Ambrosia trifida, known worldwide as an invasive species, threatens agriculture and ecosystems and causes severe allergic reactions in humans. As part of the effort to valorize this harmful plant, a phytochemical investigation of A. trifida led to the isolation of one new guaiane sesquiterpenoid (1S,7R,10R)-10,11-dihydroxy-4-guaien-3-one (1), together with two diastereomers (2 and 3). Their structures were elucidated using various spectroscopic methods, including NMR, HRMS, optical rotation, and ECD calculations. (1S,7R,10R)-11-Hydroxy-4-guaien-3-one (2) was isolated for the first time from nature. Its (1R,7R,10S)-diastereomer (3) has not been previously reported in the Compositae family. Based on network pharmacology and molecular docking analyses, the effects of 1-3 on inflammatory bowel disease (IBD) were examined. Among the isolates, only 2 exhibited anti-inflammatory and tight junction regulatory activities by targeting the JAK2/STAT3 signaling pathway in Caco-2 cells. In contrast, its diastereomer 3 was inactive, indicating that the stereochemical configuration at C-1 and C-10 plays a critical role in biological activity. This study suggests that guaiane sesquiterpenoids may be useful for the treatment of IBD, and the findings serve as a basis for a wide range of applications of this invasive plant as a useful resource.
Park et al. (Tue,) studied this question.
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