L. P. Smirnova

Flavonoids fromHieracium pilosella

From an ethanolic extract of the flowers of this plant, by column chromatography on a polyamlde sorbent we have isolated five substances of flavonoid nature (I-V). Substances (I) and (II) have been identified with the previously isolated luteolin [i] and luteolln 7-glycoside [2]. Substances (III) and (IV) have been identified on the basis of UV, IR, and NMR spectra, melting points, and elementary analyses as apigenin [3] and isorhamnetln [4, 5], respectively.

New acylated flavone glycoside fromGnaphalium uliginosum

A new acylated flavone glycoside has been isolated for the first time from the herb marsh cudweed, and for it the structure of 6″-caffeyl-7-β-D-glucopyranosyloxy-4′,5-dihydroxy-3′,6′dimethoxyflavone has been established. In addition, the aglycone, identified as 4′,5,7-trihydroxy-3′,6-dimethoxyflavone has been isolated. The identifications were made on the basis of UV, IR, PMR, and mass spectra, the products of alkaline and acid hydrolyses, and the results of elementary analysis, melting points, and specific rotations.

FLAVONOIDS OF Naumburgia thyrsiflora

Loosestrife is a common, although infrequently found, plant of marshes and swampy shores of water bodies usually growing directly in the water. In the world flora and in the flora of the Soviet Union there is a single species -Naumburgia thyrsif~ora (L.) Rchb. (Lysimachia thyrsiflora) (water loosestrife), family Prtmulaaeae [I]. In a preliminary study of this loosestrife we have previously detected saponins and flavonoids [2] and have established the structure of saponins [3, 4].

Flavonoids of Oxycoccus quadripetalis

In the leaves of Oxycoccus quadrlpetalls collected in the stage of the ripening of the fruit (September, 1974) in the Vitebsk oblast, by paper chromatography we have detected not less than six substances of flavonold nature. By chromatography on Kapron columns using aqueous ethanol of various concentrations as eluents we have isolated three substances of flavonoid nature in the individual state. On the basis of the results of UV spectroscopy with ionizing and complex-forming additives, the products of acid hydrolysis and alkaline degradation, IR and NMR spectroscopy, and mixed melting points, the substances isolated have been identified as quercetin, myrlcetin, and hyperoslde.

The structure of a flavonoid glycoside fromFilipendula ulmaria

Fractions 17-23 yielded a third ester, with the composition C1oH1oO~, mp 162-163°C, M + 194, Rf 0.35. Its saponification also formed 3,5-dihydroxycinnamic acid with mp 243-245°C. In view of the composition of the substance, it may be concluded that it is the methyl ester of the above-mentioned acid. This was confirmed by its physicochemical constants and NMR spectrum which contained a three-proton singlet at 3.62 ppm. The substances isolated from the Casouta lehmann~c~a have not been detected in the elm.

Flavonoids ofSonchus arvensis

Substance (IV) with mp 243-245°C was hydrolyzed by acids to form isorhamnetin (II) and glucose and, according to its N~ spectrum, is a monoglycoside [d 5.88 ppm (IH), J = 8 Hz and 6H in the 3.2-3.8 ppm region]. The glucose has the ~ configuration of the glycosidic center, as can be seen from the coupling constant (8 Hz) and is present in position 3. On the the basis of the facts presented, it may be concluded that substance (IV) is isorhamnetin 3-~-D-glucoside [5].