A structure and an absolute configuration of (+)-alternamin, a new coumarin from Murraya alternans having antidote activity against snake venom |
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Authors: | Hla Myoe Min Tohru Taniguchi Kenji Monde Toshiaki Nikai Yoshiaki Takaya |
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Institution: | a Department of Chemistry, University of Mandalay, Mandalay, Myanmar b Graduate School of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University, N-21, W-11, Sapporo 001-0021, Japan c Faculty of Pharmacy, Meijo University, Yagotoyama, Tempaku, Nagoya 468-8503, Japan |
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Abstract: | (+)-Alternamin (1), a new dihydrofuranocoumarin, was isolated from the aerial parts of Murraya alternans (Kurz) Swingle. The analysis 2-D NMR correlation of (+)-1 led to either of linear dihydrofuranocoumarin (2A, 2C) or angular one (2B). An IR and a vibrational circular dichroism (VCD) studies were conducted to distinguish the structure and to assign the absolute configuration. By comparison of the observed spectra with the calculated spectra for (S)-2A, (S)-2B, and (R)-2C, the molecular structure of (+)-1 was determined to be (S)-(+)-5,8-dimethoxymarmesin. The compound exhibited antidote activity against snake venom from Trimeresurus flavoviridis, affording experimental support for the pharmacological use of M. alternans. |
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Keywords: | Dihydrofuranocoumarin Antidote activity Snake venom Vibrational circular dichroism (VCD) Murraya alternans |
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