Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale
- PMID: 35268622
- PMCID: PMC8912040
- DOI: 10.3390/molecules27051521
Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale
Abstract
The roots of Melastoma malabathricum subsp. normale (D. Don) Karst. Mey have been used in traditional ethnic medicine systems in China to treat inflammation-triggered ailments, such as trauma, toothache, and fever. Therefore, the aim of this study is to screen for compounds with anti-inflammatory activity in the title plant. The extract of M. malabathricum subsp. normale roots was separated using various chromatographic methods, such as silica gel, ODS C18, MCI gel, and Sephadex LH-20 column chromatography, as well as semi-preparative HPLC. One new complex tannin, named whiskey tannin D (1), and an undescribed tetracyclic depsidone derivative, named guanxidone B (2), along with nine known polyphenols (2-10) and three known depsidone derivatives (12-14) were obtained from this plant. The structures of all compounds were elucidated by extensive NMR and CD experiments in conjunction with HR-ESI-MS data. All these compounds were isolated from this plant for the first time. Moreover, compounds 1-4, 8, and 10-14 were obtained for the first time from the genus Melastoma, and compounds 1, 2, and 11-14 have not been reported from the family Melastomataceae. This is the first report of complex tannin and depsidone derivatives from M. malabathricum subsp. normale, indicating their chemotaxonomic significance to this plant. Compounds 1-12 were investigated for their anti-inflammatory activities on the production of the nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells, and compounds 1, 11, and 12 showed anti-inflammatory activities with IC50 values of 6.46 ± 0.23 µM, 8.02 ± 0.35 µM, and 9.82 ± 0.43 µM, respectively. The structure-activity relationship showed that the catechin at glucose C-1 in ellagitannin was the key to its anti-inflammatory activity, while CH3O- at C-16 of aromatic ring A in depsidone derivatives had little effect on its anti-inflammatory activity. The study of structure-activity relationships is helpful to quickly discover new anti-inflammatory drugs. The successful isolation and structure identification of these compounds, especially complex tannin 1, not only provide materials for the screening of anti-inflammatory compounds, but also provide a basis for the study of chemical taxonomy of the genus Melastoma.
Keywords: Melastoma; Melastoma malabathricum subsp. normale (D. Don) Karst. Mey; anti-inflammatory; complex tannin; depsidone derivatives; polyphenols.
Conflict of interest statement
The authors declare no conflict of interest.
Figures
Similar articles
-
Structural Characterization and Assessment of Anti-Inflammatory and Anti-Tyrosinase Activities of Polyphenols from Melastoma normale.Molecules. 2021 Jun 26;26(13):3913. doi: 10.3390/molecules26133913. Molecules. 2021. PMID: 34206838 Free PMC article.
-
A new depsidone derivative from mangrove endophytic fungus Aspergillus sp. GXNU-A9.Nat Prod Res. 2022 Apr;36(7):1878-1882. doi: 10.1080/14786419.2020.1809400. Epub 2020 Aug 27. Nat Prod Res. 2022. PMID: 32851874
-
Antioxidant and Cytotoxicity Activities of Karamunting (Melastoma malabathricum L.) Fruit Ethanolic Extract and Quercetin.Asian Pac J Cancer Prev. 2019 Feb 26;20(2):639-643. doi: 10.31557/APJCP.2019.20.2.639. Asian Pac J Cancer Prev. 2019. PMID: 30806071 Free PMC article.
-
Antinociception of petroleum ether fraction derived from crude methanol extract of Melastoma malabathricum leaves and its possible mechanisms of action in animal models.BMC Complement Altern Med. 2016 Nov 29;16(1):488. doi: 10.1186/s12906-016-1478-1. BMC Complement Altern Med. 2016. PMID: 27899097 Free PMC article.
-
Antinociceptive, anti-inflammatory and antipyretic properties of Melastoma malabathricum leaves aqueous extract in experimental animals.Can J Physiol Pharmacol. 2006 Dec;84(12):1291-9. doi: 10.1139/y06-083. Can J Physiol Pharmacol. 2006. PMID: 17487238
Cited by
-
Curdepsidone A Induces Intrinsic Apoptosis and Inhibits Protective Autophagy via the ROS/PI3K/AKT Signaling Pathway in HeLa Cells.Mar Drugs. 2024 May 17;22(5):227. doi: 10.3390/md22050227. Mar Drugs. 2024. PMID: 38786619 Free PMC article.
-
Recent advances on natural depsidones: sources, biosynthesis, structure-activity relationship, and bioactivities.PeerJ. 2023 May 12;11:e15394. doi: 10.7717/peerj.15394. eCollection 2023. PeerJ. 2023. PMID: 37197584 Free PMC article.
References
-
- Editorial Committee of the Flora of China of Chinese Academy of Sciences . Flora Reipublicae Popularis Sinicae. 1st ed. Volume 53. Science Press; Beijing, China: 1984. pp. 154–155.
-
- Yao L.L., Liu X.Y. Advances on investigation of chemical constituents, pharmacological activities and clinical applications of Melastoma. J. Jiangxi Univ. Tradit. Chin. Med. 2010;22:52–55.
-
- Deng Z.D., Cheng A.F., Li X.L. Study on the extraction and agglutination of lectin from Melastoma dodecandrum Lour. Heilongjiang Agric. Sci. 2015;68:7654–7658.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources