10.1016/0223-5234(92)90148-T
The research focuses on the synthesis and antihepatotoxicity evaluation of Wuweizisu analogues. The purpose of the study is to develop new liver-protective agents by synthesizing and testing the efficacy of certain chemical compounds derived from Schisandra sinensis (Wuweizi), a traditional Chinese medicine known for its various pharmacological properties, especially its antihepatotoxic effects. The researchers synthesized a series of compounds, including dimethyl 4,4’-dimethoxy-5,6,5’,6’-dimethylenedioxybiphenyl-2,2’-dicarboxylate (VII) and 6-phenyl-3,9-dimethoxy-1,2-methylenedioxy-10,11-methylenedioxy-6,7-dihydro-5H-dibenz(c,e)azepin (X), using key chemicals such as gallic acid, dimethyl sulfate, bromine, aniline, and lithium aluminum hydride. The synthesized compounds were tested for their ability to protect against carbon tetrachloride-induced liver damage in primary cultured rat hepatocytes. The results showed that compound X exhibited superior antihepatotoxic activity compared to the known protective agents DDB and silymarin. This suggests that the synthesized compounds, particularly those with a dibenzoazepin structure, could serve as potential new liver-protective agents, offering a novel route for the development of such pharmaceuticals.
10.1021/jm060087k
The research investigates the antidiabetic properties of penta-O-galloyl-D-glucopyranose (PGG) and its analogues. The study explores the structure-activity relationship of PGG's R- and α-anomers, which act as insulin mimetics, stimulating glucose transport in adipocytes and reducing blood glucose and insulin levels in diabetic and obese animals. The researchers synthesized and tested various novel compounds, finding that both the glucose core and the galloyl groups are crucial for activity. The galloyl groups linked to positions 1, 2, 3, and 4 of glucose are essential, while the one at position 6 is not. Notably, 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl-R-D-glucopyranose (80) exhibited significantly higher glucose transport stimulatory activity than PGG, comparable to insulin. Key chemicals used in the research include PGG, gallic acid, methyl galloate, ellagic acid, and various derivatives of glucose and galloyl groups. The study provides insights into the development of new antidiabetic therapeutics that can address both hyperglycemia and adiposity.
10.1021/ma902762z
The research investigates the conformation and chiroptical properties of poly(dithienopyrrole)s (PDTPs) substituted with oligo(phenylenevinylene) (OPV) side chains, aiming to understand how the substitution of the OPV moiety influences these features. The study used various chemicals including gallic acid moieties to promote the formation of a helical conformation in poor solvents. The polymers were prepared by Stille-couplings and characterized by GPC, NMR, UV-vis, CD, and emission spectroscopy. The study found that OPV-PDTPs with chiral alkyl groups at the terminal gallic acid group tend to adopt a helical conformation but show no chiral expression. Additional substitution allows for discrimination of helical senses, enabling the OPV side chains to be chirally organized by the helical PDTP backbone. However, substitution in the R-position of the OPV sterically excludes helical conformation, resulting in a lamellar supramolecular structure in poor solvents. The research concludes that the conformation and chiroptical properties of PDTPs can be significantly influenced by the substitution of the OPV side chains, and the OPV side chains can contribute significantly to the optical properties of the material.
10.1016/0008-6215(87)80115-5
Heinz Schildknecht and Rainer Milde details the synthesis of the first Periodic Leaf Movement Factor (PLMF 1) and its 14C-carboxyl-labeled analog. PLMF 1, 4-O-(?-D-glucopyranosyl-6-sulfate)gallic acid, is a chemonastic compound that affects the sensitive plant Mimosa pudica L. The synthesis involved a Koenigs-Knorr reaction of a D-glucose derivative with a suitably blocked gallic acid to produce 4-O-?-D-glucopyranosylgallic acid, followed by regioselective sulfation with sulfur trioxide-pyridine to obtain PLMF 1. The 14C-labeled analog was synthesized via regioselective glucosylation of methyl [carboxy-14C]galloate with 2,3,4,6-tetra-D-acetyl-a-D-glucopyranosyl bromide and subsequent sulfation. The study confirmed the structure and biological activity of PLMF 1 through synthesis, providing a foundation for future physiological and biosynthetic studies.
10.1016/j.bmc.2020.115596
This research aimed to design, synthesize, and evaluate the inhibitory activities of amide derivatives of gallic acid (GA) against in vitro α-synuclein aggregation, which is implicated in neurodegenerative diseases like Parkinson's. The study hypothesized that modifying GA's structure could enhance its lipophilicity and improve its ability to cross the blood-brain barrier, making it a more effective inhibitor of α-synuclein aggregation. A series of amide derivatives were synthesized, featuring sheet-like conjugated structures and suitable LogP values, which are crucial for crossing the blood-brain barrier. The biological evaluation showed that some of these derivatives exhibited better anti-aggregation activities than GA itself, with IC50 values as low as 0.98 μM.