Merging total synthesis and NMR technology for deciphering the realistic structure of natural 2,6-dideoxyglycosides.

The structural identification and efficient synthesis of bioactive 2,6-dideoxyglycosides are daunting challenges. Here, we report the total synthesis and structural revision of a series of 2,6-dideoxyglycosides from folk medicinal plants Ecdysanthera rosea and Chonemorpha megacalyx, which feature pregnane steroidal aglycones bearing an 18,20-lactone and glycans consisting of 2,6-dideoxy-3-O-methyl-ß-pyranose residues, including ecdysosides A, B, and F and ecdysantheroside A. All the eight possible 2,6-dideoxy-3-O-methyl-ß-pyranoside stereoisomers (of the proposed ecdysantheroside A) have been synthesized that testify the effective gold(I)-catalyzed glycosylation methods for the synthesis of various 2-deoxy-ß-pyranosidic linkages and lays a foundation via nuclear magnetic resonance data mapping to identify these sugar units which occur promiscuously in the present and other natural glycosides. Moreover, some synthetic natural compounds and their isomers have shown promising anticancer, immunosuppressive, anti-inflammatory, and anti-Zika virus activities.

Construction of tea tree oil/salicylic acid/palygorskite hybrids for advanced antibacterial and anti-inflammatory performance.

This study describes the construction of a tailor-made clay-based hybrid with advanced dermocompatibility, antibacterial and anti-inflammatory performance by incorporating tunable ratios of tea tree oil (TTO) and salicylic acid (SA) into the naturally occurring porous structure of palygorskite (Pal). Among the three TTO/SA/Pal (TSP) systems constructed, TSP-1 with a TTO : SA ratio of 1 : 3 demonstrated the lowest 3T3 NRU predicted acute oral toxicity and dermal HaCaT cytotoxicity as well as the most pronounced antibacterial activity with a selective inhibitory action against the pathogens (E. coli, P. acnes and S. aureus) over the beneficial (S. epdermidis) species inhabiting on the human skin. Also noticeable is that exposure of these skin commensal bacteria to TSP-1 prevented the antimicrobial resistance evolution compared to the conventional antibiotic ciprofloxacin. Mechanistic investigation of its antibacterial modes of action revealed a synergy between the TTO and SA loadings on the Pal supports in reactive oxygen production, causing oxidative damage to bacterial cell membranes and increased leakage of intracellular compounds. Additionally, TSP-1 significantly decreased the proinflammatory cytokines of IL-1ß, IL-6, IL-8, and TNF-α in a bacterial lipopolysaccharide-stimulated differentiated THP-1 macrophage model, showing the potential to inhibit inflammatory responses in bacterial infections. Overall, this is the first report exploring the potential of constructing clay-based organic-inorganic hybrids as alternatives to antibiotics to combat bacterial resistance with advanced compatibility and anti-inflammatory benefits that are desired for the development of topically applied biopharmaceuticals.

Fibrous palygorskite clays as versatile nanocarriers for skin delivery of tea tree oils in efficient acne therapy.

This paper presents a facile approach to develop palygorskite (Pal), a fibrous clay mineral, as a delivery system of tea tree oil (TTO) for topical acne therapy. The obtained TTO-Pal composite showed an efficient loading of TTO (27.4%) with a selective accumulation of terpine-4-ol and 1,8-cineole (two major antimicrobial TTO constituents), sustained release of TTO at skin physiological conditions (pH5.4, 32 °C) and superior skin sebum (2.2 g/g) absorbability. In vitro toxicological assessments showed that the Pal incorporation strategy significantly reduced the acute contact toxicity of TTO. The antimicrobial results revealed a preferable bacteriostatic effect for the TTO-Pal system towards opportunistic dermal pathogens (Escherichia coli, Staphylococcus aureus and Propionibacterium acnes) over the beneficial bacterium (Staphylococcus epidermis). Moreover, TTO-Pal based formulations exhibited pronounced clinical therapeutic efficacy in treating facial acne by rapidly reducing inflamed lesions, modulating skin sebum overproduction and restoring barrier function. This is the first report of using fibrous clay as a biocompatible nanocarrier system for topical delivery of essential oils in efficient management of facial acne with both in vitro and in vivo evidences, which may open perspectives for fibrous clay-drug delivery system in topical application and expand the high added value development of this mineral resource in the advanced healthcare fields.

Diatomite encapsulated AgNPs as novel hair dye cosmetics: Preparation, performance, and toxicity.

Naturally-occurring diatomite has been successfully utilised as a unique encapsulating material to obtain a highly dispersed suspension of uniformly-sized silver nanoparticles (AgNPs). Plant derived gallic acid was used as the reducing and capping agent. High-resolution scanning and transmission electron microscopy results confirmed the attachment of AgNPs on the surface of diatom frustule and maintained an excellent dispersion stability against particle aggregation. The AgNPs obtained were employed for the colouration of bleached human hair owing to the local surface plasmonic absorption (LSPR) of the AgNPs. The effects of Ag/diatomite concentration, dyeing pH, temperature and time on the produced colour were investigated. Hair fibres treated under optimised conditions display good colour fastness toward solar radiation. The morphology and chemical composition of AgNP-dyed hair were determined by energy-dispersive spectroscopy, X-ray photoelectron spectroscopy and Fourier transform infrared spectroscopy analyses. The biocompatibility of the Ag/diatomite composite, AgNPs, and the dyebaths were confirmed by in vitro acute dermal and ocular toxicity tests. The diatomite supporting AgNPs therefore hold good promise and enormous potential to be exploited for sustainable dyeing of human hair.