Synthetic and in vitro studies to indicate that the structure of the PTP1B inhibitor isolated from Acanthopanax senticosus requires reinvestigation

Publication date: October 2018Source: Phytochemistry Letters, Volume 27Author(s): Toshiro Noshita, Ryoya Onishi, Kaori Miura, Yoshitomo Hamada, Yuki Nishino, Hidekazu Ouchi, Akihiro TaiAbstractWe herein describe the syntheses of 3,5-dimethoxy-4-{2-methoxy-4-[(1E)-3-oxoprop-1-en-1-yl]phenoxy}benzaldehyde (1) (the proposed structure for the naturally occurring protein tyrosine phosphatase 1B (PTP1B) inhibitor isolated from Acanthopanax senticosus) and its three positional isomers 3, 4, and 5. The inhibitory activities of these four compounds against PTP1B were also investigated. Comparison of the spectral data for 1, 3, 4, and 5 with the data obtained for the PTP1B inhibitor isolated from A. senticosus revealed that the original structural assignment as compound 1 was incorrect. In addition, none of the above four compounds exhibited inhibitory activity against PTP1B. Based on these results, it is apparent the structure of the PTP1B inhibitor isolated from Acanthopanax senticosus requires reinvestigation.Graphical abstract

Source: Phytochemistry Letters - September 22, 2018 Category: Chemistry Source Type: research