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Ceramicines M-P from Chisocheton ceramicus: isolation and structure-activity relationship study.
Alfarius Eko Nugroho1, Akiyo Hashimoto1, Chin-Piow Wong1
1Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-ku, Tokyo, 142-8501, Japan.
Journal of Natural Medicines
|August 20, 2017
Summary
Researchers explored new limonoids from Chisocheton ceramicus to find potent lipid droplet accumulation (LDA) inhibitors. New compounds 1-3 showed LDA inhibitory activity, with compound 3 demonstrating improved selectivity, highlighting the importance of a 7α-OH group.
Area of Science:
- Natural Product Chemistry
- Pharmacology
Background:
- Ceramicines are limonoids from Chisocheton ceramicus with diverse biological activities.
- Ceramicine B exhibits significant lipid droplet accumulation (LDA) inhibitory activity in pre-adipocytes.
Purpose of the Study:
- To isolate and characterize novel ceramicines from C. ceramicus.
- To evaluate the LDA inhibitory activity of new ceramicines and identify compounds with enhanced efficacy and selectivity compared to Ceramicine B.
Main Methods:
- Isolation and structural elucidation of four new ceramicines (1-4) using NMR and mass spectrometry.
- Evaluation of LDA inhibitory activity of compounds 1-4.
- Synthesis and evaluation of C-7 derivatives to assess substituent effects on activity.
Main Results:
- Four new ceramicines (1-4) were identified.
- Compounds 1-3 demonstrated LDA inhibitory activity.
- Compound 3 showed comparable activity to Ceramicine B but with improved selectivity.
- The presence of a 7α-OH group was confirmed as crucial for potent LDA inhibitory activity.
Conclusions:
- Novel ceramicines with LDA inhibitory properties were discovered.
- The 7α-OH group at C-7 is essential for optimal lipid droplet accumulation inhibition.
- Further investigation into C. ceramicus constituents may yield potent anti-obesity agents.
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