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.

[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.