxicity analysis and morphology were performed with different cell linesCollagen production in human fibroblasts, inhibition of metalloproteinases were demonstrated by zymography and Western blotting. Abbreviations used: AFEOR: Eperua oleifera oil-resin.

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Synthesis of (−)- and (+)-hyrtiosal and their C-16 epimers

Cited by 15 publications

References 5 publications

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid

Biological activities and cytotoxicity of Eperua oleifera Ducke oil-resin

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