Dihydro-β-agarofuran sesquiterpenes from celastraceae species as anti-tumour-promoting agents: Structure-activity relationship

Núñez, Marvin J.; Jiménez, Ignacio A.; Mendoza, Cristina R.; Chavez-Sifontes, Marvin; Martínez, Morena L.; Ichiishi, Eiichiro; Tokuda, Ryo; Tokuda, Harukuni; Bazzocchi, Isabel L.

doi:10.1016/j.ejmech.2016.01.049

Cited by 22 publications

(13 citation statements)

References 36 publications

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“…Dihydro‐ β ‐agarofurans have attracted much attention because they are considered to be privileged structures that exhibit numerous biological activities, owing to their unique molecular skeleton, which is capable of providing ligands for various biological receptors . Recently, Celastraceae‐derived dihydro‐ β ‐agarofurans have been reported to display neuroprotective, anti‐HIV, anti‐ Mycobacterium , cancer chemopreventive, multidrug‐resistance phenotype reversal, and leucine‐uptake‐inhibitory effects …”

Section: Figurementioning

confidence: 99%

Dihydro‐β‐agarofurans from the Australian Endemic Rainforest Plant Denhamia pittosporoides Inhibit Leucine Transport in Prostate Cancer Cells

et al. 2016

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Section: Figurementioning

confidence: 99%

Dihydro‐β‐agarofurans from the Australian Endemic Rainforest Plant Denhamia pittosporoides Inhibit Leucine Transport in Prostate Cancer Cells

et al. 2016

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“…Alternatively, compounds previously isolated using chromatographic instrumentation can be studied offline using suitable methodologies. Among these are the conventional usage of ECD and polarimetric measurements , chemical correlation , diasteromeric NMR analysis , X‐ray diffraction analysis , when one is lucky and obtains crystalline samples, and VCD []. The later technique has shown many advantages for the stereochemical analysis of natural substances since it can be applied in the solution state with the use of rather inexpensive computational calculations.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric high-performance liquid chromatography resolution and absolute configuration of 6β-benzoyloxy-3α-tropanol

2016

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The absolute configuration of the naturally occurring isomers of 6β-benzoyloxy-3α-tropanol (1) has been established by the combined use of chiral high-performance liquid chromatography with electronic circular dichroism detection and optical rotation detection. For this purpose (±)-1, prepared in two steps from racemic 6-hydroxytropinone (4), was subjected to chiral high-performance liquid chromatography with electronic circular dichroism and optical rotation detection allowing the online measurement of both chiroptical properties for each enantiomer, which in turn were compared with the corresponding values obtained from density functional theory calculations. In an independent approach, preparative high-performance liquid chromatography separation using an automatic fraction collector, yielded an enantiopure sample of OR (+)-1 whose vibrational circular dichroism spectrum allowed its absolute configuration assignment when the bands in the 1100-950 cm(-1) region were compared with those of the enantiomers of esters derived from 3α,6β-tropanediol. In addition, an enantiomerically enriched sample of 4, instead of OR (±)-4, was used for the same transformation sequence, whose high-performance liquid chromatography follow-up allowed their spectroscopic correlation. All evidences lead to the OR (+)-(1S,3R,5S,6R) and OR (-)-(1R,3S,5R,6S) absolute configurations, from where it follows that samples of 1 isolated from Knightia strobilina and Erythroxylum zambesiacum have the OR (+)-(1S,3R,5S,6R) absolute configuration, while the sample obtained from E. rotundifolium has the OR (-)-(1R,3S,5R,6S) absolute configuration.

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“…The relative configuration of 4 was assigned following analysis of 1 H-1 H coupling constants and the ROESY spectrum ( Figure 2). The β-orientation of H-1 and H-2 was assigned based on the small coupling constant between the two protons (J1,2 = 3.5 Hz) (Gao, et al, 2016;Núñez, et al, 2016). The ROESY spectrum of 4 exhibited correlations between H-1 and H-3β, indicating that these two atoms were co-facial.…”

Section: Resultsmentioning

confidence: 99%

“…The ROESY spectrum of 5 exhibited correlations between H3-14 and H2-15, between H2-15 and H-8, as well as H2-15 and H-6, implying the relative configuration of 5 to be the same as compound 4. Finally, on the basis of biosynthetic considerations (Núñez, et al, 2016) the absolute configuration of 5 (bilocularin E) was…”

Section: Resultsmentioning

confidence: 99%

Dihydro-β-agarofurans from the roots of the Australian endemic rainforest tree Maytenus bilocularis act as leucine transport inhibitors

et al. 2018

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Phytochemical studies of the roots of the Australian plant, Maytenus bilocularis, resulted in the identification of six previously undescribed dihydro-β-agarofuran sesquiterpenoids, bilocularins D-I, along with three known natural products, namely 1α,2α,6β,15-tetraacetoxy-9β-benzoyloxydihydro-β-agarofuran, pristimerin, and celastrol. The structures of all compounds were characterized via analysis of 1D/2D NMR and MS data. The absolute configuration of bilocularin D was defined by X-ray crystallography analysis. Bilocularins D and G, 1α,2α,6β,15-tetraacetoxy-9β-benzoyloxydihydro-β-agarofuran, and celastrol inhibited leucine transport in the human prostate cancer cell line LNCaP with IC values ranging from 2.5-27.9 μM, which were more potent than the L-type amino acid transporter (LAT) family inhibitor 2-aminobicyclo[2,2,1]-heptane-2-carboxylic acid (BCH). Bilocularins D-F are the first examples of dihydro-β-agarofurans bearing a hydroxyacetate group.

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Dihydro-β-agarofuran sesquiterpenes from celastraceae species as anti-tumour-promoting agents: Structure-activity relationship

Cited by 22 publications

References 36 publications

Dihydro‐β‐agarofurans from the Australian Endemic Rainforest Plant Denhamia pittosporoides Inhibit Leucine Transport in Prostate Cancer Cells

Dihydro‐β‐agarofurans from the Australian Endemic Rainforest Plant Denhamia pittosporoides Inhibit Leucine Transport in Prostate Cancer Cells

Enantiomeric high-performance liquid chromatography resolution and absolute configuration of 6β-benzoyloxy-3α-tropanol

Dihydro-β-agarofurans from the roots of the Australian endemic rainforest tree Maytenus bilocularis act as leucine transport inhibitors

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