Structure of the coumarins colladin and colladonin. II

Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species

“…The known compounds coladin (6) and coladonin (7) (Ban'kovskii et al, 1970;Appendino et al, 1997), feselol (8) (Ahmed, 1990), lancerodiol p-hydroxybenzoate (9) (Fraga et al, 1985) and jaeschkeanin (10) (Diab et al, 2001) were isolated and identified by comparison of their spectral data with the literature.…”

“…The biological importance of members of this genus prompted us to investigate the roots of F. vesceritensis Coss et Dur, previously not chemically investigated, to afford two new sesquiterpene coumarins (1 and 2). Also, re-investigation of the roots of F. sinaica L. yielded a new sesquiterpene coumarin 3 (named as ferulsinaic acid), an enantiomer 4 of samarcandone and a glucose derivative (5), in addition to the known compounds coladin (6) and coladonin (7) (Ban'kovskii et al, 1970;Appendino et al, 1997), feselol (8) (Ahmed 1990), lancerodiol p-hydroxybenzoate (9) (Fraga et al, 1985) and jaeschkeanin (10) (Diab et al, 2001).…”

Terpenoid Coumarins of the Genus Ferula

“…The conferol series. 137 An analysis of the 1 H NMR spectrum of the latter enabled the position of the aryloxymethyl group of C-11 to be determined and the structures of badrakemin (51), samarcandine (86), and samarcandone (88) to be corrected. 137 An analysis of the 1 H NMR spectrum of the latter enabled the position of the aryloxymethyl group of C-11 to be determined and the structures of badrakemin (51), samarcandine (86), and samarcandone (88) to be corrected.…”

“…[76] (EtOH) F. sinaica [41] (54) in an acetic acid medium with chromium trioxide gave a keto acid (117) (Figure 8). 137 The dehydration of the tertiary hydroxyl group in coumarins of samarcandin series is usually carried out in 10% ethanolic sulfuric acid solution, 76,121 together with the signals of an angular methyl group and of geminal dimethyl groups. 137 The dehydration of the tertiary hydroxyl group in coumarins of samarcandin series is usually carried out in 10% ethanolic sulfuric acid solution, 76,121 together with the signals of an angular methyl group and of geminal dimethyl groups.…”

“…Among the coumarins with acyclic monoterpene substituent, there are aurapten (137), 53,68 diversinin (138), 149 diversin (139), 149,150 diversoside (140), 151 ferulagol A (141), 152 and ferulagol B (142) 152 (Table 5 and Figure 10). …”