Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000058.xml
Download PDF
Planta Med 2023; 89(02): 208-217
DOI: 10.1055/a-1896-1098
DOI: 10.1055/a-1896-1098
Natural Product Chemistry & Analytical Studies
Original Papers
Steroidal Saponins from the Rhizomes of Smilax china and Their Inhibitory Effects on Lipopolysaccharide-Induced Proinflammatory Cytokines Expression
Supported by: Guangdong Basic and Applied Basic Research Foundation 2021A1515011094
Abstract
Four new furostanol saponins (1 – 4) and a new pregane-type saponin (5) along with six known steroidal saponins (6 – 11) were isolated from the rhizomes of Smilax china. The structures of 1 – 5 were elucidated by extensive analysis of NMR and HR-ESI-MS data in addition to enzymatic hydrolysis and other chemical methods. Compounds 1, 4, and 11 showed inhibitory activity against the expression of proinflammatory mediators, inducible nitric oxide synthase, interleukin-1β, interleukin-6, and tumor necrosis factor-α in lipopolysaccharide-induced RAW264.7 cells. Compound 1, at a concentration of 20 µM, decreased the production of inducible nitric oxide synthase, interleukin-1β, interleukin-6, and tumor necrosis factor-α by 36, 62, 72, and 67%, respectively, which is comparable to that of the positive control dexamethasone.
Supporting Information
- Supporting Information
HR-ESI-MS, 1D NMR, and 2D NMR data of compounds 1 – 5, and 1H NMR data of 1a, 1b, and 3a, acid hydrolysis, sugar analysis, and RT-qPCR analysis are available as Supporting Information.
Publication History
Received: 29 January 2022
Accepted after revision: 17 June 2022
Article published online:
28 September 2022
© 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Flora of China Editorial Committee, Chinese Academy of Sciences. Flora of China. Beijing: Science Press; 1978: 193
- 2 Meng QW, Bai ZC. The investigation of wild vegetable resource and development of Smilax genus in Chongqing mountainous area. Shanqu Kaifa 2003; 14: 35-36
- 3 Song LY, Tian LW, Ma Y, Xie Y, Feng HX, Qin F, Mo LQ, Lin S, Hou LB, Wang CX. Protection of flavonoids from Smilax china L. rhizome on phenol mucilage-induced pelvic inflammation in rats by attenuating inflammation and fibrosis. J Funct Foods 2017; 28: 194-204
- 4 Chinese Pharmacopeia Commission. Pharmacopeia of the Peopleʼs Republic of China. Beijing: China Medical Science Press; 2020: 321
- 5 Xie Y, Hu D, Zhong C, Liu KF, Fang E, Zhang YJ, Zhou C, Tian LW. Anti-inflammatory furostanol saponins from the rhizomes of Smilax china L. Steroids 2018; 140: 70-76
- 6 Shao B, Guo HZ, Cui Y, Ye M, Han J, Guo DA. Steroidal saponins from Smilax china and their anti-inflammatory activities. Phytochemistry 2007; 68: 623-630
- 7 Huang HL, Liu RH, Shao F. Structural determination of two new steroidal saponins from Smilax china . Magn Reson Chem 2009; 47: 741-745
- 8 Nikaido T, Ohmoto T, Sashida Y, Kubo S, Mimaki Y. Steroidal saponins from Smilax riparia and S. China . Phytochemistry 1992; 31: 2439-2443
- 9 Zhong C, Hu D, Hou LB, Song LY, Zhang YJ, Xie Y, Tian LW. Phenolic compounds from the rhizomes of Smilax china L. and their anti-inflammatory activity. Molecules 2017; 22: 515
- 10 Wu LS, Wang XJ, Wang H, Yang HW, Jia AQ, Ding Q. Cytotoxic polyphenols against breast tumor cell in Smilax china L. J Ethnopharmacol 2010; 130: 460-464
- 11 Feng F, Liu W, Chen Y, Liu J, Zhao S. Flavonoids and stilbenes from Smilax china . Zhongguo Yaoke Daxue Xuebao 2003; 34: 119-121
- 12 Li YL, Gan GP, Zhang HZ, Wu HZ, Li CL, Huang YP, Liu YW, Liu JW. A flavonoid glycoside isolated from Smilax china L. rhizome in vitro anticancer effects on human cancer cell lines. J Ethnopharmacol 2007; 113: 115-124
- 13 Shao B, Guo HZ, Guo DA. Flavonoids and stilbenes from Smilax china . Zhongcaoyao 2009; 40: 1700-1703
- 14 Hao Q, Yao Y, Li XL, Li RT, Li HZ. Three new dihydrokaempferol acetylated glycosides from smilax china L. Tianran Chanwu Yanjiu Yu Kaifa 2012; 24: 861-865
- 15 Jeon SY, Kwon SH, Seong YH, Bae K, Hur JM, Lee YY, Suh DY, Song KS. Beta-secretase (BACE1)-inhibiting stillbenoids from Smilax Rhizoma. Phytomedicine 2007; 14: 403-408
- 16 Ruan HL, Zhang YH, Zhao W, Tan YF, Sun ZL, Wu JZ. Studies on the chemical constituents of Smilax china L. Tianran Chanwu Yanjiu Yu Kaifa 2002; 14: 35-36 41
- 17 Zhao Z, Feng Y, Ruan J, Zhu C, Yang S. Chemical constituents of Smilax china and their antioxidant activities. Zhongcaoyao 2008; 39: 975-977
- 18 Tian LW, Zhang Z, Long HL, Zhang YJ. Steroidal saponins from the genus Smilax and their biological activities. Nat Prod Bioprospect 2017; 7: 283-298
- 19 Khan I, Nisar M, Ebad F, Nadeem S, Saeed M, Khan H, Samiullah. Khuda F, Karim N, Ahmad Z. Anti-inflammatory activities of sieboldogenin from Smilax china Linn.: experimental and computational studies. J Ethnopharmacol 2009; 121: 175-177
- 20 Liang C, Lim JH, Kim SH, Kim DS. Dioscin: A synergistic tyrosinase inhibitor from the roots of Smilax china . Food Chem 2012; 134: 1146-1148
- 21 Hirai Y, Sanada S, Ida Y, Shoji J. Studies on the Constituents of Palmae Plants. III.: The Constituents of Chamaerops humilis L. and Trachycarpus wagnerianus BECC. Chem Pharm Bull 1986; 34: 82-87
- 22 Hu K, Yao XS, Dong AJ, Kobayashi H, Iwasaki S, Jing YK. A new pregnane glycoside from Dioscorea collettii var. hypoglauca . J Nat Prod 1999; 62: 299-301
- 23 Miyamura M, Nakano K, Nohara T, Tomimatsu T, Kawasaki T. Steroid Saponins from Paris polyphylla SM.-Supplement. Chem Pharm Bull 1982; 30: 712-718
- 24 Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull 2007; 55: 899-901
- 25 Zhu XH, Tsumagari H, Honbu T, Ikeda T, Ono M, Nohara T. Peculiar steroidal saponins with opened E-ring from Solanum genera plants. Tetrahedron Lett 2001; 42: 8043-8046
- 26 Itokawa H, Xu J, Takeya K. Pregnane glycosides from an antitumour fraction of Periploca sepium . Phytochemistry 1988; 27: 1173-1179
- 27 Agrawal PK. Dependence of 1H NMR chemical shifts of geminal protons of glycosyloxy methylene (H2-26) on the orientation of the 27-methyl group of furostane-type steroidal saponins. Magn Reson Chem 2004; 42: 990-993
- 28 Dong M, Feng XZ, Wu LJ, Wang BX, Ikejima T. Two new steroidal saponins from the rhizomes of Dioscorea panthaica and their cytotoxic activity. Planta Med 2001; 67: 853-857
- 29 Tobari A, Teshima M, Koyanagi J, Kawase M, Miyamae H, Yoza K, Takasaki A, Nagamura Y, Saito S. Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides. Eur J Med Chem 2000; 35: 511-527
- 30 Yang QX, Yang CR. Cytotoxic steroidal saponins from Polygonatum punctatum . Chem Biodivers 2006; 3: 1349-1355
- 31 Lin T, Huang HL, Liu RH, Shu JC, Ren G, Shao F, Liu LS. Steroidal saponins and pregnane glycosides from Smilax microphylla . Magn Reson Chem 2012; 50: 813-817
- 32 Ahmad VU, Khaliq-uz-Zaman SM, Shameel S, Perveen S, Ali Z. Steroidal saponins from Asparagus dumosus . Phytochemistry 1998; 50: 481-484