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Planta Med 2023; 89(04): 416-422
DOI: 10.1055/a-1953-0479
Biological and Pharmacological Activity
Original Papers

Acrotrione B, a Prenylated and Highly Oxidized Xanthenoid with Antibacterial and Anti-proliferative Activities from the Roots of Acronychia pedunculata

Awat Wisetsai
1   Department of Chemistry, Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
2   Department of Industrial Chemistry, Faculty of Applied Science, King Mongkutʼs University of Technology North Bangkok, Bangkok, Thailand
,
Ratsami Lekphrom
1   Department of Chemistry, Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Thanapat Suebrasri
3   Faculty of Medicine, Department of Microbiology, Khon Kaen University, Khon Kaen, Thailand
4   Faculty of Medical Science, Nakhonratchasima College, Nakhonratchasima, Thailand
,
Sarawut Tontapha
5   Institute of Nanomaterials Research and Innovation for Energy, Khon Kaen University, Khon Kaen, Thailand
,
Thanaset Senawong
6   Department of Biochemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Khanitha Pudhom
7   Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand
,
Siwattra Choodej
7   Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand
,
Florian T. Schevenels 
1   Department of Chemistry, Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
› Author AffiliationsSupported 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 activity

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.

  • Supporting Information


Publication History

Received: 26 May 2022

Accepted after revision: 09 September 2022

Article published online:
27 October 2022

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