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Molecules (Basel, Switzerland) Feb 2022Soursop ( Lin.) is a plant belonging to the Annonaceae family that has been widely used globally as a traditional medicine for many diseases. In this review, we discuss... (Review)
Review
Soursop ( Lin.) is a plant belonging to the Annonaceae family that has been widely used globally as a traditional medicine for many diseases. In this review, we discuss the traditional use, chemical content, and pharmacological activities of . From 49 research articles that were obtained from 1981 to 2021, 's activities were shown to include anticancer (25%), antiulcer (17%), antidiabetic (14%), antiprotozoal (10%), antidiarrhea (8%), antibacterial (8%), antiviral (8%), antihypertensive (6%), and wound healing (4%). Several biological activities and the general mechanisms underlying the effects of have been tested both in vitro and in vivo. contains chemicals such as acetogenins (annomuricins and annonacin), alkaloids (coreximine and reticuline), flavonoids (quercetin), and vitamins, which are predicted to be responsible for the biological activity of .
Topics: Acetogenins; Annona; Furans; Humans; Lactones; Plant Extracts; Plant Leaves
PubMed: 35208993
DOI: 10.3390/molecules27041201 -
ChemSusChem Jul 2022The use of 5-hydroxymethylfurfural (HMF), furfural, and furan as scaffolds for designing alternative surfactants is a rapidly developing research area. This Review... (Review)
Review
The use of 5-hydroxymethylfurfural (HMF), furfural, and furan as scaffolds for designing alternative surfactants is a rapidly developing research area. This Review gathers recent examples highlighting the variety of methods for grafting the necessary polar and non-polar appendages, exploiting the specific chemical reactivity of each of these platform molecules. While the furan (or tetrahydrofuran) backbone is maintained in some targeted amphiphiles, alternatives using rearranged HMF or furfural such as cyclopentanols or furanones have also been reported. This topic is an illustration of the diversification of the use of HMF and other biobased furanic platform molecules in the field of fine and specialty chemicals. The surfactants sector, which concerns some of the most largely consumed chemicals in everyday life, and still mostly produced from fossil resources, will benefit from such alternatives enabling increased renewable carbon content and structural innovation.
Topics: Furaldehyde; Furans; Surface-Active Agents
PubMed: 35015340
DOI: 10.1002/cssc.202102660 -
Roczniki Panstwowego Zakladu Higieny 2018Coffee is the most popular hot beverage in the world. The annual coffee production in 2010, 2014 and 2016 was 8.1, 9.0 and 9.3 million tons respectively. There are more... (Review)
Review
Coffee is the most popular hot beverage in the world. The annual coffee production in 2010, 2014 and 2016 was 8.1, 9.0 and 9.3 million tons respectively. There are more than 100 coffee species, but only two of them: Arabica (Coffea arabica) and Robusta (Coffea canephora) have gained commercial importance. During roasting of green coffee beans not only desirable compounds are formed, that exert positive influence on the taste and flavour of coffee, but also small quantities of undesirable ones. Furan (C4H4O) is one of the latter. Furan is a volatile compound (boiling temp. of 31.4 oC) formed during thermal processing of food. The toxicity of furan has been well documented and it is classified as “possible human carcinogen” (Group 2B) by the International Agency for Research on Cancer. Various pathways have been reported for furan formation during food processing. It can be formed from carbohydrates, amino acids by their thermal degradation or thermal re-arrangement and by oxidation of ascorbic acid and polyunsaturated acids and carotenoids. High concentrations of furan have been reported in coffee, baked and roasted food and in food subjected to preserving in cans and jars. Furan levels in brewed coffee are typically near or below 120 μg/L, but it can approach thousands μg/kg in roasted whole beans or ground coffee. The highest concentration of furan in roasted coffee reaches the level of 7000 μg/kg. Taking into account that coffee is the most popular hot drink, it becomes the main contributor to furan exposure from dietary sources for adults. In this article the published scientific papers concerned with the presence of furan in roasted non-brewed and brewed coffee have been reviewed. The formation mechanisms and occurrence of furan in coffee and the harmful influence of furan on the consumer health have been discussed.
Topics: Coffea; Coffee; Food Contamination; Food Handling; Furans; Humans; Seeds
PubMed: 29766689
DOI: No ID Found -
Molecules (Basel, Switzerland) Mar 2022Derivatives based on pyridine-2-6- and furan-2,5-dicarboxamide scaffolds reveal numerous chemical properties and biological activities. This fact makes them an exciting...
Derivatives based on pyridine-2-6- and furan-2,5-dicarboxamide scaffolds reveal numerous chemical properties and biological activities. This fact makes them an exciting research topic in supramolecular and coordination chemistry and in discovering new pharmacologically-active compounds. This work aimed to obtain a series of symmetrical pyridine-2-6- and furan-2,5-dicarboxamides through a condensation reaction of the appropriate acyl chlorides and aromatic amides. Successful syntheses were confirmed with NMR spectroscopy. We solved their crystal structures for seven compounds; two pyridine and five furan derivatives. Based on our crystallographic studies, we were able to indicate supramolecular features of the crystals under investigation. Additionally, Hirshfeld surface analysis allowed us to calculate a distribution of intermolecular contacts in the dicarboxamide crystals.
Topics: Amides; Furans; Magnetic Resonance Spectroscopy; Pyridines
PubMed: 35335183
DOI: 10.3390/molecules27061819 -
Chemistry (Weinheim An Der Bergstrasse,... Dec 2022The dolabellane-type diterpene dictyoxetane represents a significant challenge to synthetic organic chemistry. Methodology directed towards the total synthesis of...
The dolabellane-type diterpene dictyoxetane represents a significant challenge to synthetic organic chemistry. Methodology directed towards the total synthesis of naturally occurring (+)-dictyoxetane is reported. Catalytic asymmetric synthesis of the trans-hydrindane ring system is achieved through chemoselective deoxygenation of the Hajos-Parrish ketone. An alternative to the Garst-Spencer furan annulation is developed for the synthesis of a 2,5-dimethyl, tetrasubstituted furan, employing a tandem 5-exo-dig alcohol to alkyne cyclisation/aromatisation reaction as a key step. The (4+3) cycloaddition reaction of an oxyallyl cation with a tetrasubstituted furan is established on a cyclohexanone-derived model system, and a range of related (4+3) cycloadditions investigated on a homochiral, trans-hydrindane-fused furan, where regio- and diastereoselectivity is required for the natural product synthesis. In an alternative (4+2) Diels-Alder approach, a C -symmetric vinyl sulfoxide-based chiral ketene equivalent is used to prepare oxanorbornenes with the same oxygen bridge stereochemistry found in the 2,7-dioxatricyclo[4.2.1.0 ]nonane ring system of the natural product.
Topics: Cycloaddition Reaction; Diterpenes; Furans; Biological Products; Stereoisomerism
PubMed: 36300909
DOI: 10.1002/chem.202202429 -
Plant, Cell & Environment Sep 2017The plant hormones strigolactones are synthesized from carotenoids and signal via the α/β hydrolase DWARF 14 (D14) and the F-box protein MORE AXILLARY GROWTH 2 (MAX2).... (Review)
Review
The plant hormones strigolactones are synthesized from carotenoids and signal via the α/β hydrolase DWARF 14 (D14) and the F-box protein MORE AXILLARY GROWTH 2 (MAX2). Karrikins, molecules produced upon fire, share MAX2 for signalling, but depend on the D14 paralog KARRIKIN INSENSITIVE 2 (KAI2) for perception with strong evidence that the MAX2-KAI2 protein complex might also recognize so far unknown plant-made karrikin-like molecules. Thus, the phenotypes of the max2 mutants are the complex consequence of a loss of both D14-dependent and KAI2-dependent signalling, hence, the reason why some biological roles, attributed to strigolactones based on max2 phenotypes, could never be observed in d14 or in the strigolactone-deficient max3 and max4 mutants. Moreover, the broadly used synthetic strigolactone analog rac-GR24 has been shown to mimic strigolactone as well as karrikin(-like) signals, providing an extra level of complexity in the distinction of the unique and common roles of both molecules in plant biology. Here, a critical overview is provided of the diverse biological processes regulated by strigolactones and/or karrikins. These two growth regulators are considered beyond their boundaries, and the importance of the yet unknown karrikin-like molecules is discussed as well.
Topics: Furans; Lactones; Mycorrhizae; Plant Development; Plant Proteins; Stress, Physiological
PubMed: 28558130
DOI: 10.1111/pce.12996 -
Molecules (Basel, Switzerland) Jun 20134-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF, furaneol®) and its methyl ether 2,5-dimethyl-4-methoxy-3(2H)-furanone (DMMF) are import aroma chemicals and are considered... (Review)
Review
4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF, furaneol®) and its methyl ether 2,5-dimethyl-4-methoxy-3(2H)-furanone (DMMF) are import aroma chemicals and are considered key flavor compounds in many fruit. Due to their attractive sensory properties they are highly appreciated by the food industry. In fruits 2,5-dimethyl-3(2H)-furanones are synthesized by a series of enzymatic steps whereas HDMF is also a product of the Maillard reaction. Numerous methods for the synthetic preparation of these compounds have been published and are applied by industry, but for the development of a biotechnological process the knowledge and availability of biosynthetic enzymes are required. During the last years substantial progress has been made in the elucidation of the biological pathway leading to HDMF and DMMF. This review summarizes the latest advances in this field.
Topics: Bacteria; Flavoring Agents; Fruit; Furans; Maillard Reaction; Yeasts
PubMed: 23765232
DOI: 10.3390/molecules18066936 -
Marine Drugs Aug 2015Halichondrin B is a complex, natural, polyether macrolide derived from marine sponges. Eribulin is a structurally-simplified, synthetic, macrocyclic ketone analogue of... (Review)
Review
Halichondrin B is a complex, natural, polyether macrolide derived from marine sponges. Eribulin is a structurally-simplified, synthetic, macrocyclic ketone analogue of Halichondrin B. Eribulin was approved by United States Food and Drug Administration in 2010 as a third-line therapy for metastatic breast cancer patients who have previously been treated with an anthracycline and a taxane. It has a unique microtubule dynamics inhibitory action. Phase III studies have either been completed or are currently ongoing in breast cancer, soft tissue sarcoma, and non-small cell lung cancer. Phase I and II studies in multiple cancers and various combinations are currently ongoing. This article reviews the available information on eribulin with respect to its clinical pharmacology, pharmacokinetics, pharmacodynamics, mechanism of action, metabolism, preclinical studies, and with special focus on clinical trials.
Topics: Animals; Clinical Trials as Topic; Furans; Humans; Ketones; Neoplasms; Randomized Controlled Trials as Topic
PubMed: 26262627
DOI: 10.3390/md13085016 -
Molecules (Basel, Switzerland) Aug 2022Acrylamide (AA), furan and furan derivatives, polycyclic aromatic amines (PAHs), monochloropropanediols (MCPDs), glycidol, and their esters are carcinogens that are... (Review)
Review
Acrylamide (AA), furan and furan derivatives, polycyclic aromatic amines (PAHs), monochloropropanediols (MCPDs), glycidol, and their esters are carcinogens that are being formed in starchy and high-protein foodstuffs, including bread, through baking, roasting, steaming, and frying due to the Maillard reaction. The Maillard reaction mechanism has also been described as the source of food processing contaminants. The above-mentioned carcinogens, especially AA and furan compounds, are crucial substances responsible for the aroma of bread. The other groups of bread contaminants are mycotoxins (MTs), toxic metals (TMs), and pesticides. All these contaminants can be differentiated depending on many factors such as source, the concentration of toxicant in the different wheat types, formation mechanism, metabolism in the human body, and hazardous exposure effects to humans. The following paper characterizes the most often occurring contaminants in the bread from each group. The human exposure to bread contaminants and their safe ranges, along with the International Agency for Research on Cancer (IARC) classification (if available), also have been analyzed.
Topics: Acrylamide; Bread; Carcinogens; Cooking; Food Contamination; Food Handling; Furans; Humans
PubMed: 36080171
DOI: 10.3390/molecules27175406 -
Molecules (Basel, Switzerland) Apr 2022New furan-based derivatives have been, designed, synthesized, and evaluated for their cytotoxic and tubulin polymerization inhibitory activities. DNA flow cytometric...
New furan-based derivatives have been, designed, synthesized, and evaluated for their cytotoxic and tubulin polymerization inhibitory activities. DNA flow cytometric study of pyridine carbohydrazide and -phenyl triazinone demonstrated G/M phase cell cycle disruptions. Accumulation of cells in the pre-G1 phase and positive annexin V/PI staining, which may be caused by degeneration or fragmentation of the genetic components, suggested that cell death occurs via an apoptotic cascade. Furthermore, compounds and had a strong pro-apoptotic impact through inducing the intrinsic mitochondrial mechanism of apoptosis. This mechanistic route was verified by an ELISA experiment that indicated a considerable rise in the levels of p53 and Bax and a drop in the level of Bcl-2 when compared with the control.
Topics: Antineoplastic Agents; Apoptosis; Cell Line, Tumor; Cell Proliferation; Drug Screening Assays, Antitumor; Furans; Structure-Activity Relationship
PubMed: 35458804
DOI: 10.3390/molecules27082606