| Record Information |
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| Version | 2.0 |
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| Created at | 2022-06-29 19:37:41 UTC |
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| Updated at | 2022-06-29 19:37:41 UTC |
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| NP-MRD ID | NP0139058 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Polyphyllin II |
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| Description | Polyphyllin II belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Polyphyllin II is found in Paris polyphylla. Polyphyllin II was first documented in 2013 (PMID: 24012730). Based on a literature review a significant number of articles have been published on Polyphyllin II (PMID: 33915023) (PMID: 32661907) (PMID: 35116689) (PMID: 35327385) (PMID: 34582523) (PMID: 34007265). |
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| Structure | CC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(CO)C(O)C3O)C(OC3OC(C)C(O)C(O)C3O)C2O)OC11CCC(C)CO1 InChI=1S/C44H70O16/c1-19-8-13-44(53-18-19)20(2)30-27(60-44)15-26-24-7-6-22-14-23(9-11-42(22,4)25(24)10-12-43(26,30)5)55-41-36(52)38(59-39-35(51)33(49)31(47)21(3)54-39)37(29(17-46)57-41)58-40-34(50)32(48)28(16-45)56-40/h6,19-21,23-41,45-52H,7-18H2,1-5H3 |
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| Synonyms | Not Available |
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| Chemical Formula | C44H70O16 |
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| Average Mass | 855.0280 Da |
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| Monoisotopic Mass | 854.46639 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | Not Available |
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| SMILES | CC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(CO)C(O)C3O)C(OC3OC(C)C(O)C(O)C3O)C2O)OC11CCC(C)CO1 |
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| InChI Identifier | InChI=1S/C44H70O16/c1-19-8-13-44(53-18-19)20(2)30-27(60-44)15-26-24-7-6-22-14-23(9-11-42(22,4)25(24)10-12-43(26,30)5)55-41-36(52)38(59-39-35(51)33(49)31(47)21(3)54-39)37(29(17-46)57-41)58-40-34(50)32(48)28(16-45)56-40/h6,19-21,23-41,45-52H,7-18H2,1-5H3 |
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| InChI Key | AWKXNOOUWFJCMU-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Steroidal glycosides |
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| Direct Parent | Steroidal saponins |
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| Alternative Parents | |
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| Substituents | - Steroidal saponin
- Triterpenoid
- Spirostane skeleton
- Oligosaccharide
- Delta-5-steroid
- Glycosyl compound
- O-glycosyl compound
- Ketal
- Oxane
- Tetrahydrofuran
- Secondary alcohol
- Oxacycle
- Polyol
- Acetal
- Organoheterocyclic compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - You LJ, Geng H, Yang XF, Wei GL, Zhu YD, Ge GB, Lei M, Wang DD: The comparison analysis of polyphyllin I and its analogues induced apoptosis of colon and lung cancer cells via mitochondrial dysfunction. Basic Clin Pharmacol Toxicol. 2021 Jul;129(1):15-25. doi: 10.1111/bcpt.13596. Epub 2021 May 13. [PubMed:33915023 ]
- Lu W, Pan M, Zhang P, Zheng T, Huang L, Ye F, Lei P: The Pharmacokinetics and Tissue Distributions of Nine Steroidal Saponins from Paris polyphylla in Rats. Eur J Drug Metab Pharmacokinet. 2020 Oct;45(5):665-673. doi: 10.1007/s13318-020-00633-5. [PubMed:32661907 ]
- Cheng G, Xue YY, Fang F, Sun GQ, Lu YY, Ji YQ, Qiu PC, Tang HF: Promotion of Ros-mediated Bax/Cyt-c apoptosis by polyphyllin II leads to suppress growth and aggression of glioma cells. Transl Cancer Res. 2021 Sep;10(9):3894-3905. doi: 10.21037/tcr-21-966. [PubMed:35116689 ]
- Siripuram R, Bartolek Z, Patil K, Gill SS, Pai SB: Disruption of Colorectal Cancer Network by Polyphyllins Reveals Pivotal Entities with Implications for Chemoimmunotherapy. Biomedicines. 2022 Mar 2;10(3):583. doi: 10.3390/biomedicines10030583. [PubMed:35327385 ]
- Yang Y, Yang Y, Chen M, Chen J, Wang J, Ma Y, Qian H: Injectable shear-thinning polylysine hydrogels for localized immunotherapy of gastric cancer through repolarization of tumor-associated macrophages. Biomater Sci. 2021 Sep 28;9(19):6597-6608. doi: 10.1039/d1bm01053k. [PubMed:34582523 ]
- Yang MZ, Zhang BB, Huang JC, Bai XY, Liang ZQ, Yi X, Xu N, Huang YJ, Jiao AJ: Network Pharmacology Reveals Polyphyllin II as One Hit of Nano Chinese Medicine Monomers against Nasopharyngeal Carcinoma. Bioinorg Chem Appl. 2021 Apr 29;2021:9959634. doi: 10.1155/2021/9959634. eCollection 2021. [PubMed:34007265 ]
- Wang G, Hao R, Luo C, Wang Y, Man S, Gao W: Pharmacokinetics profiles of polyphyllin II and polyphyllin VII in rats by liquid chromatography with tandem mass spectrometry. Biomed Chromatogr. 2021 Jun;35(6):e5083. doi: 10.1002/bmc.5083. Epub 2021 Feb 17. [PubMed:33544400 ]
- Qiao X, Qu C, Luo Q, Wang Y, Yang J, Yang H, Wen X: UHPLC-qMS spectrum-effect relationships for Rhizoma Paridis extracts. J Pharm Biomed Anal. 2021 Feb 5;194:113770. doi: 10.1016/j.jpba.2020.113770. Epub 2020 Nov 24. [PubMed:33288343 ]
- Niu W, Xu L, Li J, Zhai Y, Sun Z, Shi W, Jiang Y, Ma C, Lin H, Guo Y, Liu Z: Polyphyllin II inhibits human bladder cancer migration and invasion by regulating EMT-associated factors and MMPs. Oncol Lett. 2020 Sep;20(3):2928-2936. doi: 10.3892/ol.2020.11839. Epub 2020 Jul 9. [PubMed:32782609 ]
- Yang Q, Li H, Gui M, Li Z, Sun H: Development and validation of a rapid and sensitive LC-MS/MS method for the determination of polyphyllin II in rat plasma and its application in a pharmacokinetic study. Biomed Chromatogr. 2020 Aug;34(8):e4861. doi: 10.1002/bmc.4861. Epub 2020 Jun 26. [PubMed:32657482 ]
- Pang D, Yang C, Li C, Zou Y, Feng B, Li L, Liu W, Luo Q, Chen Z, Huang C: Polyphyllin II inhibits liver cancer cell proliferation, migration and invasion through downregulated cofilin activity and the AKT/NF-kappaB pathway. Biol Open. 2020 Feb 7;9(2):bio046854. doi: 10.1242/bio.046854. [PubMed:31988091 ]
- Yang Q, Li H, Gui M, Li Z, Sun H: Development and validation of a rapid and sensitive LC-MS/MS method for the determination of polyphyllin II in rat plasma and its application in a pharmacokinetic study. Biomed Chromatogr. 2020 Mar;34(3):e4780. doi: 10.1002/bmc.4780. Epub 2020 Jan 12. [PubMed:31830305 ]
- Wang W, Dong X, You L, Sai N, Leng X, Yang C, Yin X, Ni J: Apoptosis in HepaRG and HL-7702 cells inducted by polyphyllin II through caspases activation and cell-cycle arrest. J Cell Physiol. 2019 May;234(5):7078-7089. doi: 10.1002/jcp.27462. Epub 2018 Oct 26. [PubMed:30362578 ]
- Yang Y, Zhang J, Jin H, Zhang J, Wang Y: Quantitative Analysis in Combination with Fingerprint Technology and Chemometric Analysis Applied for Evaluating Six Species of Wild Paris Using UHPLC-UV-MS. J Anal Methods Chem. 2016;2016:3182796. doi: 10.1155/2016/3182796. Epub 2016 Dec 21. [PubMed:28097038 ]
- Zheng R, Jiang H, Li J, Liu X, Xu H: Polyphyllin II Restores Sensitization of the Resistance of PC-9/ZD Cells to Gefitinib by a Negative Regulation of the PI3K/Akt/mTOR Signaling Pathway. Curr Cancer Drug Targets. 2017;17(4):376-385. doi: 10.2174/1568009616666161213141608. [PubMed:28093061 ]
- Ning LH, Zhou B, Zhang YX, Li XP: [Study on hemolytic mechanism of polyphyllin II]. Zhongguo Zhong Yao Za Zhi. 2015 Sep;40(18):3623-9. [PubMed:26983211 ]
- Zhao Y, Zhang J, Yuan T, Shen T, Li W, Yang S, Hou Y, Wang Y, Jin H: Discrimination of wild Paris based on near infrared spectroscopy and high performance liquid chromatography combined with multivariate analysis. PLoS One. 2014 Feb 18;9(2):e89100. doi: 10.1371/journal.pone.0089100. eCollection 2014. [PubMed:24558477 ]
- Wang B, Ji S, Zhang H, Zhao L, Lv L, Li Y, Zhou G, Zhang G: Liquid chromatography tandem mass spectrometry in study of the pharmacokinetics of six steroidal saponins in rats. Steroids. 2013 Dec 11;78(12-13):1164-70. doi: 10.1016/j.steroids.2013.08.009. Epub 2013 Sep 5. [PubMed:24012730 ]
- Yin X, Qu C, Li Z, Zhai Y, Cao S, Lin L, Feng L, Yan L, Ni J: Simultaneous determination and pharmacokinetic study of polyphyllin I, polyphyllin II, polyphyllin VI and polyphyllin VII in beagle dog plasma after oral administration of Rhizoma Paridis extracts by LC-MS-MS. Biomed Chromatogr. 2013 Mar;27(3):343-8. doi: 10.1002/bmc.2797. Epub 2012 Aug 17. [PubMed:22903625 ]
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