514-39-6

Basic information

• Product Name: periplogenin
• Synonyms: periplogenin;3β,5,14-Trihydroxy-5β,14β-card-20(22)-enolide;3β,5,14-Trihydroxy-5β-cardanolide-20(22)-ene;5β-Hydroxydigitoxigenin;Desoxostrophanthidin;3-beta,5,14-Trihydroxy-5-beta-card-20(22)-enolide;5-beta-Card-20(22)-enolide, 3-beta,5,14-trihydroxy-;5-beta-Hydroxydigitoxigenin
• CAS NO: 514-39-6
• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.517
• Mol File: 514-39-6.mol

Chemical Properties

• Melting Point: 245-248℃
• Boiling Point: 583°Cat760mmHg
• Flash Point: 200.4°C
• Appearance: /
• Density: 1.320±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.06E-16mmHg at 25°C
• Refractive Index: 1.621
• PKA: 14.60±0.70(Predicted)
• CAS DataBase Reference: periplogenin(CAS DataBase Reference)
• NIST Chemistry Reference: periplogenin(514-39-6)
• EPA Substance Registry System: periplogenin(514-39-6)

Safety Data

• Hazardous Substances Data: 514-39-6(Hazardous Substances Data)

Usage

Uses

Used in Cancer Treatment:
Periplogenin is used as an anticancer agent for its potential ability to inhibit the growth of cancer cells. It is being studied for its potential role in the treatment of various types of cancer.
Used in Cardiovascular Disease Treatment:
Periplogenin is used as a potential therapeutic agent for cardiovascular diseases due to its pharmacological properties that may contribute to the treatment and management of such conditions.
Used in Anti-inflammatory and Analgesic Applications:
Periplogenin is used as an anti-inflammatory and analgesic agent, given its potential to reduce inflammation and alleviate pain, which is currently under investigation for its effectiveness in these areas.
Note: The specific application types and reasons are inferred from the provided materials, as the exact uses in different industries or as part of specific formulations are not detailed in the provided information. Further research is necessary to determine the exact applications and industries where periplogenin may be utilized.

InChI:InChI=1/C23H34O5/c1-20-7-3-15(24)12-22(20,26)9-5-18-17(20)4-8-21(2)16(6-10-23(18,21)27)14-11-19(25)28-13-14/h11,15-18,24,26-27H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,20+,21+,22-,23-/m0/s1

Upstream product

• 143-62-4 digitoxigenin 
• 143-62-4 (+)-digitoxigenin 
• 57-50-1 Sucrose 
• 221380-14-9 neridiginoside 

Downstream Products

• 18531-44-7 periplogenin glucoside 
• 6246-62-4 14-hydroxy-14β-carda-3,5,20(22)-trienolide 

Relevant articles and documents

Biotransformation of digitoxigenin by cultured Strophanthus hybrid cells

Hybrid cells between Strophanthus gratus and S. amboensis were obtained by electrofusion and confirmed to be hybrids through isozyme and RFLP analyses. Because a new and hybrid compound, 17βH-periplogenin β-D- glucoside, was isolated as a biotransformation product of digitoxigenin by the hybrid cells, isomerization of 17β-lactone ring on S. gratus and glucosylation on S. amboensis were demonstrated simultaneously as the biotransformation abilities in the hybrid cells. Moreover, the productivity of the hybrid compound was increased by raising the sucrose concentration.

Corchorusosides A, B, C, D, and E, new cardiotonic oligoglycosides from the seeds of Corchorus olitorius L. (Moroheiya)

The methanolic extract of the seeds of Corchorus olitorius L. (Moroheiya) was found to show inhibitory effect against Na+,K+-ATPase and positive inotropic activity in the guinea pig isolated atria. Through bioassay-guided separation from the methanolic extract, new cardenolide oligoglycosides called corchorusosides A, B, C, D, and E were isolated together with six known cardenolide oligoglycosides. The structures of new corchorusosides were determined on the basis of chemical and physicochemical evidence. All cardenolide oligoglycosides from the seeds showed potent inhibitory activity against Na+,K+-ATPase, which was equivalent to those of digitoxin and ouabain. The methanolic extract, glycoside fraction, and principal glycoside showed potent acute toxicity by intraperitoneal administration, whereas they showed little acute toxicity by oral administration. Furthermore, by means of HPLC quantitative analysis of the cardiotonic oligoglycosides, it was found that the glycosides mainly distributed in the seeds , while the edible parts such as fresh young leaves and stems contained only trace amount.

Biotransformation of digitoxigenin by cultured ginseng cells

Nine compounds, including a new compound (digitoxigenin β-D-glucoside malonyl ester), were isolated as biotransformation products of digitoxigenin by cell suspension cultures of Panax ginseng (Pg-3 cell line). At the same time, two known products were identified by TLC and HPLC.

CARDENOLIDE DIGLYCOSIDES FROM OXYSTELMA ESCULENTUM

Two new cardenolide diglycosides, named oxystelmoside and oxystelmine, were isolated from the dried roots of Oxystelma esculentum.On the basis of chemical and spectroscopic evidence their structures were established as uzarigenin 3-O-β-D-xylopyranosyl(1->4)-O-β-D-digitalopyranoside and periplogenin 3-O-6-deoxy-β-D-glucopyranosyl(1->4)-α-D-digitalopyranoside. Key Word Index - Oxystelma esculentum; Asclepiadaceae; roots; oxystelmoside; oxystelmine; steroid; cardenolide glycoside.

BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL SUSPENSION CULTURES OF STROPHANTHUS DIVARICATUS

Eight compounds, including a new compound (3-epi-17βH-gitoxigenin) were isolated as biotransformation products of digitoxigenin by cell suspension cultures of Strophanthus divaricatus.At the same time, three products were identified by TLC and HPLC. 16β-Hydroxylation and isomerization of the 17β-butenolide ring of digitoxigenin molecule were demonstrated using this cell suspension culture. Key Word Index - Strophanthus divaricatus; Apocynaceae; biotransformation; 16β-hydroxylation; isomerization of 17β-butenolide ring; cardenolides; digitoxigenin; 17βH-gitoxigenin; 3-epi-17βH-gitoxigenin.

BIOTRANSFORMATION OF DIGITOXIGENIN BY GINSENG HAIRY ROOT CULTURES

Five new compounds (three esters and two glycosides) and seven previously reported compounds were isolated as biotransformation products of digitoxigenin by ginseng hairy root cultures.The new esters and glycosides were elucidated as digitoxigenin stearate, digitoxigenin palmitate, digitoxigenin myristate, 3-epidigitoxigenin β-D-gentiobioside and digitoxigenin β-D-sophoroside using 1H and 13C NMR and FAB mass spectral data.Biotransformations involving esterification (of stearic acid, palmitic acid, myristic acid and lauric acid) and glycosylation (of gentiobiose and sophorose) of digitoxigenin have been demonstrated for the first time in the plant cell and tissue cultures.The hairy roots showed high glycosylation ability to the digitoxigenin molecule.