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547.972Teucrium hyrcanicum L. (Lamiaceae) is an endemic species, the name of which is derived from the ancient Latin name for the Caspian Sea, Marum Hyrcanum. The chemical composition and hypotensive and coagulatory activities of flavonoids from this plant have been reported [1][2][3].In continuation of research on biologically active flavonoids, a minor flavonoid component (cyanidin reaction and IR and UV spectra) was isolated from the ethylacetate fraction of the methanol extract of T. hyrcanicum [4] by column chromatography (CC) over polyamide with subsequent CC over silica gel L (40/100 µ) with elution by CHCl 3 (3% MeOH).Compound 1, C 16 H 12 O 6 , fine light-yellow needle-like crystals, mp (subl. 260°C) 290-291°C, R f 0.26 (Silufol UV-254, CHCl 3 :CH 3 OH, 19:1, system 1), 0.31 (CHCl 3 :CH 3 OH, 9:1, system 2). UV spectrum (CH 3 OH, λ max , nm): 219, 232 sh, 287, 333 (log ε 4. 51, 4.32, 4.38, 4.45). Mass spectrum (EI, 70 eV, m/z, I rel , %): 300 (100) [M] + .Comparison of TLC using system 1 found that 1 is colored brown by aqueous FeCl 3 (9%) and has a chromatographic mobility between those of cirsiliol and pedalitin.The UV spectrum of 1 with ionizing and complexing reagents according to the literature [5]: (+MeONa) 231, 253 sh, 314 sh, 375 (log J demonstrated the presence of 4′-OH, 5-OH, and 6-OH groups [6,7] in addition to a substituted hydroxyl on C-7.The mass spectrum of 1 contains fragments with m/z 182 (4) (ring A), 121 (6), 119 (12), and 118 (6) (ring B). The weakness of the quinoid ions with m/z 181 (3), 167 (3), 153 (5.5), 152 (9), 139 (9), and especially the ions for [M -CH 3 ] + with m/z 285 (1) and [M -CH 3 CO] + with m/z 257 (7) and the corresponding ions for ring A demonstrate the important difference of a flavone with a 6-OCH 3 (hypsidulin) and a 3-OCH 3 and 8-OCH 3 from that with a 7-OCH 3 [8] and confirm that the structure of 1 is 5,6,4′-trihydroxy-7-methoxyflavone (7-methylscutellarein).7-Methylscutellarein was observed in the genus Teucrium for the first time. The more polar CHCl 3 fractions (6% CH 3 OH) afforded pedalitin, luteolin, caffeic acid, and 3,4-dihydroxy-βphenylethanol, which were identified by mixed melting points with authentic samples, comparative TLC, and mass spectrometry.The methylated flavones pedalitin (5,6,3′,4′-tetrahydroxy-7-methoxyflavone) [4] and 7-methylscutellarin that were isolated from T. hyrcanicum differ from each other by one hydroxyl group, analogously to the pair cirsiliol and cirsimaritin from T. polium L. [9]. The more oxidized pedalitin and cirsiliol (6-hydroxyluteolin derivatives) dominate quantitatively over the scutellarin derivatives.

From the chloroform-soluble fraction of an aqueous extract of the epigeal part of Dracocephalum multicaule Montbr. et Auch ex Benth., Lamiaceae, we have previously isolated six polymethyoxylated flavonoids [i]. Continuing our investigation of the nonpolar fraction, by repeated rechromatography of the mixture of unseparated components of the chloroform extract, using column chromatography on silica gel L (Czechoslovakia, 40/100 mesh) with the solvent systems benzene-ether (8:1) and (6:1), we have isolated, together with the calycopterin, penduletin, and xanthomicrol previously detected in the plant [i] another two flavonoid compounds, (I) and (II), new for this species, and accompanying calycopterin and peduletin, respectively, as minor components.