Prenylated flavonoids, a unique class of flavonoids which combine a flavonoid skeleton and a lipophilic prenyl side-chain, possess great potential biological activities including cytotoxicity, ...anti-inflammation, anti-Alzheimer, anti-microbial, anti-oxidant, anti-diabetes, estrogenic, vasorelaxant and enzyme inhibition. Recently, prenylated flavonoids have become an indispensable anchor for the development of new therapeutic agents, and have received increasing from medicinal chemists. The prenylated flavonoids have been outstanding developed through isolation, semi or fully synthesis in a very short period of time, which proves the great value in medicinal chemistry researches. In this review, research progress of prenylated flavonoids including natural prenylated flavonoids, structural modification, synthetic methodologies and pharmacological activities was summarized comprehensively. Furthermore, the structure–activity relationships (SARs) of prenylated flavonoids were summarized which provided a basis for the selective design and optimization of multifunctional prenylated flavonoid derivatives for the treatment of multi-factorial diseases in clinic.
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•This article provides over 500 natural and synthetic prenylated flavonoids from 2000 to 2021.•The diverse activities and structure–activity relationships of prenylated flavonoids are summarized.•The synthetic methodologies of prenylated flavonoids are summarized.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
Inorganic cesium lead halide perovskites offer a pathway towards thermally stable photovoltaics. However, moisture‐induced phase degradation restricts the application of hole transport layers (HTLs) ...with hygroscopic dopants. Dopant‐free HTLs fail to realize efficient photovoltaics due to severe electrical loss. Herein, we developed an electrical loss management strategy by manipulating poly(3‐hexylthiophene) with a small molecule, i.e., SMe‐TATPyr. The developed P3HT/SMe‐TATPyr HTL shows a three‐time increase of carrier mobility owing to breaking the long‐range ordering of “edge‐on” P3HT and inducing the formation of “face‐on” clusters, over 50 % decrease of the perovskite surface defect density, and a reduced voltage loss at the perovskite/HTL interface because of favorable energy level alignment. The CsPbI2Br perovskite solar cell demonstrates a record‐high efficiency of 16.93 % for dopant‐free HTL, and superior moisture and thermal stability by maintaining 96 % efficiency at low‐humidity condition (10–25 % R. H.) for 1500 hours and over 95 % efficiency after annealing at 85 °C for 1000 hours.
An electrical loss management strategy by using SMe‐TATPyr molecule manipulating dopant‐free Poly(3‐hexylthiophene) (P3HT) has been developed and employed to fabricate efficient and thermally stable CsPbI2Br solar cells. The P3HT/SMe‐TATPyr presents optimized molecular orientation, favorable energy level alignment and effective defect passivation. Based on P3HT/SMe‐TATPyr HTLs, the fabricated devices yield a record‐high efficiency of 16.93 % for CsPbI2Br solar cells with dopant‐free HTLs.
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BFBNIB, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
A readily available small molecular hole‐transporting material (HTM), OMe‐TATPyr, was synthesized and tested in perovskite solar cells (PSCs). OMe‐TATPyr is a two‐dimensional π‐conjugated molecule ...with a pyrene core and four phenyl‐thiophene bridged triarylamine groups. It can be readily synthesized in gram scale with a low lab cost of around US$ 50 g−1. The incorporation of the phenyl‐thiophene units in OMe‐TATPyr are beneficial for not only carrier transportation through improved charge delocalization and intermolecular stacking, but also potential trap passivation via Pb–S interaction as supported by depth‐profiling XPS, photoluminescence, and electrochemical impedance analysis. As a result, an impressive best power conversion efficiency (PCE) of up to 20.6 % and an average PCE of 20.0 % with good stability has been achieved for mixed‐cation PSCs with OMe‐TATPyr with an area of 0.09 cm2. A device with an area of 1.08 cm2 based on OMe‐TATPyr demonstrates a PCE of 17.3 %.
A 2D hole‐transporting material with a pyrene core and four phenyl‐thiophene bridged triarylamine groups, OMe‐TATPyr, was readily synthesized at low cost on a gram scale. A power conversion efficiency (PCE) of up to 20.6 % (average PCE 20.0 %) was achieved for mixed‐cation perovskite solar cells with OMe‐TATPyr, outperforming devices with Spiro‐OMeTAD.
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BFBNIB, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
Understanding the nature of quantum chromodynamics (QCD) matter is important but challenging due to the presence of non-perturbative dynamics under extreme conditions. We construct a holographic ...model describing the gluon sector of QCD at finite temperatures in the non-perturbative regime. The equation of state as a function of temperature is in good accordance with the lattice QCD data. Moreover, the Polyakov loop and the gluon condensation, which are proper order parameters to capture the deconfinement phase transition, also agree quantitatively well with the lattice QCD data. We obtain a strong first-order confinement/deconfinement phase transition at
T
c
= 276.5 MeV that is consistent with the lattice QCD prediction. Based on our model for a pure gluon hidden sector, we compute the stochastic gravitational waves and primordial black hole (PBH) productions from this confinement/deconfinement phase transition in the early Universe. The resulting stochastic gravitational-wave backgrounds are found to be within detectability in the International Pulsar Timing Array and Square Kilometre Array in the near future when the associated productions of PBHs saturate the current observational bounds on the PBH abundances from the LIGO-Virgo-Collaboration O3 data.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
Since the discovery of penicillin,
has become one of the most attractive fungal genera for the production of bioactive molecules. Marine-derived
has provided numerous excellent pharmaceutical leads ...over the past decades. In this review, we focused on the cytotoxic metabolites * (* Cytotoxic potency was referred to five different levels in this review, extraordinary (IC
/LD
: <1 μM or 0.5 μg/mL); significant (IC
/LD
: 1~10 μM or 0.5~5 μg/mL); moderate (IC
/LD
: 10~30 μM or 5~15 μg/mL); mild (IC
/LD
: 30~50 μM or 15~25 μg/mL); weak (IC
/LD
: 50~100 μM or 25~50 μg/mL). The comparative potencies of positive controls were referred when they were available). produced by marine-derived
species, and on their cytotoxicity mechanisms, biosyntheses, and chemical syntheses.
Daphne giraldii Nitsche., a member of the genus Daphne (Thymelaeaceae), is a deciduous shrub with mild toxicity. Its rhizome bark, generally called ‘Zushima’ in Chinese, has many medicinal folkloric ...uses and good therapeutic effects. Previous studies investigating the chemical constituents and pharmacological activities of D. giraldii have focused on several major classes of compounds, such as coumarins, lignans and flavonoids, especially the interesting enantiomeric flavans. Extracts and pure compounds of D. giraldii were found to possess anti-inflammatory, anti-nociceptive, cytotoxicity, antimalarial, immunomodulating, sedative and hypnotic effects. They have also been reported to influence the cardiovascular functions and blood activities. This comprehensive review will describe the advances in the phytochemistry, pharmacology, medicinal uses and clinical applications of D. giraldii and its formulations covering the literature published from 1970 to 2018. Almost half of the reviewed studies were originally published in non-English languages (mainly in Chinese). Collectively, the aim of this article is to open new avenues for further in-depth pharmacological studies on D. giraldii.
The medicinal uses, clinical application, phytochemistry and pharmacology of D. giraldii were reviewed. The main chemicals were coumarins and flavonoids with multiple prenyl substitutions. The structure-activity relationships (SAR) and mechanism of biological action were discussed. Display omitted
•This review summarizes the phytochemistry, pharmacology, medicinal uses and clinical application of D. giraldii.•The review expands the interest in the structure-activity relationships of flavones with multiple prenyl substitutions.•Biological activities and mechanism of both isolates and individual compounds are gathered and analyzed.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
Background: MicroRNAs (miRs) play a crucial role in inflammatory diseases, including periodontitis. Meanwhile, miRs act as biomarkers for predicting diabetes mellitus (DM). However, the regulatory ...mechanism of miR‐126 on development of periodontitis in patients with DM still remains unclear.
Methods: Human gingival fibroblasts were cultured with low (5.5 mmol/L), medium (15 mmol/L), and high (25 mmol/L) glucose, respectively. Expressions of miR‐126, tumor necrosis factor (TNF) receptor associated factor (TRAF) 6, and related cytokines were analyzed by real‐time polymerase chain reaction (PCR). After transfection with miR‐126 mimic, PCR and western blot were performed to detect level of TRAF6, and luciferase reporter assay confirmed if TRAF6 is the direct target of miR‐126. Production of cytokines was measured using enzyme‐linked immunosorbent assay.
Results: Increased glucose significantly suppressed miR‐126 expression in human gingival fibroblasts (P <0.05). Also, high glucose increased TRAF6, interleukin (IL)‐6, TNF‐α, and chemical chemokine ligand (CCL) 2 levels, whereas it decreased IL‐10 level. MiR‐126 mimic significantly decreased TRAF6 mRNA and protein levels under high glucose (P <0.05). Also, miR‐126 directly targeted TRAF6 through binding to its 3′ untranslated region in human gingival fibroblasts. Overexpression of miR‐126 significantly abrogated high glucose–induced secretion of proinflammatory cytokines such as IL‐6, TNF‐α, and CCL2 and promoted production of IL‐10.
Conclusion: These data suggest that miR‐126 inhibits inflammation of human gingival fibroblasts under high glucose through targeting TRAF6, which may be a potential therapeutic target for periodontitis concomitant with DM.
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BFBNIB, CMK, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
Hepatocellular carcinoma has been known as the most frequent subtype of liver cancer with a high rate of spread, metastases, and recurrence, also dismal treatment effects. However, effective ...therapies for HCC are still required. Nowadays, natural products have been known as a valuable source for drug discovery. In this research, 44 sesquiterpene lactones isolated from the Elephantopus scaber Linn. (Asteraceae) were tested by MTT assay for the antitumor activities. Deoxyelephantopin (DET) was found to exert significant cytotoxicity on HepG2 and Hep3B cells. Moreover, we found that DET treatment markedly reduced the growth of HCC cells in a concentration‐dependent manner, which was better than sorafenib. Furthermore, DET induced mitochondrial dysfunction, oxidative stress, and cellular apoptosis. Additionally, we found that DET and sorafenib synergistically induced apoptosis and mitochondrial dysfunction in HCC cells. DET combined with sorafenib was also efficacious in tumor xenograft model. Molecular docking experiments revealed that DET had a potentially high binding affinity with Hsp90α. Moreover, Drug Affinity Responsive Target Stability assay suggested that DET could directly target Hsp90α. Additionally, the expression of Hsp90α was both decreased in vitro and in vivo. Altogether, this study revealed that DET might be a promising agent for HCC therapy by targeting Hsp90α.
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BFBNIB, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
Red raspberry (Rubus idaeus L.) is an edible fruit-producing species belonging to the Rosaceae family. In our search for the health-promoting constituents from this fruit, four pairs of enantiomeric ...phenylpropanoids (1a/1b–4a/4b), including three new compounds (1a and 2a/2b), were isolated from red raspberry. Their structures were elucidated by a combination of the extensive NMR spectroscopic data analyses, high-resolution electrospray ionization mass spectrometry and comparison between the experimental measurements of electronic circular dichroism (ECD) and calculated ECD spectra by time-dependent density functional theory (TDDFT). In addition, their neuroprotective effects against H2O2-induced oxidative stress in human neuroblastoma SH-SY5Y cells were investigated, and the results showed enantioselectivity, in which that 3a exhibited noticeable neuroprotective activity, while its enatiomer 3b exhibited no obvious protective effect. Further study demonstrated that 3a could selectively inhibit the apoptosis induction and reactive oxygen species (ROS) accumulation by enhancing the activity of catalase (CAT) in H2O2-treated human neuroblastoma SH-SY5Y cells. These findings shed much light on a better understanding of the neuroprotective effects of these enantiomers and provide new insights into developing better treatment of neurodegenerative diseases in the future.
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IJS, KILJ, NUK, PNG, UL, UM, UPUK
Recently, ciquitins A and B isolated from the powdered and defatted airdried aerial parts of Leucophyllum ambiguum were reported as a mixture of conformers in a solution at room temperature. ...Considering the existence of a hemiacetal hydroxyl fragment in the ciquitins A and B, they are more likely to exist in the form of epimer rather than the mixture of conformers. To confirm this hypothesis, the NMR calculations of two epimers at C-9 (1-a and 1-b) were performed and the results matched well with experimental NMR data of mixtures (1). Moreover, a brief discussion on the reason for this hypothesis was also presented.
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BFBNIB, DOBA, GIS, IJS, IZUM, KILJ, KISLJ, NUK, PILJ, PNG, SAZU, UILJ, UKNU, UL, UM, UPUK
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