Novel synthesis of oxa[9]helicenes by Lawesson’s reagent-mediated cyclization of helical quinone derivatives

New oxa[9]helicenes which possess one furan ring have been readily prepared by reactive helical quinone with Lawesson’s reagent or phosphorus pentasulfide in good yields. The versatility of this protocol has been demonstrated with various substituted helical quinones.     

Virtual Screening for Potential Phytobioactives as Therapeutic Leads to Inhibit NQO1 for Selective Anticancer Therapy

NAD(P)H:quinone acceptor oxidoreductase-1 (NQO1) is a ubiquitous flavin adenine dinucleotide-dependent flavoprotein that promotes obligatory two-electron reductions of quinones, quinonimines, nitroaromatics, and azo dyes. NQO1 is a multifunctional antioxidant enzyme whose expression and deletion are linked to reduced and increased oxidative stress susceptibilities. NQO1 acts as both a tumor suppressor and tumor promoter; thus, the inhibition of NQO1 results in less tumor burden. In addition, the high expression of NQO1 is associated with a shorter survival time of cancer patients. Inhibiting NQO1 also enables certain anticancer agents to evade the detoxification process. In this study, a series of phytobioactives were screened based on their chemical classes such as coumarins, flavonoids, and triterpenoids for their action on NQO1. The in silico evaluations were conducted using PyRx virtual screening tools, where the flavone compound, Orientin showed a better binding affinity score of −8.18 when compared with standard inhibitor Dicumarol with favorable ADME properties. An MD simulation study found that the Orientin binding to NQO1 away from the substrate-binding site induces a potential conformational change in the substrate-binding site, thereby inhibiting substrate accessibility towards the FAD-binding domain. Furthermore, with this computational approach we are offering a scope for validation of the new therapeutic components for their in vitro and in vivo efficacy against NQO1.     

Optimization Method for Phenolic Compounds Extraction from Medicinal Plant (Juniperus procera) and Phytochemicals Screening

Juniperus procera is a natural source of bioactive compounds with the potential of antitumor, antimicrobial, insecticidal, antifungal, and antioxidant activities. An optimization method was developed for total phenolic content (TPC), total flavonoid content (TFC), and total tannin content (TTC) in leaf and seed extract of Juniperus procera. Organic solvents (methanol (99.8%), ethanol (99%), and acetone (99.5%)), and deionized water (DI) were used for extraction. The estimation of TPC, TFC, and TTC in plant materials was carried out using UV-spectrophotometer and HPLC with the standards gallic acid, quercetin, and tannic acid. Recovery of TPC in leaf extract ranged from 2.9 to 9.7 mg GAE/g DW, TFC from 0.9 to 5.9 mg QE/g DW, and TTC ranged from 1.5 to 4.3 mg TA/g DW while the TPC value in the seed extract ranged from 0.53 to 2.6 mg GAE/g DW, TFC from 0.5 to 1.6 mg QE/g DW, and TTC ranged from 0.5 to 1.4 mg TA/g DW. This result revealed that methanol is the best solvent for recovery of the TPC value (9.7 mg) from leaf extract in comparison to other solvents. Ethanol recorded the highest result of TFC (5.9 mg) in leaf extract among the solvents whereas acetone was the best for TTC yield recovery from leaf extract (4.3 mg). In the case of the seed extract, ethanol was the best solvent for both TPC (2.6 mg), and TFC (1.6 mg) recovery in comparison to other solvents. Total tannin content in methanol resulted in significant recovery from seed extract (1.4 mg). Separation and quantification of gallic acid, quercetin, and tannic acid in plant materials were undertaken using HPLC. Gallic acid in leaf and seed of J. procera ranged from 6.6 to 9.2, 6.5 to 7.2 µg/g DW, quercetin from 6.3 to 18.2, 0.9 to 4.2 µg/g DW, and tannic acid from 16.2 to 29.3, 6.6 to 9.3 µg/g DW, respectively. Solvents have shown a significant effect in the extraction of phenolic compounds. Moreover, phytochemicals in plant materials were identified using GC-MS and resulted in very important bioactive compounds, which include anti-inflammatory, antibacterial, and antitumor agents such as ferruginol, phenanthrene, and n-hexadecanoic acid. In conclusion, the optimal solvent for extraction depends on the part of the plant material and the compounds that are to be isolated.     

Molecular Networking and Cultivation Profiling Reveals Diverse Natural Product Classes from an Australian Soil-Derived Fungus Aspergillus sp. CMB-MRF324

This study showcases the application of an integrated workflow of molecular networking chemical profiling (GNPS), together with miniaturized microbioreactor cultivation profiling (MATRIX) to successfully detect, dereplicate, prioritize, optimize the production, isolate, characterize, and identify a diverse selection of new chemically labile natural products from the Queensland sheep pasture soil-derived fungus Aspergillus sp. CMB-MRF324. More specifically, we report the new tryptamine enamino tripeptide aspergillamides E–F (7–8), dihydroquinoline-2-one aflaquinolones H–I (11–12), and prenylated phenylbutyrolactone aspulvinone Y (14), along with an array of known co-metabolites, including asterriquinones SU5228 (9) and CT5 (10), terrecyclic acid A (13), and aspulvinones N-CR (15), B (16), D (17), and H (18). Structure elucidation was achieved by a combination of detailed spectroscopic and chemical analysis, biosynthetic considerations, and in the case of 11, an X-ray crystallographic analysis.     

Ultrasound irradiation in heterocycle synthesis: An overview

The synthesis of heterocyclic compounds has been a hot topic for several decades. Synthetic organic chemists are always in search of new methodologies which are greener for the synthesis of heterocyclic compounds. The ultrasound-assisted reactions have contributed much to this field. This review focuses on the impact of sonochemistry in the synthesis of heterocyclic compounds and covers the literature from 2009 to 2020.     

Cubosome particles of a novel Guerbet branched chain glycolipid

Cubic liquid crystalline nanoparticles (cubosomes) of bicontinuous nature with internal networks of water channels have received great interests in nanomedicine applications, particularly as potential vehicle for loading and release of therapeutic agents. These nanoparticles have been most commonly produced using monoolein and phytantriol. In this study, we explore the use of a Guerbet branched chain glycolipid, namely 2-hexyl-decyl-β-D glucopyranoside (β-Glc?OC₁₀C₆), as a new and alternative material for cubosomes production. The fully hydrated glycolipid assumes a reverse bicontinuous cubic liquid crystal phase of an Ia3d space group with lattice parameter of ca. 74 Å, as confirmed using a small-angle X-ray scattering. Dynamic light scattering and a conventional transmission electron microscopy were used to investigate the average size and morphology of the cubosomes. The effectiveness of Poloxamer 407 (stabiliser typically used in other cubosome systems against aggregations and particle coalescence) in providing steric stabilisation of the glycolipid cubosomes was assessed through visual assessment.     

Crystal structures of bis(4-dimethylaminopyridinium) tetrachlorocobaltate(II) and bis-[1,3-di (ammoniummethyl)benzene]tetrachlorocobaltate(II)

The crystal structures consist of organoammonium cations hydrogen bonded to tetrahedral CoCl₄ ^2– anions. In the 4-dimethylaminopyridinium salt, [(CH₃)₂NC₅H₅NH]₂CoCl₄, pairs of cations hydrogen bond in an asymmetric fashion to two of the chlorines in each anion. The planar cations form two sets of – stacks, first parallel to the a axis and the second parallel to the b axis. The anions lie between these two nonintersecting sets of stacks. In contrast, for the second compound, [C₆H₄(CH₂NH₃)₂]CoCl₄, the tetrahedral CoCl₄ ^2– anions form layers lying parallel to the bc plane. The 1,3-di(ammoniummethyl)benzene cations crosslink adjacent anionic layers, forming a lamellar structure of alternating organic and inorganic layers.