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Three Further Triterpenoid Saponins from Gleditsia Caspica Fruits and Protective Effect of the Total Saponin Fraction on Cyclophosphamide-Induced Genotoxicity in Mice

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Three Further Triterpenoid Saponins from Gleditsia Caspica Fruits and Protective Effect of the Total Saponin Fraction on Cyclophosphamide-Induced Genotoxicity in Mice Z. Naturforsch. 2015; 70(1-2)c: 31–37 Farouk R. Melek, Fawzia A. Aly, Iman A.A. Kassem*, Mona A.M. Abo-Zeid, Ayman A. Farghaly and Zeinab M. Hassan Three further triterpenoid saponins from Gleditsia caspica fruits and protective effect of the total saponin fraction on cyclophosphamide-induced genotoxicity in mice Abstract: Three triterpenoidal saponins were isolated 1 Introduction from the saponin fraction derived from a Gleditsia caspica Desf. methanolic fruit extract. The isolated saponins were The genus Gleditsia (family Fabaceae) comprises 14 identified as gleditsiosides B, C, and Q based on spectral species of deciduous trees [1]. Gleditsia caspica (Caspian data. The saponin-containing fraction was evaluated in locust), a tree that grows up to 12 m, is cultivated in public vivo for genotoxic and antigenotoxic activities. The frac- gardens in Egypt mainly for ornamental purposes due tion caused no DNA damage in Swiss albino male mice to its graceful habit, elegant form, and delicate fern-like treated with a dose of 45 mg/kg body weight for 24 h, foliage. Gleditsia species have been widely used in folk although it significantly inhibited the number of chromo- medicine. The thorns of G. sinensis have been used for the somal aberrations induced by cyclophosphamide (CP) in treatment of carbuncles, scabies, and suppurate skin dis- bone marrow and germ cells when applied before or after eases, whereas the mature pods and anomalous fruits are CP administration. The inhibitory indices in chromosomal mainly used for treating apoplexy, headache, productive aberrations were 59% and 41% for bone marrow and 48% cough, and asthma. The dried fruits of G. japonica Miq. and 43% for germ cells, respectively. In addition, the have long been known in oriental medicine as diuretic saponin fraction was found to reduce the viability of the and expectorant [2]. Saponins, the main constituents of human tumor cell line MCF-7 in a dose-dependent manner Gleditsia fruits, were previously reported from fruits of with an extrapolated IC value in the range of 220 μg/mL. 50 different Gleditsia species [3–10]. From G. caspica, we recently reported the isolation and characterisation of 11 Keywords: antigenotoxicity; Gleditsia caspica; triterpe- new triterpenoidal and acylated triterpenoidal saponins noidal saponins. named caspicaosides A–K [11, 12], as well as the known Gleditsia saponins C′ and E′ and gleditsioside I [13]. DOI 10.1515/znc-2014-4132 As a part of our continuous interest in bioactive sapo- Received July 24, 2014; revised September 27, 2014; accepted nins from plants cultivated in Egypt [12, 14–19], we report February 10, 2015 here the isolation and identification of three further sapo- nins from the saponin fraction of G. caspica fruits (SFGC). Also, the genotoxic and antigenotoxic activities of SFGC are presented. *Corresponding author: Iman A.A. Kassem, National Research Centre, Chemistry of Natural Compounds Department, Dokki 12622, 2 Materials and methods Giza, Egypt, E-mail: [email protected] Farouk R. Melek and Zeinab M. Hassan: National Research Centre, Chemistry of Natural Compounds Department, Dokki, Giza, Egypt 2.1 General Fawzia A. Aly and Ayman A. Farghaly: National Research Centre, Genetics and Cytology Department, Dokki, Giza, Egypt 1H (400 MHz) and 13C (100 MHz) NMR spectra were recorded on an Jeol Mona A.M. Abo-Zeid: National Research Centre, Genetics and α-400 FT-NMR spectrometer (Tokyo, Japan), and chemical shifts are Cytology Department, Dokki, Giza, Egypt; and Cancer Biology given as δ values with tetramethylsilane (TMS) as internal standard at Laboratory, Center of Excellence for Advanced Sciences, National 35 °C in pyridine-d5. High-performance liquid chromatography (HPLC) Research Centre, Dokki, Giza, Egypt was performed on a Jasco system 800 instrument (Tokyo, Japan). 32 Melek et al.: Saponins of Gleditsia caspica and their antigenotoxic activity 2.2 Chemicals (1H, dd, J = 10.5, 2.0 Hz, H-8a), 5.53 (1H, dd, J = 17.0, 2.0 Hz, H-8b), 6.11 (1H, dd, J = 17.0, 10.5 Hz, H-7), 7.20 (1H, t, J = 8.0 Hz, H-3). – 13C NMR (C H N, 100 MHz): [6]. Cyclophosphamide (CP) and all other material used in cell culture 5 5 were purchased from Sigma-Aldrich (St. Louis, MO, USA). All other chemicals used in extraction and isolation of saponins were pur- 2.6 Gleditsioside B (2) chased from ADWIC (Cairo, Egypt). 1 Amorphous powder (20 mg). – H NMR (C5H5N, 400 MHz): aglycone: 2.3 Plant material δ 0.87, 0.91, 0.97, 0.99, 1.08, 1.33, 1.36 (each 3H, s), 5.47 (1H, br t, J = 3.0 Hz, H-12); sugar units: δ 1.76 (3H, d, J = 6.1 Hz, Rha Me-6), 4.97 (1H, d, J = 7.0 Hz, Xyl H-1), 5.06 (1H, d, J = 7.0 Hz, Xyl′ H-1), 5.14 (1H, d, J = 5.2 Hz, Fruits of G. caspica were collected from El-Orman public garden, Ara H-1), 5.17 (1H, d, J = 7.8, Xyl″ H-1), 6.13 (1H, d, J = 9.0 Hz, Glc′ H-1), Giza, Egypt, in November 2012. A voucher specimen was deposited in 6.35 (1H, d, J = 1.3 Hz, Rha H-1); monoterpene unit (MT): δ 1.44 (3H, s, the herbarium of the National Research Centre (CAIRC), Giza, Egypt. Me-10), 5.14 (1H, dd, J = 10.8, 1.8 Hz, H-8a), 5.53 (1H, dd, J = 17.3, 1.8 Hz, H-8b), 6.10 (1H, dd, J = 17.3, 10.8 Hz, H-7), 7.23 (1H, t, J = 7.9 Hz, H-3). – 13C NMR (C H N, 100 MHz): [5]. 2.4 Preparation of the saponin fraction of G. caspica 5 5 (SFGC) and isolation of saponins 2.7 Gleditsioside C (3) The air-dried fruits of G. caspica (2.0 kg) were defatted with n-hexane, then extracted twice with CHCl , followed by MeOH until exhaustion. 1 3 Amorphous powder (10 mg). – H NMR (C5H5N, 400 MHz): aglycone δ The combined MeOH extract was evaporated under reduced pres- 0.92, 0.94, 0.99, 1.08, 1.11, 1.31, 1.84 (each 3H, s), 5.19 (1H, br s, H-16), sure to dryness. The residue (66 g) was dissolved in the least pos- 5.64 (1H, br t, J = 3.0 Hz, H-12); sugar units: δ 1.62 (3H, d, J = 6.5 Hz, Rha sible amount of MeOH, and the solution was diluted with the 10-fold Me-6), 4.92 (1H, d, J = 7.5 Hz, Glc H-1), 4.99 (1H, d, J = 6.9 Hz, Xyl H-1), amount of acetone to precipitate 18 g of a crude saponin mixture. 5.10 (1H, d, J = 7.5 Hz, Xyl′ H-1), 5.11 (1H, d, J = 7.0 Hz, Xyl″ H-1), 5.12 (1H, The mixture was dissolved in H2O (0.2%), and the aqueous solution d, J = 5.0 Hz, Ara H-1), 5.15 (1H, d, J = 10.5 Hz, Gal H-1), 5.93 (1H, d, J = 9.0 passed through a chromatographic column packed with 500 g Diaion Hz, Glc′ H-1), 6.43 (1H, d, J = 1.3 Hz, Rha H-1); monoterpene unit (MT): HP-20 polymer gel (Mitsubishi, Tokyo, Japan). After washing the col- δ 1.45 (3H, s, Me-10), 5.15 (1H, dd, J = 10.8, 1.8 Hz, H-8a), 5.53 (1H, dd, umn with distilled water for several times, elution was carried out J = 17.3, 1.8 Hz, H-8b), 6.10 (1H, dd, J = 17.3, 10.8 Hz, H-7), 7.22 (1H, t, with 25%, 50%, 60%, 75% aqueous MeOH and finally with 100% 13 J = 7.8 Hz, H-3). – C NMR (C5H5N, 100 MHz): [5]. MeOH. The collected fractions were examined by silica gel thin layer chromatography (TLC) (Merck, Darmstadt, Germany) using the sol- 2.8 Animals vent systems CHCl3/MeOH/H2O (60:30:5, v/v/v) and n-BuOH/EtOH/ NH4OH (7:2:5) and visualized by spraying with 20% sulfuric acid in MeOH followed by heating at 110 °C. Based on TLC analysis, simi- Laboratory-bred strain Swiss albino male mice, 10–12 weeks old lar fractions were combined. Fractions eluted with 75% and 100% with an average weight of 25±2.5 g were obtained from the National MeOH were found similar and contained saponin constituents. The Research Centre, Giza, Egypt. Animals were housed in groups (five two fractions were combined, and part of the combined fraction animals/group) and maintained under standard conditions of tem- (SFGC) (3 g) was kept in a refrigerator until used for the biological perature, humidity, and light. The animals were given standard food study. The remainder (2.5 g) was applied onto a chromatographic and water ad libitum. column packed with 120 g PSQ 100B silica gel (Fuji Silysia, Nagoya, Japan) and eluted with CHCl3/MeOH/H2O with increasing polarity (70:27:3–58:35:7). A total of 50 fractions, 50 mL each, were collected. 2.9 In vitro study Similar fractions were combined after TLC analysis to yield 20 sub- fractions, A–T. Subfractions A (605 mg) and B (410 mg) were sub- 2.9.1 Cell culture: The breast cancer cell line (MCF-7) (ATCC, Rock- jected to repeated HPLC (column, TSK gel ODS-80TS, 5 mm × 60 cm; ville, MD, USA) was routinely cultured in RPMI-1640 media sup- solvent, 30%–45% CH3CN in H2O, linear gradient; flow rate, 45 mL/ plemented with 10% fetal bovine serum (FBS), 2 mM glutamine, min; detection, UV at 205 nm).
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