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DOI: 10.1055/a-1953-0479
Acrotrione B, a Prenylated and Highly Oxidized Xanthenoid with Antibacterial and Anti-proliferative Activities from the Roots of Acronychia pedunculata
Supported by: the Science Achievement Scholarship of Thailand (SAST)Supported by: Khon Kaen University
Supported by: the National Research Council of Thailand (NRCT) NRCT5-TRG63003-01
Supported by: the Center of Excellence for Innovation in Chemistry (PERCH−CIC)
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Abstract
A new prenylated xanthenoid with a highly oxidized core, acrotrione B (1), together with six previously reported acetophenones (2 – 7), were isolated from the roots of Acronychia pedunculata. The structures of the isolated compounds were elucidated by thorough analysis of their 1D and 2D NMR spectroscopic data. The relative and absolute configurations of acrotrione B were determined by electronic circular dichroism (ECD) calculations. Acrotrione B is an unusual, oxidized xanthenoid with a cyclohexadienone core that has not been previously reported. It thus represents a new skeletal type within the xanthenoid class. Acrotrione B (1) exhibited anti-proliferative activity against Hela (IC50 = 16.0 µM) and A549 (IC50 = 16.3 µM) cell lines. 5′-Prenylacrovestone (4) and acrovestone (5) were even more potent with IC50 values of 5.1 µM and 0.77 µM, respectively, against Hela cells and 11.8 µM and 1.13 µM, respectively, against A549 cells. Moreover, acrotrione B (1) displayed moderate antibacterial activities against Staphylococcus aureus, Bacillus cereus, and Bacillus subtilis, with MIC values in the range of 16 – 64 µg/mL. Finally, acropyrone (6) showed a significant suppression of lipopolysaccharide (LPS) induced NO production in murine macrophage J774.A1 cells (IC50 = 8.9 µM).
Key words
Acronychia pedunculata - Rutaceae - xanthene - anti-inflammatory activity - anti-proliferative activity - antibacterial activitySupporting Information
- Supporting Information
MS, IR, UV, CD, and 1D and 2D NMR spectra of compound 1 and detailed calculation of electronic circular dichroism spectra are available as Supporting Information. Copies of the original spectra are obtainable from the corresponding author.
Publication History
Received: 26 May 2022
Accepted after revision: 09 September 2022
Article published online:
27 October 2022
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