Chiral resolution, absolute configuration, and bioactivity of a new racemic asarone derivative from the rhizome of Acorus tatarinowii. 2017

En Gao, and Fei-Fei Ren, and Jian Zou, and Yang Yu, and Hong-Xia Fan, and Zheng-Qun Zhou, and Guo-Dong Chen, and Rong-Rong He, and Xin-Sheng Yao, and Hao Gao
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, People's Republic of China.

A new asarone-derived racemate (1) was isolated from the rhizome of Acorus tatarinowii. The structure of 1 was established by comprehensive spectroscopic analyses, and it was successfully resolved by chiral HPLC, demonstrating that it is racemic. The absolute configurations of 1a [(-)-acortatarone A] and 1b [(+)-acortatarone A] were determined using quantum chemical calculations. Compounds 1a and 1b were the first cases of asarone derivatives with the 5,7-dialkyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one core. The α-glucosidase inhibitory and acetylcholinesterase (AChE) inhibitory activities of 1 were evaluated, and it exhibited α-glucosidase inhibitory activity with potency close to that of the positive control (acarbose).

UI MeSH Term Description Entries
D000081248 Allylbenzene Derivatives Compounds that include a single 1-phenyl-2-propene moiety in their structure. 1-Methyl-1-phenylethylene Derivatives,1-Phenyl-2-propene Derivatives,2-Propenylbenzene Derivatives,3-Ethenylmethylbenzene Derivatives,Allylbenzenes,Vinyl Toluene Derivatives
D000110 Acetylcholinesterase An enzyme that catalyzes the hydrolysis of ACETYLCHOLINE to CHOLINE and acetate. In the CNS, this enzyme plays a role in the function of peripheral neuromuscular junctions. EC 3.1.1.7. Acetylcholine Hydrolase,Acetylthiocholinesterase,Hydrolase, Acetylcholine
D000520 alpha-Glucosidases Enzymes that catalyze the exohydrolysis of 1,4-alpha-glucosidic linkages with release of alpha-glucose. Deficiency of alpha-1,4-glucosidase may cause GLYCOGEN STORAGE DISEASE TYPE II. Acid Maltase,Lysosomal alpha-Glucosidase,Maltase,Maltases,Maltase-Glucoamylase,Neutral Maltase,Neutral alpha-Glucosidase,alpha-Glucosidase,Lysosomal alpha Glucosidase,Maltase Glucoamylase,Neutral alpha Glucosidase,alpha Glucosidase,alpha Glucosidases,alpha-Glucosidase, Lysosomal,alpha-Glucosidase, Neutral
D000840 Anisoles A group of compounds that are derivatives of methoxybenzene and contain the general formula R-C7H7O. Methylphenyl Ethers,Ethers, Methylphenyl
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D027343 Rhizome Root-like underground horizontal stem of plants that produces shoots above and roots below. Distinguished from true roots which don't have buds and nodes. Similar to true roots in being underground and thickened by storage deposits. Rhizomes
D029023 Acorus A plant genus of the family ACORACEAE, order Arales, subclass Arecidae most notable for Acorus calamus L. root which contains asarone and has been used in TRADITIONAL MEDICINE. Calamus Root,Sedge, Sweet,Acorus calamus,Acorus gramineus,Flagroot,Sweet Flag,Sweetflag,Calamus Roots,Root, Calamus,Roots, Calamus,Sedges, Sweet,Sweet Sedge,Sweet Sedges
D065089 Glycoside Hydrolase Inhibitors Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. alpha-Glucosidase Inhibitor,alpha-Glucosidase Inhibitors,Intestinal alpha-Amylase Inhibitors,Pancreatic alpha-Amylase Inhibitors,alpha-Amylase Inhibitors, Pancreatic,Hydrolase Inhibitors, Glycoside,Inhibitor, alpha-Glucosidase,Inhibitors, Glycoside Hydrolase,Inhibitors, Intestinal alpha-Amylase,Inhibitors, Pancreatic alpha-Amylase,Inhibitors, alpha-Glucosidase,Intestinal alpha Amylase Inhibitors,Pancreatic alpha Amylase Inhibitors,alpha Amylase Inhibitors, Pancreatic,alpha Glucosidase Inhibitor,alpha Glucosidase Inhibitors,alpha-Amylase Inhibitors, Intestinal

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