Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide Derivatives
Phytochemical investigation of the whole plant of <i>Tradescantia albiflora</i> Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (<b>1</b>), that was isolated from natural sources for the first time, a new butenolide, 5-<i>O</i>-acet...
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| Format: | Article |
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MDPI AG
2019-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/18/3336 |
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| author | Ping-Chen Tu Han-Chun Tseng Yu-Chia Liang Guan-Jhong Huang Te-Ling Lu Tzong-Fu Kuo Yueh-Hsiung Kuo |
| author_facet | Ping-Chen Tu Han-Chun Tseng Yu-Chia Liang Guan-Jhong Huang Te-Ling Lu Tzong-Fu Kuo Yueh-Hsiung Kuo |
| author_sort | Ping-Chen Tu |
| collection | DOAJ |
| description | Phytochemical investigation of the whole plant of <i>Tradescantia albiflora</i> Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (<b>1</b>), that was isolated from natural sources for the first time, a new butenolide, 5-<i>O</i>-acetyl bracteanolide A (<b>2</b>), and a new apocarotenoid, 2<i>β</i>-hydroxyisololiolide (<b>11</b>), together with 25 known compounds (compounds <b>3</b>−<b>10</b> and <b>12</b>−<b>28</b>). 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 <b>4a</b>−<b>4d</b> 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 <i>n</i>-butyl bracteanolide A (<b>4d</b>) showed enhanced NO inhibitory activity compared to the original compound, with an IC<sub>50</sub> value of 4.32 ± 0.09 μg/mL. |
| first_indexed | 2024-12-14T22:37:49Z |
| format | Article |
| id | doaj.art-33b15c007fe748f798c8bab39a7b9f5a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-14T22:37:49Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-33b15c007fe748f798c8bab39a7b9f5a2022-12-21T22:45:05ZengMDPI AGMolecules1420-30492019-09-012418333610.3390/molecules24183336molecules24183336Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide DerivativesPing-Chen Tu0Han-Chun Tseng1Yu-Chia Liang2Guan-Jhong Huang3Te-Ling Lu4Tzong-Fu Kuo5Yueh-Hsiung Kuo6The Ph.D. Program for Cancer Biology and Drug Discovery, China Medical University and Academia Sinica, Taichung 404, TaiwanDepartment of Chemistry, National Taiwan University, Taipei 106, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, TaiwanSchool of Pharmacy, China Medical University, Taichung 404, TaiwanDepartment of Post-Baccalaureate Veterinary Medicine, Asia University, Taichung 413, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, TaiwanPhytochemical investigation of the whole plant of <i>Tradescantia albiflora</i> Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (<b>1</b>), that was isolated from natural sources for the first time, a new butenolide, 5-<i>O</i>-acetyl bracteanolide A (<b>2</b>), and a new apocarotenoid, 2<i>β</i>-hydroxyisololiolide (<b>11</b>), together with 25 known compounds (compounds <b>3</b>−<b>10</b> and <b>12</b>−<b>28</b>). 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 <b>4a</b>−<b>4d</b> 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 <i>n</i>-butyl bracteanolide A (<b>4d</b>) showed enhanced NO inhibitory activity compared to the original compound, with an IC<sub>50</sub> value of 4.32 ± 0.09 μg/mL.https://www.mdpi.com/1420-3049/24/18/3336<i>Tradescantia albiflora</i>butenolidesanti-inflammatory activity |
| spellingShingle | Ping-Chen Tu Han-Chun Tseng Yu-Chia Liang Guan-Jhong Huang Te-Ling Lu Tzong-Fu Kuo Yueh-Hsiung Kuo Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide Derivatives Molecules <i>Tradescantia albiflora</i> butenolides anti-inflammatory activity |
| title | Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide Derivatives |
| title_full | Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide Derivatives |
| title_fullStr | Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide Derivatives |
| title_full_unstemmed | Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide Derivatives |
| title_short | Phytochemical Investigation of <i>Tradescantia Albiflora</i> and Anti-Inflammatory Butenolide Derivatives |
| title_sort | phytochemical investigation of i tradescantia albiflora i and anti inflammatory butenolide derivatives |
| topic | <i>Tradescantia albiflora</i> butenolides anti-inflammatory activity |
| url | https://www.mdpi.com/1420-3049/24/18/3336 |
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