Absolute Configuration and Biological Evaluation of Novel Triterpenes as Possible Anti-Inflammatory or Anti-Tumor Agents.

Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE

Original Publication: Basel, Switzerland : MDPI, c1995-

Antineoplastic Agents*/pharmacology ; Oleanolic Acid*/pharmacology ; Triterpenes*/chemistry ; Triterpenes*/pharmacology; Acetals ; Aldehydes ; Anti-Inflammatory Agents/chemistry ; Anti-Inflammatory Agents/pharmacology ; Lipopolysaccharides/pharmacology ; Molecular Structure

Two new compounds, ardisiapunine B ( 1 ) and ardisiapunine C ( 2 ), were isolated from Ardisia lindleyana D. Dietr. Their structures were examined using HR-ESI-MS, IR, (1D, 2D) NMR spectroscopic analyses, single-crystal X-ray diffraction, and ECD calculation. It was found that the two new compounds belong to unusual oleanane-type triterpenes, with compound 1 bearing an acetal unit and a C-13-C-18 double bond, and compound 2 bearing a C-28 aldehyde group and a C-18-C-19 double bond. The anti-inflammatory properties of compounds 1 and 2 were tested on NO production and cellular morphology using RAW264.7 cells, and their anti-tumor properties were tested on cytotoxic activities, cellular morphology, cell apoptosis, and cell cycle. The results showed that compound 1 exhibited a potent cytotoxicity against HepG2 cell lines with an IC 50 of 12.40 μM. Furthermore, it is possible that compound 1 inhibits cell proliferation by blocking the cell G2/M phase and promoting cell apoptosis. Compound 2 exhibited a potential anti-inflammatory activity by decreasing the production of NO in LPS-stimulated RAW264.7 cells. Comparative analysis of the structures of compounds 1 and 2 revealed that the acetal structure and double bond positions were the main differences between them, and these are presumed to be the main reasons for the extreme differences in their cytotoxicity and anti-inflammatory activities. From these new findings, two promising lead compounds were identified for the future development of potential anti-inflammatory or anti-tumor agents.

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Keywords: Ardisia lindleyana D. Dietr; absolute configurations; ardisiapunine B; ardisiapunine C; biological activity; single–crystal X–ray diffraction; triterpene

0 (Acetals)
0 (Aldehydes)
0 (Anti-Inflammatory Agents)
0 (Antineoplastic Agents)
0 (Lipopolysaccharides)
0 (Triterpenes)
6SMK8R7TGJ (Oleanolic Acid)

Date Created: 20221014 Date Completed: 20221017 Latest Revision: 20221019

20231215

PMC9572544

10.3390/molecules27196641

36235179