New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Compound Characterization Data
3.5. Acid Hydrolysis and GC Analysis of the Sugar Moieties in 1–4
3.6. Cytotoxicity Assay for Compounds 1–10
3.7. Statistical Analysis
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
- Liu, Y.; Tian, X.; Hua, D.; Cheng, G.; Wang, K.; Zhang, L.; Tang, H.; Wang, M. New steroidal saponins from the rhizomes of Paris delavayi and their cytotoxicity. Fitoterapia 2016, 111, 130–137. [Google Scholar] [CrossRef] [PubMed]
- Wen, F.Y.; Yin, H.X.; Chen, C.; Liu, X.B.; Xue, D.; Chen, T.Z.; He, J.; Zhang, H. Chemical characteristics of saponins from Paris fargesii var. brevipetala and cytotoxic activity of its main ingredient, paris saponin H. Fitoterapia 2012, 83, 627–635. [Google Scholar] [CrossRef] [PubMed]
- Watanabe, S.; Suzuki, T.; Hara, F.; Yasui, T.; Uga, N.; Naoe, A. Polyphyllin D, a steroidal saponin in Paris polyphylla, induces apoptosis and necroptosis cell death of neuroblastoma cells. Pediatric Surg. Int. 2017, 33, 713–719. [Google Scholar] [CrossRef] [PubMed]
- Zheng, L.; Zheng, J.; Zhao, Y.; Wang, B.; Wu, L.; Liang, H. Three anti-tumor saponins from Albizia julibrissin. Bioorg. Med. Chem. Lett. 2006, 16, 2765–2768. [Google Scholar] [CrossRef] [PubMed]
- Kawabata, T.; Cui, M.Y.; Hasegawa, T.; Takano, F.; Ohta, T. Anti-inflammatory and anti-melanogenic steroidal saponin glycosides from Fenugreek (Trigonella foenum-graecum L.) seeds. Planta Medica 2011, 77, 705–710. [Google Scholar] [CrossRef] [PubMed]
- Deng, D.; Lauren, D.R.; Cooney, J.M.; Jensen, D.J.; Wurms, K.V.; Upritchard, J.E.; Cannon, R.D.; Wang, M.Z.; Li, M.Z. Antifungal saponins from Paris polyphylla Smith. Planta Medica 2008, 74, 1397–1402. [Google Scholar] [CrossRef] [PubMed]
- Tian, Y.; Zheng, L.H.; Xu, Z.Y.; Sun, L.Q.; Gao, C.K.; Zheng, Q.Z.; Zhang, Z.H.; Shu, Y. Clinical and pharmacological study of the hemostatic action of Rhizoma Paridis by contraction of uterus. J. Tradit. Chin. Med. 1986, 6, 178–182. [Google Scholar] [PubMed]
- Zaki, A.A.; Ali, Z.; Wang, Y.H.; El-Amier, Y.A.; Khan, S.I.; Khan, I.A. Cytotoxic steroidal saponins from Panicum turgidum Forssk. Steroids 2017, 125, 14–19. [Google Scholar] [CrossRef] [PubMed]
- Jing, S.S.; Wang, Y.; Li, X.; Man, S.L.; Gao, W.Y. Chemical constituents and antitumor activity from Paris polyphylla Smith var. yunnanensis. Nat. Prod. Res. 2017, 31, 660–666. [Google Scholar] [CrossRef] [PubMed]
- Yang, B.Y.; Bi, X.Y.; Liu, Y.; Li, G.Y.; Yin, X.; Kuang, H.X. Four New Glycosides from the Rhizoma of Anemarrhena asphodeloides. Molecules 2017, 22, 1995. [Google Scholar] [CrossRef] [PubMed]
- Pereira, G.M.; Ribeiro, M.G.; da Silva, B.P.; Parente, J.P. Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property. Bioorg. Med. Chem. Lett. 2017, 27, 4345–4349. [Google Scholar] [CrossRef] [PubMed]
- Li, H. The Genus Paris (Trilliaceae); Science Press: Beijing, China, 1998; pp. 26–28. [Google Scholar]
- Huang, Y.; Cui, L.J.; Wang, Q.; Ye, W.C. Separation and identification of active constituents of Paris vietnamensis. Acta Pharm. Sin. 2006, 40, 361–364. [Google Scholar]
- Chen, P.Y.; Chen, C.H.; Kuo, C.C.; Lee, T.H.; Kuo, Y.H.; Lee, C.K. Cytotoxic steroidal saponins from Agave sisalana. Planta Medica 2011, 77, 929–933. [Google Scholar] [CrossRef] [PubMed]
- Liu, H.; Chou, G.X.; Wang, J.M.; Ji, L.L.; Wang, Z.T. Steroidal saponins from the rhizomes of Dioscorea bulbifera and their cytotoxic activity. Planta Medica 2011, 77, 845–848. [Google Scholar] [CrossRef] [PubMed]
- Zhao, Y.; Kang, L.P.; Liu, Y.X.; Liang, Y.G.; Tan, D.W.; Yu, Z.Y.; Cong, Y.W.; Ma, B.P. Steroidal saponins from the rhizome of Paris polyphylla and their cytotoxic activities. Planta Medica 2009, 75, 356–363. [Google Scholar] [CrossRef] [PubMed]
- Agrawal, P.K.; Jain, D.C.; Pathak, A.K. NMR spectroscopy of steroidal sapogenins and steroidal saponins: An update. Magn. Reson. Chem. 1995, 33, 923–953. [Google Scholar] [CrossRef]
- Agrawal, P.K.; Jain, D.C.; Gupta, R.K.; Thakur, R.S. Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry 1985, 24, 2479–2496. [Google Scholar] [CrossRef]
- Xiao, C.M.; Huang, J.; Zhong, X.M.; Tan, X.Y.; Deng, P.C. Two New Homo-aro-cholestane Glycosides and a New Cholestane Glycoside from the Roots and Rhizomes of Paris polyphylla var. Pseudothibetica. Helv. Chim. Acta 2010, 92, 2587–2595. [Google Scholar] [CrossRef]
- Agrawal, P.K. Assigning stereodiversity of the 27-Me group of furostane-type steroidal saponins via NMR chemical shifts. Steroids 2005, 70, 715–724. [Google Scholar] [CrossRef] [PubMed]
- Zhang, J.; Ma, B.P.; Kang, L.P.; Yu, H.S.; Yang, Y.; Yan, X.Z. NMR studies of two furostanol saponins isolated from Polygonatum Kingianum. Chin. J. Magn. Reson. 2006, 23, 30–40. [Google Scholar]
- Mahato, S.B.; Sahu, N.P.; Ganguly, A.N. Steroidal saponins from Dioscorea floribunda: Structures of floribundasaponins A and B. Phytochemistry 1981, 20, 1943–1946. [Google Scholar] [CrossRef]
- Tian, X.; Feng, J.; Tang, H.; Zhao, M.; Li, Y.; Hai, W.; Zhang, X. New cytotoxic triterpenoid saponins from the whole plant of Clematis lasiandra Maxim. Fitoterapia 2013, 90, 233–239. [Google Scholar] [CrossRef] [PubMed]
- Kasai, R.; Okihara, M.; Asakawa, J.; Mizutani, K.; Tanaka, O. 13C NMR study of α-anomeric and β-anomeric pairs of d-mannopyranosides and l-rhamnopyranosides. Tetrahedron 1979, 35, 1427–1432. [Google Scholar] [CrossRef]
- Zhang, Y.; Yang, C.R.; Zhang, Y.J. Steroidal saponins from the rhizomes of Polygonatum prattii. J. Asian Nat. Prod. Res. 2016, 18, 268–273. [Google Scholar] [CrossRef] [PubMed]
- Xie, B.B.; Liu, H.Y.; Ni, W.; Chen, C.X. Ypsilandrosides C-G, five new spirostanol saponins from Ypsilandra thibetica. Steroids 2009, 12, 950–955. [Google Scholar] [CrossRef] [PubMed]
- Kang, L.P.; Huang, Y.Y.; Zhan, Z.L.; Liu, D.H.; Peng, H.S.; Nan, T.G.; Zhang, Y.; Hao, Q.X.; Tang, J.F.; Zhu, S.D.; et al. Structural characterization and discrimination of the Paris polyphylla var. yunnanensis and Paris vietnamensis based on metabolite profiling analysis. J. Pharm. Biomed. Anal. 2017, 142, 252–261. [Google Scholar] [CrossRef] [PubMed]
- Tang, L.Y.; Wang, Z.J.; Wu, H.W.; Yokosuka, A.; Mimaki, Y. Steroidal glycosides from the underground parts of Dracaena thalioides and their cytotoxic activity. Phytochemistry 2014, 107, 102–110. [Google Scholar] [CrossRef] [PubMed]
- Khodakov, G.V.; Akimov, Y.A.; Shashkov, A.S.; Kintia, P.K.; Grishkovets, V.I. Triterpene and steroid saponins isolated from two Melilotus species. Oxyg. Transp. Tissue XXXIII 1996, 405, 211–222. [Google Scholar]
- Li, Y.H.; Liu, C.X.; Xiao, D.; Han, J.; Yue, Z.G.; Sun, Y.; Fan, L.; Zhang, F.; Meng, J.; Zhang, R.; et al. Trillium tschonoskii steroidal saponins suppress the growth of colorectal Cancer cells in vitro and in vivo. J. Ethnopharmacol. 2015, 168, 136–145. [Google Scholar] [CrossRef] [PubMed]
- Lee, H.J.; Watanabe, B.; Nakayasu, M.; Onjo, M.; Sugimoto, Y.; Mizutani, M. Novel steroidal saponins from Dioscorea esculenta (Togedokoro). Biosci. Biotechnol. Biochem. 2017, 81, 2253–2260. [Google Scholar] [CrossRef] [PubMed]
- Lu, Y.Y.; Luo, J.G.; Huang, X.F.; Kong, L.Y. Four new steroidal glycosides from Solanum torvum and their cytotoxic activities. Steroids 2009, 74, 95–101. [Google Scholar] [CrossRef] [PubMed]
- Tian, X.R.; Tang, H.F.; Lin, H.W.; Cheng, G.; Wang, S.W.; Zhang, X. Saponins: The potential chemotherapeutic angents in pursuing new anti-glioblastoma drugs. Mini-Rev. Med. Chem. 2013, 13, 1709–1724. [Google Scholar] [CrossRef] [PubMed]
- Fu, Q.; Zan, K.; Zhao, M.; Zhou, S.; Shi, S.; Jiang, Y.; Tu, P. Triterpene saponins from Clematis chinensis and their potential anti-inflammatory activity. J. Nat. Prod. 2010, 73, 1234–1239. [Google Scholar] [CrossRef] [PubMed]
- Lin, H.; Zhang, X.; Cheng, G.; Tang, H.F.; Zhang, W.; Zhen, H.N.; Cheng, J.X.; Liu, B.L.; Cao, W.D.; Dong, W.P.; et al. Apoptosis induced by ardipusilloside III through BAD dephosphorylation and cleavage in human glioblastoma U251MG cells. Apoptosis 2008, 13, 247–257. [Google Scholar] [CrossRef] [PubMed]
- Dang, Y.; Wu, W.; Xu, Y.; Mu, Y.; Xu, K.; Wu, H.; Zhu, Y.; Zhang, C. Effects of low-level laser irradiation on proliferation and functional protein expression in human RPE cells. Lasers Med. Sci. 2015, 9, 2295–2302. [Google Scholar] [CrossRef] [PubMed]
- Wang, Z.Y.; Yang, J.; Xu, G.; Wang, W.; Liu, C.H.; Yang, H.H.; Yu, Z.B.; Lei, Q.Q.; Xiao, L.; Xiong, J.; et al. Targeting miR-381-NEFL axis sensitizes glioblastoma cells to temozolomide by regulating stemness factors and multidrug resistance factors. Oncotarget 2014, 6, 3147–3164. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Samples of the compounds 1–10 are available from the authors. |
Aglycone | R1 | R2 | R3 | R4 | Configuration of C-25 | |
---|---|---|---|---|---|---|
1 | I | S1 | COCH3 | OH | CH3 | 25R |
2 | I | S1 | H | OH | CH2OH | 25R |
3 | II | S1 | H | - | - | 25R |
4 | II | S2 | H | - | - | 25R |
5 | I | S1 | H | OH | CH3 | 25R |
6 | I | S1 | H | OH | CH3 | 25S |
7 | I | S3 | H | OH | CH3 | 25R |
8 | I | S4 | H | H | CH3 | 25R |
9 | I | S5 | H | OH | CH3 | 25R |
10 | I | S1 | H | H | CH3 | 25R |
1 a | 2 a | 3 b | 4 b | |||||
---|---|---|---|---|---|---|---|---|
1 | 38.74 | 1.08 m, 1.90 m | 38.75 | 1.09 m, 1.90 m | 37.68 | 1.24 m, 2.01 m | 37.69 | 1.21 m, 2.00 m |
2 | 30.97 | 1.30 m, 1.59 m | 30.91 | 1.29 m, 1.92 m | 30.56 | 1.72 m, 2.05 m | 30.57 | 1.72 m, 2.05 m |
3 | 80.09 | 3.53 m | 79.32 | 3.62 m | 78.05 | 3.79 m | 78.04 | 3.77 m |
4 | 39.77 | 2.45 m, 2.30 t (11.1) | 39.66 | 2.45 m, 2.30 t (11.2) | 39.61 | 2.48 m, 2.73 m | 39.61 | 2.46 m, 2.72 m |
5 | 142.03 | − | 142.06 | − | 46.62 | 2.49 m | 46.60 | 2.46 m |
6 | 122.80 | 5.40 br s | 122.75 | 5.39 br s | 204.57 | − | 204.49 | − |
7 | 32.66 | 1.57 m, 1.70 m | 33.83 | 1.64 m, 1.83 m | 126.59 | 5.73 br s | 126.59 | 5.73 br s |
8 | 33.44 | 1.65 m | 33.64 | 1.65 m | 169.05 | − | 169.06 | − |
9 | 51.61 | 0.95 m | 51.63 | 0.94 m | 51.37 | 1.48 m | 51.37 | 1.47 m |
10 | 38.13 | − | 38.15 | − | 40.08 | − | 40.09 | − |
11 | 21.85 | 1.52 m, 1.62 m | 21.70 | 1.51 m, 1.62 m | 21.85 | 1.65 m | 21.85 | 1.60 m, 1.70 m |
12 | 33.00 | 1.59 m, 1.69 m | 32.44 | 1.44 m, 1.58 m | 32.67 | 1.53 m, 1.65 m | 32.67 | 1.53 m, 1.70 m |
13 | 46.00 | − | 46.25 | − | 46.66 | − | 46.66 | − |
14 | 54.07 | 1.72 m | 53.87 | 1.71 m | 47.27 | 2.03 m | 47.27 | 2.00 m |
15 | 32.24 | 1.27 m, 2.06 m | 32.28 | 1.26 m, 2.06 m | 34.22 | 1.39 m, 2.84 m | 34.22 | 1.35 m, 2.80 m |
16 | 90.68 | 4.01 m | 90.08 | 4.08 dd (5.84, 7.68) | 90.59 | 4.05 dd (6.45, 7.75) | 90.58 | 4.04 dd (6.4, 7.76) |
17 | 91.45 | − | 91.45 | − | 90.11 | − | 90.13 | − |
18 | 17.67 | 0.84 s | 17.34 | 0.86 s | 17.81 | 0.84 s | 17.81 | 0.84 s |
19 | 19.98 | 1.05 s | 19.99 | 1.06 s | 17.83 | 1.25 s | 17.83 | 1.27 s |
20 | 45.68 | 2.10 q (7.12) | 53.15 | 2.25 dd (5.84, 8.56) | 45.33 | 2.08 m | 45.53 | 2.06 m |
21 | 9.26 | 0.90 d (7.2) | 59.55 | 3.61 m, 3.80 dd (8.64, 11.2) | 9.45 | 0.90 d (7.20) | 9.44 | 0.90 d (7.28) |
22 | 110.10 | − | 110.17 | − | 111.11 | − | 111.10 | − |
23 | 33.35 | 1.58 m, 2.03 m | 33.37 | 1.56 m, 2.02 m | 32.31 | 1.32 m, 1.39 m | 32.31 | 1.32 m, 1.39 m |
24 | 29.59 | 1.45 m, 1.63 m | 29.59 | 1.42 m, 1.60 m | 29.56 | 1.46 m, 1.62 m | 29.57 | 1.43 m, 1.61 m |
25 | 31.44 | 1.61 m | 31.37 | 1.61 m | 31.42 | 1.61 m | 31.43 | 1.60 m |
26 | 67.85 | 3.34 m, 3.49 m | 67.85 | 3.34 m, 3.47 m | 67.82 | 3.35 m, 3.49 m | 67.82 | 3.33 m, 3.48 m |
27 | 17.64 | 0.80 d (6.4) | 17.62 | 0.79 d (6.4) | 17.64 | 0.86 d (6.3) | 17.65 | 0.81 d (6.4) |
Glc | ||||||||
1 | 101.04 | 4.51 d (7.76) | 100.66 | 4.48 d (7.76) | 100.89 | 4.52 d (7.75) | 100.87 | 4.53 d (7.76) |
2 | 79.07 | 3.37 m | 79.18 | 3.35 m | 78.88 | 3.41 m | 78.88 | 3.36 m |
3 | 79.33 | 3.48 m | 79.54 | 3.46 m | 77.89 | 3.38 m | 77.91 | 3.27 m |
4 | 75.10 | 3.44 m | 77.89 | 3.24 m | 79.42 | 3.78 m | 79.43 | 3.48 m |
5 | 71.98 | 3.27 m | 71.99 | 3.26 m | 71.94 | 3.49 m | 71.94 | 3.27 m |
6 | 64.09 | 4.20 q (6.08), 4.35 dd (2.16, 11.92) | 62.92 | 3.64 m, 3.85 m | 62.90 | 3.65 m, 3.85 m | 62.89 | 3.63 m, 3.83 m |
-COCH3 | ||||||||
1 | 172.89 | − | ||||||
2 | 20.89 | 2.05 s | ||||||
Rha | ||||||||
1 | 102.33 | 5.20 br s | 102.33 | 5.19 br s | 102.16 | 5.22 br s | 102.18 | 5.21 br s |
2 | 72.36 | 3.91 m | 72.38 | 3.91 m | 72.30 | 3.92 m | 72.31 | 3.92 m |
3 | 72.52 | 3.66 m | 72.53 | 3.66 m | 72.51 | 3.66 m | 72.51 | 3.65 m |
4 | 74.09 | 3.40 m | 74.09 | 3.39 m | 74.07 | 3.40 m | 74.06 | 3.38 m |
5 | 69.91 | 4.12 dd (6.24, 9.60) | 69.90 | 4.14 dd (6.24, 9.60) | 69.85 | 4.12 dd (6.25, 9.50) | 69.86 | 4.12 dd (6.24, 9.60) |
6 | 18.12 | 1.26 d (6.24) | 18.11 | 1.24 d (6.24) | 18.13 | 1.26 d (6.3) | 18.13 | 1.25 d (6.24) |
Compounds | Astrocytes | Cell Lines | |
---|---|---|---|
U251 | U87MG | ||
1 | >100 | >100 | 52.04 ± 1.28 |
2 | >100 | >100 | >100 |
3 | >100 | >100 | >100 |
4 | >100 | >100 | >100 |
5 | >100 | >100 | >100 |
6 | >100 | >100 | >100 |
7 | >100 | >100 | >100 |
8 | >100 | 2.16 ± 0.65 | 2.33 ± 1.03 |
9 | >100 | 3.14 ± 1.26 | 2.97 ± 0.94 |
10 | >100 | >100 | >100 |
ACNU b | >100 | 0.96 ± 0.05 | 0.88 ± 0.04 |
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Liu, Y.; Wang, M.; Liu, K.; Qiu, P.; Zhang, S.; Lu, Y.; Tang, N.; Tang, H. New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity. Molecules 2018, 23, 588. https://doi.org/10.3390/molecules23030588
Liu Y, Wang M, Liu K, Qiu P, Zhang S, Lu Y, Tang N, Tang H. New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity. Molecules. 2018; 23(3):588. https://doi.org/10.3390/molecules23030588
Chicago/Turabian StyleLiu, Yang, Minchang Wang, Ke Liu, Pengcheng Qiu, Shan Zhang, Yunyang Lu, Na Tang, and Haifeng Tang. 2018. "New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity" Molecules 23, no. 3: 588. https://doi.org/10.3390/molecules23030588