-(±)-TTPG-B Attenuates Cell Cycle Progression and Inhibits Cell Proliferation on Cholangiocarcinoma Cells.

This research aimed to determine the target protein and molecular mechanism of -(±)-kusunokinin ((±)-KU) derivatives (-(±)-ARC and -(±)-TTPG-B). Molecular docking was used to predict potential synthesized (±)-KU targets among 22 proteins. The (±)-TTPG-B bound HSP90α better than EC44, native (±)-KU and (-)-KU, and (±)-KU and (-)-ARC.

-(±)-Kusunokinin Binding to AKR1B1 Inhibits Oxidative Stress and Proteins Involved in Migration in Aggressive Breast Cancer.

Synthetic -(±)-kusunokinin ((±)KU), a potential anticancer substance, was revealed to have an inhibitory effect on breast cancer. According to the computational modeling prediction, AKR1B1, an oxidative stress and cancer migration protein, could be a target protein of -(-)-kusunokinin. In this study, we determined the binding of (±)KU and AKR1B1 on triple-negative breast and non-serous ovarian cancers.

Anticancer Activity of (±)-Kusunokinin Derivatives towards Cholangiocarcinoma Cells.

This study aimed to investigate the cytotoxicity and anticancer activity of (±)-kusunokinin derivatives ((±)-TTPG-A and (±)-TTPG-B). The cytotoxicity effect was performed on human cancer cells, including breast cancer, cholangiocarcinoma, colon and ovarian cancer-cells, compared with normal cells, using the MTT assay. Cell-cycle arrest and apoptosis were detected using flow-cytometry analysis.

Trans-(-)-Kusunokinin: A Potential Anticancer Lignan Compound against HER2 in Breast Cancer Cell Lines?

Trans-(-)-kusunokinin, an anticancer compound, binds CSF1R with low affinity in breast cancer cells. Therefore, finding an additional possible target of trans-(-)-kusunokinin remains of importance for further development. Here, a computational study was completed followed by indirect proof of specific target proteins using small interfering RNA (siRNA).

(-)-Kusunokinin as a Potential Aldose Reductase Inhibitor: Equivalency Observed via AKR1B1 Dynamics Simulation.

(-)-Kusunokinin performed its anticancer potency through CFS1R and AKT pathways. Its ambiguous binding target has, however, hindered the next development phase. Our study thus applied molecular docking and molecular dynamics simulation to predict the protein target from the pathways.

Inhibition of CSF1R and AKT by (±)-kusunokinin hinders breast cancer cell proliferation.

Kusunokinin, a lignan compound, inhibits cancer cell proliferation and induces apoptosis; however, the role of kusunokinin is not fully understood. Here, we aimed to identify a target protein of (-)-kusunokinin and determine the protein levels of its downstream molecules. We found that (-)-kusunokinin bound 5 possible target proteins, including CSF1R, MMP-12, HSP90-α, CyclinB1 and MEK1 with ΔG less than -10.

Antimalarial 9-Methoxystrobilurins, Oudemansins, and Related Polyketides from Cultures of Basidiomycete Species.

Fourteen new compounds, oudemansins -, oudemansinols -, favolasins -, favolasinin (), polyketides -, and (,)-2,4-dimethyl-5-phenyl-4-pentene-2,3-diol (), together with nine known compounds were isolated from the basidiomycete fungus sp. BCC 18686. Two new compounds, favolasin E () and 9-oxostrobilurin E (), were isolated from the closely related organism BCC 36684 along with nine β-methoxyacrylate-type derivatives.

Secondary metabolites from cultures of the ant pathogenic fungus BCC 2728.

Five new compounds, iranginins A-E (-), together with sixteen known compounds were isolated from the insect pathogenic fungus BCC 2728. The structures and the absolute configurations of the new compounds were established by spectroscopic analyses, the application of modified Mosher's method (for ), ECD calculation (for ), and X-ray crystallographic analysis (for ). LL-Z1640-5 and mucorisocoumarin C were active against (MIC 41.

Anticancer activity of synthetic (±)-kusunokinin and its derivative (±)-bursehernin on human cancer cell lines.

Kusunokinin is a potent lignan compound with a several biological properties including antitrypanosomal and anticancer. In this study, (±)-kusunokinin and its derivative, (±)-bursehernin, were synthesized and investigated for their anticancer activities on cell viability, cell cycle arrest and apoptosis in cancer cell lines including breast cancer (MCF-7, MDA-MB-468 and MDA-MB-231), colon cancer (HT-29) and cholangiocarcinoma (KKU-K100, KKU-M213 and KKU-M055) cells. The result showed that (±)-kusunokinin and (±)-bursehernin represented the strongest growth inhibition against breast cancer (MCF-7) and cholangiocarcinoma (KKU-M213) cells with the IC values of 4.

F-THENA: a chiral derivatizing agent for the determination of the absolute configuration of secondary aromatic alcohols with a self-validating system.

F-THENA is designed as an alternative fluorine-containing chiral derivatizing agent (CDA). The fluorine atom functions exclusively as a reporter which can directly sense an anisotropic effect from an aromatic substituent of a chiral alcohol. In combination with chemical shift differences from both F NMR and H NMR, the F-THENA method can successfully be used for determining the absolute configuration of chiral secondary aromatic alcohols with a self-validating system.

Eremophilane Sesquiterpenes and Diphenyl Thioethers from the Soil Fungus Penicillium copticola PSU-RSPG138.

Four new compounds including two eremophilane sesquiterpenes, penicilleremophilanes A (1) and B (2), as well as two sulfur-containing biphenols, penicillithiophenols A (3) and B (4), were isolated from the soil fungus Penicillium copticola PSU-RSPG138 together with 16 known compounds. Their structures were elucidated by spectroscopic methods. Known sporogen AO-1 exhibited significant antimalarial activity against Plasmodium falciparum with an IC50 value of 1.

Bioactive metabolites from cultures of basidiomycete Favolaschia tonkinensis.

Two strobilurins, 9-methoxystrobilurin B (1) and 9-methoxystrobilurin G (2), two monochlorinated 2,3-dihydro-1-benzoxepin derivatives, 3 and 4a, and butenolide 5, together with four known compounds, strobilurin B, 9-methoxystrobilurin A, and oudemansins A and B, were isolated from culture BCC 18689 of the fungus Favolaschia tonkinensis. 9-Methoxystrobilurins A, B (1), and G (2) and oudemansins A and B exhibited antimalarial, antifungal, and cytotoxic activities, while compounds 3, 4a, and 5 displayed only cytotoxic activity.

Stereoselective synthesis of naturally occurring alpha-methylenebis-gamma-butyrolactones: an application of novel oxiranyl "remote" anions.

Stereospecific deprotonation of the epoxy proton at the beta-position of the alpha,beta-epoxy esters 5 and 6 yielded oxiranyl "remote" anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, respectively, epoxy lactones 11 and 13 with high stereoselectivity. Generation of the remote anions as well as their stereoselective reactions served as a new synthetic route to the naturally occurring alpha-methylenebis-gamma-butyrolactones, 1.

Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations.

The questions considered in this paper are why, as agents for resolving helicenols, camphanate esters are particularly effective, and why, in all 19 examples studied, when the (1S)-camphanates of (P)- and (M)-helicen-1-ols are chromatographed on silica gel, the former has the lower R(f)(). Models are proposed for the favored conformations of the esters, and to support the models, evidence is provided from five X-ray diffraction analyses and four ROESY analyses supplemented by molecular mechanics calculations. The essential discovery is that, presumably to avoid a steric interaction between a methyl on the camphanate's bridge and the helicene skeleton, the O=CCO conformation is anti-periplanar in (M)-helicenol camphanates and syn-periplanar in (P)-helicenol camphanates.