Abstract
Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.
Highlights
Tradescantia albiflora Kunth (Commelinaceae) is native to tropical rainforests
Previous research described the inhibitory activity against xanthine oxidase (XO), which plays a central role in metabolic disorders such as hyperuricemia and gout, of the methanol extract and compounds isolated from the leaves of
Phytochemical investigation of the whole plants of T. albiflora Kunth led to the isolation and characterization of three new compounds and 25 known compounds, which were identified by comparison with literature spectroscopic data and determined as 4-(3’,4’-dihydroxyphenyl)furan-2(5H)- one (3) [3], bracteanolide A (4) [2], bracteanolide B (5) [2], methyl 3,4-dihydroxybenzoate (6) [4], hydroxytyrosol
Summary
Tradescantia albiflora Kunth (Commelinaceae) is native to tropical rainforests. It has been used as a traditional medicine for treating hyperuricemia and gout in Taiwan. Previous research described the inhibitory activity against xanthine oxidase (XO), which plays a central role in metabolic disorders such as hyperuricemia and gout, of the methanol extract and compounds isolated from the leaves of. The butenolide bracteanolide A (4) was the most abundant compound among the isolates, and it has been reported to show inhibitory ability against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. This inhibition was associated with its selective suppression on inducible NO synthase (iNOS) induction [2], indicating its potential to Molecules 2019, 24, 3336; doi:10.3390/molecules24183336 www.mdpi.com/journal/molecules
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