Spiro-meroterpenoids, Syzygioblanes D-H, Isolated from Indonesian Medicinal Plant .

Syzygioblanes A-C (-), isolated from the Indonesian traditional herbal medicine (), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D-H (-), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule.

Mild boroxazolidone formation and dissociation: application toward target identification of bioactive molecules.

We successfully found that boroxazolidone can dissociate under aqueous conditions, which were applicable to a solution containing proteins. The immobilization of a newly synthesized diarylborinic acid on beads enabled the capture and release of target proteins of bioactive compounds through boroxazolidone formation and dissociation.

Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant .

The isolation, structure determination, and biological evaluation of constituents from the organic extract of Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, and a 7-keto sterol). Among the new compounds, is the first triterpenoid with a trioxaspiro[4.4]nonane side chain, while - are the first 17-γ-lactone tetranortriterpenoids with four oxygenated functional groups at C-1, -3, -6, and -7.

Cyclic Sesquiterpene-Flavanone [4+2] Hybrids, Syzygioblanes A-C, Found in an Indonesian Traditional Medicine, "Jampu Salo" ().

A plant used in an Indonesian traditional herbal medicine as a diabetes treatment and known locally as "Jampu Salo" was collected on Sulawesi Island, Indonesia. It was identified as (C. B.

Total Synthesis of a TNBC-Selective Cytotoxic Bromo Nor-eremophilane, PC-A, and Its Preliminary Structure-Activity Relationships.

PC-A (), a bromo nor-eremophilane, showed selective antiproliferative activity against a triple-negative breast cancer (TNBC) cell line. This unique activity prompted us to establish a total synthesis to facilitate a structure-activity relationship (SAR) study and selectivity optimization. An enantioselective first total synthesis of was achieved starting from ()-carvone through a side chain extension with a Mukaiyama aldol reaction and decalin construction.

Unusual Vilasinin-Class Limonoids from .

Eight vilasinin-class limonoids, including the unusually chlorinated rubescins K-M (-), the 2,3-epoxylated rubescin N (), and rubescins O-R (-), were newly isolated from . The structures of the isolated compounds were determined through spectroscopic and spectrometric analyses, as well as ECD calculations. The natural occurrence of chlorinated limonoids - was confirmed by chemical methods and HPLC analysis of a roughly fractionated portion of the plant extract.

Caged Xanthones and Biphenyls Isolated from the Tropical Plant .

Four cytotoxic heptacyclic caged-xanthones [gambogefic acids B-E (-)], a cytotoxic hexacyclic caged-xanthone [garcilatelic acid ()], and four biphenyl derivatives [garcilatelibiphenyls A-D (-)] were newly isolated in a phytochemical study of a 50% MeOH/CHCl extract of (Clusiaceae). The isolated compounds were evaluated for antiproliferative activity against five human tumor cell lines including a vincristine-resistant line. The new caged-xanthones displayed potent activity with IC values from 0.

Cytotoxicity Activity, Metabolite Profiling, and Isolation Compound from Crude Hexane Extract of Cleome rutidospermae.

Objective: This study isolated the chemical compounds and evaluated the cytotoxic activity of the crude hexane extract of Cleome rutidospermae herb (CRH).

Methods: The isolate was purified using silica gel, column chromatography, and preparative thin layer chromatography (PTLC). Furthermore, the structure of the compounds was identified by spectroscopic methods using 1D, 2D NMR, and mass spectrometry.

Total Synthesis of Waltherione A, a Quinolone Alkaloid Fused with Oxabicyclo[3.2.1]octane.

Waltherione A (), a unique quinolone alkaloid fused with oxabicyclo[3.2.1]octane, was isolated originally from and recently by us from a methanol extract of along with the related 3,4-dimethoxyquinoline paliasanines A-E.

Novel α-Trifluoromethyl Chalcone Exerts Antitumor Effects Against Prostate Cancer Cells.

Background/aim: Despite treating advanced prostate cancer (PCa) with androgen deprivation therapy, it eventually progresses to castration-resistant PCa. Subsequently, taxanes are administered, but when PCa becomes resistant to taxanes, another treatment is needed, which has not yet been established. We previously synthesized a novel α-trifluoromethyl chalcone, YS71, and reported its antitumor effects against PCa cells.

A New Bis-indole Alkaloid, Spermaocymine A, and an Anthraquinone from Spermacoce ocymoides.

A phytochemical study on Spermacoce ocymoides has led to the isolation of a novel bis-indole alkaloid, spermaocymine A (2), together with the known alkaloid 4-methyl-borreverine (1), as well as an anthraquinone, 8-hydroxy-2-(hydroxymethyl)-1-methoxyanthracene-9,10-dione (3). The structures of the isolated compounds were elucidated by analyzing spectroscopic and spectrometric data, including one-dimensional (1D)- and 2D-NMR and high resolution (HR)-MS. Newly isolated alkaloid 2 was a C-3,14-stereoisomer of 1, the first natural stereoisomer of related bis-indoles containing an indeno[1,2-b]indole skeleton with an epiminoethano bridge.

Suppression of androgen receptor signaling induces prostate cancer migration via activation of the CCL20-CCR6 axis.

The suppression of androgen receptor (AR) expression exacerbates the migration potential of prostate cancer. This study identified a previously unrecognized regulation of the AR-controlled pathway that promotes migration potential in prostate cancer cells. Prostate cancer cells that pass through a transwell membrane (mig cells) have a higher migration potential with a decreased AR expression than parental cells.

Synthesis of a Model Compound of the Unique Meroterpenoids Cryptolaevilactones.

Cryptolaevilactones (CLs) A-L, found in the leaves and twigs of Cryptocarya laevigata, are unique natural meroterpenoids with a spiro[3.5]nonane skeleton. We report the total synthesis of a simplified model compound of CLs A-C.

Tapered self-written waveguide for a silicon photonic chip I/O.

An optical coupling method with high alignment tolerance by self-written waveguide (SWW) formation is a promising candidate for co-packaged optics (CPO) by silicon photonics (SiPh). However, conventional SWWs cannot be used with Si waveguides because visible light for SWW formation cannot radiate from the waveguide facet. Here, we devised a new, to the best of our knowledge, optical circuit with SiON waveguides for SWW formation from an SiPh chip.

Vitamin E Enhances Cancer Immunotherapy by Reinvigorating Dendritic Cells via Targeting Checkpoint SHP1.

Unlabelled: Despite the popular use of dietary supplements during conventional cancer treatments, their impacts on the efficacies of prevalent immunotherapies, including immune-checkpoint therapy (ICT), are unknown. Surprisingly, our analyses of electronic health records revealed that ICT-treated patients with cancer who took vitamin E (VitE) had significantly improved survival. In mouse models, VitE increased ICT antitumor efficacy, which depended on dendritic cells (DC).

Chemical Space Expansion of Flavonoids: Induction of Mitotic Inhibition by Replacing Ring B with a 10π-Electron System, Benzo[]thiophene.

Natural products, which are enzymatically biosynthesized, have a broad range of biological activities. In particular, many flavonoids are known to contribute to human health with low toxicity. We previously reported that novel benzo[]thiophenyl (BT) flavones with a 10π-electron BT ring B replacing the usual 6π-electron phenyl ring showed potent antiproliferative activity against human tumor cell lines.

Radiosynthesis and in Vivo and ex Vivo Evaluation of Isomeric [C]methoxy Analogs of Nimesulide as Brain Cyclooxygenase-2-Targeted Imaging Agents.

Our previous studies identified that nimesulide analogs which bear a methoxy substituent at the para-position of the phenyl ring could be potential radiotracer candidates for detecting disorders related to cyclooxygenase-2 (COX-2) expression and activity in vivo using positron emission tomography (PET) in the brain. The present study was conducted to evaluate the in vivo characteristics of C-labeled para-methoxy nimesulide ([C]1d) as a brain COX-2-targeted imaging agent compared to other isomeric methoxy analogs of nimesulide ([C]1b and [C]1c). [C]1b-d were synthesized with reasonable yield and purity by the methylation of the O-desmethyl precursor with [C]methyl triflate in the presence of NaOH at room temperature.

The allergy mediator histamine confers resistance to immunotherapy in cancer patients via activation of the macrophage histamine receptor H1.

Reinvigoration of antitumor immunity remains an unmet challenge. Our retrospective analyses revealed that cancer patients who took antihistamines during immunotherapy treatment had significantly improved survival. We uncovered that histamine and histamine receptor H1 (HRH1) are frequently increased in the tumor microenvironment and induce T cell dysfunction.

Effects of substituent pattern on the intracellular target of antiproliferative benzo[b]thiophenyl chromone derivatives.

A new biological scaffold was produced by replacing the 6π-electron phenyl ring-B of a natural flavone skeleton with a 10π-electron benzothiophene (BT). Since aromatic rings are important for ligand protein interactions, this expansion of the π-electron system of ring-B might change the bioactivity profile. One of the resulting novel natural product-inspired compounds, 2-(benzo[b]thiophen-3-yl)-5-hydroxy-7-isopropoxy-6-methoxyflavone (6), effectively arrested the cell cycle at the G2/M phase and displayed significant antiproliferative effects with IC values of 0.

α-Trifluoromethyl Chalcones as Potent Anticancer Agents for Androgen Receptor-Independent Prostate Cancer.

α-Trifluoromethyl chalcones were prepared and evaluated for their antiproliferative activities against androgen-independent prostate cancer cell lines as well as five additional types of human tumor cell lines. The most potent chalcone showed superior antitumor activity in vivo with both oral and intraperitoneal administration at 3 mg/kg. Cell-based mechanism of action studies demonstrated that induced cell accumulation at sub-G1 and G2/M phases without interfering with microtubule polymerization.

Synthesis of Thio-lignan Analogues, Bioequivalent Salvinal without Unfavored Aldehyde.

The oxygen in the benzofuran (BF) of three antiproliferative natural neolignans, salvinal (), obovaten (), and 2-[7-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran-5-yl]ethanol (), was replaced with sulfur to form the new biological scaffold benzothiophene (BT) thio-lignans -. Compounds - and synthesized derivatives were evaluated for antiproliferative activity against five human cancer cell lines, including a multidrug-resistant cell line. Thio-salvinal () displayed significant antiproliferative effects with half-maximal inhibitory concentration (IC) values of 0.

Rise and fall of Landau's quasiparticles while approaching the Mott transition.

Landau suggested that the low-temperature properties of metals can be understood in terms of long-lived quasiparticles with all complex interactions included in Fermi-liquid parameters, such as the effective mass m. Despite its wide applicability, electronic transport in bad or strange metals and unconventional superconductors is controversially discussed towards a possible collapse of the quasiparticle concept. Here we explore the electrodynamic response of correlated metals at half filling for varying correlation strength upon approaching a Mott insulator.

Bicyclic Chalcones as Mitotic Inhibitors for Overcoming Androgen Receptor-Independent and Multidrug-Resistant Prostate Cancer.

To improve the biological effects of the lead compound 5'-chloro-2,2'-dihydroxychalcone (Cl-DHC), bicyclic aromatic chalcones were designed, synthesized, and evaluated against androgen-independent prostate cancer (PCa) DU145 and PC-3 cell proliferation. Newly synthesized bi-naphthyl derivatives and suppressed the proliferation of these two cell lines and also taxane-resistant prostate cancer cell lines at a submicromolar level. The two compounds were 4-18 times more potent than the parent molecule Cl-DHC.