Four new aspidosperma-type alkaloids, melosuavines J-M (1-4) were isolated from the leaves of Melodinus suaveolens. Their structures with absolute configurations were elucidated by extensive HRESIMS and NMR spectroscopic analysis, as well as ECD calculations and Mosher's method. Their cytotoxic activities against four human cancer cell lines were also evaluated.
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http://dx.doi.org/10.1016/j.fitote.2020.104588 | DOI Listing |
J Nat Med
June 2024
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-Ku, Tokyo, 142-8501, Japan.
A novel trimeric monoterpenoid indole alkaloid, vincarostine A (1) consisting of an aspidosperma-iboga-aspidosperma type skeleton, was isolated from the whole plant of Catharanthus roseus. The structure including absolute stereochemistry was elucidated on the basis of 2D NMR data and CD spectrum. Vincarostine A (1) showed anti-malarial activity.
View Article and Find Full Text PDFChemistry
May 2024
Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecular & Life Sciences (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081, HZ Amsterdam, The Netherlands.
We present an Ugi multicomponent approach to explore the chemical space around Aspidosperma-type monoterpene indole alkaloids. By variation of the isocyanide and carboxylic acid inputs we demonstrate the rapid generation of molecular diversity and the possibility to introduce handles for further modification. The key Ugi three-component reaction showed full diastereoselectivity towards the cis-fused ring system, which can be rationalized by DFT calculations that moreover indicate that the reaction proceeds via a Passerini-type hydrogen bonding mechanism.
View Article and Find Full Text PDFJ Nat Med
March 2024
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-Ku, Tokyo, 142-8501, Japan.
Redox Biol
April 2024
State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macau, China; Department of Food Science and Nutrition, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China; Research Centre for Chinese Medicine Innovation, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, China. Electronic address:
Neuroinflammation and oxidative stress play a crucial role in the pathogenesis of neurodegenerative diseases, including Alzheimer's disease. The triggering receptor expressed on myeloid cells 2 (TREM2), highly expressed by microglia in the central nervous system (CNS), can modulate neuroinflammatory responses. Currently, there are no approved drugs specifically targeting TREM2 for CNS diseases.
View Article and Find Full Text PDFBioorg Chem
November 2023
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address:
Four monoterpenoid indole alkaloid dimers (MIADs), axidimins A-D (1-4), which possesses unprecedented apidosperma-aspidosperma-type skeletons, along with twelve known MIAs were isolated from Melodinus axillaris. Their structures were established by comprehensive analysis of the HRESIMS, NMR, ECD calculation and DP4 + analysis. A possible biosynthetic pathway for axidimins A-D was proposed.
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