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Comprehensive Summary The EDA complex‐mediated reactions involving oxime esters have been few studied. Herein, an EDA complex formed by thiophenolate anion and oxime ester is reported for photoinduced divergent synthesis of thioethers, depending on different types of oxime esters. Operational simplicity, mild reaction conditions, and flexible options of leaving group demonstrate the generality and synthetic utility of this approach. Such an approach can also enable an interesting thiol‐catalysis for the synthesis of phenanthridines. [ABSTRACT FROM AUTHOR]

Comprehensive Summary The EDA complex‐mediated reactions involving oxime esters have been few studied. Herein, an EDA complex formed by thiophenolate anion and oxime ester is reported for photoinduced divergent synthesis of thioethers, depending on different types of oxime esters. Operational simplicity, mild reaction conditions, and flexible options of leaving group demonstrate the generality and synthetic utility of this approach. Such an approach can also enable an interesting thiol‐catalysis for the synthesis of phenanthridines. [ABSTRACT FROM AUTHOR]

Difluoroalkyl sulfide (‐CF2S‐) moieties are an important class of skeletons in medicinal chemistry. Herein, a photoredox radical‐polar crossover reaction is reported for the three‐component thiofluorination, thiohydroxylation, thioalkoxylation, thioaminolation, and thiochlorination of gem‐difluoroalkenes towards diverse α‐functionalized difluoroalkyl sulfides. Such an approach features mild conditions, operational simplicity, and good substrate scope. [ABSTRACT FROM AUTHOR]

In this DFT study, we have evaluated the reaction mechanism of lithium polysulfide (Li2S6) with the electrolyte additive methyl trifluoroacetate (CH3TFA) in the gas and solvent (dimethoxyethane (DME)) phase at room temperature (298 K) by locating transition states (TS) for the methyl group transfer from CH3TFA to Li2S6, which is reported to produces organosulfur ((CH3)2S6). All the reported methyl transfer reactions that lead to the formation of organosulfur are having high barrier energy. The barrier energy difference between gas and solvent phase is maximum of 7 kcal/mol, and both the reactions are in extremely slow regime, therefore, the methyl transfer reaction for the formation of organosulfur implausible at room temperature. [ABSTRACT FROM AUTHOR]

Scorodocarpus borneensis (Baill.) Becc. is attracting increased attention as a potential commercial medicinal plant product in Southeast Asia. This review summarizes the current knowledge on the taxonomy, habitat, distribution, medicinal uses, natural products, pharmacology, toxicology, and potential utilization of S. borneesis in the pharmaceutical/nutraceutical/functional cosmetic industries. All data in this review were compiled from Google Scholar, PubMed, Science Direct, Web of Science, ChemSpider, PubChem, and a library search from 1866 to 2022. A total of 33 natural products have been identified, of which 11 were organosulfur compounds. The main organosulfur compound in the seeds is bis-(methylthiomethyl)disulfide, which inhibited the growth of a broad spectrum of bacteria and fungi, T-lymphoblastic leukemia cells, as well as platelet aggregation. Organic extracts evoked anti-microbial, cytotoxic, anti-free radical, and termiticidal effects. S. borneensis and its natural products have important and potentially patentable pharmacological properties. In particular, the seeds have the potential to be used as a source of food preservatives, antiseptics, or termiticides. However, there is a need to establish acute and chronic toxicity, to examine in vivo pharmacological effects and to perform clinical studies. [ABSTRACT FROM AUTHOR]

Hydrogen sulfide (H2S), known for many decades exclusively for its toxicity and the smell of rotten eggs, has been re-discovered for its pleiotropic effects at the cardiovascular and non-cardiovascular level. Therefore, great attention is being paid to the discovery of molecules able to release H2S in a smart manner, i.e., slowly and for a long time, thus ensuring the maintenance of its physiological levels and preventing "H2S-poor" diseases. Despite the development of numerous synthetically derived molecules, the observation that plants containing sulfur compounds share the same pharmacological properties as H2S led to the characterization of naturally derived compounds as H2S donors. In this regard, polysulfuric compounds occurring in plants belonging to the Alliaceae family were the first characterized as H2S donors, followed by isothiocyanates derived from vegetables belonging to the Brassicaceae family, and this led us to consider these plants as nutraceutical tools and their daily consumption has been demonstrated to prevent the onset of several diseases. Interestingly, sulfur compounds are also contained in many fungi. In this review, we speculate about the possibility that they may be novel sources of H2S-donors, furnishing new data on the release of H2S from several selected extracts from fungi. [ABSTRACT FROM AUTHOR]

A simple and transition-metal-free HFIP-induced allylation reaction of tertiary allylic alcohols with thiols or sulfonyl hydrazine derivatives was reported for the efficient and highly selective synthesis of allylic sulfides and allylic sulfones. Herein, HFIP played a vital role in not only activating the allylic alcohol, but also stabilizing the allylic cation intermediate to accelerate the subsequent transformations. [ABSTRACT FROM AUTHOR]

Scorodocarpus borneensis (Baill.) Becc. is attracting increased attention as a potential commercial medicinal plant product in Southeast Asia. This review summarizes the current knowledge on the taxonomy, habitat, distribution, medicinal uses, natural products, pharmacology, toxicology, and potential utilization of S. borneesis in the pharmaceutical/nutraceutical/functional cosmetic industries. All data in this review were compiled from Google Scholar, PubMed, Science Direct, Web of Science, ChemSpider, PubChem, and a library search from 1866 to 2022. A total of 33 natural products have been identified, of which 11 were organosulfur compounds. The main organosulfur compound in the seeds is bis-(methylthiomethyl)disulfide, which inhibited the growth of a broad spectrum of bacteria and fungi, T-lymphoblastic leukemia cells, as well as platelet aggregation. Organic extracts evoked anti-microbial, cytotoxic, anti-free radical, and termiticidal effects. S. borneensis and its natural products have important and potentially patentable pharmacological properties. In particular, the seeds have the potential to be used as a source of food preservatives, antiseptics, or termiticides. However, there is a need to establish acute and chronic toxicity, to examine in vivo pharmacological effects and to perform clinical studies.

Aquaculture growth will unavoidably involve the implementation of innovative and sustainable production strategies, being functional feeds among the most promising ones. A wide spectrum of phytogenics, particularly those containing terpenes and organosulfur compounds, are increasingly studied in aquafeeds, due to their growth promoting, antimicrobial, immunostimulant, antioxidant, anti-inflammatory and sedative properties. This trend relies on the importance of the mucosal barrier in the fish defense. Establishing the phytogenics’ mode of action in mucosal tissues is of importance for further use and safe administration. Although the impact of phytogenics upon fish mucosal immunity has been extensively approached, most of the studies fail in addressing the mechanisms underlying their pharmacological effects. Unstandardized testing as an extended practice also questions the reproducibility and safety of such studies, limiting the use of phytogenics at commercial scale. The information presented herein provides insight on the fish mucosal immune responses to phytogenics, suggesting their mode of action, and ultimately encouraging the practice of reliable and reproducible research for novel feed additives for aquafeeds. For proper screening, characterization and optimization of their mode of action, we encourage the evaluation of purified compounds using in vitro systems before moving forward to in vivo trials. The formulation of additives with combinations of compounds previously characterized is recommended to avoid bacterial resistance. To improve the delivery of phytogenics and overcome limitations associated to compounds volatility and susceptibility to degradation, the use of encapsulation is advisable. Besides, newer approaches and dedicated methodologies are needed to elucidate the phytogenics pharmacokinetics and mode of action in depth.

Aquaculture growth will unavoidably involve the implementation of innovative and sustainable production strategies, being functional feeds among the most promising ones. A wide spectrum of phytogenics, particularly those containing terpenes and organosulfur compounds, are increasingly studied in aquafeeds, due to their growth promoting, antimicrobial, immunostimulant, antioxidant, anti-inflammatory and sedative properties. This trend relies on the importance of the mucosal barrier in the fish defense. Establishing the phytogenics' mode of action in mucosal tissues is of importance for further use and safe administration. Although the impact of phytogenics upon fish mucosal immunity has been extensively approached, most of the studies fail in addressing the mechanisms underlying their pharmacological effects. Unstandardized testing as an extended practice also questions the reproducibility and safety of such studies, limiting the use of phytogenics at commercial scale. The information presented herein provides insight on the fish mucosal immune responses to phytogenics, suggesting their mode of action, and ultimately encouraging the practice of reliable and reproducible research for novel feed additives for aquafeeds. For proper screening, characterization and optimization of their mode of action, we encourage the evaluation of purified compounds using in vitro systems before moving forward to in vivo trials. The formulation of additives with combinations of compounds previously characterized is recommended to avoid bacterial resistance. To improve the delivery of phytogenics and overcome limitations associated to compounds volatility and susceptibility to degradation, the use of encapsulation is advisable. Besides, newer approaches and dedicated methodologies are needed to elucidate the phytogenics pharmacokinetics and mode of action in depth. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • Reactions between arynes and organosulfurs are reviewed. • S(II), S(IV), and S(VI) organosulfurs have distinctive reactivities with arynes. • Various aromatic organosulfurs are now synthesizable via aryne intermediates. Abstract The recent progress made on transformations involving the reactions between aryne intermediates and organosulfur compounds has been reviewed. A wide variety of aromatic organosulfurs are now synthesizable by generating arynes in the presence of organosulfur compounds. Organosulfurs have distinctive reactivities with arynes, which depend on the sulfur atom's valence state, that is, S(II), S(IV), and S(VI), as well as the presence or absence of other intra- or intermolecular reactive moieties. These novel transformations have enabled the diversity-oriented synthesis of unique aromatic organosulfurs that were once difficult to prepare by the conventional methods, paving the way for the development of molecules that are beneficial across numerous disciplines, including pharmaceutical science and materials science. [ABSTRACT FROM AUTHOR]

Purpose: Methimazole is a drug widely used in hyperthyroidism. However, life-threatening hepatotoxicity has been associated with its clinical use. No protective agent has been found to be effective against methimazole-induced hepatotoxicity yet. Hence, the capacity of organosulfur compounds to protect rat hepatocytes against cytotoxic effects of methimazole and its proposed toxic metabolite, N-methylthiourea was evaluated. Methods: Hepatocytes were prepared by the method of collagenase enzyme perfusion via portal vein. Cells were treated with different concentrations of methimazole, N-methylthiourea, and organosulfur chemicals. Cell death, protein carbonylation, reactive oxygen species formation, lipid peroxidation, and mitochondrial depolarization were assessed as toxicity markers and the role of organosulfurs administration on them was investigated. Results: Methimazole caused a decrease in cellular glutathione content, mitochondrial membrane potential (ΔΨm) collapse, and protein carbonylation. In addition, an increase in reactive oxygen species (ROS) formation and lipid peroxidation was observed. Treating hepatocytes with N-methylthiourea caused a reduction in hepatocytes glutathione reservoirs and an elevation in carbonylated proteins, but no significant ROS formation, lipid peroxidation, or mitochondrial depolarization was observed. N-acetyl cysteine, allylmercaptan, and diallyldisulfide attenuated cell death and prevented ROS formation and lipid peroxidation caused by methimazole. Furthermore, organosulfur compounds diminished methimazole-induced mitochondrial damage and reduced the carbonylated proteins. In addition, these chemicals showed protective effects against cell death and protein carbonylation induced by methimazole metabolite. Conclusion: Organosulfur chemicals extend their protective effects against methimazole-induced toxicity by attenuating oxidative stress caused by this drug and preventing the adverse effects of methimazole and/or its metabolite (s) on subcellular components such as mitochondria.

This study presented the methanol/ethanol extraction of organosulfurs from a commercially available garlic capsule, commonly used as a herbal drug supplement, comparing with fresh and its baked garlic clove followed by its antioxidant activity evaluation by both 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 1,10-phenanthroline (Phen) methods. Using various ratios of methanol or ethanol in deionized water under stirring at ambient temperature, the highest antioxidant activities of the crude extract obtained from garlic (powder) capsule, fresh garlic clove and baked garlic powder were 224, 189 and 253 µg BHT/g DW for DPPH assay, and 9.5, 9.2 and 9.6 µg Fe/g DW for Phen assay, respectively. However, the garlic crude extract contained rather high contents of total phenolics, as determined by Folin-Ciocalteu reagent, of 554, 1866 and 536 µg GAE/g DW, respectively. When removal of total phenolics at least 10 folds using C18-SPE expecting only for an allicin, its antioxidant activity of the garlic capsule drastically decreased (88%) as the total phenolics decreased about 91%. Concerning the powder of the baked garlic clove, its antioxidant activity also decreased (82%) with removal of the phenolics (93%). While that of fresh garlic remained increase of 14% as its total phenolics decreased 92%. Therefore, the obtained antioxidant activity of which the organosulfurs in the garlic extract would be synergic results from the residual phenolics. [ABSTRACT FROM AUTHOR]

Purpose: Methimazole is a drug widely used in hyperthyroidism. However, life-threatening hepatotoxicity has been associated with its clinical use. No protective agent has been found to be effective against methimazole-induced hepatotoxicity yet. Hence, the capacity of organosulfur compounds to protect rat hepatocytes against cytotoxic effects of methimazole and its proposed toxic metabolite, N-methylthiourea was evaluated. Methods: Hepatocytes were prepared by the method of collagenase enzyme perfusion via portal vein. Cells were treated with different concentrations of methimazole, N-methylthiourea, and organosulfur chemicals. Cell death, protein carbonylation, reactive oxygen species formation, lipid peroxidation, and mitochondrial depolarization were assessed as toxicity markers and the role of organosulfurs administration on them was investigated. Results: Methimazole caused a decrease in cellular glutathione content, mitochondrial membrane potential (??m) collapse, and protein carbonylation. In addition, an increase in reactive oxygen species (ROS) formation and lipid peroxidation was observed. Treating hepatocytes with N-methylthiourea caused a reduction in hepatocytes glutathione reservoirs and an elevation in carbonylated proteins, but no significant ROS formation, lipid peroxidation, or mitochondrial depolarization was observed. N-acetyl cysteine, allylmercaptan, and diallyldisulfide attenuated cell death and prevented ROS formation and lipid peroxidation caused by methimazole. Furthermore, organosulfur compounds diminished methimazole-induced mitochondrial damage and reduced the carbonylated proteins. In addition, these chemicals showed protective effects against cell death and protein carbonylation induced by methimazole metabolite. Conclusion: Organosulfur chemicals extend their protective effects against methimazole-induced toxicity by attenuating oxidative stress caused by this drug and preventing the adverse effects of methimazole and/or its metabolite (s) on subcellular components such as mitochondria. [ABSTRACT FROM AUTHOR]