Nomenclature
CAS number: 13137-64-9
3β-[(2,6-Dideoxy-4-
O-β-
d-glucopyranosyl-β-
d-
ribo-hexopyranosyl)oxy]-5β,14-dihydroxycard-20(22)-enolide; glucoperiplocymarin; periplocoside.
C
36H
56O
13; mol wt 696.82.
C 62.05%, H 8.10%, O 29.85%.
Description and references
Isoln from Periploca graeca L., Asclepiadaceae: Lehmann, Arch. Pharm. 235, 157 (1897); W. A. Jacobs, A. Hoffmann, J. Biol. Chem. 79, 519 (1928);
from Strophanthus preussii Engl. and Pax., Apocynaceae: Ruppol, Trukovic, J. Pharm. Belg. 10, 221 (1955), C.A. 50, 12089d (1956). Structure: Stoll, Renz, Helv. Chim. Acta 22, 1193 (1939).
Pharmacology and toxicity: M. H. MacKeith, J. Pharmacol. Exp. Ther. 27, 449 (1926).
Properties
Amorphous yellowish powder. Readily sol in water.
Acid hydrolysis yields
periplogenin,
q.v., and periplobiose (cymarose + glucose, C
13H
24O
9, [α]
D20 +32°). Enzymatic hydrolysis
with strophanthobiase splits off glucose, yielding periplocymarin.
The biose is attached to the hydroxyl group at C-3 of the aglycon.
LD in rabbits, rats (mg/kg): 10, 480 s.c. (MacKeith).
Derivative
Dihydrate.
Properties
Fine needles from water. Becomes anhydr after
drying for one hour in high vacuum at 105°. mp 224° when bath is preheated to 200°. [α]D20 +23° (c = 0.7 in alcohol). One gram dissolves in ≈20 ml boiling
water, at 25° the soly is ≈1:2500. Freely sol in alcohol. Almost
insol in ether, chloroform.Derivative
Tetraacetylperiplocin.
C
44H
64O
17; mol wt 864.97.
C 61.10%, H 7.46%, O 31.44%.
Properties
Six-sided prisms from alcohol, mp 195°. [α]D20 +20° (c = 0.5 in
alcohol). Sol in alcohol, chloroform; very slightly sol in
water.