G. K. Nikonov

Coumarins of Ferula kopetdaghensis and the structure of kopeolin and kopeoside

SummaryThe roots ofFerula kopetdaghensis Eug. Kor. have yielded five coumarins — umbelliferone and four new compounds (kopetin, kopeodin, kopeolin, and kopeoside).On the basis of NMR, mass, and IR spectroscopy, derivatives, and transformation products, the structures of two of the new coumarins kopeolin and kopeoside have been established. It has been shown that kopeolin is a derivative of farnesiferol C and kopeoside is kopeolin 3-O-β-D-glucoside.

Kamolone from the roots of Ferula kopetdaghensis

Continuing a study of the coumarins of the above-named plant, from the ethereal fraction after the elimination of the galbanic acid [1] we have isolated another lactone, with the composition C24H3204, M + 382, mp 189-190°C (methanol), [a]~ + 63 ° (c 1.0; chloroform), Rf 0.21 [petroleum e the r -e thy l acetate (5 : 1) system]. From its chemical composition and UV spectrum [244,255, and 327 nm (log £ 3.64, 3.38, and 4.29, respectively)] it belongs to the 7-hydroxycoumarin derivatives. Its IR spectrum contains absorption bands at (cm-1): 1733 (carbonyl of an ~-pyrone), 1617, 1562 (aromatic nucleus), 2990, 2965, 2940, and 1380-1360 (C-methyl groups), and 1.713 (carbonyl group of a saturated ketone). Acid hydrolysis of the lactone gave umbelliferone CsH603 with mp 229-231°C (from water), which was identified by the absence of a depression of the melting point in a mixture with 7-hydroxycoumarin.

Coumarins of Ferula kopetdaghensis — Kopetdaghin and kopeodin (farnesiferol B)

SummaryFrom the roots ofFerula kopetdaghensis Eug. Kor. a new coumarin has been isolated which has been called kopetdaghin. On the basis of the hydrolysis products, the results of hydrogenation and acetylation, and spectroscopy, it has been established that kopetdaghin is an ether of 7-hydroxycoumarin and 1-(3-hydroxy-2,2,6-trimethylcyclohex-5-enyl)-3-methylpent-2-en-1-ol, i.e., an isomer of farnesiferol B.Furthermore, farnesiferol B has been shown to consist of a natural mixture of kopetdaghin (30%) and a component with the structure previously proposed for it (70%).

Phenols of Ferula prangifolia

SummaryFrom the roots ofFerula prangifolia (Boiss) Korov. two phenolic components have been isolated that are esters of p-hydroxybenzoic acid and sesquiterpene alcohols. On the basis of their physicochemical constants and hydrolysis products it has been shown that one of them isl-chimgin (borneol p-hydroxybenzoate) and the second, which has been called ferungin, is ferutinol p-hydroxybenzoate.

Feligoside and feloside — New phenol glycosides from Ferula kopetdaghensis

SummaryTwo new phenol glycosides have been isolated from the roots ofFerula kopetdaghensis: feligoside (I) and feloside (II). On the basis of physicochemical and spectral characteristics and also of chemical transformations, the structure of 1-(4′,6′-dimethoxy-5′-0-β-D-glucopyranosyloxy-2′-propylphenyl)-1-(3″,5″-dimethoxy-4″-hydroxyphenyl)propane is proposed for (I) and 1-(3′,5′-dimethoxy-4′-β-D-glucopyranosyloxyphenyl)-2-β-d-glucopyranosyloxypropane for (II).