7540. Plumieride

Nomenclature

CAS number: 511-89-7
(1S,2′R,4aS,7aS)-1-(β-d-Glucopyranosyloxy)-4a,7a-dihydro-4′-[(1S)-1-hydroxyethyl]-5′-oxospiro[cyclopenta[c]pyran-7(1H),2′(5′H)-furan]-4-carboxylic acid methyl ester; agoniadin.
C21H26O12; mol wt 470.42.
C 53.62%, H 5.57%, O 40.81%.

Description and references

Found in bark of Plumeria lancifolia Muell.-Arg., Apocynaceae, also in P. acutifolia and P. rubra var. alba: Peckolt, Arch. Pharm. [2] 142, 40 (1870); E. Merck's Jahresber. 1895, 11; Boorsma, Mededeel. Lands Plant. 13, 27 (1894); 31, 132 (1899); Franchimont, Rec. Trav. Chim. 18, 334, 477 (1899); 19, 350 (1900); Halpern, Schmid, Helv. Chim. Acta 41, 1109 (1958). Structure: Albers-Sch"onberg, Schmid, ibid. 44, 1447 (1961). Biosynthesis: D. A. Yeowell, H. Schmid, Experientia 20, 250 (1964); K. Inoue et al., Chem. Pharm. Bull. 27, 3115 (1979).

Chemical structure

Properties

Monohydrate, bitter crystals, mp 156-158°. When anhydrous, mp 224-225°. [α]D20 -114°; [α]D20 -80° (methanol). Broad uv absorption: 217-238 nm. Sol in water, alcohol, ethyl acetate.