Periplocin

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.[2][3]

Periplocin
Names
IUPAC name
3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.208.699
EC Number
  • 683-188-2
UNII
  • 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/s1
    Key: KWBPKUMWVXUSCA-AXQDKOMKSA-N
  • C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
Properties
C36H56O13
Molar mass 696.831 g·mol−1
Hazards
GHS labelling:[1]
GHS06: ToxicGHS08: Health hazard
Danger
H300, H330, H373
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 [77 °F], 100 kPa).
Infobox references

CPP's healing activities have long been recognized in traditional Chinese medicine[3] where it has been used to treat rheumatoid arthritis.[2] 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.[2] 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.[2]

Higher doses of periplocin are toxic as a cardiac glycoside.[4]

Potential medical applications of periplocin are focused on these areas:[2]

  • 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,[5] have also shown some pharmacological effects.

Potential senolytic activity was suggested by an AI structural analysis of over 4,000 chemicals in 2013.[6]

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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