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Phytochemical Investigation of Vinca Minor Cultivated in Iran

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Phytochemical Investigation of Vinca Minor Cultivated in Iran Iranian Journal of Pharmaceutical Research (2011), 10 (4): 777-785 Copyright © 2011 by School of Pharmacy Received: Juanary 2011 Shaheed Beheshti University of Medical Sciences and Health Services Accepted: May 2011 Original Article Phytochemical Investigation of Vinca minor Cultivated in Iran Behnaz Farahanikiaa, Tahmineh Akbarzadehb, Akbar Jahangirzadeha, Narguess Yassaa, Mohammad Reza Shams Ardekania, Tahmineh Mirnezamia, Abbas Hadjiakhoondia and Mahnaz Khanavia* aDepartment of Pharmacognosy and Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran. bDepartment of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran. Abstract Lesser Periwinkle (Vinca minor L.), a member of Apocynaceae, is not only an ornamental plant with lilac-blue flowers, but also a medical plant producing an important alkaloid, vincamine, found in the leaves which shows a pronounced cerebrovasodilatory and neuroprotective activity. This plant is native to northern Spain, western France, central and southern Europe, and Caucasus. It has been recently cultivated for pharmaceutical purposes by Zardband Botanical Garden in Iran. Since the quality of herb material and alkaloid concentration is greatly influenced by environmental conditions, in this study, we report the isolation and identification of major alkaloids along with the quantification of vincamine as the pharmacologically most important component. Alkaloids from the aerial parts of V. minor were isolated and purified using different chromatographic methods. The structures of these alkaloids were determined on the basis of their physical and spectroscopic data. The concentration of vincamine was determined by high performance liquid chromatography using Tracer Excel 120 ODS A C18 column. Five indole alkaloids including vincaminorine, vincaminoreine, minovine, minovincine, and vincamine (Figure 1) were isolated from the aerial parts of V. minor. Vincamine was found to be the dominant alkaloid in this plant with the content of 0.057% of the dried plant mass. This plant may be used as a natural source for pharmaceutical purposes in Iran, due to the presence of biologically active alkaloids especially vincamine as the major alkaloid in Lesser Periwinkle cultivated. Keywords: Vinca minor; Apocynaceae; Indole alkaloids; Vincamine. Introduction to northern Spain, through western France, eastward via central and southern Europe as far The genus Vinca (Apocynaceae) comprises as the Caucasus; it has been naturalized in many about seven species in the world. In Iran, it is regions. In folk medicine, it is used internally represented by V. herbacea Waldst and Kit for circulatory disorders, cerebral circulatory as a native plant with two other species being impairment and brain’s metabolism support (3). introduced or cultivated including V. minor L. So far, more than 50 alkaloids of indole type and V. major L. (1, 2). Vinca minor or Lesser have been isolated from the aerial parts and the Periwinkle is a perennial subshrub, indigenous root of this plant, a few of which have quaternary structures such as 4-methylraucubaininium * Corresponding author: chloride, 4-methylstrictaminium chloride E-mail: [email protected] and 4-methylakuammicinium chloride (4). Farahanikia B et al. / IJPR (2011), 10 (4): 777-785 Figure 1. Structures of alkaloids isolated from the aerial parts of Vinca minor (compounds 1-5). Vincarubine is the only alkaloid with bisindole is used for the prevention and treatment of structure reported from this plant that has cerebrovascular insufficiencies and disorders. shown a considerable cytotoxic effect against A large body of clinical evidence indicates the P388 leukemia cells (5). V.minor contains a favorable effect of vincamine in a number monomeric eburnamine-type indole alkaloids of brain disorders of elderly patients, such including vincamine which has modulatory as memory disturbances, vertigo, transient effects on brain circulation and neuronal ischemic deficits, and headache. It increases homeostasis as well as antihypoxic and cerebral blood flow, oxygen consumption and neuroprotective potencies (6). Vincamine glucose utilization (7, 8). In general, Vinca 778 Phytochemical Investigation of Vinca Minor Cultivated in Iran minor is known to be a valuable medicinal 125 MHz, respectively, are relative to TMS as plant in folk medicine and it also serves as a an internal standard. Chemical shifts (δ) are natural source for the industrial production expressed in ppm and coupling constants (J) of medicaments for stimulating the brain in Hz. HPLC analysis was performed using a blood flow (9). Vinca minor has been recently Waters Alliance system. The column used was cultivated by Zardband Botanical Garden in Tracer Excel 120 ODS A C18 column (150 × 5 Gonbad Qabus, Golestan Province, in large mm, 5 µm). Merck silica gel 60 (70-230 mesh), scale for pharmaceutical purposes. In view of the Merck silica gel 60 (230-400 mesh), Merck fact that different parameters including climate TLC silica gel 60 F254 aluminium sheets (20 × and soil requirements, agricultural measures 20 cm) and Merck silica gel 60 GF254 were used such as propagation, planting, fertilization for column chromatography, medium pressure and harvest date vastly influence the quality liquid chromatography (MPLC), analytical and of plant material and alkaloid concentration, preparative TLC, respectively. With the exception the analysis of the alkaloid content of the plant of vincamine standard which was obtained grown in Iran proves invaluable. It has been from Sigma-Aldrich, all other chemicals were shown that nitrogenous fertilizers significantly purchased from Merck Company. increase the content of alkaloids. Besides, the Alkaloid spots on chromatograms were content of alkaloids reaches its maximum at the detected under UV-light or by spraying with flowering stage (May to September). Proper air Dragendroff›s reagent. temperature and humidity as well as sufficient soil moisture during growth and development Plant material of the plant are important factors for growing The aerial parts of V. minor were collected and dry matter production of Vinca minor (10, from Zardband Botanical Garden in Gonbad 11). All of the aforementioned factors should Qabus, Golestan Province, in June 2006. The be taken into consideration in order to optimize plant was identified and authenticated by Dr. the growth and alkaloid yield of the herb. We Gholamreza Amin and the voucher specimen have previously reported the cytotoxicity of (TEH-6654) was deposited at the Herbarium of the alkaloid fractions of this plant (12). This the Faculty of Pharmacy in Tehran University of is the first phytochemical report of Vinca Medical Sciences (Tehran, Iran). minor cultivated in Iran. We report here the isolation and characterization of alkaloids Extraction and isolation vincaminorine, vincaminoreine, minovine, The air-dried and powdered aerial parts minovincine, and vincamine along with a of the plant (800 g) were extracted with 80% validated HPLC quantification of vincamine MeOH at room temperature for 72 h. The (Figure 1). procedure was repeated until the negative test against Dragendroff›s reagent. The MeOH Experimental extracts were concentrated to give 287 g of crude extract (yield: 35.87%). The crude General extract was dissolved in CHCl3 (500 mL) and Melting points (uncorrected) were determined extracted with 2N HCl (200 mL × 10). The on a Reichert-Jung apparatus. Optical rotations acidic fraction was washed with CHCl3 (200 were measured in 2 cm cells on a Perkin-Elmer mL × 3). The pH of the aqueous solution was 142 automatic spectropolarimeter. FT-IR spectra adjusted to 2. The combined acid fraction was were recorded on a Nicolet 550-A spectrometer basified with 25% NH3 on the ice chest (pH 10- (KBr pellets). EI-MS spectra were measured 12) and extracted with CHCl3 (300 mL × 10). by Agilent Technology (HPTM) instrument CHCl3 was removed under reduced pressure to with 5973 Network Mass Selective Detector give 10.9 g of a crude mixture of alkaloids. A (MS model). 1H- and 13C-NMR spectra of mass of 3 g crude alkaloid extract was initially CDCl3 solution, running with a Bruker Avance subjected to column chromatography on silica DRX 500 spectrometer operating at 500 and gel (70-230 mesh), eluted with CHCl3-MeOH 779 Farahanikia B et al. / IJPR (2011), 10 (4): 777-785 in a step gradient (99:1, 98:2, 97:3, 96:4, 95:5, 1568, 1519, 1491, 1342, 1225, 1073, 760. EI- 90:10, 80:20, 70:30, 60:40, 50:50, 25:75, MS 70 eV, m/z (rel. int.): 354 (83, M+), 339 (3), and 10:90 v/v; 500 mL each) to give twelve 325 (3), 295 (8), 268 (9), 229 (100), 210 (60), fractions. Fractions with similar TLC behavior 184 (13), 170 (19), 149 (9), 124 (43). 1H-NMR were combined to yield the following three (500 MHz, CDCl3) δ: 7.50 (d, J = 7.1, 1H, H-9), major fractions: 1 (0.72 g), 2 (0.85 g) and 3 7.24 (1H, covered by solvent peak, H-12), 7.17 (0.97 g). (t, J = 7, 1H, H-10), 7.07 (t, J = 7, 1H, H-11), Fraction 1 was purified using a medium 3.70 (s, 3H, OMe), 3.52 (s, 3H, NMe), 3.16 (d, pressure liquid chromatography (MPLC) over J = 15, 1H, H-21a), 2.93–2.95 (m, 2H, CH2-17), silica gel (230-400 mesh) with the solvent 2.49–2.51 (m, 1H, H-3a), 2.29–2.33 (m, 1H, system of Hexane-EtOAc (8:2) to give 4.2 mg H-5a), 2.27–2.29 (m, 1H, H-5b), 2.24–2.27 (m, of vincaminorine (1), 4.5 mg of vincaminoreine 1H, H-3b), 1.93–1.96 (m, 1H, H-16), 1.61 (d, J (2), 12.5 mg of minovine (3), and 6 mg of = 15, 1H, H-21b), 1.47 – 1.54 (m, 1H, H-14a), minovincine (4). 1.36–1.41 (m, 1H, H-6a), 1.30–1.35 (m.1H, Fraction 2 was subjected to repeated prep. H-15a), 1.25–1.29 (m, 1H, H-14b), 1.20–1.25 TLC (20 × 20 cm, 0.8 mm thickness) over silica (m, 2H, CH2-19), 1.18 – 1.20 (m, 1H, H-15b), gel eluted with EtOAc-MeOH (9:1) to give 80 1.16 – 1.18 (m, 1H, H-6b), 0.93 (t, J = 7.2, 3H, 13 mg of vincamine (compound 5) (R:0.40).
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