Periplocin

Modify Date: 2024-01-02 11:03:55

Periplocin Structure
Periplocin structure
Common Name Periplocin
CAS Number 13137-64-9 Molecular Weight 682.795
Density 1.4±0.1 g/cm3 Boiling Point 877.4±65.0 °C at 760 mmHg
Molecular Formula C36H56O13 Melting Point 205°C
MSDS N/A Flash Point 272.8±27.8 °C

 Use of Periplocin


Periplocin is a cardiotonic steroid isolated from Periploca forrestii. Periplocin promotes tumor cell apoptosis and inhibits tumor growth. Periplocin has the potential to facilitate wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase[1][2].

 Names

Name 3-[(3S,5S,10R,13R,14S,17R)-3-[(2R,5R)-6-[[(3R,6S)-4,6-dihydroxy-2-methyloxan-3-yl]oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-5,14-dihydroxy-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
Synonym More Synonyms

 Periplocin Biological Activity

Description Periplocin is a cardiotonic steroid isolated from Periploca forrestii. Periplocin promotes tumor cell apoptosis and inhibits tumor growth. Periplocin has the potential to facilitate wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase[1][2].
Related Catalog
Target

Apoptosis[2]

In Vitro Periplocin (5-20 μM; 48 hours; L929 cells) treatment shows increased proliferation up to 131% at 20 μM[1]. Periplocin (5-20 μM; 30-120 minutes; L929 cells) increases phosphorylation of Src, ERK, PI3K and Akt at active sites in a dosedependent and time-dependent manner.Periplocin (5-20 μM; 48 hours) significantly promotes migration of fibroblast cell[1]. Periplocin (5-20 μM; 48 hours) increases collagen production in L929 fibroblast[1]. Periplocin induces Na/KATPase mediates the activation of Src/ERK and PI3K/Akt pathways[1]. Cell Viability Assay[1] Cell Line: L929 cells Concentration: 5 μM, 10 μM, 20 μM Incubation Time: 48 hours Result: Showed increased proliferation up to 131% at 20 μM. Western Blot Analysis[1] Cell Line: L929 cells Concentration: 5 μM, 10 μM, 20 μM Incubation Time: 30 minutes, 60 minutes, 120 minutes Result: Increased phosphorylation of Src, ERK, PI3K and Akt at active sites in a dosedependent and time-dependent manner.
In Vivo Periplocin (5-20 mg/kg; intraperitoneal injection; daily; for 14 days; female SCID mice) treatment represses the growth of hepatocellular carcinoma (HCC) in xenograft tumor model in mice[2]. Animal Model: Female SCID mice (6-8 weeks old) injected with Huh-7 cells[2] Dosage: 5 mg/kg, 20 mg/kg Administration: Intraperitoneal injection; daily; for 14 days Result: Repressed the growth of hepatocellular carcinoma (HCC) in xenograft tumor model in mice.
References

[1]. Chen L, et al. Periplocin promotes wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase. Phytomedicine. 2019 Apr;57:72-83.

[2]. Cheng CF, et al. Antitumor Effect of Periplocin in TRAIL-Resistant Human Hepatocellular Carcinoma Cells through Downregulation of IAPs. Evid Based Complement Alternat Med. 2013;2013:958025.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 877.4±65.0 °C at 760 mmHg
Melting Point 205°C
Molecular Formula C36H56O13
Molecular Weight 682.795
Flash Point 272.8±27.8 °C
Exact Mass 682.356445
PSA 193.83000
LogP -1.36
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.624
Storage condition 2-8C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FH4919700
CHEMICAL NAME :
Card-20(22)-enolide, 3-((2,6-dideoxy-4-O-beta-D-glucopyranosyl-3-O-methyl- beta-D-ribo- hexopyranosyl)oxy)-5,14-dihydroxy-, (3-beta,5-beta)-
CAS REGISTRY NUMBER :
13137-64-9
BEILSTEIN REFERENCE NO. :
0075742
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C36-H56-O13
MOLECULAR WEIGHT :
696.92
WISWESSER LINE NOTATION :
L E5 B666TJ A1 E1 IQ MQ F- DT5OV EHJ& OO- FT6OTJ B1 CQ DO- BT6OTJ CQ DQ EQ F1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
480 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
2500 ug/kg
TOXIC EFFECTS :
Behavioral - muscle weakness Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - nausea or vomiting
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
120 ug/kg
TOXIC EFFECTS :
Behavioral - muscle weakness Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - nausea or vomiting
REFERENCE :
85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,193,1963
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
121 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,151,1963
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Cardiac - arrhythmias (including changes in conduction) Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
34 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926

 Synonyms

Card-20(22)-enolide, 3-[(2,6-dideoxy-4-O-β-D-glucopyranosyl-β-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-, (3β,5β)-
Glucoperiplocymarin
corchorusoside C
(3β,5β)-3-{[2,6-Dideoxy-4-O-(β-D-glucopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-5,14-dihydroxycard-20(22)-enolide
(3β,5β)-3-{[2,6-Dideoxy-4-O-(β-D-glucopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-5,14-dihydroxycard-20(22)-enolido(2-)
Periplogenin + D-cymarose + D-glucose [German]
periplocin
Periplogenin + D-cymarose + D-glucose
Periplocoside
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Price: ¥1230/10 mM * 1 mL in DMSO

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