Skip to main content
Erschienen in: Journal of Natural Medicines 3/2018

26.02.2018 | Note

Two flavonol glycosides from Liparis bootanensis

verfasst von: Shuai Huang, Run Wu, Feng Gao, Chunying Li, Xianli Zhou

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2018

Einloggen, um Zugang zu erhalten

Abstract

Two new flavonol glycosides, bootanenside I and II (1 and 2), along with ten known compounds (312), were isolated from whole plant of Liparis bootanensis Griff. Their structures were elucidated on the basis of extensive spectroscopic analyses, including high-resolution electrospray-ionization mass spectrometry (HR–ESIMS) and one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR). The cytotoxicity of the compounds was investigated against HCT116 human cancer cell line, revealing that none of them possessed considerable cytotoxic activity. Bioassays of the new metabolites showed that compounds 1 and 2 displayed moderate in vitro antiinflammatory activity by inhibiting expression of inducible nitric oxide synthase (iNOS) protein in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.
Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Chen SC, Ormerod P, Wood JJ (2009) Orchidaceae. In: Wu ZY, Raven PH, Hong DY (eds) Flora of China, Vol 25. Science Press, Beijing, and Missouri Botanical Garden Press, St., pp 211–228 Chen SC, Ormerod P, Wood JJ (2009) Orchidaceae. In: Wu ZY, Raven PH, Hong DY (eds) Flora of China, Vol 25. Science Press, Beijing, and Missouri Botanical Garden Press, St., pp 211–228
2.
Zurück zum Zitat Nishikawa K, Hirata Y (1967) Chemotaxonomical alkaloid studies. I. Structure of nervosine. Tetrahedron Lett 8:2591–2596CrossRef Nishikawa K, Hirata Y (1967) Chemotaxonomical alkaloid studies. I. Structure of nervosine. Tetrahedron Lett 8:2591–2596CrossRef
3.
Zurück zum Zitat Nishikawa K, Hirata Y (1968) Chemotaxonomical alkaloid studies. 3. Further studies of Liparis alkaloids. Tetrahedron Lett 9:6289–6291CrossRef Nishikawa K, Hirata Y (1968) Chemotaxonomical alkaloid studies. 3. Further studies of Liparis alkaloids. Tetrahedron Lett 9:6289–6291CrossRef
4.
Zurück zum Zitat Huang S, Zhou XL, Wang CJ, Wang HY, Wang YS, Shan LH, Weng J (2013) New nervogenic acid derivatives from Liparis nervosa. Planta Med 79:281–287CrossRef Huang S, Zhou XL, Wang CJ, Wang HY, Wang YS, Shan LH, Weng J (2013) New nervogenic acid derivatives from Liparis nervosa. Planta Med 79:281–287CrossRef
5.
Zurück zum Zitat Huang S, Zhou XL, Wang CJ, Wang YS, Xiao F, Shan LH, Guo ZY, Weng J (2013) Pyrrolizidine alkaloids from Liparis nervosa with inhibitory activities against LPS-induced NO production in RAW264.7 macrophages. Phytochemistry 93:154–161CrossRef Huang S, Zhou XL, Wang CJ, Wang YS, Xiao F, Shan LH, Guo ZY, Weng J (2013) Pyrrolizidine alkaloids from Liparis nervosa with inhibitory activities against LPS-induced NO production in RAW264.7 macrophages. Phytochemistry 93:154–161CrossRef
6.
Zurück zum Zitat Huang S, Pan MF, Zhou XL, Zhou ZL, Wang CJ, Shan LH, Weng J (2013) Five new nervogenic acid derivatives from Liparis nervosa. Chin Chem Lett 24:734–736CrossRef Huang S, Pan MF, Zhou XL, Zhou ZL, Wang CJ, Shan LH, Weng J (2013) Five new nervogenic acid derivatives from Liparis nervosa. Chin Chem Lett 24:734–736CrossRef
7.
Zurück zum Zitat Huang S, Zhong DX, Shan LH, Zheng YZ, Zhang ZK, Bu YH, Ma HW, Zhou XL (2016) Three new pyrrolizidine alkaloids derivatives from Liparis nervosa. Chin Chem Lett 27:757–760CrossRef Huang S, Zhong DX, Shan LH, Zheng YZ, Zhang ZK, Bu YH, Ma HW, Zhou XL (2016) Three new pyrrolizidine alkaloids derivatives from Liparis nervosa. Chin Chem Lett 27:757–760CrossRef
8.
Zurück zum Zitat Zhao Y, Hu S, Wang C, Zheng Y, Xu X (2013) Chemical constituents from Liparis nervosa. Chin Tradit Herb Drugs 44:2955–2959 Zhao Y, Hu S, Wang C, Zheng Y, Xu X (2013) Chemical constituents from Liparis nervosa. Chin Tradit Herb Drugs 44:2955–2959
9.
Zurück zum Zitat Wu R, Huang S, Shan LH, Li SY, Wei Y, Zhou X (2016) A new flavone glycoside from Liparis bootanensis. Chin J Org Chem 36:2735–2738CrossRef Wu R, Huang S, Shan LH, Li SY, Wei Y, Zhou X (2016) A new flavone glycoside from Liparis bootanensis. Chin J Org Chem 36:2735–2738CrossRef
10.
Zurück zum Zitat Hua YX, Liu SF, Yang ZQ (1999) The Chinese herbal, vol 12. Shanghai Science and Technology Publishing House, Shanghai, p 997 Hua YX, Liu SF, Yang ZQ (1999) The Chinese herbal, vol 12. Shanghai Science and Technology Publishing House, Shanghai, p 997
11.
Zurück zum Zitat Yang J, Wang L, Zhou X, Yuan J, Zhang T, Liu F (2014) Chemical constituents from Melilotus officinalis. Tradit Herb Drugs 45:622–625 Yang J, Wang L, Zhou X, Yuan J, Zhang T, Liu F (2014) Chemical constituents from Melilotus officinalis. Tradit Herb Drugs 45:622–625
12.
Zurück zum Zitat Li Y, Zhou Y, Chen G, Pei Y, Qin X (2014) Isolation and identification of phenols from Cynanchum paniculatum. J Shenyang Pharm Univ 31:444–447 Li Y, Zhou Y, Chen G, Pei Y, Qin X (2014) Isolation and identification of phenols from Cynanchum paniculatum. J Shenyang Pharm Univ 31:444–447
13.
Zurück zum Zitat Asahina H, Yoshikawa H, Shuto Y (1998) Effects of batatasin III and its analogs on gibberellic acid-dependent α-amylase induction in embryoless barley seeds and on cress growth. Biosci Biotechnol Biochem 62:1619–1620CrossRef Asahina H, Yoshikawa H, Shuto Y (1998) Effects of batatasin III and its analogs on gibberellic acid-dependent α-amylase induction in embryoless barley seeds and on cress growth. Biosci Biotechnol Biochem 62:1619–1620CrossRef
14.
Zurück zum Zitat Reisch J, Bathory M, Novak I, Szendrei K (1970) Structure and biochemistry of natural phenanthrene derivatives. Herba Hung 9:43–48 Reisch J, Bathory M, Novak I, Szendrei K (1970) Structure and biochemistry of natural phenanthrene derivatives. Herba Hung 9:43–48
15.
Zurück zum Zitat Kozma A, Deden T, Carreras J, Wille C, Petuskova J, Rust J, Alcarazo M (2014) Coordination chemistry of cyclopropenylidene-stabilized phosphenium cations: synthesis and reactivity of Pd and Pt complexes. Chem Eur J 20:2208–2214CrossRef Kozma A, Deden T, Carreras J, Wille C, Petuskova J, Rust J, Alcarazo M (2014) Coordination chemistry of cyclopropenylidene-stabilized phosphenium cations: synthesis and reactivity of Pd and Pt complexes. Chem Eur J 20:2208–2214CrossRef
16.
Zurück zum Zitat Rethy B, Kovacs A, Zupko I, Forgo P, Vasas A, Falkay G, Hohmann J (2006) Cytotoxic phenanthrenes from the rhizomes of Tamus communis. Planta Med 72:767–770CrossRef Rethy B, Kovacs A, Zupko I, Forgo P, Vasas A, Falkay G, Hohmann J (2006) Cytotoxic phenanthrenes from the rhizomes of Tamus communis. Planta Med 72:767–770CrossRef
17.
Zurück zum Zitat Wu YP, Liu WJ, Zhong WJ, Chen YJ, Chen DN, He F, Jiang L (2017) Phenolic compounds from the stems of Flickingeria fimbriata. Nat Prod Res 31:1518–1522CrossRef Wu YP, Liu WJ, Zhong WJ, Chen YJ, Chen DN, He F, Jiang L (2017) Phenolic compounds from the stems of Flickingeria fimbriata. Nat Prod Res 31:1518–1522CrossRef
18.
Zurück zum Zitat Rao KV, Damu AG, Jayaprakasam B, Gunasekar D (1999) Flavonol glycosides from Cassia hirsuta. J Nat Prod 62:305–306CrossRef Rao KV, Damu AG, Jayaprakasam B, Gunasekar D (1999) Flavonol glycosides from Cassia hirsuta. J Nat Prod 62:305–306CrossRef
19.
Zurück zum Zitat Adhikari DP, Schutzki RE, DeWitt DL, Nair MG (2006) Effects of Amelanchier fruit isolates on cyclooxygenase enzymes and lipid peroxidation. Food Chem 97:56–56CrossRef Adhikari DP, Schutzki RE, DeWitt DL, Nair MG (2006) Effects of Amelanchier fruit isolates on cyclooxygenase enzymes and lipid peroxidation. Food Chem 97:56–56CrossRef
20.
Zurück zum Zitat Wang X, Li L, Zhu R, Zhang J, Zhou J, Lou H (2017) Bibenzyl-based meroterpenoid enantiomers from the Chinese Liverwort Radula sumatrana. J Nat Prod 80:3143–3150CrossRef Wang X, Li L, Zhu R, Zhang J, Zhou J, Lou H (2017) Bibenzyl-based meroterpenoid enantiomers from the Chinese Liverwort Radula sumatrana. J Nat Prod 80:3143–3150CrossRef
Metadaten
Titel
Two flavonol glycosides from Liparis bootanensis
verfasst von
Shuai Huang
Run Wu
Feng Gao
Chunying Li
Xianli Zhou
Publikationsdatum
26.02.2018
Verlag
Springer Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 3/2018
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-018-1189-7

Weitere Artikel der Ausgabe 3/2018

Journal of Natural Medicines 3/2018 Zur Ausgabe