Planta Med 2006; 72 - P_146
DOI: 10.1055/s-2006-949946

Identification of spiroketal polyacetylenes as the main components of an oil extract of chamomile (Chamomilla recutita L. Rausch.) flowers

AN Shikov 1, I Laakso 3, ON Pozharitskaya 1, HJD Dorman 3, VG Makarov 1, VP Tikhonov 2, R Hiltunen 3
  • 1Interregional Center “Adaptogen“, 47/5, Piskarevsky pr, 195067, St-Petersburg, Russia
  • 2Open joint-stock company “Diod“, 11-A, ul. Derbenevskaya, 115114, Moscow, Russia
  • 3Faculty of Pharmacy, Division of Pharmaceutical Biology, University of Helsinki, P.O. Box 56 (Viikinkaari 5E), FIN-00014 Helsinki, Finland

The composition of Chamomilla recutita L. Raush. (family Asteraceae) flowers extract obtained by polar solvents (water, ethanol) is well investigated. They contain flavonoids, coumarins, arene carboxylic acids, sesquiterpene lactones as precursors of chamazulene, etc. However, the extracts of this plant obtained by non-polar, natural plant fixed oils (soybean, olive, etc.) are significantly enriched by more hydrophobic compounds. This report is devoted to the identification of main compounds of an oil extract from the flowers of C. recutita.

Chamomile oil extract have been obtained by original technology at the flowers/oil ratio 1:10 [1]. In our previous studies, it has been shown that the oil extract of the flowers contains flavonoids and coumarins and two major compounds. For concentration of these compounds, flowers were ground and extracted with diethyl ether/saturated sodium hydrogen carbonate solution (1:1, v/v).

The non-silylated and silylated samples were injected into a GC-MS system consisting of an HP 5980 gas chromatograph coupled with an HP 5790A quadrupole mass selective detector operating at EI mode with electron energy of 70 eV and mass range of m/z 40–400. The injector and detector were set at 250°C. The analyses were performed on an NB-54 capillary column (15 m x 0.25mm i.d., Nordion, Finland) with split injection mode. Identification of compounds was done by comparing the retention times and spectral data obtained from GC-MS library and literature. Total ion analyses of the sample showed excellent resolution between the two compounds. Retention times were 17.8±0.1min and 18.0±0.1min, and their molecular weights were 200. Both compounds had molecular ions at m/z 200 and other fragments at m/z 185, 170, 157, 144, 141, 128, 115, 102, 76. Based upon the library and literature data, the compounds were identified as en-yn-dicycloethers (spiroketal polyacetylenes) (E)-2-[2,4-hexadiyniliden]-1,6-dioxaspiro[4,4]-non-3-ene and (Z)-2-[2,4-hexadiyniliden]-1,6-dioxaspiro[4,4]-non-3-ene.

Spiroketal polyacetylenes are powerful inhibitors of NFκB activity, and they occur in chamomile [2], where they might synergize the activity of other inflammatory principles, like the bisabolane-type sesquiterpenoids and chamazulene.

References: 1. Shikov, A.N. et al. (2004), Plants oil and oily extracts: technology, standardization, properties. M, Russky vrach. 2. Redaelli, C., Formentini, L. (1981), J. Chrom. A 209: 110–112.