|Year : 2013 | Volume
| Issue : 2 | Page : 148-154
Desmutagenic and antimutagenic potential of phenolics from Khaya grandifoliola (C.DC.), Meliaceae
Fatma A Hashem1, Elsayed A Aboutabl2, Sahar S EL Souda3, Maysa Moharam4, Amal A Mammoun1, Manal Shabana5
1 Department of Pharmacognosy, National Research Centre, Dokki, Giza, Egypt
2 Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo, Egypt
3 Department of Chemistry of Natural Compounds, National Research Centre, Dokki, Giza, Egypt
4 Department of Microbiology, National Research Centre, Dokki, Giza, Egypt
5 Department of Phytochemistry and Plant Systematics, National Research Centre, Dokki, Giza, Egypt
|Date of Submission||02-May-2013|
|Date of Acceptance||20-Aug-2013|
|Date of Web Publication||31-Dec-2013|
Fatma A Hashem
Department of Pharmacognosy, National Research Centre, Elbehous street, 12311 Dokki, Giza
Source of Support: None, Conflict of Interest: None
Background and objectives
Antimutagenic or protective effects have been attributed to many classes of phytocompounds, mainly flavonoids and phenolic compounds, present in foods. Anticancer, antioxidant and anti-inflammatory activities of Khaya spp. have been reported, but their desmutagenic and antimutagenic activities were not studied. The aim of this study was to identify the phenolic contents of Khaya grandifoliola and correlate the desmutagenic and antimutagenic activities of these compounds.
Materials and methods
Desmutagenic and antimutagenic activities of specimen extracts of K. grandifoliola leaves and flowers were evaluated by measuring the inhibition of Salmonella typhimurium TA100 His + revertants induced by ethyl methanesulphonate and ribose lysine. The phenolic contents of K. grandifoliola leaf extracts were determined using column and paper chromatography. Spectroscopic analysis UV, 1 H NMR, 13 C NMR and electrospray ionization were applied to identify the isolated compounds.
Results and conclusion
Five phenolic compounds were isolated for the first time from K. grandifoliola leaves. These compounds were identified as quercetin 3-O-rhamnoglucoside (rutin), quercetin 3-O-rhamnoside, quercetin 3-O-glucoside, quercetin and 6-methoxycoumarin-7-O arabinofuranoside. The alcoholic extracts of both leaves and flowers (total and successive) of K. grandifoliola, rutin and quercetin rhamnoside isolated from the leaves, exhibited desmutagenic and antimutagenic activity against ethyl methanesulphonate-induced and ribose lysine-induced reversion.
Keywords: ethyl methanesulphonate, Khaya grandifoliola, Meliaceae, ribose lysine, rutin, Salmonella typhimurium TA100 (His - ), scopoletin 7-O-a-arabinofuranoside
|How to cite this article:|
Hashem FA, Aboutabl EA, EL Souda SS, Moharam M, Mammoun AA, Shabana M. Desmutagenic and antimutagenic potential of phenolics from Khaya grandifoliola (C.DC.), Meliaceae. Egypt Pharmaceut J 2013;12:148-54
|How to cite this URL:|
Hashem FA, Aboutabl EA, EL Souda SS, Moharam M, Mammoun AA, Shabana M. Desmutagenic and antimutagenic potential of phenolics from Khaya grandifoliola (C.DC.), Meliaceae. Egypt Pharmaceut J [serial online] 2013 [cited 2022 Nov 26];12:148-54. Available from: http://www.epj.eg.net/text.asp?2013/12/2/148/124018
| Introduction|| |
Plants of the family Meliaceae Juss are trees, shrubs or rarely herbs that may be laticiferous (rarely, with a milky juice exuding from the bark). Plants of this family are distributed in tropical, subtropical and occasionally warm temperate regions. The genus Khaya comprises seven species native to tropical Africa and Madagascar. Limonoids are heavily oxygenated modified triterpenes dominant in the plants of this family and exhibit anticancer activity and antifeedant activity against insects. Compounds other than limonoids were isolated from Khaya grandifoliola (African Mahogany), which include catechin from the bark seed  and steroid hormone from the bark  , whereas rutin and quercetin flavonoids were isolated from Khaya senegalensis leaves  . Antimalarial  , schistosomicidal  , hypoglycaemia and hypocholesterolaemic  activities were reported for K. grandifoliola stem bark. As the mutagens are involved in the initiation and promotion of several human diseases including cancer, the significance of novel bioactive phytocompounds in counteracting the promutagenic and carcinogenic effects are important. Such chemicals that reduce the mutagenicity of physical and chemical mutagens are called antimutagens. Numerous studies have been carried out to identify compounds that might protect humans against DNA damage and its consequences. The antimutagenic and anticarcinogenic properties of a wide variety of dietary constituents and plant secondary metabolites have been reported ,, . Natural antimutagens from edible and medicinal plants are of particular importance, as they may be useful for human cancer prevention and have no undesirable xenobiotic effects on living organisms , . Anticancer  , antioxidant  , and anti-inflammatory  activities of Khaya spp. have been reported, but desmutagenic and antimutagenic activities were not studied. Directly assaying potential carcinogens by testing their ability to form tumours in animals is difficult and expensive. In addition to causing tumours in animal cells, most carcinogens are mutagens ,, . Hence, the objective of this work was the evaluation of the desmutagenic and antimutagenic potential of the plant.
| Experimental|| |
Ultraviolet (UV) spectra were obtained on a Shimadzu UV 240, Shimadzu Corporation (Tokyo, Japan) spectrometer. NMR Jeol ECA spectrometer, Jeol Corporation (Tokyo, Japan) 500 MHz for 1 H NMR and 125 MHz for 13 C NMR were used with DMSO-d6 as the solvent. All chemical shifts (d) are given in ppm units with reference to TMS as an internal standard and the coupling constants (J) are given in Hz. Paper chromatography (Whatman No. 1 and 3 mm; Whatman, International Ltd, Maidstone, England, UK), mass spectrometer, electrospray ionization mass spectrometry (ESI-MS), and Thermo Finnigan, Finnigan Corporation, California, USA (ion trap) were used.
| Materials and methods|| |
Fresh leaves and flowers of K. grandifoliola (C.DC.), Meliaceae, grown in Egypt were collected from Giza Zoo (Giza, Egypt). They were confirmed by Dr Mohamed El-Gebaly, a plant taxonomist.
Preparation of successive extracts
Air-dried powdered leaves (600 g) and flowers (100 g) were successively and separately extracted with petroleum ether, chloroform, ethyl acetate and 95% ethanol in a Soxhlet apparatus. The solvents were evaporated to dryness under reduced pressure at 40°C; the yield of leaf extracts was 25.2, 24.3, 0.3, and 60 g, respectively, whereas those of flowers were 2.5, 1.5, 1.7 and 10 g, respectively.
Preparation of 90% ethanol extracts
The crude extract was prepared by percolating the air-dried powdered leaves (500 g) and flowers (50 g) with 90% ethanol till exhaustion. The filtered percolate, in each case, was evaporated to dryness under vacuum at 40°C to yield 129 and 8 g, respectively.
Ethanol extracts from successive extractions were subjected to two-dimensional paper chromatography for the detection of flavonoids using Whatman No. 1 and solvent systems (s 1 ) n-butanol : acetic acid : water (3 : 1 : 1 v/v) and (s 2 ) acetic acid : water (15 : 85 v/v) for development. Chromatograms were examined under UV light (365 nm) before and after exposure to ammonia vapour and spraying with AlCl 3 solution.
Isolation of phenolics
Successive ethanol extracts of K. grandifoliola leaves (60 g) were fractionated on a reversed-phase polyamide column, with the gradient solvent system starting from 100% water to 100% methanol. The fractions were purified on subcolumns of Sephadex (LH-20) using butanol saturated with water as the eluent to yield compound I (20 mg), whereas compound V (14 mg) was isolated from the 30% (methanol/water) fraction, purified on a silica gel column using gradient elution from petroleum ether to chloroform, and then a column of Sephadex (LH-20) with methanol as eluent to yield yellow needle crystals. Compounds II, III and IV (6, 4 and 15 mg, respectively) were isolated from the ethyl acetate extract using preparative paper chromatography and were purified on columns of Sephadex (LH-20). Spots were detected in each fraction, their Rf values in systems s 1 and s 2 and their colours being recorded in [Table 1]. Purified compounds were subjected to UV spectral analysis and 1 H NMR, 13 C NMR determinations. Spectroscopic UV data of these compounds were compared with the published data  and are represented in [Table 2]. The NMR assignments are showed in [Table 3] and [Table 4]. Compound III was identified after acidic hydrolysis. The compound was completely dissolved in 6% aqueous HCl (5 ml) and minimal methanol. The solution was heated on a steam bath for 45 min, then cooled and extracted by shaking with ether to yield the aglycon in the ethereal layer after drying on anhydrous sodium sulphate and the sugar moiety in the aqueous layer  .
|Table 2: UV ( λ methanol max ) spectral data of compounds I, II, III and IV|
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Inhibition of mutagen-Induced revertants in Salmonella More Details typhimurium
Desmutagenic and antimutagenic activities of leaves and flowers of K. grandifoliola extracts were detected using the bacterial strain Salmonella typhimurium TA100 (His - ). The concentration of each mutagen used was as follows: 25 μl in 100 μl DMSO, ethyl methanesulphonate (EMS); ribose lysine (RL), 0.5 mol/l in water , . Ascorbic acid was used as the reference desmutagenic and antimutagenic compound  .
Various amounts of the ethanolic extracts (total and successive) of K. grandifoliola (leaves and flowers), compound I (rutin), compound II (quercetin-3-O-α-L-rhamnopyranoside), ascorbic acid (as the reference drug) and the mutagen were mixed with sterile distilled water (1 ml final volume) containing 100 μmol phosphate buffer (pH 7.4). The mixture was incubated at 37°C for 30 min, and 100 ml of a 24-h bacterial culture of TA100 His - strain (10 8 cells) and 2 ml of molten top agar (45°C) were poured with the mixture onto minimal glucose agar plates. The plates were incubated once more for h at 37°C. The number of His + -induced revertants was scored after incubation for 48 h at 37°C.
Various concentrations of ethanolic extract (total and successive), compound I, compound II and ascorbic acid (as the reference drug) were added to sterile distilled water (1 ml final volume) containing 100 μl of the 24-h culture of the TA100 His - test strain and 100 μmol of phosphate buffer pH 7.4. After incubation at 37°C for h, cells were collected by centrifugation, washed twice with phosphate buffer to remove the antimutagen (tested compounds) and finally suspended in 1 ml of the buffer. After addition of the mutagen and 2 ml of soft agar, the mixture was poured onto minimal glucose agar plates. After incubation for 48 h at 37°C, revertant colonies (His + ) were counted.
Desmutagenic and antimutagenic activities were calculated as the percentage of decrease in induced revertants according to Amara-Mokrane and colleagues , after subtraction of the corresponding spontaneous reversion according to the equation: %inhibition = 100-(N/N0 × 100), where N is the revertant/plate induced by the mutagen in the presence of increasing amounts of the tested material and N0 is the reversion induced in the control [Table 6] and [Table 7].
|Table 6: Desmutagenic and antimutagenic potential of ethanolic extracts, compound I and compound II isolated from Khaya grandifoliola using EMS-induced and RL-induced revertants|
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|Table 7: % Potency of compound I and compound II as desmutagenic and antimutagenic agents using EMS-induced revertants relative to ascorbic acid as the reference drug |
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| Results and discussion|| |
Identification of isolated compounds
Compound I was expected to be quercetin-3-O-glycoside on the basis of its chromatographic properties (Rf values, colour under UV/NH 3 and AlCl 3 )  [Table 1]. UV spectra [Table 2] show a bathochromic shift in band I (51 nm), on addition of NaOMe, accompanied by an increase in the intensity, which was an evidence of free 4′-OH. The bathochromic shift in band II (16 nm), on addition of NaOAc, referred to a free 7-OH. A bathochromic shift of 43 nm in band I in the presence of AlCl 3 /HCl confirms the presence of 5-OH. In addition, a bathochromic shift of 21 nm in band I in the presence of NaOAc/H 3 BO 3 and a hypsochromic shift of more than 21 nm of band I in AlCl 3 /HCl spectrum relative to band I in the spectrum of AlCl 3 confirmed the presence of ortho-dihydroxyl groups in the B ring  . The 1 H, 13 C NMR spectra [Table 3] and [Table 4] of compound I revealed the presence of glucose, rhamnose and quercetin. The 1 H NMR spectrum showed an overlapping signal at d 7.51 for H-2′, 6′ and a doublet at d 6.81 (J = 8.4 Hz) for H-5′ due to ortho-coupling with H-6′ and two doublets of two aromatic protons at d 6.35 and 6.15 (J = 1.5 Hz), each proton assigned for H-8 and H-6, respectively.
A β-D-rutinoside moiety at C-3 was deduced from the downfield signal of C-3 to 133.81 ppm and the two anomeric carbons appeared at 101.70 and 101.26 ppm, together with two anomeric proton signals at d 5.29 (d, J = 6.8 Hz) and d 4.34 (singlet) and a doublet of three protons at d 0.96 (J = 6.0 Hz) for Me-6′′′. A 1′′′;6′′′ interglycosidic linkage was followed from the characteristic up-field location of H-1′′′ as a singlet at d 4.34. Therefore, compound I was identified as rutin [quercetin-3-O-α-L-rhamnopyranosyl-(1′′′;6′′′)-O-β-D-glucopyranoside]. Rutin was previously isolated from K. senegalensis (A. Juss) leaves  , but this is the first report for its isolation from the K. grandifoliola.
The UV spectra of compound II [Table 2] show a bathochromic shift (44 nm) in band I with an increase in the intensity relative to that of MeOH upon addition of NaOMe, indicating free 4′-OH. It also showed a characteristic bathochromic shift in band II (15 nm) on addition of NaOAc attributed to a free 7-OH group. In contrast, there was a bathochromic shift of 44 nm in band I in the presence of AlCl 3 /HCl, confirming the presence of 5-OH. In addition, a bathochromic shift of 17 nm in band I in the presence of NaOAc/H 3 BO 3 and a hypsochromic shift about 37 nm of band I in AlCl 3 /HCl spectrum relative to band I in the spectrum of AlCl 3 confirmed the presence of ortho-dihydroxyl groups in the B ring  .
1 H, 13 C NMR spectra of compound II [Table 3] and [Table 4] revealed the presence of quercetin and rhamnose. The 1 H NMR spectrum showed an overlapping signal at d 7.25 for H-2′, 6′ and a doublet at d 6.81 (J = 8.4 Hz) for H-5′ due to ortho-coupling with H-6′. Two doublets at d 6.13 and 6.32 ppm assigned H-6 and H-8, respectively. The downfield signal of C-3 in 13 C NMR to 134.63 ppm confirmed the flavonol structure. The anomeric carbon of rhamnose appeared at 102.29 ppm, with the anomeric proton appearing as a doublet of small J value at d 5.21 ppm, whereas protons of the methyl group showed a doublet with J = 6 Hz at d 1.19 ppm appearing in 13 C NMR at 18.02 ppm. Hence, compound II was identified as quercetin- 3-O-α-L-rhamnopyranoside.
UV spectra [Table 2] show a bathochromic shift in band I (40 nm), on addition of NaOMe, with no decrease in the intensity, which was an evidence of free 4′-OH. In addition, a characteristic bathochromic shift in band II (20 nm) on addition of NaOAc referred to a free 7-OH group confirmed by a new peak appearing at 330 nm upon addition of NaOMe. A bathochromic shift of 31 nm in band I in the presence of AlCl 3 /HCl confirmed the presence of 5-OH. In addition, a bathochromic shift of 15 nm in band I in the presence of NaOAc/H 3 BO 3 and a hypsochromic shift of more than 27 nm of band I in AlCl 3 /HCl spectrum relative to band I in the spectrum of AlCl 3 confirmed the presence of ortho-dihydroxyl groups in the B ring  . The compound was expected to be quercetin-3-O-glycoside on the basis of its chromatographic properties. The sugar moiety was determined after complete acid hydrolysis to yield glucose in the aqueous phase and quercetin in the organic phase (copaper chromatography with authentics using Aniline phthalate reagent for sugars and AlCl 3 for the aglycone). Hence, compound III was identified as quercetin-3-O-α-L-glucopyranoside.
Compound IV was expected to be quercetin on the basis of its chromatographic properties. The bathochromic and hypsochromic shifts observed in the UV spectra [Table 2] were in good agreement with quercetin aglycone  .
UV spectra show a bathochromic shift in band I (47 nm), on addition of NaOMe, accompanied by an increase in the intensity, which was an evidence of free 4′-OH. The bathochromic shift in band II (11 nm), on addition of NaOAc, referred to a free 7-OH. A bathochromic shift of 55 nm in band I in the presence of AlCl 3 /HCl was observed, confirming the presence of 5-OH. In addition, a bathochromic shift of 16 nm in band I in the presence of NaOAc/H 3 BO 3 and a hypsochromic shift of 23 nm in band I in the AlCl 3 /HCl spectrum relative to band I in the spectrum of AlCl 3 confirmed the presence of ortho-dihydroxyl groups in the B ring  .
The 1 H, 13 C NMR spectra [Table 3] and [Table 4] of compound IV revealed the presence of a flavonol structure with a downfield signal of C-3 in 13 C NMR to 135.59 ppm. The 1 H NMR spectrum showed a signal at d 7.64 for H-6′ d,d, with J = 8.4 Hz, due to ortho-coupling with 5′, which appeared as a doublet at d 6.95 ppm and (J = 2.2 Hz) due to meta-coupling with 2′′, which appeared as a doublet at d 8.4 ppm and two doublets of two aromatic protons at d 6.47 and 6.21 (J = 1.5 Hz), each proton assigned for H-8 and H-6, respectively. Hence, compound IV was identified as quercetin.
Compound I: R = rutinoside; compound II: R = rhamnoside; compound III: R = glucoside; compound IV: R = H.
Compound V appeared as a blue fluorescent spot on TLC (Silica gel 60GF 254 precoated plates), turning yellow on exposure to ammonia vapour (Rf = 0.39; benzene : ethyl acetate, 7 : 3).
UV λmax : 261, 288, 339, 363 nm (in methanol).
ESI-MS: (m/z, rel. int.) C 15 H 16 O 8 [M+H] +1 , 325.
The UV absorption bands at 288 and 339 nm could be attributed to the benzene and the pyrone rings, respectively. The NMR data [Table 5] shows signals corresponding to methoxy substituents in an aromatic system at d 3.9 ppm, confirmed by 13 C NMR at 55.5 ppm. Signals corresponding to H-3 and H-4 appeared at 6.2 and 7.8 ppm, respectively, with J3,4 = 9.15 Hz, confirming ortho-coupling. Two other singlets appeared at 6.7 and 7.1 ppm, corresponding to H-5 and H-8, respectively, confirming (with the 13 C NMR spectrum) the structure of 6,7-disubstituted coumarin. The signal appearing at 5.2 ppm in 1 H NMR with J = 1 Hz assigned the anomeric proton of the sugar moiety, which is identified by 13 C NMR as arabinose and confirmed by acid hydrolysis and cochromatography with authentic sugar. From these data, compound V was identified as 6-methoxycoumarin-7-O-arabinofuranoside (scopoletin 7-O-α-arabinofuranoside). This is the first isolation of this compound from the family Meliaceae.
Desmutagenic and antimutagenic potential
Desmutagenic and antimutagenic activities of specimen extracts of K. grandifoliola leaves and flowers were ascertained by measuring the inhibition of TA100 His + revertants induced by EMS and RL. The results in [Table 6] showed that the desmutagenic and antimutagenic activity of flower extract is higher than that of leaf extract especially in case of EMS. Tests on EMS-induced reversion showed good activity of all the extract specimens. In contrast, desmutagenic and antimutagenic activities of RL were variable, whereas rutin and quercetin rhamnoside showed somewhat similar results in case of EMS and RL. The %potency of the two compounds was calculated relative to ascorbic acid as the reference drug  . Results illustrated in [Table 7] show a higher %potency of quercetin rhamnoside than rutin as an antimutagenic agent in case of EMS-induced revertants. This phenomenon can be interpreted by the different action mechanisms of these mutagens, or presumably due to the selective activity of the antimutagen compound.
The antimutagenic factors are divided into two main classes according to differences in their modes of action: one is the desmutagen, which inhibits the formation of mutagens out of the cell or taking the mutagens into the cell, or inactivates or destroys mutagens directly or indirectly out of the cell, and pre-incubation treatment is designed to evaluate the desmutagenic effect. The other type is called a bioantimutagen, which suppresses the process of mutagenesis itself in the cell; for example, it eliminates radicals or increases DNA repair systems; other antimutagens exert this effect by acting as blocking agents  . Recent research has confirmed that plant flavonoids inhibit the mutagenicity induced by chemical mutagens  .
Antimutagenic or protective effects have been attributed to many classes of phytocompounds, mainly flavonoids and phenolic compounds, present in food. However, such compounds have also been reported to exhibit a wide range of other biological activities such as antimicrobial, anti-inflammatory, antioxidant and free-radical scavenging , . In this study, rutin and quercetrin were the major flavonoids showing desmutagenic and antimutagenic activity similar to ascorbic acid. These compounds were reported for their antioxidant  , anticancer  and anti-inflammatory  activities.
| Conclusion|| |
Alcoholic extracts of both leaves and flowers (total and successive) of K. grandifoliola, rutin and quercetin rhamnoside isolated from the leaves, exhibited desmutagenic and antimutagenic activity against EMS-and RL-induced reversion.
| Acknowledgements|| |
The authors thank the National Research Centre (Egypt) for funding this work.
Conflicts of interest
There are no conflicts of interest.
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[Table 1], [Table 2], [Table 3], [Table 4], [Table 5], [Table 6], [Table 7]
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