Esters from Ferula samarcandica
In continuation of research on terpenoid plants of the Ferula L. genus (Apiaceae), we studied components of the roots of Samarkand ferula ( Ferula samarcandica Korov.) collected in Tashkent district. The terpenoid coumarins samarcandin and samarcandone were isolated previously from Samarkand ferula [1]. Later, a study of Samarkand ferula misidentified as mogoltav ferula ( F. mogoltavica Lipsky ex Korov.) isolated the terpenoid coumarins samarcandin, samarcandone, mogoltadone, gummosin, and farnesiferol A [2-4]. Air-dried ground roots were extracted with ethanol. The alcohol extract was evaporated, diluted with water (1:2), and treated with ethylacetate. The combined ethylacetate extract was distilled to produce a thick extract that was placed on a col umn of KSK silica gel (d = 3 cm, h = 80 cm) and eluted by benzine:ethylacetate (9:1) with a subsequent increase of ethylace tate concentration. Fractions of 100 mL were collected. The separation of the total terpenoids was monitored using TLC (hydrocarbons:ethylacetate, 4:1; developer, 1% vanillin in conc. H 2SO4). Four terpenoid esters were isolated: 1, C17H22O3, mp 155-156°C; 2, C18H24O4, mp 84-85°C; 3, C18H24O4, [α]D 22 -30 (c 0.5, ethanol); 4, C22H28O5, mp 129-130°C. Comparison of the PMR, UV, IR, and mass spectra of 1 and 2 with those in the literature identified them as tschimgin and tschimganin [5]. The IR spectrum (KBr, ν, cm) of 3 exhibited absorption bands typical of hydroxyl (3534), ester carbonyl (1693), and an aromatic ring (1598, 1514) [6]. The mass spectrum of 3 was similar to that of esters of monoterpene alcohols and had peaks for ions with m/z 304 [M]+, 168 (C8H8O4), 148, 123, 95, 93. The PMR spectrum (100 MHz, DMSO-d 6, δ, ppm, J/Hz) of 3 exhibited signals at 0.70, 0.80, and 1.02 (each 3H, s), 3.65 (3H, s, OCH 3), 7.10 (1H, d, J = 9.0, H-3 ′), 7.72 (1H, d, J = 2, H-6 ′), 7.75 (1H, q, J 1 = 9.0, J2 = 2, H-2′), 4.90 (1H, d, J1 = J2 = 7.5) and 5.15 (1H, br.d, J = 10). The two signals at 4.90 and 5.15 ppm in the range of geminal protons indicate that 3 is a natural mixture of tschimganin and iso-tschimganin. Similar mixtures of tschimgin/ iso-tschimgin and tschimganin/ isotschimganin were isolated from F. dshizakensis Korov. and F. angreni Korov. [7, 8]. The neutral part of the hydrolysate from base hydrolysis of 3 by aqueous KOH (5%) afforded a monoterpene alcohol of composition C10H18O with mp 201-202 °C that was identified as borneol [5]. Comparison of the PMR, IR, and mass spectra of 4 with those of known carotane esters showed that this compound was lancerodiol p-hydroxybenzoate, which was isolated earlier from F. lancerottensis [9]. Thus, it is found for the first time that Samarkand ferula contains esters of terpenoid alcohols in addition to terpenoid coumarins.
Chemical constituents from Ferula oopoda (Boiss. & Buhse) Boiss
Abstract Eleven compounds including three monoterpene-phenyl esters (1-3), a monoterpene glucoside (4), five sesquiterpenoids/sesquiterpene-phenyl esters (5-9), a phenolic acid glucoside (10), and uridine (11) were isolated from the aerial parts of Ferula oopoda (Boiss. & Buhse) Boiss. Structures of the isolated compounds were elucidated by 1D and 2D NMR spectroscopic methods and comparison with previously reported data. Compound 1 was found to be new compound. NMR data of compounds 5 and 6 are reported here for the first time. Moreover, these compounds were reported for the first time from this species. This paper deals with the isolation and structure elucidation of the metabolites from F. oopoda and their chemotaxonomic significance.
Linkiol, a new sesquiterpene from Ferula linkii
Abstract A new sesquiterpene ester, linkiol with a daucane skeleton was isolated from Ferula linkii .