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

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).

Antioxidant, Cytotoxic, Anti‐Glycation, and Anti‐Tyrosinase Compounds from the Leaves of Uvaria Siamensis

“…Several of these compounds exhibited cytotoxicity. [10][11][12] As part of our ongoing research to discover new bioactive constituents derived from natural sources, [13][14][15][16] we have chosen to investigate the secondary metabolites present in the leaves of U. siamensis. We hereby present the separation, purification, and identification of the secondary metabolites obtained from the leaves of this plant.…”

Passifetilactones A–E, Fatty Acid Lactones from the Fruit and Flowers of Passiflora foetida with Cytotoxic Activity

“…In continuation of our efforts to identify new bioactive natural products from plants growing in Thailand, − we decided to investigate the fruit and the flowers of P . foetida .…”