Chemistry:Periplocin
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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
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C36H56O13 | |
| Molar mass | 696.831 g·mol−1 |
| Hazards | |
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| GHS Signal word | Danger |
| H300, H330, H373 | |
| P260, P264, P270, P271, P284, P301+316Script error: No such module "Preview warning".Category:GHS errors, P304+340, P316Script error: No such module "Preview warning".Category:GHS errors, P319Script error: No such module "Preview warning".Category:GHS errors, P320, P321, P330, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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]
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
- ↑ "Periplocin" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/14463159#section=Safety-and-Hazards.
- ↑ 2.0 2.1 2.2 2.3 2.4 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. PMID 27973416.
- ↑ 3.0 3.1 Guo, Hao; Mao, Haoping; Pan, Guixiang; Zhang, Han; Fan, Ganwei; Li, Weiwei; Zhou, Kun; Zhu, Yan et al. (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.
- ↑ 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.
- ↑ Wang, Shuyao; Yu, Xin; Wu, Siyang; Yang, Wei; Gao, Yang; Wang, Weihua; Wang, Qiutao; Wei, Mengmeng et al. (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.
- ↑ NN (June 15, 2023). "AI and anti-aging research: Unveiling the latest drug discovery". Open Access Government. https://www.openaccessgovernment.org/ai-anti-aging-research-drugs-malfunctioning-cells/161082/.
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