731 0009-3130/09/4505-0731 © 2009 Springer Science+Business Media, Inc. Chemistry of Natural Compounds, Vol. 45, No. 5, 2009 FLAVONOIDS FROM Senecio viscosus E. M. Suleimenov, 1* R. A. Jose, 2 S. B. Rakhmadieva, 1 UDC 547.972 W. De Borggraeve, 2 and W. Dehaen 2 Raw material of Senecio viscosus L. (Compositae) first yielded the pyrrolizidine alkaloid senecionine in 0.06–0.075% yield [1] and then the alkaloids squalidine and S-F were isolated by chromatography and their structures were elucidated [2]. We established the component composition of the aerial part of S. viscosus collected in the National Park near Bayanaul Pavlodar Oblast′ of the Republic of Kazakhstan at the beginning of August 2007. The CHCl 3 extract of the finely ground aerial part of S. viscosus was separated by column chromatography over silica gel with elution by heptane:EtOAc (7:3) to isolate β-sitosterol (1), which was identified by mass spectral and PMR data. Further elution isolated 2 as yellow crystals, mp 164–168°C. Its molecular formula C 18 H 16 O 7 was proved by high-resolution mass spectrometry by production of an ion [M] + with m/z 344.08929. The UV spectrum showed strong absorption maxima at 253 and 355 nm that were indicative of conjugated chromophores. According to PMR and 13 C NMR data (Table 1), 2 was identified as 5,4′-dihydroxy-3,3′,7-trimethoxyflavone (or 3,3′,7-trimethyl ether of quercetin, pachypodol), which was isolated earlier from S. viscosissimus [3], Artemisia heptapotamica Poljak [4], A. annua L. [5], Plectranthus cylindraceus [6], Varthemia iphionoides Boiss. [7], and others. 1) L. N. Humilev Eurasian National University, 010008, Astana, Munaitpasov, 5, Republic of Kazakhstan, fax: +7 (7172) 35 98 72, e-mail: syerlan75@yandex.ru; 2) Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium, fax: +32 16 32 79 90, e-mail: wim.dehaen@chem.kuleuven.be. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 612–613, September–October, 2009. Original article submitted March 29, 2009. TABLE 1. 1 H and 13 C Spectral Data for 2 and 3 (DMSO-d 6 , δ, ppm, J/Hz) 2 3 C atom δ H δ C δ H δ C 2 3 4 5 6 7 8 9 10 1′ 2′ 3′ 4′ 5′ 6′ 5-OH 4′-OH 3-OMe 3′-OMe 7-OMe – – – – 6.34 (d, J = 1.83) – 6.73 (d, J = 1.83) – – – 7.65 d – – 6.96 (d, J = 8.22) 7.62 (dd, J = 8.22; 2.1) 12.66 s 9.97 s 3.81 s 3.87 s 3.85 s 156.20 138.40 178.49 161.36 98.21 165.56 92.83 156.71 105.62 121.15 112.51 147.94 150.37 116.10 122.77 – – 60.14 56.52 56.22 – 6.94 s – – 6.37 (d, J = 2.3) – 6.80 (d, J = 2.3) – – – 7.58 (d, J = 2.2) – – 6.94 (d, J = 8.4) 7.59 (dd, J = 8.4; 2.2) 12.97 s 9.98 s – 3.87 s 3.90 s 164.33 103.84 182.36 161.50 98.46 165.49 93.18 157.60 105.02 121.72 110.73 148.40 151.23 116.23 120.95 – – – 56.53 56.53