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

Awat Wisetsai; Ratsami Lekphrom; Thanapat Suebrasri; Sarawut Tontapha; Thanaset Senawong; Khanitha Pudhom; Siwattra Choodej; Florian T. Schevenels

doi:10.1055/a-1953-0479

Planta Medica, Inhaltsverzeichnis

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

¹Department of Chemistry, Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand

²Department of Industrial Chemistry, Faculty of Applied Science, King Mongkutʼs University of Technology North Bangkok, Bangkok, Thailand

,

Ratsami Lekphrom

¹Department of Chemistry, Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand

,

Thanapat Suebrasri

³Faculty of Medicine, Department of Microbiology, Khon Kaen University, Khon Kaen, Thailand

⁴Faculty of Medical Science, Nakhonratchasima College, Nakhonratchasima, Thailand

,

Sarawut Tontapha

⁵Institute of Nanomaterials Research and Innovation for Energy, Khon Kaen University, Khon Kaen, Thailand

,

Thanaset Senawong

⁶Department of Biochemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand

,

Khanitha Pudhom

⁷Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand

,

Siwattra Choodej

⁷Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand

,

Florian T. Schevenels

¹Department of Chemistry, Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand

› Institutsangaben

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

Volltext

Referenzen

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