RESUMEN

The chemical variability and the in vitro anti-inflammatory activity of the leaf essential oil from Ivorian Isolona dewevrei were investigated for the first time. Forty-seven oil samples were analyzed using a combination of CC, GC(RI), GC-MS and 13C-NMR, thus leading to the identification of 113 constituents (90.8-98.9%). As the main components varied drastically from sample to sample, the 47 oil compositions were submitted to hierarchical cluster and principal components analyses. Three distinct groups, each divided into two subgroups, were evidenced. Subgroup I-A was dominated by (Z)-ß-ocimene, ß-eudesmol, germacrene D and (E)-ß-ocimene, while (10ßH)-1ß,8ß-oxido-cadina-4-ene, santalenone, trans-α-bergamotene and trans-ß-bergamotene were the main compounds of Subgroup I-B. The prevalent constituents of Subgroup II-A were germacrene B, (E)-ß-caryophyllene, (5αH,10ßMe)-6,12-oxido-elema-1,3,6,11(12)-tetraene and γ-elemene. Subgroup II-B displayed germacrene B, germacrene D and (Z)-ß-ocimene as the majority compounds. Germacrene D was the most abundant constituent of Group III, followed in Subgroup III-A by (E)-ß-caryophyllene, (10ßH)-1ß,8ß-oxido-cadina-4-ene, germacrene D-8-one, and then in Subgroup III-B by (Z)-ß-ocimene and (E)-ß-ocimene. The observed qualitative and quantitative chemical variability was probably due to combined factors, mostly phenology and season, then harvest site to a lesser extent. The lipoxygenase inhibition by a leaf oil sample was also evaluated. The oil IC50 (0.020 ± 0.005 mg/mL) was slightly higher than the non-competitive lipoxygenase inhibitor NDGA IC50 (0.013 ± 0.003 mg/mL), suggesting a significant in vitro anti-inflammatory potential.

Asunto(s)

Annonaceae/química , Antiinflamatorios/química , Antiinflamatorios/farmacología , Aceites Volátiles/química , Aceites Volátiles/farmacología , Aceites de Plantas/química , Aceites de Plantas/farmacología , Antiinflamatorios/aislamiento & purificación , Côte d'Ivoire , Evaluación Preclínica de Medicamentos , Cromatografía de Gases y Espectrometría de Masas , Técnicas In Vitro , Lipooxigenasa/efectos de los fármacos , Inhibidores de la Lipooxigenasa/química , Inhibidores de la Lipooxigenasa/aislamiento & purificación , Inhibidores de la Lipooxigenasa/farmacología , Espectroscopía de Resonancia Magnética , Aceites Volátiles/clasificación , Hojas de la Planta/química , Aceites de Plantas/clasificación , Plantas Medicinales/química , Glycine max/enzimología

RESUMEN

The title compound, C(25)H(23)N(3)S, crystallizes with two independent mol-ecules in the asymmetric unit. The seven-membered fused-ring adopts a boat conformation, with the two bridgehead C atoms representing the stern and the C atom bearing the exocyclic double bond the prow.

RESUMEN

The seven-membered ring in the title compound, C(18)H(16)N(2)O, adopts a boat conformation with the two phenyl-ene carbons representing the stern and the methyl-ene C atom the prow. The dihedral angle between the best plane through the seven-membered ring and the phenyl ring is 62.13 (3)°.

RESUMEN

The seven-membered ring in the title compound, C(19)H(18)N(2)O(3), adopts a boat conformation with the two phenyl-ene C atoms representing the stern and the methyl-ene C atom the prow. The dihedral angle between the best plane through the seven-membered ring (r.m.s deviation = 0.343 Å) and the phenyl substituent is 31.9 (1)°. The dihedral angle between this best plane and the best plane through the eth-oxy-carbonyl-methyl substituent (r.m.s. deviation = 0.058 Å) is 72.2 (1)°.

RESUMEN

The seven-membered ring in the title compound, C(20)H(19)N(3)O(3), adopts a boat conformation with the two phenyl-ene C atoms representing the stern and the methyl-ene C atom the prow. The dihedral angle between the best plane through the seven-membered ring (r.m.s deviation = 0.358 Å) and the phenyl substituent is 55.8 (1)°. The two rings at either ends of the ethyl chain are staggered [N-CH(2)-CH(2)-N torsion angle = 57.5 (4)°].