4452. Glucofrangulin

Nomenclature

CAS number: 52731-38-1
Erbalax-N (Erba); Irgalax (Novartis).
C27H30O14; mol wt 578.52.
C 56.05%, H 5.23%, O 38.72%.

Description and references

Anthraquinone glycoside from bark of Rhamnus frangula L., Rhamnaceae (alder buckthorn): Casparis, Maeder, Bull. Soc. Chim. Biol. 9, 324 (1927); Cucu, Jarpo, Pharmazie 14, 316 (1959); Knap et al., CS 110024 (1964), C.A. 61, 4159e (1964). Consists of two isomers, glucofrangulin A and glucofrangulin B, which differ by the linkage to the sugar moiety at the 3 position of the aglycone. Structure: Schindler, Helv. Chim. Acta 29, 411 (1946); Hrhammer et al., Naturwissenschaften 51, 310 (1964); Longo et al., Arch. Pharm. 297, 248 (1964); Wagner, Hrhammer, Naturwissenschaften 53, 585 (1966). Proof of structure of glucofrangulin A and partial synthesis: eidem, Z. Naturforsch. 24B, 1408 (1969).

Chemical structure

Derivative

Glucofrangulin A.

Nomenclature

CAS number: 21133-53-9
3-[(6-Deoxy-α-l-mannopyranosyl)oxy]-1-(β-d-glucopyranosyloxy)-8-hydroxy-6-methyl-9,10-anthracenedione.

Derivative

Glucofrangulin A octaacetate.
C43H46O22; mol wt 914.81.
C 56.46%, H 5.07%, O 38.48%.

Properties

Needles from methanol, mp 228-230°. [α]D20 124° (c = 1.16 in acetone). uv max: 212, 264, 360 nm (log ε 4.57, 4.56, 4.26).

Therapeutic Category

Cathartic.

Keywords

Laxative/Cathartic