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Record Information
Version2.0
Created at2022-06-29 19:37:41 UTC
Updated at2022-06-29 19:37:41 UTC
NP-MRD IDNP0139058
Secondary Accession NumbersNone
Natural Product Identification
Common NamePolyphyllin II
DescriptionPolyphyllin 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).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC44H70O16
Average Mass855.0280 Da
Monoisotopic Mass854.46639 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
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
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
InChI KeyAWKXNOOUWFJCMU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Paris polyphyllaLOTUS Database
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal saponins
Alternative Parents
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
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46200821
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]