title: Erinacerins C-L, isoindolin-1-ones with α-glucosidase inhibitory activity from cultures of the medicinal mushroom Hericium erinaceus.
abstract: The well-known edible and medicinal mushroom Hericium erinaceus produces various bioactive secondary metabolites. Ten new isoindolin-1-ones, named erinacerins C-L (1-10), together with (E)-5-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one (11) were isolated from the solid culture of H. erinaceus. The structures of new metabolites were established by spectroscopic methods. The absolute configurations of 3, 4, 9, and 10 were assigned by comparing their specific rotations with those of related phthalimidines (13-20). Compounds 5 and 6, 7 and 8, and 9 and 10 are double-bond positional isomers. In a α-glucosidase inhibition assay, compounds 2-11 showed inhibitory activity with IC50 values ranging from 5.3 to 145.1 μM. Preliminary structure-activity analysis indicated that the terpenoid side chain and the phenolic hydroxy groups contributed greatly to the α-glucosidase inhibitory activity of 1-11. In a cytotoxicity assay, compound 11 also presented weak cytotoxicity against two cell lines, A549 and HeLa, with IC50 values of 49.0 and 40.5 μM.
authors.affiliation: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences , No. 1 Beichenxi Road, Chaoyang District, Beijing 100101, People's Republic of China.
authors.forename: Kai
authors.initials: K
authors.lastname: Wang
authors.forename: Li
authors.initials: L
authors.lastname: Bao
authors.forename: Qiuyue
authors.initials: Q
authors.lastname: Qi
authors.forename: Feng
authors.initials: F
authors.lastname: Zhao
authors.forename: Ke
authors.initials: K
authors.lastname: Ma
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Pei
authors.forename: Hongwei
authors.initials: H
authors.lastname: Liu
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D065089:Glycoside Hydrolase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006367:HeLa Cells; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D054833:Isoindoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000187:drug effects*
chemical_list: C000595948:(E)-5-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-6-methoxy-2-phenethylisoindolin-1-one; D000970:Antineoplastic Agents; D065089:Glycoside Hydrolase Inhibitors; D006575:Heterocyclic Compounds, 3-Ring; D054833:Isoindoles; C505044:erinacerin A; D000520:alpha-Glucosidases