Periplocin

Names

[ Name ]:
Periplocin

[Synonym ]:
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

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]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[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