Title: Periplocin
CAS Registry Number: 13137-64-9
CAS Name: 3b-[(2,6-Dideoxy-4-O-b-D-glucopyranosyl-b-D-ribo-hexopyranosyl)oxy]-5b,14-dihydroxycard-20(22)-enolide
Additional Names: glucoperiplocymarin; periplocoside
Molecular Formula: C36H56O13
Molecular Weight: 696.82
Percent Composition: C 62.05%, H 8.10%, O 29.85%
Literature 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, C13H24O9, [a]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).
Optical Rotation: [a]D20 +32°
Toxicity data: LD in rabbits, rats (mg/kg): 10, 480 s.c. (MacKeith)
Derivative Type: 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°. [a]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.
Melting point: mp 224° when bath is preheated to 200°
Optical Rotation: [a]D20 +23° (c = 0.7 in alcohol)
Derivative Type: Tetraacetylperiplocin
Molecular Formula: C44H64O17
Molecular Weight: 864.97
Percent Composition: C 61.10%, H 7.46%, O 31.44%
Properties: Six-sided prisms from alcohol, mp 195°. [a]D20 +20° (c = 0.5 in alcohol). Sol in alcohol, chloroform; very slightly sol in water.
Melting point: mp 195°
Optical Rotation: [a]D20 +20° (c = 0.5 in alcohol)
|