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Evaluation and improvement of CuI-mediated 11C-cyanation
2023 / Journal of Labelled Compounds and RadiopharmaceuticalsCuI-mediated 11C-cyanation was evaluated by synthesizing [11C]perampanel ([11C]5) as a model compound and compared with previous reports. To a DMF solution with 5′-(2-bromophenyl)-1′-phenyl-[2,3′-bipyridin]-6′(1′H)-one (4) and CuI, [11C]NH4CN in a stream of ammonia/nitrogen (5:95, v/v) gas was bubbled. Subsequently, the reaction mixt...
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Utilization of the By-Product of Corn: Guided Identification of Bioactive Terpenoids from Stigma Maydis (Corn Silk)
2023 / Journal of Agricultural and Food ChemistryStigma maydis (corn silk) (S. maydis) is a food-based by-product of maize and possesses great nutritional and pharmaceutical value. This study aimed to explore bioactive components from S. maydis. By the guidance of bioactivity-guided approach and Global Natural Products Social (GNPS) molecular networking, 12 terpenoids were discovered from S. maydis. The structure...
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Antibiotic Guanacastane Diterpenoids with Two New Skeletons from Psathyrella candolleana Uncovered by Semisolid and Liquid Media
2023 / Journal of Agricultural and Food ChemistryThe culture of Psathyrella candolleana in host Dioscorea opposite medium produced seven new guanacastane diterpenoids, psayamin (1) as an unprecedented 5/7/6/6/6/6/7/5-fused octacyclic spiro scaffold both under liquid and semisolid conditions, psathins A–C (4–6) with a 5/7/6 tricyclic backbone by liquid medium, psathins D–E (7–8) as the same...
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Influence of Arabinan Fine Structure, Galacturonan Backbone Length, and Degree of Esterification on the Emulsifying Properties of Acid-Extracted Sugar Beet Pectins
2023 / Journal of Agricultural and Food ChemistrySugar beet pectins (SBPs) are known for their emulsifying properties, but it is yet unknown which structural elements are most important for functionality. Recent results indicated that the arabinose content has a decisive influence, but the approach applied did not allow causality to be established. In this study, a mostly intact SBP was selectively modified and t...
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Study of Serial Exposures of an Astringent Green Tea Flavonoid Extract with Oral Cell-Based Models
2023 / Journal of Agricultural and Food ChemistryIt is well known that repeated exposure to phenolic compounds (PCs) raises astringency perception. However, the link between this increase and the oral cavity’s interactions with salivary proteins (SPs) and other oral constituents is unknown. To delve deeper into this connection, a flavonoid-rich green tea extract was tested in a series of exposures to two or...
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Eugeniifoline, a Pentacyclic Indole Alkaloid from Leuconotis eugeniifolia, and Configurational Revision of Synthetic Eugeniifoline Isolated from a Diversity-Enhanced Extract
2023 / Journal of Natural ProductsEugeniifoline (1), a pentacyclic indole alkaloid with a five-membered ring E, was isolated for the first time as a natural product from the stem-bark extract of Leuconotis eugeniifolia. Eugeniifoline (1) was previously reported as a synthetic product from a diversity-enhanced extract, but with the configuration at C-21 reported as S (1a). The configuration at C-21 ...
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In Vitro Hypoglycemic Diterpenoids from the Roots of Croton yunnanensis
2023 / Journal of Natural ProductsFifteen compounds including nine new diterpenes were isolated from the roots of Croton yunnanensis. By HRESIMS, NMR, ECD data, and X-ray diffraction analysis, the new compounds were characterized as eight neo-clerodane diterpenes (compounds 1–8) and one 15,16-dinor-ent-pimarane diterpene (9). All diterpenes were assayed for their hypoglycemic activities. Comp...
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Daphnepedunins A–F, Anti-HIV Macrocyclic Daphnane Orthoester Diterpenoids from Daphne pedunculata
2022 / Journal of Natyral ProductsFrom the whole plant of Daphne pedunculata, 12 macrocyclic daphnane diterpenoids, including six new compounds, daphnepedunins A–F (1–4, 9, and 10), were isolated. Their structures were elucidated by physiochemical and spectroscopic data analysis, the modified Mosher’s method, and X-ray crystallography. The isolated compounds were evaluated for ant...
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Enhanced antioxidant and cytotoxic activity of ferrocenyl-substituted curcumin via stabilization of promoter c-MYC silencer element
2022 / Journal of Biomolecular Structure and DynamicsWe are reporting a successful attachment of ferrocenyl moiety at the active methylene carbon atom of β-diketone of curcumin via Knoevenagel condensation reaction, to utilize the optimum selectivity toward biological targets. The formation of ferrocenyl curcumin (i.e., Fc-cur) has been confirmed by 1H NMR, 13C NMR, and FT-IR spectra analysis. Further, circular ...
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Heat-triggered thermo-irreversible gelation of curdlan to control crystallisation and in vitro release of nobiletin
2022 / International Journal of Food Science & TechnologyMany kinds of flavonoids with poor water solubility and high crystallisation properties tend to crystallise in the system, which negatively affects their processing, storage and bioavailability. Hence, controlling crystal growth is an effective pathway to achieve stabilisation. Inspired by the properties of heat-triggered gelation of curdlan (Cur), the nobiletin ...
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Inhibitors of Asexual Reproduction of the Plant Pathogen Phytophthora from Tomato Juice: Structure–Activity Relationships and Transcriptome Analysis
2022 / Journal of Agricultural and Food ChemistryPhytophthora is a genus of fungus-like microorganisms that damages important crops, such as potatoes and tomatoes. Its asexual reproduction, which results in the production of numerous motile zoospores, is the cause of quick and severe outbreaks and crop damage. The search for substances that selectively inhibit the asexual reproduction of Phytophthora led to the i...
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Major Carotenoids of Meiothermus ruber Are Deinoxanthin Glucoside Esters, Not Meiothermoxanthin Glucoside Esters
2022 / Journal of Naturral ProductsMeiothermus ruber DSMZ 1279T was isolated from a hot spring in Kamchatka and was red in color. The major carotenoid present was reported to be 1′-(β-d-glucopyranosyloxy)-3,4,3′,4′-tetradehydro-1′,2′-dihydro-β,ψ-caroten-2-one after saponification (Burgess et al. J. Nat. Prod. 1999, 62, 859−863). In this study, we pur...
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Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
2022 / Journal of Natural ProductsThe stereoselective synthesis of C40-all-trans-carotenoids with the formal hexahydrobenzofuran skeletons aurochrome, auroxanthin, and equinenone-5′,8′-epoxide is reported. The synthesis is based on a one-pot or stepwise double Horner–Wadsworth–Emmons (HWE) reaction of a terminal enantiopure C15-5,6-epoxycyclohexadienylphosphonate and a centr...
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Vegetable seeds: A new perspective in future food development
2022 / Journal of Food Processing and PreservationTraditionally, vegetables are consumed as ingredients of daily household meals. Before cooking, vegetables are washed thoroughly, unpeeled, and deseeded, followed by chopping into desired shapes and sizes. Vegetable peels and seeds are also byproducts of various food industries. If they are not used, they will contribute significantly to global garbage. On the...
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Polyprenylated Benzophenones and Tocotrienol Derivatives from the Edible Fruits of Garcinia oblongifolia Champ. ex Benth. and Their Cytotoxicity Activity
2022 / Journal of Agricultural and food chemistryThe fruits of Garcinia oblongifolia Champ. ex Benth. were famous as an edible fruit in tropical regions of China. Because of its unique taste and great nutritional value, the ripe fresh fruits of G. oblongifolia could be eaten directly or used as raw materials for natural beverages and food supplements. In this work, six new polyprenylated benzophenones (1–6)...
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