Yun-chao Wang, Yu-wei Zhang, Li-hua Zheng
Feb 1, 2013
Citations
0
Influential Citations
9
Citations
Journal
Helvetica Chimica Acta
Abstract
Four compounds with similar structures and UV spectra were isolated from the fermentation broth of Armillaria mellea by means of preparative HPLC. Their structures were established as methyl (2S)-1- (2-(furan-2-yl)-2-oxoethyl)-5-oxopyrrolidine-2-carboxylate (1), (2S)-1-(2-(furan-2-yl)-2-oxoethyl)-5-oxo- pyrrolidine-2-carboxylic acid (2), 1-(2-(furan-2-yl)-2-oxoethyl)pyrrolidin-2-one (3) and 1-(2-(furan-2- yl)-2-oxoethyl)piperidin-2-one (4) on the basis of their 1D- and 2D-NMR, and HR-MS data. The absolute configurations of compounds 1 and 2 were determined by comparison of the experimental and calculated electronic circular dichroism (ECD) data. Additionally, four known compounds, 5 - 8, were also isolated. Introduction. - Armillaria mellea (Ticholomataceae) is a well-known edible and medicinal fungus, symbiotic with the famous Chinese medicinal herb Gastrodia elata (Orchidaceae). Its fruit bodies (calledZhenmoin Chinese) are widely used for the treatment of epilepsy, pain on haunch, and stroke in Chinese folk medicine. Studies have shown that the mycelium and broth from liquid fermentation of A. mellea had similar pharmacological activities as G. elata itself (1). As A. mellea can be mass- produced by industrial liquid fermentation, it has been used as an alternative to G. elata. In China, A. mellea is added to many formulations used clinically for the treatment of geriatric patients with palsy, dizziness, headache, neurasthenia, insomnia, numbness in limbs, and infantile convulsion (2). Many studies about the chemical constituents of A. mellea have been performed, and a range of compounds has been reported (2) (3). In this study, four new alkaloids with similar structures were isolated from the AcOEt extract of A. mellea fermentation broth using preparative HPLC. In addition, four known compounds were also isolated. Their structures were deduced from NMR and HR-MS data. The absolute configurations of the chiral compounds were determined by comparison of the experimental electronic circular dichroism (ECD) spectra with the quantum-theory calculated ones.