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.
Chemistry of spices: bornyl 4-methoxybenzoate from Ferula ovina (Boiss.) Boiss. (Apiaceae) induces hyperalgesia in mice.
UNLABELLED
Ferula ovina (Boiss.) Boiss. is a traditional Iranian flavoring agent used as an ingredient of spices and condiments.


METHODS AND RESULTS
GC-MS analyses of F. ovina aerial parts' essential oil revealed the presence of a number of rare aromatic esters of monoterpenic alcohols. The structures of these esters were corroborated by synthesis, and one of them, bornyl 4-methoxybenzoate, turned out to be a new natural compound. The antinociceptive activities of the oil and the new ester were assessed in mice using several different laboratory models. The oil exerted strong peripheral and moderate central analgesic activities. Surprisingly, mice treated with bornyl 4-methoxybenzoate had an increased sensitivity to the noxious stimulus compared to that of the control group. A dynamic hot plate test was used to demonstrate that bornyl 4-methoxybenzoate induces hyperalgesia and not allodynia.


CONCLUSION
Essential oil constituents impart this spice with both antinociceptive and hyperalgesic potentially flavor-related properties.
Six sesquiterpene alcohol esters from ferula elaeochytris
Abstract Two new salicyloyl and angeloyl esters of jaeschkeanadiol, together with the known benzoic, p -hydroxybenzoic, p -methoxybenzoic and vanillic acid esters, were isolated from Ferula elaeochytris . A new ketone, 3-hydroxy-4,5-methylenedioxypropiophenone, was also obtained.