3-Methoxy-4,5-Methylenedioxypropiophenone and Ferocinin from Ferula kelleri
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B R I E F C O M M U N I CAT I O N S
3-METHOXY-4,5-METHYLENEDIOXYPROPIOPHENONE AND FEROCININ FROM Ferula kelleri
S. M. Adekenov,1* A. S. Kishkentayeva,1 M. M. Zhakanov,1 and I. Yu. Bagryanskaya2,3
The genus Ferula L. (Apiaceae) numbers >130 species, of which 48 grow in Kazakhstan. F. kelleri Koso-Pol. inhabits grassy slopes and grows among bushes in the middle mountain belt [1]. The terpenoid coumarin kellerin was previously isolated from roots of F. kelleri [2]. In continuation of work on the chemistry of F. kelleri, roots of the plant collected in July 2018 in Ushkonyr gorge in Karasay District, Almaty Region, Republic of Kazakhstan, were extracted with EtOH. Raw material (1 kg) was extracted (3×) with EtOH. The extracts were evaporated under vacuum. The condensed extract was worked up (4×) with Et2O. The Et2O extract was evaporated. The obtained total compounds (129 g) were chromatographed over a column of KSK silica gel in a 1:9 (compound–gel) ratio with elution by petroleum ether–EtOAc (98:2 and 96:4) to isolate colorless crystalline 1 and 2. The stereochemistry of 1 was studied by an X-ray crystal structure analysis (XSA). Figure 1 shows its molecular structure. Crystals of 1 were monoclinic, space group P21/c with unit-cell constants a = 8.7877(9), b = 15.7285(17), c = 7.7702(7) A° , β = 110.311(4)°, V = 1007.2(2) A° 3, Z = 4, C11H12O4, dcalcd = 1.373 g/cm3, μ = 0.105 mm–1, crystal size 0.10 × 0.20 × 0.90 mm, maximum angle 2θ = 59.4°, transmission 0.8264–0.8622. Intensities of 2511 independent reflections were measured. The final refinement parameters were wR2 = 0.1357, S = 1.008, number of refined parameters 138 (R = 0.0430 for 1880 F > 4σ). The geometric parameters of 1 were within 3σ of the mean statistical values [3]. Dimeric pairs formed in the crystal through weak C6–H6a…O2 H-bonds with H6a…O2 = 2.51 A° , C6…O2 = 3.429(2) A° , and angle C6–H6a…O2 = 168°. The stereochemistry of 2 was studied by an XSA (Fig. 2). °, Crystals of 2 were monoclinic, space group C2 with unit-cell constants a = 16.9194(8), b = 6.4397(4), c = 21.1062(2) A β = 112.809(2)°, V = 2119.8(2) A° 3, Z = 4, C23H30O4, dcalcd = 1.161 g/cm3, μ = 0.078 mm–1, crystal size 0.30 × 0.30 × 0.80 mm, maximum angle 2θ = 55.1°, transmission 0.7017–0.7456. Intensities of 4816 independent reflections were measured. The final refinement parameters were wR2 = 0.1463, S = 1.038, number of refined parameters 249 (R = 0.0526 for 4003 F > 4σ). The XSAs were performed on a Bruker Kappa APEX II diffractometer (Mo Kα-radiation, graphite monochromator, CCD detector). Absorption corrections were applied using the SADABS program [4]. The structures were solved by direct methods using the program SHELXS-97 [5] and refined anisotropically and isotropically (for H atoms) using the SHELXL-97 program [5]. Positions of H atoms were geometrically calculated. Parameters of H atoms were refined isotropically using a rider model. The structural data for 1 and 2 were deposited in the Cambridge Crystallographic Data Centre under numbers CCDC 1978204 and 1978205 and can be
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