7175. Periplocymarin

Nomenclature

CAS number: 32476-67-8
(2,6-Dideoxy-3-O-methyl-β-d-ribo-hexopyranosyl)oxy-5,14-dihydroxy-card-20(22)-enolide.
C30H46O8; mol wt 534.68.
C 67.39%, H 8.67%, O 23.94%.

Description and references

By extracting bark and wood of Periploca graeca L., Asclepiadaceae with 70% alcohol and treating with the enzyme strophanthobiase from seeds of Strophanthus courmonti Sacleux, Apocynaceae: Jacobs, Hoffmann, J. Biol. Chem. 79, 519 (1928); Katz, Reichstein, Pharm. Acta Helv. 19, 231 (1944); from S. hypoleucus Stapf: von Euw, Reichstein, Helv. Chim. Acta 33, 544 (1950); from S. ledienii Stein: Lichti et al., ibid. 39, 1914 (1956); from S. eminii Asch. et Pax.: Zelnik, Schindler, ibid. 40, 2110 (1957). Structure: von Euw, Reichstein, ibid. 31, 883 (1948). Acid hydrolysis yields one mol periplogenin and one mol cymarose, q.q.v.. The cymarose is attached to the hydroxyl group at C-3 of the aglycon.

Properties

Lustrous needles from methanol contg approx one mol CH3OH of crystn. Bitter taste, but not nearly so marked as that of cymarin. Becomes solvent-free at 100° in vacuo. Sinters at 138°. mp 148°. [α]D27 +29° (c = 0.94 in 95% alcohol for the anhydr substance). Readily sol in alcohol, chloroform, acetone; less readily in methanol; very sparingly sol in water and practically insol in ether. Readily hydrolyzed in the cold.