New Isorhamnetin Glycosides and other Phenolic Compounds from Calendula officinalis
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NEW ISORHAMNETIN GLYCOSIDES AND OTHER PHENOLIC COMPOUNDS FROM Calendula officinalis
UDC 582.71:547.918
D. N. Olennikov* and N. I. Kashchenko
A total of 39 known compounds and two new flavonoid glycosides that were identified as isorhamnetin-3-O(2s-acetyl)-E-D-glucopyranoside and isorhamnetin-3-O-(2s,6s-diacetyl)- E-D-glucopyranoside were isolated from florets of Calendula officinalis (Asteraceae). The distribution of phenolic compounds in morphological groups of C. officinalis was studied. It was found that peripheral florets had the highest flavonoid content (36.66 mg/g); tubular florets (9.95 mg/g) and leaves (9.65 mg/g), phenylpropanoids. Anthocyanins, among which cyanidin derivatives dominated, were identified for the first time in C. officinalis florets. Keywords: Calendula officinalis, Asteraceae, isorhamnetin-3-O-(2s-acetyl)-E-D-glucopyranoside, isorhamnetin-3O-(2s,6s-diacetyl)-E-D-glucopyranoside, flavonoids, anthocyanins, HPLC. Calendula officinalis L. is an annual herbaceous plant of the family Asteraceae that is widely used in medical practice. Chemical studies found in C. officinalis various classes of compounds including terpenes, phenols, lipids, carbohydrates, etc. [1]. C. officinalis is a cultivated species that is remarkable for its adaptability that enables it to be grown even in inhospitable agricultural zones, in particular, in the Transbaikal territory. Several double-flowered varieties (Big Orange, Egypt Sun, Flame Dancer, Geisha Girl, Indian Prince, Radio, Red Black Centered) were recommended for cultivation of C. officinalis in the Republic of Buryatiya. These are characterized by high productivity and a prolonged vegetative period. Information on the chemical compositions of these varieties has not been published. Therefore, the goal of the present work was to study phenolic compounds from seven C. officinalis varieties introduced into the Republic of Buryatiya. Preliminary studies of florets of the studied C. officinalis varieties for the presence of the principal compound groups showed that the contents of essential oil, carotenoids, and water-soluble polysaccharides in them were 1.4–2.9, 5.14–7.59, and 14.51–28.81 mg/g, respectively (Table 1). The total flavonoid concentration varied from 10.52 (Flame Dancer) to 26.79 mg/g (Big Orange), which was greater than that for raw material grown in the central part of Russia (2.6–9.1 mg/g) [2], Estonia (2.1–6.8 mg/g) [3], Italy (2.8–7.5 mg/g) [4], and Brazil (14.1–14.4 mg/g) [5]. Then, we studied the phenolic components from florets of Big Orange variety, from which fractionation and chromatographic separation of the extracted compounds identified 41 compounds including 39 known compounds and two new flavonoids 1 and 2. OCH3 3'
OH 4'
HO
O
7
3
O
O
5
OH
O
O
1'' 2''
O RO
6''
CH3 OH OH
1, 2
1: R = H; 2: R = Ac
Institute of General and Experimental Biology, Siberian Branch, Russian Academy of Sciences, 670047, Ulan-Ude, Ul. Sakhcyanovoi, 6, fax: 7 (3012) 43 47 43, e-mail: [email protected]. Translated from Khimiya Prirodnykh Soedi
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