PERUVOSIDE Property

Melting point:

161-164°C

alpha 

D22 -71.7° (c = 1.54 in methanol)

Boiling point:

540.83°C (rough estimate)

Density 

1.1277 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

12.92±0.70(Predicted)

form 

powder

color 

light yellow

Safety

Hazard Codes 

T

Risk Statements 

23/24/25

Safety Statements 

36/37/39-45

WGK Germany 

3

RTECS 

FH4915000

Toxicity

cat,LD50,intravenous,145ug/kg (0.145mg/kg),GASTROINTESTINAL: NAUSEA OR VOMITINGCARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)CARDIAC: CHANGE IN RATE,Archives Internationales de Pharmacodynamie et de Therapie. Vol. 126, Pg. 412, 1960.

Hazard and Precautionary Statements (GHS)

PERUVOSIDE Chemical Properties,Usage,Production

Originator

Peruvoside ,Indena

Uses

Peruvoside is a cardiac glycoside with the same inotropic and chronotropic effects on heart function as Ouabain (O714500).

Definition

ChEBI: Peruvoside is a cardenolide glycoside.

Manufacturing Process

Peruvoside is obtained employing the fruit or seeds of ApocynaceaThevetia peruviana by the fermentation and the separation the extracted glucoside mixture by chromatography.
Two kilograms of the ground fruit of ApocynaceaThevetia peruviana is mixed with 100 g of grain chaff and moistened with 900 ml of hot water (approximately 60°C). The mixture is mixed with 20 ml of toluene and maintained at 45°-55°C in a closed vessel for 5 days. The thus fermented material is extracted six times with 1200 ml portions of acetone. The combined extracts are concentrated at 30°C under reduced pressure, until there remains about 600 ml of a dark colored aqueous concentrate. The latter is shaken out with an equal volume of petroleum ether. The organic phase is discarded after recovering the petroleum ether. The thus degreased aqueous concentrate is extracted six times with 500 ml portions of dichloromethane. The dichloromethane extracts are dried over sodium sulfate, combined, and concentrated to about 100 ml. Then the residue is stirred into 250 ml of petroleum ether. After standing overnight, the thus-separated crystallized product is vacuum-filtered, washed petroleum ether and dried at about 40°C. The thus obtained crude glycoside mixture (21 g) is dissolved in a mixture of chloroform/methanol and chromatographed on a column of silica gel. There is thus isolated a small amount of oil and fat, a total of 15.5 g of cerberine, acetylperuvoside and neriifolin, 2.2 g of pure peruvoside, MP: 160°-163°C; [α]22d=70° (c = 1.3 in CH3OH), corresponding to a yield 0.11%, based on the quantity of fruit of Thevetia peruviana employed as the starting material.
One kilogram of ground seeds of Thevetia peruviana is mixed with 300 g of grain chaff and moistened with 500 ml of hot water (60°C). After addition of 10 ml of toluene the mixture is allowed to stand in a sealed vessel for 5 days at 45°-55°C. Thereafter, the moist drug material is extracted six times with 500 ml portions of methanol. The extracts are concentrated at about 30°C to about 300 ml. Without degreasing, glycosides are extracted from this aqueous concentrate with three 300 ml portions followed by three 100 ml portions of chloroform. The chloroform extracts are concentrated at about 40°C to a volume of about 200 ml. This concentrate is then mixed with 500 ml of petroleum ether. After standing overnight, the crystallized product, which separated, is vacuum-filtered, washed with petroleum ether, and dried at 40°C. Yield of rude glycoside: 46.9 g. From this product, after the usual separation by chromatography, 5.1 g of pure peruvoside is obtained, MP: 161°-164°C. Yield 0.51%, based on the weight of the non-degreased seeds of Thevetia peruviana.

Therapeutic Function

Cardiotonic

Enzyme inhibitor

This cardiotonic glycoside or cardenoide (FW = 548.67 g/mol; CAS 1182- 87-2), named systematically as (3b,5b)-3-(6-deoxy-3-O-methyl-a-Lglucopyranosyl)oxyl-14-hydroxy-19-oxocard-20(22)-enolide, a component of neriperside from Thevetia neriifolia (yellow oleander) resembles oubain in its inotropic (force of contraction) and chronotropic (rate of contraction) effects on heart function. Orally administered peruvoside is effective in treating congestive heart failure. Note the structural similarities of the aglycon to digitoxigenin. Target(s): Na+ /K+ -exchanging ATPase.