Biologically Active Compounds from Dorycnium graecum Growing in Azerbaijan
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BIOLOGICALLY ACTIVE COMPOUNDS FROM Dorycnium graecum GROWING IN AZERBAIJAN
I. S. Movsumov, D. Yu. Yusifova, T. A. Suleymanov, and E. A. Garaev*
Two of the twelve species of Dorycnium L. growing mainly in the Mediterranean, Canary Islands, and Caucasus regions are found in Azerbaijan [1]. The species D. graecum (L.) Ser. (Fabaceae) was studied by us for the rational use of domestic plant resources to find new sources of biologically active compounds. According to our results, all organs of the perennial herbaceous plant D. graecum (flowers, leaves, stems) contain flavonoids. Preparations of D. graecum leaves are used in folk medicine for hemorrhoids [2]. The flavonoid kaempferitrin was previously isolated from flowers and leaves of the plant growing in the Caucasus [3]. Raw material of D. graecum was collected in the middle of July 2018 in the vicinity of Altiaghaj, Khizi District. The dried and ground aerial part (1.0 kg) of D. graecum was extracted (3×) with EtOH (80%) at room temperature for 24 h. The extracts were combined, evaporated to a watery residue, and worked up sequentially with hexane, CHCl3, hexane–EtOAc, and EtOAc. The hexane extract afforded 1 (0.05 g); CHCl3 extract, 2 (0.6 g); hexane–EtOAc extract, 3 (0.3 g); and EtOAc extract, 4 (0.6 g). Then, the mother liquor was subjected to acid hydrolysis (4% H2SO4, 4 h) to give total flavonoid aglycons consisting of the three compounds kaempferol, quercetin, and myricetin. Preparative paper chromatography isolated 3, 5, and 6. β-Sitosterol (1), mp 138–140°C (aqueous EtOH), [α]D20 –40° (c 0.25, CHCl3). IR spectra of 1 and β-sitosterol agreed [4]. 20 +54° (c 0.5, MeOH) [4]. Ursolic acid (2), mp 280–282°C (EtOH), [α]D Myricetin (3), yield 0.3 g, mp 350–352°C (aqueous EtOH). UV spectrum (MeOH, λmax, nm): 256, 378, 340sh. A Bryant reaction showed that the compound was a flavonoid aglycon. Compound 3 and a reference standard of myricetin were identical [5]. 20 –124° (c 0.6, MeOH). Acid hydrolysis (4% H SO , 4 h) Myricitrin (4), yield 0.22 g, mp 200–202°C (EtOH), [α]D 2 4 formed the aglycon (myricetin, 63.3%) and L-rhamnose. UV spectrum of 4 (MeOH, λmax, nm): 257, 305, 355. Compound 4 agreed with myricitrin [5]. Kaempferol (5), mp 272–274°C (CHCl3–MeOH). UV spectrum of 5 (EtOH, λmax, nm): 370, 268, mp of the tetraacetate 180–182°C (hexane–CHCl3). Compound 5 was identical to kaempferol [6]. Quercetin (6), mp 300–302°C (CHCl3–MeOH). UV spectrum (MeOH, λmax, nm): 255, 374. All parameters of 6 agreed with those of quercetin [6]. Azerbaijan has significant reserves of D. graecum that could provide a source for preparing a cholegogic preparation [2, 7].
Azerbaijan Medical University, 23 Bakikhanova St., Baku, AZ 1022, Azerbaijan, e-mail: [email protected]. Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2020, p. 815. Original article submitted February 21, 2020. 0009-3130/20/5605-0953
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Springer Science+Business Media, LLC
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REFERENCES 1. 2. 3. 4. 5. 6. 7.
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Flora of Azerbaijan [in Russian], Vol. V, Baku, 1957, 309 pp. Plant Reso
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