Periplocin

Last updated
Periplocin
Periplocin.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 683-188-2
PubChem CID
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]
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
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).

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]

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]

Related Research Articles

<span class="mw-page-title-main">Cardiac glycoside</span> Class of organic compounds

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.

<span class="mw-page-title-main">Ginseng</span> Root of a plant used in herbal preparations

Ginseng is the root of plants in the genus Panax, such as Korean ginseng, South China ginseng, and American ginseng, typically characterized by the presence of ginsenosides and gintonin. Ginseng is most commonly used in the cuisines and medicines of China and Korea.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

<span class="mw-page-title-main">Naringenin</span> Chemical compound

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs.

<i>Adonis vernalis</i> Species of flowering plant in the buttercup family Ranunculaceae

Adonis vernalis, known variously as pheasant's eye, spring pheasant's eye, yellow pheasant's eye and false hellebore, is a perennial flowering plant in the buttercup family Ranunculaceae. It is found in dry meadows and steppes in Eurasia. More specifically, this plant grows in a wide range of locations which include open forests, forest clearings, dry meadows, mesic steppe, and mostly calcareous soil. Isolated populations are found from Spain in the west across Central Europe with fine examples in Valais, Switzerland, and southern Europe, reaching southern Sweden in the north and Abruzzo in the south, with its main area of distribution being the Pannonian Basin and the West Siberian Plain. In contrast to most other European Adonis species, the flowers appear in springtime, and are up to 80 mm (3.1 in) in diameter, with up to 20 bright yellow petals. Not only do the flowers begin to grow, but so do the plants aerial organs, from around April to May.

<span class="mw-page-title-main">Ursolic acid</span> Pentacyclic chemical compound found in fruits

Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

<span class="mw-page-title-main">Ginsenoside</span> Class of steroids

Ginsenosides or panaxosides are a class of natural product steroid glycosides and triterpene saponins. Compounds in this family are found almost exclusively in the plant genus Panax (ginseng), which has a long history of use in traditional medicine that has led to the study of pharmacological effects of ginseng compounds. As a class, ginsenosides exhibit a large variety of subtle and difficult-to-characterize biological effects when studied in isolation.

<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.

<span class="mw-page-title-main">Baicalin</span> Chemical compound

As baicalin is a flavone glycoside, it is a flavonoid. It is the glucuronide of baicalein.

<span class="mw-page-title-main">Salidroside</span> Chemical compound

Salidroside (rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It has been studied, along with rosavin, as one of the potential compounds responsible for the putative antidepressant and anxiolytic actions of this plant. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardized for rosavin content rather than salidroside.

<span class="mw-page-title-main">Arenobufagin</span> Chemical compound

Arenobufagin is a cardiotoxic bufanolide steroid secreted by the Argentine toad Bufo arenarum. It has effects similar to digitalis, blocking the Na+/K+ pump in heart tissue.

<span class="mw-page-title-main">Cinobufagin</span> Chemical compound

Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad Bufo gargarizans. It has similar effects to digitalis and is used in traditional Chinese medicine.

<span class="mw-page-title-main">Protopanaxadiol</span> Chemical compound

Protopanaxadiol (PPD) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng and in notoginseng.

<span class="mw-page-title-main">Ampelopsin</span> Chemical compound

Ampelopsin, also known as dihydromyricetin and DHM, when purported as an effective ingredient in supplements and other tonics, is a flavanonol, a type of flavonoid. It is extracted from the Japanese raisin tree and found in Ampelopsis species japonica, megalophylla, and grossedentata; Cercidiphyllum japonicum; Hovenia dulcis; Rhododendron cinnabarinum; some Pinus species; and some Cedrus species, as well as in Salix sachalinensis.

<span class="mw-page-title-main">Palmatine</span> Chemical compound

Palmatine is a protoberberine alkaloid found in several plants including Phellodendron amurense, Coptis Chinensis and Corydalis yanhusuo, Tinospora cordifolia, Tinospora sagittata, Phellodendron amurense, Stephania yunnanensis.

<span class="mw-page-title-main">Pseudoginsenoside F11</span> Chemical compound

Pseudoginsenoside F11 is a chemical natural product found in American ginseng but not in Asian ginseng, although it has similar properties to the Asian ginseng compound ginsenoside Rf. The molecule is a triterpenoid saponin member of the dammarane family and contains a four-ring rigid skeleton. Compounds in the ginsenoside family are found almost exclusively in plants of the genus Panax. A wide variety of difficult-to-characterize in vitro effects have been reported for the compounds in isolation. Pseudoginsenoside F11 and its derivatives are sometimes referred to as having an ocotillol-type skeleton structure.

<span class="mw-page-title-main">Geniposide</span> Chemical compound

Geniposide, the glycoside form of genipin, is a bioactive iridoid glycoside that is found in a wide variety of medicinal herbs, such as Gardenia jasminoides (fruits) . Geniposide shows several pharmacological effects including neuroprotective, antidiabetic, hepatoprotective, anti-inflammatory, analgesic, antidepressant-like, cardioprotective, antioxidant, immune-regulatory, antithrombotic and antitumoral activity. These pharmacology benefits arise through the modulating action of geniposide on several proteins and genes that are associated with inflammatory and oxidative stress processes.

<span class="mw-page-title-main">Ginsenoside Rb1</span> Chemical compound

Ginsenoside Rb1 (or Ginsenoside Rb1 or GRb1 or GRb1) is a chemical compound belonging to the ginsenoside family.

<span class="mw-page-title-main">Forsythoside B</span>

Forsythoside B is a natural product from the phenylpropanoid glycoside group, which is found in a number of plant species such as Marrubium alysson, Phlomis armeniaca, Scutellaria salviifolia, Phlomoides tuberosa, Phlomoides rotata, Pedicularis longiflora and Teucrium chamaedrys, several of which are used in Chinese traditional medicine in preparations such as Shuanghuanglian (双黄连). It acts as an inhibitor of inflammatory mediators such as TNF-alpha, IL-6, IκB and NF-κB, as well as the temperature sensitive channel TRPV3, but also activates the RhoA/ROCK signaling pathway which can cause hypersensitivity reactions when it is injected intravenously.

<span class="mw-page-title-main">Ciprofol</span> Intravenous medication used in general anaesthesia

Ciprofol is a novel 2,6-disubstituted phenol derivative that is used for the intravenous induction of general anesthesia. A short-acting and highly selective γ-aminobutyric acid agonist, ciprofol is 4–6 times more potent than other phenol derivatives such as propofol or fospropofol.

References

  1. "Periplocin". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 3 4 5 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. 1 2 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.