nach oben

Journal of Natural Medicines

Erschienen in:

26.07.2018 | Original Paper

Three new C-glycosyflavones with acetyl substitutions from Swertia mileensis

verfasst von: Xiaolong Liu, Yanhong Shi, Haijun Hu, Jia Li, Chunge Li, Li Yang, Zhengtao Wang

Erschienen in: Journal of Natural Medicines | Ausgabe 4/2018

Einloggen, um Zugang zu erhalten

Abstract

Three new acetylated C-glycosylflavones, 3″,6″-di-O-acetylswertiajaponin (1), 4″,6″-di-O-acetylswertiajaponin (2), and 6″-O-acetylswertiajaponin (3), together with six known compounds were isolated from the whole herb of Swertia mileensis. Their structures were elucidated on extensive NMR experiments and mass spectrometry studies. ¹H and ¹³C NMR data exhibited doublet signals at room temperature. Variable temperature ¹H NMR experiments were carried out to investigate the presence of rotational isomerism of C-glycosylflavones. All compounds showed potential antioxidant activities against apoptosis of H₂O₂-induced human embryo liver L02 cells.

Nur mit Berechtigung zugänglich

Li P, Leeuwenberg AJM, Middleton DJ (1995) Gentianaceae. In: Flora of China. Sci Press (Beijing), Miss Bot Garden (St Louis) vol. 16, p 115

Ho T, Liu S (2015) A worldwide monograph of Swertia and its allies. Science Press, Beijing

Chinese Pharmacopoeia Commission (2015) Pharmacopoeia of the People’s Republic of China. China Medical Science and Technology Press, Beijing, vol 1, p 196

Li YL, Shang MY, Chen JJ, Cai SQ (2013) Application of microscopy for discrimination of eight Swertia species utilized in the traditional Chinese medicine “Qingyedan”. Microsc Res Techn 76:296–310CrossRef

Li YL, Shang MY, Geng CA, Zhang XM, Chen JJ, Cai SQ (2013) Simultaneous determination of five constituents in eight Qingyedan species derived from Swertia plants by HPLC. China J Chinese Materia Medica 38:1394–1400

Brahmachari G, Mondal S, Gangopadhyay A, Gorai D, Mukhopadhyay B, Saha S, Brahmachari AK (2004) Swertia (Gentianaceae): chemical and pharmacological aspects. Chem Biodivers 1:1627–1651CrossRefPubMed

Reen RK, Karan M, Singh K, Karan V, Johri RK, Singh J (2001) Screening of various Swertia species extracts in primary monolayer cultures of rat hepatocytes against carbon tetrachloride- and paracetamol-induced toxicity. J Ethnopharmacol 75:239–247CrossRefPubMed

Davoust D, Massias M, Molho D (1980) ¹³C NMR investigation of flavonoid C-β-D-glucosides. Detection of a conformational equilibrium. Magn Reson Chem 13:218–219

Kato T, Morita Y (1990) C-Glycosylflavones with acetyl substitution from Rumex acetosa L. Chem Pharm Bull 38:2277–2280CrossRef

10.

Frank JH, Powdergeorge YL, Ramsewak RS, William FR (2012) Variable-temperature ¹H-NMR studies on two C-glycosylflavones. Molecules 17:7914–7926CrossRefPubMed

11.

Kikuzaki H, Kawasaki Y, Kitamura S, Nakatani N (1996) Secoiridoid glucosides from Swertia mileensis. Planta Med 62:35–38CrossRefPubMed

12.

Zhou GH, Wu HW, Wang T, Guo RX, Xu J, Zhang Q, Tang LY, Wang ZJ (2017) C-glycosylflavone with rotational isomers from Vaccaria hispanica (Miller) Rauschert seeds. Phytochem Lett 19:241–247CrossRef

13.

Rayyan S, Fossen T, Nateland HS, Andersen OM (2005) Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug ‘Crataegi folium cum flore’ (hawthorn). Phytochem Analysis 16:334–341CrossRef

14.

Camargo LMD, Férézou JP, Tinoco LW, Kaiser CR, Costa SS (2012) Flavonoids from Mimosa xanthocentra, (Leguminosae: Mimosoideae) and molecular modeling studies for isovitexin-2″-O-α-l-rhamnopyranoside rotamers. Phytochem Lett 5:427–431CrossRef

15.

Zhou GH, Wu HW, Wang T, Guo RX, Xu J, Zhang LY, Wang ZJ (2017) C-glycosylflavone with rotational isomers from Vaccaria hispanica (Miller) Rauschert seeds. Phytochem Lett 19:241–247CrossRef

16.

Pi H, Xu S, Zhang L, Li Y, Xie J, Tian L, He M, Lu Y, Li M, Zhang Y, Zhong M, Xiang Y, Deng L, Zhou Z, Yu Z (2013) Dynamin 1-like-dependent mitochondrial fission initiates overactive mitophagy in the hepatotoxicity of cadmium. Autophagy 9:1780–1800CrossRefPubMed

17.

Hu CF, Sun LP, Yang QH, Lu DX, Luo S (2016) Ginsenosides from stems and leaves of Ginseng prevent ethanol-induced lipid accumulation in human L02 hepatocytes. Chin J Integr Med 23:438–444CrossRefPubMed

18.

Battelli MG, Musiani S, Valgimigli M, Gramantieri L, Tomassoni F, Bolondi L, Stirpe F (2001) Serum xanthine oxidase in human liver disease. Am J Gastroenterol 96:1194–1199CrossRefPubMed

19.

Halliwell B, Whiteman M (2004) Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean? Br J Pharmacol 142:231–255CrossRefPubMedPubMedCentral

20.

Kamata H, Hirata H (1999) Redox regulation of cellular signalling. Cell Signal 11:1CrossRefPubMed

21.

Liu S, Luo R, Xiang Q, Xu X, Qiu L, Pang J (2015) Design and synthesis of novel Xyloketal derivatives and their protective activities against H₂O₂-induced HUVEC injury. Mar Drugs 13:948–973CrossRefPubMedPubMedCentral

22.

Oliveria EBD, Humeau C, Maia ER, Chebil L, Ronat E, Monard G, Ruiz-Lopez MF, Ghoul M, Engasser JM (2010) An approach based on density functional theory (DFT) calculations to assess the Candida antarctica lipase B selectivity in rutin, isoquercitrin and quercetin acetylation. J Mol Catal B-Enzym 66:325–331CrossRef

23.

Jaeschke H (2006) Mechanisms of liver injury. II. Mechanisms of neutrophil-induced liver cell injury during hepatic ischemia-reperfusion and other acute inflammatory conditions. Am J Physiol Gastrointest Liver Physiol 290:1083–1088CrossRef

Titel: Three new C-glycosyflavones with acetyl substitutions from Swertia mileensis
verfasst von: Xiaolong Liu
Yanhong Shi
Haijun Hu
Jia Li
Chunge Li
Li Yang
Zhengtao Wang
Publikationsdatum: 26.07.2018
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 4/2018
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-018-1225-7

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 4/2018

Genistein has the function of alleviating and treating disseminated intravascular coagulation caused by lipopolysaccharide

New podolactones from the seeds of Podocarpus nagi and their anti-inflammatory effect

Correction to: Naturally occurring cell adhesion inhibitors

Dandelion root extract protects NCM460 colonic cells and relieves experimental mouse colitis

Morin protects glucocorticoid-induced osteoporosis through regulating the mitogen-activated protein kinase signaling pathway

Use of a Caco-2 permeability assay to evaluate the effects of several Kampo medicines on the drug transporter P-glycoprotein