Design and synthesis of bis(indolyl)-hydrazide-hydrazone derivatives and their antifungal activities against plant pathogen fungi.

A series of bis(indolyl)-hydrazide-hydrazone derivatives were synthesised, and their structures were characterised using 1H-NMR and HRMS. The antifungal activity of the prepared compounds was evaluated against Pyricularia oryzae Cav., Colletotrichum -gloeosporioides Penz., Botrytis cinerea Pers.: Fr. and Rhizoctonia solani Kühn using the mycelial growth rate method. The preliminary bioassays revealed that most of the synthesised compounds exhibited antifungal activity against the four tested fungi and displayed a remarkable inhibitory effect on the mycelium growth of R. solani. In particular, compounds 3b, 3c, and 3k demonstrated significant antifungal activity against R. solani, with EC50 values of 26.42, 20.74, and 22.41 µM, respectively, outperforming the positive control shenqinmycin (47.18 µM) and carvacrol (49.13 µM).

Novel Perbutyrylated Glucose Derivatives of (-)-Epigallocatechin-3-Gallate Inhibit Cancer Cells Proliferation by Decreasing Phosphorylation of the EGFR: Synthesis, Cytotoxicity, and Molecular Docking.

Lung cancer is one of the most commonly occurring cancer mortality worldwide. The epidermal growth factor receptor (EGFR) plays an important role in cellular functions and has become the new promising target. Natural products and their derivatives with various structures, unique biological activities, and specific selectivity have served as lead compounds for EGFR. D-glucose and EGCG were used as starting materials. A series of glucoside derivatives of EGCG (7-12) were synthesized and evaluated for their in vitro anticancer activity against five human cancer cell lines, including HL-60, SMMC-7721, A-549, MCF-7, and SW480. In addition, we investigated the structure-activity relationship and physicochemical property-activity relationship of EGCG derivatives. Compounds 11 and 12 showed better growth inhibition than others in four cancer cell lines (HL-60, SMMC-7721, A-549, and MCF), with IC50 values in the range of 22.90-37.87 µM. Compounds 11 and 12 decreased phosphorylation of EGFR and downstream signaling protein, which also have more hydrophobic interactions than EGCG by docking study. The most active compounds 11 and 12, both having perbutyrylated glucose residue, we found that perbutyrylation of the glucose residue leads to increased cytotoxic activity and suggested that their potential as anticancer agents for further development.

Chemical composition and antifungal activity of essential oil from Origanum vulgare against Botrytis cinerea.

In this study, the chemical composition of the essential oil (EO) of Origanum vulgare was characterized, and the antifungal activity of the EO and some individual components against Botrytis cinerea (Y-BC-1) was determined. Twenty-one components were identified by gas chromatography-mass spectrometry and gas chromatography-flame ionization detection, constituting 95.7% of the EO. The major components were methyleugenol (16.5%), myristicin (15.6%), carvacrol (15.0%), thymol (9.8%), apioline (9.4%), and (Z)-ß-farnesene (8.7%). B. cinerea in vitro mycelial growth and spore germination were strongly inhibited by the EO and two of its main components, thymol and carvacrol. In vivo vapor contact assays, the antifungal activity of the EO at 250 mg/L suppressed the decay of cherry tomatoes 96.39%. Moreover, thymol and carvacrol at 125 mg/L completely suppressed the gray mold. Thus, the EO of O. vulgare is a potentially nontoxic and ecofriendly botanical fungicide for postharvest control of gray mold.

Inhibitory activities of flavonoids from Eupatorium adenophorum against acetylcholinesterase.

Fifteen flavonoids isolated from the Eupatorium adenophorum showed inhibitory activities against acetylcholinesterase (AChE) isolated from Caenorhabditis elegans and Spodoptera litura. Their IC50 values ranged from 12.54 to 89.06µg/mL and 12.08 to 86.01µg/mL, respectively against the AChE isolated from the nematode and insect species. AChE was inhibited in a dose-dependent manner by all tested flavonoids, The isolated compound quercetagetin-7-O-(6-O-caffeoyl-ß-D-glucopyranoside) displayed the highest inhibitory effect against AChE from C. elegans and S. litura, with IC50 values of 12.54 µg/mL and 12.58 µg/mL, respectively. The structure-activity relationship of flavonoids on the inhibitory activities indicated that additional phenolic hydroxyl groups in the glucose were favorable for their inhibitory effects and the degree of increase in inhibitory activity also depended on the number of phenolic hydroxyl groups. The Lineweaver-Burk and Dixon plots indicated that quercetagetin-7-O-(6-O-caffeoyl-ß-d-glucopyranoside) is a reversible inhibitor against AChE. Quercetagetin-7-O-(6-O-caffeoyl-ß-d-glucopyranoside), 5,4'-Dihydroxytlavone and quercetin-3-O-ß-d-glucopyranoside inhibited AChE in a mixed-type competitive manner and these compounds might be the dual binding site AChE inhibitors. Further, nine compounds showed poisonous effects against C. elegans and inhibitory effects on the growth and development of S. litura.

[Chemical composition and allelopathic potential of essential oil isolated from Origanum vulgare]. / ç‰›è‡³æŒ¥å‘æ²¹çš„åŒ–å­¦æˆåˆ†åŠå ¶åŒ–æ„Ÿä½œç”¨.

This study aimed to explore the chemical composition of essential oil isolated from Origanum vulgare and investigated its allelopathic potential. The essential oil isolated by hydro-distillation from the whole plant of O. vulgare was analyzed by GC and GC-MS. Fourteen different components were identified, constituting 93.56% of the total area of peaks. The major components were methyleugenol (16.5%), myristicin (15.6%), carvacrol (15.0%), thymol (9.8%), and apioline (9.4%). We examined the inhibitory effects of essential oil on seed germination and seedling growth of wheat (Triticum aestivum), mung bean (Vigna radiata), and radish (Raphanus sativus). The results showed that essential oil of O. vulgare inhibited seed germination of all tested crops, with wheat being the most susceptible, followed by radish and mung bean. The inhibitory effects of essential oil on growth of the aboveground part of tested crops were greater than that of underground part. The inhibitory effects of essential oil on the seedling length of all tested crops increased in a dose-dependent manner, with the same pattern for radicle length of wheat and radish as well. Meanwhile, essential oil could stimulate radicle growth of V. radiata at low concentration, but inhibit the growth at high concentration. Our results confirmed the existence of allelochemicals in the essential oil of O. vulgare. However, what the compounds will be and how about their allelopathic mechanism needs further investigation.

Antifungal activity of phenolic monoterpenes and structure-related compounds against plant pathogenic fungi.

The aim of this work is to explore the possibility of using the phenolic monoterpenes (PMs) as leading compounds with antifungal activity against plant disease. The in vitro antifungal activities of carvacrol and thymol against seven kinds of plant pathogenic fungi were evaluated on mycelium growth rate method, and the results showed that carvacrol and thymol exhibited broad spectrum antifungal activity. Structure requirement for the antifungal activity of PMs was also investigated. The preliminary conclusion was that phenolic hydroxyl and monoterpene were basic structures for the antifungal activity of PMs, and the position of phenolic hydroxyl showed less effect. Ester derivatives of carvacrol and thymol were more effective than carvacrol and thymol against plant pathogenic fungi. We suggested that carvacrol, thymol and their ester derivatives could potentially be used as new fungicide leading compounds.

Synthesis and antifungal activity of carvacrol and thymol esters with heteroaromatic carboxylic acids.

Aiming to obtain the more effective pathogen inhibitive ingredients and explore the influence of introducing different heterocyclic units to carvacrol and thymol esters, twenty ester derivatives with different heterocyclic units were synthesized. And the in vitro antifungal activity of title compounds against five plant pathogenic fungi was evaluated by mycelium growth rate method. The results showed that some carvacrol and thymol esters showed good to excellent antifungal activity, and compound 9d (4-bromo-5-isopropyl-2-methylphenyl picolinate) exhibited a broad antifungal spectrum. Preliminary study indicated that the introduction of furan, thiophene and pyridine unit could enhance the antifungal activity of carvacrol and thymol esters against Botrytis cinerea and a bromine atom on the para position of benzene moiety could enhance their antifungal activity.

Novel Competitive Fluorescence Sensing Platform for L-carnitine Based on Cationic Pillar[5]Arene Modified Gold Nanoparticles.

Supramolecular host-guest interaction and sensing between cationic pillar[5]arenes (CP5) and L-carnitine were developed by the competitive host-guest recognition for the first time. The fluorescence sensing platform was constructed by CP5 functionalized Au nanoparticles (CP5@Au-NPs) as receptor and probe (rhodamine 123, R123), which shown high sensitivity and selectivity for L-carnitine detection. Due to the negative charge and molecular size properties of L-carnitine, it can be highly captured by the CP5 via electrostatic interactions and hydrophobic interactions. The host-guest mechanism between PP5 and L-carnitine was studied by ¹H NMR and molecular docking, indicating that more affinity binding force of CP5 with L-carnitine. Therefore, a selective and sensitive fluorescent method was developed. It has a linear response of 0.1⁻2.0 and 2.0⁻25.0 µM and a detection limit of 0.067 µM (S/N = 3). The fluorescent sensing platform was also used to detect L-carnitine in human serum and milk samples, which provided potential applications for the detection of drugs abuse and had path for guarding a serious food safety issues.

Liquid crystalline 2-thienyl-4,6-diamino-1,3,5-triazines exhibiting Im3[combining macron]m and Pm3[combining macron]n micellar cubic phases in an inverted sequence.

Two micellar cubic phases with different structures were observed for the first time in the order Im3[combining macron]m-Pm3[combining macron]n in a thermotropic phase sequence of 4,6-diaminotriazine terminated rod-like liquid crystals upon increasing alkyl chain length or rising temperature.