periplocin profile

periplocin: isolated from Periploca calophylla [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Periploca	genus	A plant genus of the family Apocynaceae. It is a source of periplocosides (pregnane steroid glycosides).[MeSH]	Apocynaceae	The dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]
Periploca calophylla	species	[no description available]	Apocynaceae	The dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

ID Source	ID
PubMed CID	14463159
MeSH ID	M0487436

Synonym
glucoperiplocymarin
periplocin
periplogenin + d-cymarose + d-glucose [german]
periplocoside
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)-
brn 0075742
S9181
periplogenin + d-cymarose + d-glucose
199x940o3k ,
unii-199x940o3k
4-18-00-02439 (beilstein handbook reference)
13137-64-9
AC-34379
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.)-
periplocin [mi]
periplogenin 3-o-(.beta.-d-glucopyranosyl-(1->4)-.beta.-d-cymaropyranoside)
AS-75113
(3?,5?)-3-[(2,6-dideoxy-4-o-?-d-glucopyranosyl-3-o-methyl-?-d-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-card-20(22)-enolide; periplocin (6ci,7ci,8ci); (3?,5?)-3-[(2,6-dideoxy-4-o-?-d-glucopyranosyl-3-o-methyl-?-d-ribo-hexopyranosyl)oxy]-5,14-dihydroxycard-20
AKOS030573522
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]
card-20(22)-enolide, 3-[(2,6-dideoxy-4-o-beta-d-glucopyranosyl-3-o-methyl-beta-d-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-, (3beta,5beta)-
CS-0016801
HY-N1381
CCG-270383
Q27252090
DTXSID501030586

Research Excerpts

Overview

Piplocin is a cardiac glycoside and has been used widely in the clinic for its cardiotonic, anti-inflammatory and anti-tumor effects. It shows poor absorption when administered orally.

Excerpt	Reference	Relevance
"Periplocin is a monomeric compound that exhibits anti-tumor activities. "	( Periplocin inhibits the growth of pancreatic cancer by inducing apoptosis via AMPK-mTOR signaling. Chen, B; Li, Y; Sun, L; Wang, C; Xie, G, 2021)	3.51
"Periplocin is a cardiac glycoside and has been used widely in the clinic for its cardiotonic, anti-inflammatory and anti-tumor effects. "	( Tissue distribution study of periplocin and its two metabolites in rats by a validated LC-MS/MS method. Azietaku, JT; Chang, Y; Gao, X; He, J; Liu, H; Ouyang, H; Sun, M; Tang, Z; Wang, M; Zhang, D, 2018)	2.21
"Periplocin is an active digitalis-like component from Cortex Periplocae, which has been widely used in the treatment of heart diseases in China for many years. "	( Gene expression profiling of the proliferative effect of periplocin on mouse cardiac microvascular endothelial cells. Gao, XM; Hu, LM; Jiang, M; Liu, H; Liu, Y; Wang, XY; Zhang, BL; Zhang, H, 2010)	2.05
"Periplocin is an important compound of Cortex Periplocae, which shows poor absorption when administered orally. "	( The assessment of absorption of periplocin in situ via intestinal perfusion of rats by HPLC. Gao, XM; Liu, CX; Pan, GX; Ren, XL; Xie, YS, 2008)	2.07

Actions

Periplocin could increase cell viability to a level lower than ouabain in the MTT analysis, but decrease LDH release simultaneously.

Excerpt	Reference	Relevance
"Periplocin displays a promising mechanism of action in sarcoma cells because altering the death receptor expression is an interesting target in sarcoma treatment especially to overcome TRAIL resistance."	( Periplocin, the most anti-proliferative constituent of Periploca sepium, specifically kills liposarcoma cells by death receptor mediated apoptosis. Bauer, R; Kaltenegger, H; Kretschmer, N; Kunert, O; Leithner, A; Lohberger, B; Rinner, B; Stuendl, N; Wagner, S; Wohlmuther, J, 2018)	3.37
"Periplocin could increase cell viability to a level lower than ouabain in the MTT analysis, but decrease LDH release simultaneously. "	( Gene expression profiling of the proliferative effect of periplocin on mouse cardiac microvascular endothelial cells. Gao, XM; Hu, LM; Jiang, M; Liu, H; Liu, Y; Wang, XY; Zhang, BL; Zhang, H, 2010)	2.05

Treatment

Excerpt	Reference	Relevance
"Periplocin is used for treatment of rheumatoid arthritis, reinforcement of bones and tendons, palpitations or shortness of breath and lower extremity edema in traditional medicine. "	( Comparative proteomic analysis of anti-cancer mechanism by periplocin treatment in lung cancer cells. Kang, J; Lu, Z; Song, Q; Yang, J; Yang, P; Zhang, X; Zhao, X, 2014)	2.09

Toxicity

Excerpt	Reference	Relevance
" Orally ingesting periplocin in high doses or over prolonged periods would cause serious adverse reactions, especially cardiotoxicity, which limits the applications of periplocin in clinical therapy."	( Metabolomics study on the periplocin-induced cardiotoxicity and the compatibility of periplocin and Panax notoginseng saponins in reducing cardiotoxicity in rats by GC-MS. Fan, Y; He, J; Huang, X; Li, L; Ouyang, H; Wang, S; Wang, W; Xue, Z, 2021)	1.26

Pharmacokinetics

The proposed method was successfully applied to evaluating the pharmacokinetic studies of periplocin and its metabolites in rats. Using this method, the concentrations were established after oral administration of Cortex Periplocae extract to rats.

Excerpt	Reference	Relevance
" The validated method was applied to the pharmacokinetic study of periplocin in rat plasma after intravenous and intramuscular administration."	( Determination and pharmacokinetics of periplocin in rat plasma by LC-MS. Bi, K; Che, S; Chen, X; Liu, W; Lu, D; Yi, L; Zhang, Q, 2010)	0.87
" The proposed method was successfully applied to evaluating the pharmacokinetic studies of periplocin and its metabolites (periplocymarin and periplogenin) in rats after a single oral administration of periplocin at 50 mg/kg."	( A validated LC-MS/MS assay for the simultaneous determination of periplocin and its two metabolites, periplocymarin and periplogenin in rat plasma: Application to a pharmacokinetic study. Azietaku, JT; Bo, F; Chang, Y; Dou, T; Gao, X; He, J; Liu, H; Ouyang, H; Tu, Y, 2015)	0.88
" Using this method, the concentrations of periplocin, PM, PG, PSM and PSN were established after oral administration of Cortex Periplocae extract to rats, and the pharmacokinetic characteristics of periplocin, PM, PG, PSM and PSN were assessed."	( Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study. Gao, Y; Li, Y; Wang, Q; Wang, S; Wang, W; Wei, M; Wu, J; Wu, S; Yang, W; Yu, X; Yuan, Z; Zhu, M, 2022)	1.27

Compound-Compound Interactions

Excerpt	Reference	Relevance
" No obvious indications of metabolism were observed in the in vitro incubation system, which suggests that periplocin did not interact with the hepatic drug metabolic enzymes."	( P-glycoprotein- and organic anion-transporting polypeptide-mediated transport of periplocin may lead to drug-herb/drug-drug interactions. Deng, F; He, X; Koomson, E; Liang, S; Martey, ON; Shi, X; Wen, H; Xing, H, 2014)	0.84

Bioavailability

Excerpt	Reference	Relevance
" The efflux function of P-gp may be partly responsible for the low permeability and bioavailability of periplocin."	( P-glycoprotein- and organic anion-transporting polypeptide-mediated transport of periplocin may lead to drug-herb/drug-drug interactions. Deng, F; He, X; Koomson, E; Liang, S; Martey, ON; Shi, X; Wen, H; Xing, H, 2014)	0.84

Dosage Studied

Excerpt	Relevance	Reference
" In this study, a sensitive and reliable liquid chromatography-tandem mass spectrometry method was developed and validated to identify and quantify periplocin and its two metabolites in rat tissue after a single dosage of perplocin at 50 mg/kg."	( Tissue distribution study of periplocin and its two metabolites in rats by a validated LC-MS/MS method. Azietaku, JT; Chang, Y; Gao, X; He, J; Liu, H; Ouyang, H; Sun, M; Tang, Z; Wang, M; Zhang, D, 2018)	0.97

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (8.57)	18.7374
1990's	0 (0.00)	18.2507
2000's	5 (14.29)	29.6817
2010's	17 (48.57)	24.3611
2020's	10 (28.57)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	36 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.02	1	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.11	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.05	1	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
desoxycorticosterone acetate Desoxycorticosterone Acetate: The 21-acetate derivative of desoxycorticosterone.	2.6	1	corticosteroid hormone
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.11	1	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
periplogenin periplogenin: structure	3.1	4
lanthanum [no description available]	2.06	1	f-block element atom; lanthanoid atom; scandium group element atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.06	1	copper group element atom; elemental silver	Escherichia coli metabolite
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	1.92	1	D-glucopyranose	epitope; mouse metabolite
arabinose [no description available]	2.02	1	L-arabinose	Escherichia coli metabolite; mouse metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	2.05	1	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
glycosides [no description available]	2.64	3
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.05	1	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
digitoxigenin Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).	3.1	4	14beta-hydroxy steroid; 3beta-hydroxy steroid
beta-escin [no description available]	4.82	31
periplocymarin periplocymarin: has antineoplastic activity; isolated from both Periploca sepium and Periploca graeca	3.1	4
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.05	1

Condition	Relationship Strength	Studies
Cardiac Remodeling, Ventricular [description not available]	2.6	1
Cardiac Failure [description not available]	2.38	2
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	7.38	2
Bone Loss, Osteoclastic [description not available]	2.6	1
Innate Inflammatory Response [description not available]	2.76	2
Age-Related Osteoporosis [description not available]	2.6	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.76	2
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	7.6	1
Hepatocellular Carcinoma [description not available]	7.6	1
Cancer of Liver [description not available]	2.6	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.6	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.6	1
Colorectal Cancer [description not available]	7.6	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.6	1
Esophageal Squamous Cell Carcinoma A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.	7.21	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.21	1
Rheumatoid Arthritis [description not available]	7.25	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.25	1
Cancer of Pancreas [description not available]	2.31	1
Invasiveness, Neoplasm [description not available]	2.31	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.31	1
Germinoblastoma [description not available]	2.31	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	7.31	1
Cardiac Toxicity [description not available]	2.59	2
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.59	2
Adjuvant Arthritis [description not available]	2.15	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.49	2
Atypical Lipomatous Tumor [description not available]	2.17	1
Liposarcoma A malignant tumor derived from primitive or embryonal lipoblastic cells. It may be composed of well-differentiated fat cells or may be dedifferentiated: myxoid (LIPOSARCOMA, MYXOID), round-celled, or pleomorphic, usually in association with a rich network of capillaries. Recurrences are common and dedifferentiated liposarcomas metastasize to the lungs or serosal surfaces. (From Dorland, 27th ed; Stedman, 25th ed)	7.17	1
Cancer of Stomach [description not available]	2.57	2
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.57	2
Cancer of Lung [description not available]	2.48	2
Lung Neoplasms Tumors or cancer of the LUNG.	2.48	2
Cancer of Colon [description not available]	2.46	2
Colonic Neoplasms Tumors or cancer of the COLON.	2.46	2
Benign Neoplasms [description not available]	2.05	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.05	1
Carcinoma, Anaplastic [description not available]	2.05	1
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.05	1

periplocin

Description

Cross-References

Synonyms (26)

Research Excerpts

Overview

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Research

Studies (35)

Market Indicators

Research Demand Index: 30.70

Study Types

periplocin

Description

Related Flora

Cross-References

Synonyms (26)

Research Excerpts

Overview

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Research

Studies (35)

Market Indicators

Research Demand Index: 30.70

Study Types

Related Drugs (17)

Related Conditions (39)