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Periplocin

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Periplocin
Names
IUPAC name 3-oxyoxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopentaphenanthren-17-yl]-2H-furan-5-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.208.699 Edit this at Wikidata
EC Number
  • 683-188-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C36H56O13/c1-18-31(49-32-30(41)29(40)28(39)25(16-37)48-32)24(44-4)14-27(46-18)47-20-5-9-33(2)22-6-10-34(3)21(19-13-26(38)45-17-19)8-12-36(34,43)23(22)7-11-35(33,42)15-20/h13,18,20-25,27-32,37,39-43H,5-12,14-17H2,1-4H3/t18-,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1Key: KWBPKUMWVXUSCA-AXQDKOMKSA-N
SMILES
  • C1((C(O1)O2CC3(4CC5((CC5(4CC3(C2)O)O)C6=CC(=O)OC6)C)C)OC)O7((((O7)CO)O)O)O
Properties
Chemical formula C36H56O13
Molar mass 696.831 g·mol
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS08: Health hazard
Signal word Danger
Hazard statements H300, H330, H373
Precautionary statements P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P319, P320, P321, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Periplocin is a plant-derived glycoside whereby the sugar moiety is linked to a steroid. It can be extracted from cortex periplocae (CPP), the dry root of Periploca sepium.

CPP's healing activities have long been recognized in traditional Chinese medicine where it has been used to treat rheumatoid arthritis. Scientific studies of CPP have identified over 100 components of which periplocin has been a major focus both for its toxicity as well as for its potential beneficial pharmaceutical effects. Besides the cardiac glycosides with periplocin as its main constituent, the CPP contains different C21-steroidal glycosides such as periplocodides and pregnene derivatives, fatty acids, volatile oils, terpenes, and others.

Higher doses of periplocin are toxic as a cardiac glycoside.

Potential medical applications of periplocin are focused on these areas:

  • Anti-inflammatory effects. Periplocin and its derivatives have shown anti-inflammatory effects.
  • Antitumor activity. A number of in vivo and in vitro studies suggest that periplocin inhibits tumor growth. Studies show both inhibition of growth as well as induction of apoptosis.
  • Cardiotonic activity. Traditional use includes an application for heart failure. Structure and function of cardiac muscle were improved in rats.

Periplocin's metabolites, periplocymarin and periplogenin, have also shown some pharmacological effects.

Potential senolytic activity was suggested by an AI structural analysis of over 4,000 chemicals in 2013.

References

  1. "Periplocin". pubchem.ncbi.nlm.nih.gov.
  2. ^ Li, Yang; Li, Jin; Zhou, Kun; He, Jun; Cao, Jun; An, Mingrui; Chang, Yan-Xu (2016). "A Review on Phytochemistry and Pharmacology of Cortex Periplocae". Molecules. 21 (12): 1702. doi:10.3390/molecules21121702. PMC 6272874. PMID 27973416.
  3. ^ Guo, Hao; Mao, Haoping; Pan, Guixiang; Zhang, Han; Fan, Ganwei; Li, Weiwei; Zhou, Kun; Zhu, Yan; Yanagihara, Nobuyuki; Gao, Xiumei (2013). "Antagonism of Cortex Periplocae extract-induced catecholamines secretion by Panax notoginseng saponins in cultured bovine adrenal medullary cells by drug combinations". Journal of Ethnopharmacology. 147 (2): 447–455. doi:10.1016/j.jep.2013.03.036. PMID 23524165.
  4. Wang, Wei; Fan, Yuqi; Huang, Xuhua; Li, Li; Wang, Songrui; Xue, Zixiang; Ouyang, Huizi; He, Jun (2021). "Metabolomics study on the periplocin-induced cardiotoxicity and the compatibility of periplocin and Panax notoginseng saponins in reducing cardiotoxicity in rats by GC-MS". Journal of Separation Science. 44 (14): 2785–2797. doi:10.1002/jssc.202001262. PMID 33961332. S2CID 233985785.
  5. Wang, Shuyao; Yu, Xin; Wu, Siyang; Yang, Wei; Gao, Yang; Wang, Weihua; Wang, Qiutao; Wei, Mengmeng; Zhu, Mingying; Wu, Jiarui; Yuan, Zheng; Li, Yingfei (2022). "Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study". Biomedical Chromatography. 36 (3): e5283. doi:10.1002/bmc.5283. PMID 34816469. S2CID 244529941.
  6. NN (June 15, 2023). "AI and anti-aging research: Unveiling the latest drug discovery". Open Access Government.
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