Anti-Inflammatory and Antioxidant Components from Hygroryza aristata
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. DPPH Free-Radical Scavenging Activity
3.5. Preparation of Human Neutrophils
3.6. Measurement of Superoxide Anion (O2•−) Generation
4. Conclusions
Acknowledgements
References
- Hsu, C.C.; Kuoh, C.S.; Lin, W.C.; Liu, H.Y. Flora of Taiwan, 2nd ed.; Epoch Publishing Co., Ltd.: Taipei, Taiwan, 2000; Volume 5, pp. 320–321. [Google Scholar]
- Takara, K.; Matsui, D.; Wada, K.; Ichiba, T.; Chinen, I.; Nakasone, Y. New phenolic compounds from Kokuto, non-centrifuged cane sugar. Biosci. Biotechnol. Biochem. 2003, 67, 376–379. [Google Scholar] [CrossRef] [PubMed]
- Su, D.G.; Tang, W.Z.; Hu, Y.C.; Liu, Y.B.; Yu, S.S.; Ma, S.G.; Qu, J.; Yu, D.Q. Lignan glycosides from Neoalsomitra integrifoliola. J. Nat. Prod. 2008, 71, 784–788. [Google Scholar] [CrossRef] [PubMed]
- Ghosal, S.; Srivastava, R.S. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry 1973, 12, 193–197. [Google Scholar] [CrossRef]
- Ponchet, M.; Jean, F.B.; Hauteville, M.; Riccl, P. Dianthramides (N-benzoyl and N-paracoumarylanthranilic acid derivativies) from elicited tissues of Dianthus caryophyllus. Phytochemistry 1988, 27, 2725–2730. [Google Scholar] [CrossRef]
- Goetz, G.; Fkyerat, A.; Metais, N. Resistance factors to grey mould in grape berries: Identification of some phenolics inhibitors of Botrytis cinerea stilbene oxidase. Phytochemistry 1999, 52, 759–767. [Google Scholar] [CrossRef]
- Fan, W.; Tezuka, Y.; Kadota, S. Proly endopeptidase inhibitory activity of fourteen kampo formulas and inhibitory constituents of Tokaku-joki-to. Chem. Pharm. Bull. 2000, 48, 1055–1061. [Google Scholar] [CrossRef] [PubMed]
- Houck, D.R.; Hanners, J.L.; Unkefer, C.J. Biosynthesis of pyrroloquinoline quinine.1. Identification of biosynthetic precursors using 13C labeling and NMR spectroscopy. J. Am. Chem. Soc. 1988, 110, 6920–6921. [Google Scholar] [CrossRef]
- Liu, J.X.; Di, D.L.; Shi, Y.P. Diversity of chemical constituents from Saxifraga montana H. J. Chin. Chem. Soc. 2008, 55, 863–870. [Google Scholar] [CrossRef]
- Slimestad, R.; Andersen, M.; Francis, G.W.; Marston, A.; Hostettmann, K. Syringetin 3-O-(6"-acetyl)-β-glucopyranoside and other flavonols from needles of Norway spruce, Picea abies. Phytochemistry 1995, 40, 1537–1542. [Google Scholar] [CrossRef]
- Wu, T.S.; Leu, Y.L.; Chan, Y.Y. Aristolochic acids as a defensive substance for the Aristolochiaceous plant-feeding swallowtail butterfly, Pachliopta aristolochiae interpositus. J. Chin. Chem. Soc. 2000, 47, 221–226. [Google Scholar] [CrossRef]
- Kitajima, J.; Tanaka, T.; Ida, Y. Water-soluble constituents of fennel. IX. glucosides and nucleosides. Chem. Pharm. Bull. 1999, 47, 988–992. [Google Scholar] [CrossRef]
- Sako, M.; Kawada, H. A new and efficient synthetic method for 15N3-labeled cytosine nucleoside: dimroth rearrangement of cytidine N3-oxides. J. Org. Chem. 2004, 69, 8148–8150. [Google Scholar] [CrossRef] [PubMed]
- Lin, Y.L.; Wang, W.Y.; Kuo, Y.H.; Chen, C.F. Nonsteroidal constituents from Solanum incanum L. J. Chin. Chem. Soc. 2000, 47, 247–251. [Google Scholar] [CrossRef]
- Leu, Y.L.; Chan, Y.Y.; Hsu, M.Y.; Chen, I.S.; Wu, T.S. The constituents of the stem and roots of Aristolochia foveolata. J. Chin. Chem. Soc. 1998, 45, 539–541. [Google Scholar] [CrossRef]
- Kosuge, K.; Mitsunaga, K.; Koike, K.; Ohmoto, T. Studies on the constituents of Ailanthus integrifolia. Chem. Pharm. Bull. 1994, 29, 1669–1671. [Google Scholar] [CrossRef]
- Shen, C.C.; Syu, W.J.; Li, S.Y.; Lin, C.H.; Lee, G.H.; Sun, C.M. Antimicrobial activities of naphthazarins from Arnebia euchroma. J. Nat. Prod. 2002, 65, 1857–1862. [Google Scholar] [CrossRef] [PubMed]
- Chen, C.Y.; Chang, F.R.; Teng, C.M.; Wu, Y.C. Cheritamine, a new N-fatty acyl tryptamine and other constituents from the stems of Annona cherimola. J. Chin. Chem. Soc. 1999, 46, 77–86. [Google Scholar] [CrossRef]
- Wu, T.S.; Yeh, J.H.; Wu, P.L. The heartwood constituents of Tetradium glabrifolium. Phytochemistry 1995, 40, 121–124. [Google Scholar] [CrossRef]
- Lin, W.Y.; Kuo, Y.H.; Chang, Y.L.; Teng, C.M.; Wang, E.C.; Tsutomu, I.; Chen, I.S. Anti-platelet aggregation and chemical constituents from the rhizome of Gynura japonica. Planta Med. 2003, 69, 757–764. [Google Scholar] [PubMed]
- Wang, E.C.; Shih, M.H.; Liu, M.C.; Chen, M.T.; Lee, G.H. Studies on constituents of Saururus chinensis. Heterocycles 1996, 43, 969–975. [Google Scholar] [CrossRef]
- Lee, C.K.; Chang, M.H. The chemical constituents from the heartwood of Eucalyptus citriodora. J. Chin. Chem. Soc. 2000, 47, 555–560. [Google Scholar] [CrossRef]
- Wu, T.S.; Chang, F.C.; Wu, P.L.; Kaoh, C.S.; Chen, I.S. Constituents of Tetradium glabrifolium. J. Chin. Chem. Soc. 1995, 42, 929–934. [Google Scholar] [CrossRef]
- Susumu, K.; Toshiro, I.; Ken, Y.; Sakae, Y.; Michio, T. (+)-α-Viniferin an antiflammatory compound from Caragana chamlagu root. Chem. Pharm. Bull. 1990, 38, 432–435. [Google Scholar]
- Wolters, A.M.; Jayawickrama, D.A.; Larive, C.K.; Sweedler, J.V. Capillary isotachophoresis/NMR: Extension to trace impurity analysis and improved instrumental coupling. Anal. Chem. 2002, 74, 2306–2313. [Google Scholar] [CrossRef] [PubMed]
- Shimada, K.; Fujikawa, K.; Yahara, K.; Nakamura, T. Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion. J. Agric. Food Chem. 1992, 40, 945–948. [Google Scholar] [CrossRef]
- Hwang, T.L.; Su, Y.C.; Chang, H.L.; Leu, Y.L.; Chung, P.J.; Kuo, L.M.; Chang, Y.J. Suppression of superoxide anion and elastase release by C18 unsaturated fatty acids in human neutrophils. J. Lipid Res. 2009, 50, 1395–1408. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Samples of the compounds 1, 3-28 are available from the authors. |
Position | δC | δH |
---|---|---|
1 | 133.2 | |
2, 6 | 103.9 | 6.75 (2H, s) |
3, 5 | 148.3 | |
4 | 135.2 | |
7 | 83.6 | 5.10 (1H, d, J = 8.4 Hz) |
8 | 50.9 | 2.34 (1H, m) |
9a 9b | 68.6 | 3.62 (1H, m) 4.01 (1H, dd, J = 10.0, 4.8 Hz) |
1’ | 133.2 | |
2’, 6’ | 104.0 | 6.79 (2H, s) |
3’, 5’ | 148.4 | |
4’ | 135.3 | |
7’ | 83.3 | 5.01 (1H, d, J = 8.4 Hz) |
8’ | 53.5 | 2.46 (1H, m) |
9’a 9’b | 60.1 | 3.67 (1H, m) 3.74 (1H, dd, J = 11.6, 4.4 Hz) |
3, 5, 3’, 5’-OCH3 | 55.9 | 3.87 (12H, s) |
Xyl-1 | 104.3 | 4.23 (1H, d, J = 7.6 Hz) |
Xyl-2 | 73.9 | 3.20 (1H, m) |
Xyl-3 | 77.0 | 3.31 (1H, m) |
Xyl-4 | 70.2 | 3.48 (1H, m) |
Xyl-5 | 66.0 | 3.20 (1H, m) 3.84 (1H, dd, J = 6.4, 2.4 Hz) |
Position | δC | δH |
---|---|---|
2 | 123.5 | 7.09 (1H, d, J = 2.4 Hz) |
3 | 112.1 | |
4 | 112.0 | 7.19 (1H, d, J = 8.4 Hz) |
5 | 111.9 | 6.70 (1H, dd, J = 8.4, 2.0 Hz) |
6 | 151.1 | |
7 | 103.0 | 7.03 (1H, d, J = 2.0 Hz) |
8 | 132.0 | |
9 | 128.8 | |
1’ | 26.1 | 2.89 (2H, t, J = 7.6 Hz ) |
2’ | 40.2 | 3.59 (2H, dd, J = 13.6, 7.6 Hz) |
1” | 166.1 | |
2” | 119.4 | 7.48 (1H, d, J = 16.0 Hz) |
3” | 139.6 | 6.49 (1H, d, J = 16.0 Hz) |
4” | 127.3 | |
5”, 9” | 129.6 | 7.42 (2H, d, J = 8.4 Hz) |
6”, 8” | 116.1 | 6.85 (2H, d, J = 8.4 Hz) |
7” | 159.3 | |
1-NH | 7.74 (1H, br.s) | |
3’-NH | 7.30 (1H, br.s) | |
6-OH | 8.86 (1H, br.s) | |
7”-OH | 9.75 (1H, br.s) |
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Chung, Y.-M.; Lan, Y.-H.; Hwang, T.-L.; Leu, Y.-L. Anti-Inflammatory and Antioxidant Components from Hygroryza aristata. Molecules 2011, 16, 1917-1927. https://doi.org/10.3390/molecules16031917
Chung Y-M, Lan Y-H, Hwang T-L, Leu Y-L. Anti-Inflammatory and Antioxidant Components from Hygroryza aristata. Molecules. 2011; 16(3):1917-1927. https://doi.org/10.3390/molecules16031917
Chicago/Turabian StyleChung, Yu-Ming, Yu-Hsuan Lan, Tsong-Long Hwang, and Yann-Lii Leu. 2011. "Anti-Inflammatory and Antioxidant Components from Hygroryza aristata" Molecules 16, no. 3: 1917-1927. https://doi.org/10.3390/molecules16031917