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
• Article Data: 6

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

General Description

Periplogenin is a naturally occurring chemical compound found in various plants, including Periploca aphylla and Periploca graeca. It belongs to the class of compounds known as cardenolides, which are glycosides of the steroid nucleus. Periplogenin has been studied for its potential pharmacological properties, including its ability to inhibit the growth of cancer cells and its potential role in the treatment of cardiovascular diseases. Additionally, it has been investigated for its potential anti-inflammatory and analgesic effects. Research on periplogenin is ongoing, and further studies are needed to fully understand its biological activities and potential therapeutic applications.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.