Periplocin

Periplocin is a plant-derived glycoside whereby the sugar moiety is linked to a steroid. First reported in 1897 from the stem bark of Periploca graeca from the southwest Caucasus in the Black Sea region.^[2][3] It can also be extracted from Periploca calophylla, Periploca forrestii, Periploca omeiensis^[2] and the traditional Chinese medicine cortex periplocae (CPP), the dry root bark of Periploca sepium.^[2][4][5]

Quick facts Names, Identifiers ...

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
CAS Number	13137-64-9 N
3D model (JSmol)	Interactive image
ChemSpider	16739442
ECHA InfoCard	100.208.699
EC Number	683-188-2
PubChem CID	14463159
UNII	199X940O3K
CompTox Dashboard (EPA)	DTXSID501030586
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/s1 Key: KWBPKUMWVXUSCA-AXQDKOMKSA-N
SMILES 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
Chemical formula	C36H56O13
Molar mass	696.831 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
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 [77 °F], 100 kPa). Infobox references

Close

High doses of periplocin are toxic as a cardiac glycoside.^[2][6]

CPP's healing activities have long been recognized in traditional Chinese medicine^[5] where it has been used to treat rheumatoid arthritis.^[4] 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.^[4] 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.^[4]

Potential medical applications of periplocin are focused on these areas:^[4]

• 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,^[7] have also shown some pharmacological effects.

Potential senolytic activity was suggested by an AI structural analysis of over 4,000 chemicals in 2013.^[8]