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Flavonoids from Moraea Sisyrinchium (L.) Ker Gawl. (Iridaceae) in Egypt

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Flavonoids from Moraea Sisyrinchium (L.) Ker Gawl. (Iridaceae) in Egypt See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/257136398 Flavonoids from Moraea sisyrinchium (L.) Ker Gawl. (Iridaceae) in Egypt Conference Paper · September 2013 CITATIONS READS 0 132 1 author: Mona Marzouk National Research Center, Egypt 32 PUBLICATIONS 82 CITATIONS SEE PROFILE Some of the authors of this publication are also working on these related projects: Chemosystematic and biological studies of some Egyptian flora View project All content following this page was uploaded by Mona Marzouk on 28 January 2017. The user has requested enhancement of the downloaded file. All in-text references underlined in blue are added to the original document and are linked to publications on ResearchGate, letting you access and read them immediately. 2013 International Conference on Applied Life Sciences (ICALS2013) UAE. September 15-17, 2013 Flavonoids from Moraea sisyrinchium (L.) Ker Gawl. (Iridaceae) in Egypt Mona O.A. El Shabrawy 1, Mona M. Marzouk 1+, Salwa A. Kawashty 1, Hassnaa A. Hosni 2, Ibrahim A. El Garf 2 and Nabiel A.M. Saleh 1 1 Department of Phytochemistry and Plant Systematic, National Research Center, Cairo, Egypt. 2 Department of Botany, Cairo University, Cairo, Egypt. Abstract. Seven flavonoids were isolated from the aerial part of Moraea sisyrinchium (L.) Ker Gawl. They were identified as apigenin, apigenin 7-O-β-glucopyranoside, luteolin 7-O-β- glucopyranoside, isovitexin, orientin, isoorientin and saponarin. Their structures were established on the basis of chemical and spectroscopic analysis and by comparison with the literature data. Keywords: Moraea sisyrinchium; Iridaceae; flavones; flavone O-glycosides; flavone C-glycosides. 1. Introduction The Iridaceae family is comprised about 92 genera and 1800 species, distributed throughout the world [1]. Iridaceae are of considerable economic importance in ornamental horticulture and the cut-flower industry. In the flora of Egypt, this family is represented by two genera (Iris L. and Moraea Mill., nom. Conserve). Moraea sisyrinchium (L.) Ker Gawl. (Syns. Gynandriris sisyrinchium (L.) Parl. and Iris sisyrinchium L.) is one of two Moraea species growing wild in Egypt [2]. Previous phytochemical screening studies on Iridaceae species revealed the presence of flavone C-glycosides, isoflavones, flavonones, quinones and terpenoids [3-9]. Williams et al. 1989 reported the presence of flavone C-glycosides and the absence of flavonols in M. sisyrinchium [9]. A recent study identified the essential oil constituents of M. sisyrinchium leaves and bulbs, which were reported to have a strong antimicrobial activity against gram positive strains [10]. Flavonoids are often described as biologically active secondary metabolites and have been found to possess anti-protozoal, anti-inflammatory, anticancer, antioxidant, insecticidal, antifungal and antibacterial activities [11]. In the present study, we aim to investigate the flavonoid constituents of M. sisyrinchium which have not yet been reported. 2. Material and Methods 2.1. General Ultra-Violet spectra were recorded using UV visible spectrophotometer (Shimadzu model 2401PC). NMR measurements were carried out using Jeol EX-500 spectroscopy: 500MHz (1H NMR) and 125 MHz (13C NMR). ESIMS: LCQ Advantage Thermo Finnigan spectrometer. CC Polyamide S6 (Riedel-De-Haen AG, Seelze Haen AG, Seelze Hanver, Germany) using MeOH/H2O as eluent. PC (descending) Whatman No. 1 and 3 MM papers, using solvent systems 1) H2O, 2) 15% HOAc (H2O–HOAc 85:15), 3) BAW (n-BuOH– HOAc–H2O 4:1:5, upper layer), 5) (C6H6–n-BuOH–H2O–pyridine 1:5:3:3, upper layer). Solvents 4 and 5 were used for sugar identification, Sephadex LH-20 (Pharmazia) for purification. Complete acid hydrolysis + Corresponding author. Tel.: + 20233335455; fax: +20233370931. E-mail address: [email protected] 33 for O-glycosides (2 N HCl, 2 h, 100°C) were carried out and followed by paper co-chromatography with authentic samples to identify the aglycones and sugar moieties. The sugar units of C-glycoside flavonoids were determined using ferric chloride degradation [12]. 2.2. Plant Material A fresh sample of M. sisyrinchium was collected from Alexandria-Mersa Matruh desert road, in March 2012. Samples were identified by Prof. Dr. Salwa A. Kawashty, and voucher specimen (No.785) was deposited in the herbarium of the National Research Centre (CAIRC). 2.3. Extraction and Isolation Air-dried, ground, whole plant of Moraea sisyrinchium (250 g) was defatted with light petroleum ether (40-60oC) and extracted four times at room temperature with 70% methanol/water. The aqueous methanol extract was evaporated under reduced pressure and temperature affording 72 g (28.8%) residue. It was subjected to a polyamide column (90 x 4 cm) starting with water as eluent then decreasing the polarity by increasing the concentration of methanol. Five main fractions (I-V) were obtained by combining similar fractions according to their PC profile using H2O, 15% HOAc and BAW as eluents. Three compounds (1, 58 mg; 2, 88 mg and 3, 95 mg) were separated from fractions VI and V by fractionation over preparative paper chromatography (PPC) using BAW and HOAc: H2O (1:1). Compounds (4, 45 mg; 5, 67 mg; 6, 60 mg and 7, 24 mg) were separated from fractions I-III by fractionation over Sephadex column (35 x 2.5 cm) using MeOH/H2O (decreasing polarity) for elution then PPC to the sub fractions using 15% HOAc, H2O and BAW. Fig. 1: Chemical structure of compounds 1-7. 4. Results and Discussion Fractionation of the aqueous methanol extract of M. sisyrinchium resulted in the isolation of seven compounds (Fig. 1). These were identified as apigenin (1), apigenin 7-O-β-glucopyranoside (2), luteolin 7- O-β-glucopyranoside (3), isovitexin [apigenin 6-C-β-glucopyranoside] (4), orientin [luteolin 8-C-β- 34 glucopyranoside] (5), isoorientin [luteolin 6-C-β-glucopyranoside] (6) and saponarin [apigenin 6-C-β- glucopyranoside-7-O-β-glucopyranoside] (7). Table 1. UV and ESIMS data of compounds (1-7). UV spectral data, λ (nm) [M-H]- Comp. max MeOH MeOH/NaOMe AlCl3 AlCl3/HCl NaOAc NaOAc/H3BO3 m/z (1) 272, 331. 268, 332, 400. 279,306, 279,304, 281,306, 268,342. 269.2 351,387. 346, 386. 387. (2) 273, 332. 279,342,394. 279,304, 280,304, 275,300sh, 273,334. 431.28 344,385. 345,390. 385. (3) 255,268, 264, 401. 275,295, 275,295, 259,359. 259,374. 447.34 348. 356,386. 356,386. (4) 268,330. 271,345,388. 275,299, 276,298, 266,335, 267,334. 431.17 340,387. 339, 380. 394. (5) 256,299sh, 268, 334, 409. 275,299, 263,277sh, 272,326sh, 263, 378, 439. 447.02 352. 426. 300sh,362, 380. 387. (6) 258,270sh, 268, 335,407. 275,300, 263,278sh, 273,325sh, 263,377, 447.13 350. 423. 299sh,362 379. 440. ,389. (7) 269, 322 279, 394 276,303, 277, 303, 279, 389 270, 319, 345 593,16 346, 382 343, 381 Table 2. 1H NMR data of compounds (1-7). 1H NMR, 500 MHz, DMSO-d6, δ, ppm (J/Hz) H (1) (2) (3) (4) (5) (6) (7) 3 6.7 , s 6.85, s 6.72, s 6.61 , s 6.65, s 6.6, s 6.78, s 5 12.95, br s 12.98, br s 12.88, br s 13.64, br s 13.53, br s 13.56, br s 13.7, br s (OH) (OH) (OH) (OH) (OH) (OH) (OH) 6 6.2 , d 6.44, d 6.43, d C-glucose 6.24, d C-glucose C-glucose (2.0) (2.0) (2.0) (2.0) 7 OH O-glucose O-glucose OH OH OH O-glucose 8 6.5, d 6.82, d 6.78, d 6.45, d C-glucose 6.5, d 6.75, d (2.0) (2.0) (2.0) (2.0) (2.0) (2.0) 2′ 7.9, d 7.96, d 7.44, m 8.02, d 7.43, m 7.4, m 8.02, d (8.5) (8.5) (8.5) (8.5) 3′ 6.9, d 6.9 , d OH 6.83, d OH OH 6.95, d (8.5) (8.5) (8.5) (8.5) 4′ OH OH OH OH OH OH OH 5′ 6.9, d 6.95, d 6.93, d 6.83, d 6.89, d 6.9, d 6.95, d (8.5) (8.5) (8.5) (8.5) (8.5) (8.5) (8.5) 6′ 7.9, d 7.96,d (8.5) 7.44, m 8.02, d 7.43, m 7.4, m 8.02, d (8.5) (8.5) (8.5) 1′′ - 5.04, d 5.05, d 4.62, d 4.72, d 4.6, d 4.77, d (7.2) (7.5) (9) (9.5) (9.5) (9.5) 1′′′ - - - - - - 5.01, d (7.2) 2′′-6′′ - 3-4 (overlapped with OH) 2′′′-6′′′ - 35 The structures of these compounds were elucidated by their chromatographic behaviors, chemical analysis and spectroscopic analysis using UV and ESI/MS (Table 1), 1H-NMR (Table 2) and 13C–NMR (Table 3). The obtained data coincidence with those published in previous work [13, 14]. The UV spectral data revealed that all compounds belonging to flavone nuclei. Compounds 1, 4, 5 and 6 showed a free OH groups at positions 5, 7 and 4', while 7-OH is substituted in compounds 2, 3 and 7. Ortho dihydroxy groups are assigning to compounds 3, 5 and 6 [11-12]. 1HNMR spectrum revealed the presence of apigenin nucleolus in compounds; 1, 2, 4 and 7 represented as aglycone, 7-O-β-glucopyranoside (H-1'' at δ5.04, d, J=7.2 Hz), 6-C-β-glucopyranoside (H-1'' at δ4.6, d, J=9 Hz) and 6-C-β-glucopyranoside-7-O-β- glucopyranoside (H-1'' at δ 4.77, J=9.5 Hz & H-1'' at δ5.01, J=7.2 Hz), respectively [14].
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