Periplogenin | CAS# 514-39-6 | Cardiac glycoside

MedKoo Cat#: 413577 | Name: Periplogenin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Periplogenin, also known as PPN is a natural cardiac glycoside which exerts anti-inflammatory and analgesic effects in diseases by inhibiting cell growth and migration. Periplogenin is an active ingredient in the anti-rheumatic and anti-inflammatory herb, cortex periplocae.

Chemical Structure

Periplogenin

CAS#514-39-6

Theoretical Analysis

MedKoo Cat#: 413577

Name: Periplogenin

CAS#: 514-39-6

Chemical Formula: C23H34O5

Exact Mass: 390.2406

Molecular Weight: 390.52

Elemental Analysis: C, 70.74; H, 8.78; O, 20.48

Price and Availability

Size	Price	Availability
1mg	USD 240.00	2 Weeks
5mg	USD 540.00	2 Weeks
10mg	USD 860.00	2 Weeks
25mg	USD 1,390.00	2 Weeks

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Related CAS #

No Data

Synonym

Periplogenin; Desoxostrophanthidin; UNII-B6808P7IY9

IUPAC/Chemical Name

5-beta-Card-20(22)-enolide, 3-beta,5,14-trihydroxy-

InChi Key

QJPCKAJTLHDNCS-FBAXFMHRSA-N

InChi Code

InChI=1S/C23H34O5/c1-20-7-3-15(24)12-22(20,26)9-5-18-17(20)4-8-21(2)16(6-10-23(18,21)27)14-11-19(25)28-13-14/h11,15-18,24,26-27H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,20+,21+,22-,23-/m0/s1

SMILES Code

O=C1OCC([C@H]2CC[C@]3(O)[C@]4([H])CC[C@]5(O)C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]23C)=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 390.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ma X, Yang Y, Li H, Luo Z, Wang Q, Yao X, Tang F, Huang Y, Ling Y, Ma W. Periplogenin inhibits pyroptosis of fibroblastic synoviocytes in rheumatoid arthritis through the NLRP3/Caspase-1/GSDMD signaling pathway. Int Immunopharmacol. 2024 May 30;133:112041. doi: 10.1016/j.intimp.2024.112041. Epub 2024 Apr 17. PMID: 38636373. 2: Gan K, Lian H, Yang T, Huang J, Chen J, Su Y, Zhao J, Xu J, Liu Q. Periplogenin attenuates LPS-mediated inflammatory osteolysis through the suppression of osteoclastogenesis via reducing the NF-κB and MAPK signaling pathways. Cell Death Discov. 2024 Feb 17;10(1):86. doi: 10.1038/s41420-024-01856-0. PMID: 38368392; PMCID: PMC10874423. 3: Zhong X, Feng W, Liu L, Liu Q, Xu Q, Liu M, Liu X, Xu S, Deng M, Lin C. Periplogenin inhibits pathologic synovial proliferation and infiltration in rheumatoid arthritis by regulating the JAK2/3-STAT3 pathway. Int Immunopharmacol. 2024 Feb 15;128:111487. doi: 10.1016/j.intimp.2024.111487. Epub 2024 Jan 5. PMID: 38183911. 4: Li Y, Feng X, Qiu F. Determination of Two Wound Healing Components in Streptocaulon juventas (Lour.) Merr.: Periplogenin and Digitoxigenin. Chem Biodivers. 2024 Jan;21(1):e202301585. doi: 10.1002/cbdv.202301585. Epub 2023 Dec 19. PMID: 38061998. 5: Fan Z, Wang S, Xu C, Yang J, Cui B. Mechanisms of action of Fu Fang Gang Liu liquid in treating condyloma acuminatum by network pharmacology and experimental validation. BMC Complement Med Ther. 2023 Apr 20;23(1):128. doi: 10.1186/s12906-023-03960-7. PMID: 37081536; PMCID: PMC10116837. 6: He H, Sun W, Chang J, Hu S, Yang J, Yi X, Yan F, Long Y. Multi-component immune knockout: A strategy for studying the effective components of traditional Chinese medicine. J Chromatogr A. 2023 Mar 15;1692:463853. doi: 10.1016/j.chroma.2023.463853. Epub 2023 Feb 7. PMID: 36780848. 7: Wang S, Yu X, Wu S, Yang W, Gao Y, Wang W, Wang Q, Wei M, Zhu M, Wu J, Yuan Z, Li Y. Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study. Biomed Chromatogr. 2022 Mar;36(3):e5283. doi: 10.1002/bmc.5283. Epub 2021 Dec 8. PMID: 34816469. 8: Hu Y, Liu F, Jia X, Wang P, Gu T, Liu H, Liu T, Wei H, Chen H, Zhao J, Yang R, Chen Y, Dong Z, Liu K. Periplogenin suppresses the growth of esophageal squamous cell carcinoma in vitro and in vivo by targeting STAT3. Oncogene. 2021 Jun;40(23):3942-3958. doi: 10.1038/s41388-021-01817-2. Epub 2021 May 13. PMID: 33986510. 9: Ye H, Wei X, Meng C, Wei Y, Liang G, Huang Z, Guo L, Su W. Mechanism of Action of Periplogenin on Nasopharyngeal Carcinoma Based on Network Pharmacology and Experimental Study of Vitamin E Coupled with Periplogenin Self-Assembled Nano-Prodrug for Nasopharyngeal Carcinoma. J Biomed Nanotechnol. 2020 Sep 1;16(9):1406-1415. doi: 10.1166/jbn.2020.2978. PMID: 33419494. 10: Zhang BD, Zhu WF, Akihisa T, Kikuchi T, Ukiya M, Maya F, Xu J, Liu WY, Feng F, Zhang J. Cardiac glycosides from the roots of Streblus asper Lour. and their apoptosis-inducing activities in A549 cells. Phytochemistry. 2021 Jan;181:112544. doi: 10.1016/j.phytochem.2020.112544. Epub 2020 Oct 30. PMID: 33130375. 11: Yang Y, Liu Y, Zhang Y, Ji W, Wang L, Lee SC. Periplogenin Activates ROS-ER Stress Pathway to Trigger Apoptosis via BIP-eIF2α- CHOP and IRE1α-ASK1-JNK Signaling Routes. Anticancer Agents Med Chem. 2021;21(1):61-70. doi: 10.2174/1871520620666200708104559. PMID: 32640963. 12: Yang X, Li MY, Yan CY, Xiao ZJ, Jiang WQ, Wang XY, Cui XX, Li WX, Yao KN, Liu CX. [Research progress on chemical composition and pharmacological effects of Periplocae Cortex and predictive analysis on Q-marker]. Zhongguo Zhong Yao Za Zhi. 2020 Jun;45(12):2772-2783. Chinese. doi: 10.19540/j.cnki.cjcmm.20200327.202. PMID: 32627450. 13: Bui XH, Dang PH, Vo TT, Nguyen NYT, Nguyen MD, Tran QL. A new cardenolide glycoside from the roots of Streptocaulon juventas (lour.) merr. (Asclepiadaceae). Nat Prod Res. 2021 Apr;35(7):1192-1198. doi: 10.1080/14786419.2019.1641806. Epub 2019 Aug 1. PMID: 31368357. 14: Li Z, Li Y, Li J, Liu R, Hao J, He J, Chang YX. An LC-MS/MS Method for Simultaneous Determination of the Toxic and Active Components of Cortex Periplocae in Rat Plasma and Application to a Pharmacokinetic Study. Int J Anal Chem. 2019 Feb 13;2019:1639619. doi: 10.1155/2019/1639619. PMID: 30894874; PMCID: PMC6393897. 15: Lohberger B, Wagner S, Wohlmuther J, Kaltenegger H, Stuendl N, Leithner A, Rinner B, Kunert O, Bauer R, Kretschmer N. Periplocin, the most anti- proliferative constituent of Periploca sepium, specifically kills liposarcoma cells by death receptor mediated apoptosis. Phytomedicine. 2018 Dec 1;51:162-170. doi: 10.1016/j.phymed.2018.10.008. Epub 2018 Oct 11. PMID: 30466613. 16: Liu H, Zhang D, Tang Z, Sun M, Azietaku JT, Ouyang H, Chang Y, Wang M, He J, Gao X. Tissue distribution study of periplocin and its two metabolites in rats by a validated LC-MS/MS method. Biomed Chromatogr. 2018 Oct;32(10):e4302. doi: 10.1002/bmc.4302. Epub 2018 Jun 26. PMID: 29809276. 17: Knittel DN, Lorenz P, Huber U, Stintzing FC, Kammerer DR. Characterization of the cardiac glycoside and lipid profiles of Strophanthus kombé Oliv. seeds. Z Naturforsch C J Biosci. 2016 Mar;71(3-4):55-64. doi: 10.1515/znc-2015-0186. PMID: 26974139. 18: Zhang HY, Xu WQ, Wang YW, Omari-Siaw E, Wang Y, Zheng YY, Cao X, Tong SS, Yu JN, Xu XM. Tumor targeted delivery of octreotide-periplogenin conjugate: Synthesis, in vitro and in vivo evaluation. Int J Pharm. 2016 Apr 11;502(1-2):98-106. doi: 10.1016/j.ijpharm.2016.02.024. Epub 2016 Feb 18. PMID: 26899980. 19: Zhang WJ, Song ZB, Bao YL, Li WL, Yang XG, Wang Q, Yu CL, Sun LG, Huang YX, Li YX. Periplogenin induces necroptotic cell death through oxidative stress in HaCaT cells and ameliorates skin lesions in the TPA- and IMQ-induced psoriasis- like mouse models. Biochem Pharmacol. 2016 Apr 1;105:66-79. doi: 10.1016/j.bcp.2016.02.001. Epub 2016 Feb 3. PMID: 26850986. 20: He J, Bo F, Tu Y, Azietaku JT, Dou T, Ouyang H, Chang Y, Liu H, Gao X. A validated LC-MS/MS assay for the simultaneous determination of periplocin and its two metabolites, periplocymarin and periplogenin in rat plasma: Application to a pharmacokinetic study. J Pharm Biomed Anal. 2015 Oct 10;114:292-5. doi: 10.1016/j.jpba.2015.06.008. Epub 2015 Jun 10. PMID: 26093244.