ChemInform Abstract: Three Cyclohexene Oxides from Uvaria grandiflora.

Xu, Lizhen; Yang, S.‐L.; Dai, Jie; Zhen, Y.‐S.; Zhu, Min; Sun, Na-Bo

doi:10.1002/chin.199741309

Cited by 4 publications

(12 citation statements)

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“…To further evaluate the scope of the microwave-assisted protocol, ortho -quinol dimers (+)- 15 , 11 16 , 24 17 , and 18 25 were subjected to optimized reaction conditions (μW, SiC, mesitylene, 170 °C, 15 min, Table 4). In all cases, good to excellent isolated yield of the desired cycloadducts 19 to 25 were obtained as single diastereomers.…”

Section: Resultsmentioning

confidence: 99%

“…Hyperconjugative effects (Cieplak-Fallis model) 29 from the methyl group in the transition state may also contribute to facial selectivity. 24, 30 Dienone 4 has a high lying HOMO (−6.9 eV) and a low-lying LUMO (−2.3 eV) and as a consequence reacts with both electron-rich and electron-poor dienophiles. In every case, the preferred regiochemistry follows initial bonding to C5 of the dienone which maximizes resonance stabilization in the asynchronous transition state.…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H, 13 C NMR, IR, and HRMS of 16 were identical to literature reported data. 24,39 [α] 22 D = −5.1° ( c = 0.57, CHCl 3 ; lit. S5 [α] 22 D = −13.6°, c = 0.728, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

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Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions ofo-Quinol Dimers

et al. 2011

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We have accomplished a parallel screen of cycloaddition partners for ortho-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels-Alder/Diels-Alder cascades of ortho-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels-Alder cycloadditions of ortho-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions ofo-Quinol Dimers

et al. 2011

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“…Zeylenone was isolated from Uvaria grandiflora Roxb (DSC purity > 99%) according to a previous protocol (Liao et al ., ). Emodin was obtained from the National Institute for the Control of Pharmaceutical and Biological Products (Beijing, China).…”

Section: Methodsmentioning

confidence: 97%

“…) is a naturally occurring cytotoxic agent that exhibited remarkable antitumor activity and strong inhibition of nucleoside transport in Ehrlich carcinoma cells. The compound also displayed equal potency against sensitive and multidrug‐resistant cell lines with IC 50 values for mammary carcinoma MCF‐7 cell line and its resistant MCF‐7/ADM subline being 2.2 and 2.6 µ m determined by MTT [3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide] assay (Liao et al ., ). Zeylenone is regarded as a cytotoxic soft drug since it is an ester‐containing compound and the benzoate ester bonds are hydrolyzed and inactivated rapidly in the blood owing to the presence of esterases.…”

Section: Introductionmentioning

confidence: 97%

Stabilization of zeylenone in rat plasma by the presence of esterase inhibitors and its LC‐MS/MS assay for pharmacokinetic study

Wei

Han

et al. 2012

Biomedical Chromatography

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Six esterase inhibitors, namely EDTA·2Na(+), NaF, phenylmethanesulfonyl fluoride, dichlorvos, bis-nitrophenyl phosphate (BNPP) and thenoyltrifluoroacetone, and the mixture of NaF and BNPP, were evaluated for the stabilization of labile benzoate containing zeylenone in rat plasma. The mixture appeared to exhibit the most effectively stabilizing effect with the degraded content of zeylenone decreasing from >60% (in the absence of inhibitors) to <6%. Following the stabilization by the addition of NaF (5 mM) and BNPP (5 mM), the analytes in rat plasma were acidified by formic acid and extracted into ethyl acetate at 0°C. After chromatographic separation, the detection of zeylenone was performed on a 3200 Q-Trap with positive ion electrospray mode, monitoring the ion transition m/z 383.2 → 105.0. The method was validated over the range from 2.68 to 1340 ng/mL with inter- and intra-run precision for the quality control samples being less than 6.8%. The assay accuracy was within 100 ± 7.0%. The validated method was successfully applied to a pharmacokinetic study in rats after the intratracheal administration of zeylenone in free drug or polymeric micellar solutions. The results showed that the pulmonary absorption of zeylenone loaded in micelles was significantly retarded compared with that of free drug solutions.

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Polyoxygenated Cyclohexenes from Uvaria grandiflora with Multi-Enzyme Targeting Properties Relevant in Type 2 Diabetes and Obesity

et al. 2022

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Shikimic acid-derived polyoxygenated cyclohexene natural products commonly occurring in several species of the Uvaria represent natural products with promising biological activities. While a number of derivatives have been reported from Uvaria grandiflora (U. grandiflora), further studies are needed to discover additional bioactive congeners, particularly derivatives with multi-protein target inhibitory properties implicated in diseases such as diabetes and obesity. In this paper, isolation and identification of a new highly oxygenated cyclohexene, uvagrandol (1), along with the known compound (-)-zeylenone (2) from the DCM sub-extract of U. grandiflora following in vitro and in silico assessment of their enzyme inhibitory properties against αglucosidase, dipeptidyl peptidase IV, porcine lipase, and human recombinant monoacylglycerol lipase are reported. The structure of 1 was elucidated using 1D and 2D NMR data analysis. The absolute configuration of 1 was established by quantum chemical calculations via the Gauge-Independent Atomic Orbital (GIAO) NMR method followed by TDDFT-Electronic Circular Dichroism (ECD) calculations. The structures of the eight possible stereoisomers were optimized by means of DFT calculations (B3LYP/6-31+G [d,p] in vacuum), and then their isotropic shielding tensors were obtained using the GIAO method at mPW1PW91/6-31G(d,p) in chloroform. Through DP4+, the isomer of configuration (1S,2S,3R,6R) for 1 was predicted with 96.3% probability. Compounds 1 and 2 significantly inhibited the four target enzymes in vitro. Binding studies through molecular docking simulations showed strong binding affinities for (-)-zeylenone (2), thus validating the in vitro results. Our findings suggest the potential of polyoxygenated cyclohexenes, in particular (-)-zeylenone (2), in anti-diabetic and anti-obesity drug discovery.

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ChemInform Abstract: Three Cyclohexene Oxides from Uvaria grandiflora.

Cited by 4 publications

References 1 publication

Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions ofo-Quinol Dimers

Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions ofo-Quinol Dimers

Stabilization of zeylenone in rat plasma by the presence of esterase inhibitors and its LC‐MS/MS assay for pharmacokinetic study

Polyoxygenated Cyclohexenes from Uvaria grandiflora with Multi-Enzyme Targeting Properties Relevant in Type 2 Diabetes and Obesity

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