RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000058.xml
PDF herunterladen
Planta Med 2019; 85(17): 1374-1382
DOI: 10.1055/a-1023-8940
DOI: 10.1055/a-1023-8940
Biological and Pharmacological Activity
Original Papers
Alkaloid Enantiomers from Isatis tinctoria with Neuroprotective Effects against H2O2-Induced SH-SY5Y Cell Injury
Authors
Gefördert durch: National Natural Science Foundation of China 81973462 Gefördert durch: China Postdoctoral Science Foundation 2016M593031 Gefördert durch: China Postdoctoral Science Foundation 2018T111135 Gefördert durch: Natural Science Foundation of Liaoning Province of China 2019-MS-303 Gefördert durch: Career Development Support Plan for Young, Middle-aged Teachers in Shenyang Pharmaceutical University ZQN2018006
Weitere Informationen
Publikationsverlauf
received 29. August 2019
revised 28. September 2019
accepted 06. Oktober 2019
Publikationsdatum:
04. November 2019 (online)
Abstract
Six pairs of alkaloid enantiomers including 11 new alkaloids (1a/1b–5a/5b, 6a) were isolated from the leaves of Isatis tinctoria. Their structures were established by extensive spectroscopic analyses. Enantiomers were separated successfully by chiral chromatographic column and the absolute configurations of all isolates were determined by comparison of experimental and calculated electronic circular dichroism spectra. The isolated alkaloids were evaluated for their neuroprotective activities against H2O2-induced cell injury in human neuroblastoma SH-SY5Y cells. The results showed that 5a/5b and 6a/6b exhibited potent neuroprotective activities at 50 µM compared with the H2O2-treated group.
Supporting Information
- Supporting Information (PDF)
NMR, HRESIMS, UV, ECD spectrum, chiral HPLC chromatograms, and further detailed experimental information are available as Supporting Information.
-
References
- 1 Jiangsu New Medical College. Dictionary of traditional Chinese medicine. Shanghai: Shanghai Science and Technology Publishing House; 1985: 1250-1252
- 2 Chang HN, Huang ST, Yeh YC, Wang HS, Wang TH, Wu YH, Pang JHS. Indigo naturalis and its component tryptanthrin exert anti-angiogenic effect by arresting cell cycle and inhibiting Akt and FAK signaling in human vascular endothelial cells. J Ethnopharmacol 2015; 174: 474-481
- 3 Chen MH, Gan LS, Lin S, Wang XL, Li L, Li YH, Zhu CG, Wang YN, Jiang BY, Jiang JD, Yang YC, Shi JG. Alkaloids from the root of Isatis indigotica . J Nat Prod 2012; 75: 1167-1176
- 4 Wu XY, Liu YH, Sheng WY, Sun J, Qin GW. Chemical constituents of Isatis indigotica . Planta Med 1997; 63: 55-57
- 5 Wu XY, Qin GW, Cheung KK, Cheng KF. New alkaloids from Isatis indigotica . Tetrahedron 1997; 53: 13323-13328
- 6 Wu YX, Zhang ZX, Hu H, Li DM, Qiu GF, Hu XM, He XJ. Novel indole-glycosides from Isatis indigotica and their potential cytotoxic activity. Fitoterapia 2011; 82: 288-292
- 7 He LW, Li X, Chen JW, Sun DD, Ju WZ, Wang KC. Chemical constituents from water extract of Radix isatidis . Acta Pharm Sin 2006; 41: 1193-1196
- 8 Zuo L, Li JB, Xu J, Yang JZ, Zhang DM, Tong YL. Studies on chemical constituents in root of Isatis indigotica . China J Chin Mater Med 2007; 32: 688-691
- 9 Liu JF, Zhang XM, Xue DQ, Jiang ZY, Qiong GU, Chen JJ. Studies on chemical constituents from leaves of Isatis indigotica . China J Chin Mater Med 2006; 31: 1961-1965
- 10 Sun DD, Dong WW. Isolation, structural determination and cytotoxic activity of two new ceramides from the root of Isatis indigotica . Sci China Chem 2009; 52: 621-625
- 11 Li B, Chen WS, Yang GJ, Zhang WD, Qiao CZ. Organic acids of tetraploid Isatis indigotica . Acad J Second Mil Med Univ 2000; 21: 207-208
- 12 Liu HL, Wu LJ, Li H, Wang J. Study on the chemical constituents of Isatis indigotica Fort. J Shenyang Pharm Univ 2002; 19: 93-95
- 13 Hsuan SL, Chang SC, Wang SY, Liao TL, Jong TT, Chien MS, Lee WC, Chen SS, Liao JW. The cytotoxicity to leukemia cells and antiviral effects of Isatis indigotica extracts on pseudorabies virus. J Ethnopharmacol 2009; 123: 61-67
- 14 Ho YL, Chang YS. Studies on the antinociceptive, anti-inflammatory and anti pyretic effects of Isatis indigotica root. Phytomedicine 2002; 9: 419-424
- 15 Liu SF, Zhang YY, Zhou L, Lin B, Huang XX, Wang XB, Song SJ. Alkaloids with neuroprotective effects from the leaves of Isatis indigotica collected in the Anhui Province, China. Phytochemistry 2018; 149: 132-139
- 16 Huang S, Meng N, Liu ZM, Guo L, Dong LS, Li B, Ye Q. Neuroprotective Effects of Taraxacum officinale Wigg. Extract on Glutamate-Induced Oxidative Stress in HT22 Cells via HO-1/Nrf2 Pathways. Nutrients 2018; 10: 926-937
- 17 Sherer TB, Betarbet R, Stout AK, Lund S, Baptista M, Panov AV, Cookson MR, Greenamyre JT. An in vitro model of Parkinsonʼs disease: linking mitochondrial impairment to altered α-synuclein metabolism and oxidative damage. J Neurosci 2002; 22: 7006-7015
- 18 Finefield JM, Sherman DH, Kreitman M, Williams RM. Enantiomeric natural products: occurrence and biogenesis. Angew Chem Int Ed Engl 2012; 51: 4802-4836
- 19 Liu HJ, Xia YL, Cai WD, Zhang YN, Zhang XQ, Du ST. Enantioselective oxidative stress and oxidative damage caused by Rac- and S-metolachlor to Scenedesmus obliquus . Chemosphere 2017; 173: 22-30
- 20 Zhang WJ, Cheng C, Chen L, Di SS, Liu CX, Diao JL, Zhou ZQ. Enantioselective toxic effects of cyproconazole enantiomers against Chlorella pyrenoidosa . Chemosphere 2016; 159: 50-57
- 21 Liu SF, Lin B, Xi YF, Zhou L, Lou LL, Huang XX, Wang XB, Song SJ. Bioactive spiropyrrolizidine oxindole alkaloid enantiomers from Isatis indigotica Fortune. Org Biomol Chem 2018; 16: 9430-9439
- 22 Xi YF, Zhou L, Bai M, Wang J, Lin B, Wang XB, Huang XX, Song SJ. N-acylanthranilic acid derivatives with anti-Aβ 1–42 aggregation activity from the leaves of Isatis indigotica Fortune. Fitoterapia 2018; 128: 169-174
- 23 Xi YF, Liu SF, Hong W, Song XY, Lou LL, Zhou L, Yao GD, Lin B, Wang XB, Huang XX, Song SJ. Discovery of cycloneolignan enantiomers from Isatis indigotica Fortune with neuroprotective effects against MPP+-induced SH-SY5Y cell injury. Bioorg Chem 2019; 88: 102926-102931
- 24 Chen BC, Zhou P, Davis FA, Ciganek E. α-Hydroxylation of Enolates and Silyl Enol Ethers. Org React 2003; 62: 1-356
- 25 Kafka S, Proisl K, Kašpárková V, Urankar D, Kimmel R, Košmrlj J. Oxidative ring opening of 3-hydroxyquinoline-2, 4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids. Tetrahedron 2013; 69: 10826-10835
- 26 Stadlbauer W, Lutschounig H, Schindler G, Witoszynskyj T, Kappe T. Synthesis of 3-nitro- and 3-aminoquinoline-2, 4-diones. An unexpected route to 3-hydroxyquinoline-2, 4-diones. J Heterocycl Chem 1992; 29: 1535-1540
- 27 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich A, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 09, A.01 ed. Wallingford: Gaussian, Inc.; 2016
- 28 Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 2013; 25: 243-249