Sesquiterpenic lactones from smyrnium olusatrum L. roots

✍ Scribed by A. Ulubelen; S. Öksüz; Z. Samek; M. Holub

• Book ID: 104248336
• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 133 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)97467-2

✦ Synopsis

Recently the presence of two flavonoid glycosidea in the leaves and stelas of Smyrnium olusatrum L. (Umbelliferae) has been described'. We investigated WOK the componente from the roots of the mentioned species and isolated two eesquiterpenic lactones to which we gave the names istanbulind and istanbulin-B.

Istanbulin A, m.p. 246'C and [ti]F+81.5', has the composition C15H2004 (m/e 264). From its II? (CRC1 3 ) and W spectra (ethenol) it followed that a keto-group in a six-membered or larger -1

ring is probably present in its molecule (1711 cm ; 285 run, log L 2.2), further an a$-unsaturated y-lactone group (1758 cm?; 221 nm, log L. 4.16), and a free hydroxy-group (33w) and 3565 cm?).

In the PWR-spectrum of istanbulind (HA-100; CDC13, TRS) the hydroxy-group proton gave a broad signal at 4.05 ppm, and after conversion to an amidic proton with trichloroacetylisoeyanate2 a broadened ainglet at 9.35 ppm (1 PI). In the PMR-spectrum of istanbulin-A and of its edduct with trichloroacetyliaocyanate2 no characteristic signals of the Cg-0 type protons or of vinylic protons