Short Communication | Volume: 9, Issue: 6, June, 2019

C-glycosyl flavonoids-rich extract of Dipcadi erythraeum Webb & Berthel. bulbs: Phytochemical and anticancer evaluations

Mona M. Marzouk Ahmed Elkhateeb Rasha R. Abdel Latif El-Sayed S. Abdel-Hameed Salwa A. Kawashty Sameh R. Hussein   

Open Access   

Published:  Jun 05, 2019

DOI: 10.7324/JAPS.2019.90613
Abstract

Dipcadi erythraeum Webb & Berthel. is a wild edible species belonging to family Asparagaceae and commonly used in folk medicine. The D. erythraeum bulbs extract was subjected to chemical investigation using Liquid Chromatography-Electrospray Ionization Mass Spectrometry (LC-ESI-MS) technique to identify its polar active constituents and evaluated against four human carcinoma cell lines; MCF7, HEPG2, A549, and HCT116. The D. erythraeum bulbs extract revealed 22 phenolic compounds characterized for the first time from the studied species, 14 of them were identified as C-glycosyl flavonoids. Moreover, the studied extract showed moderate activity against MCF7 and HCT116 at 100 μg/ml with cell viability of 43.6% and 48.4%, respectively. From the chemotaxonomic point of view, the presence of C-glycosyl flavonoids supported that D. erythraeum has a closer relationship with the species of Asparagaceae family than Liliaceae.


Keyword:     Dipcadi erythraeum C-glycosyl flavonoids LC-ESI-MS cytotoxic activity.


Citation:

Marzouk MM, Elkhateeb A, Abdel Latif RR, Abdel-Hameed ES, Kawashty SA, Hussein SR. C-glycosyl flavonoids-rich extract of Dipcadi erythraeum bulbs: Phytochemical and anticancer evaluations. J Appl Pharm Sci, 2019; 9(06): 094–098.

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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INTRODUCTION

The genus Dipcadi is recently belonging to the subfamily Scilloideae of the family Asparagaceae. It is reported mainly from Africa, peninsular India, Madagascar, and neighboring Pakistan. Ten species of this genus are reported, of which D. erythraeum Webb & Berthel. is distributed in India as well as in different tropical regions of the world such as the Canary Islands, Arabia, Egypt, and Saudi Arabia (Boulos, 2009).

Dipcadi erythraeum [Syn. Dipcadi unicolor (Stocks) Baker, Uropetalum unicolor, Hooker’s, Ornithogalum erythraeum (Webb & Berthel.) J. C. Manning & Goldblatt, Uropetalon erythraeum (Webb & Berthel.) Boiss.] is observed in rocky and gravelly habitats where rainwater collects for some days. The leaves are narrowly linear, while the flowers are greenish in color. Flowers and fruits appear during the months of August–September (Bhandari, 1990).

Dipcadi erythraeum is a medicinal plant with great folk uses. The bulbs and capsules are eaten raw during the famine (Jongbloed et al., 2000; Mandaville, 1990). The leaves are laxative and used as an ointment for wounds (Moussaid et al., 2013), while the whole plant is used for a cough, biliousness, diabetes, urinary and discharge. Phytochemical screening of Dipcadi species revealed the presence of tannins, alkaloids, flavonoids, and saponins (Abdulkareem et al., 2014; Adly et al., 2015; Ali, 2005). El-Shabrawy et al. (2016) reported the isolation of two flavonol aglycones (kaempferol and quercetin), one flavonol glycoside (quercetin 3-O-rutinoside-7-O-α-rhamnopyranoside), and four C-glycosyl flavones (vitexin, isovitexin, orientin, and isoorientin) from the defatted aqueous methanol extract of D. erythraeum whole plant.

There are no biological activities reported for D. erythraeum, therefore, the objective of the present study is to further our knowledge about its phytochemical constituent using Liquid Chromatography-Electrospray Ionization Mass Spectrometry (LC-ESI-MS) and evaluate its cytotoxic activity against breast (MCF7), hepatocellular (HEPG2), lung (A549), and colon (HCT116) cell lines.


EXPERIMENTAL

Plant material and extraction

Dipcadi erythraeum was collected 120 km Cairo-Alexandria desert road, in March 2017 and identified by M. El-Shabrawy. A voucher specimen (s.n. MS6) was deposited in the herbarium of the National Research Center (CAIRC). The bulbs were dried and grinded, then extracted three times with 70% MeOH/H2O (Mabry et al., 1970). The solvent was evaporated under reduced pressure at 50°C and then the dried extract was defatted with petroleum ether.

LC-ESI-MS analysis

Dipcadi erythraeum aqueous methanol extract was analyzed by LC-ESI-MS system [High Performance Liquid Chromatography (Waters Alliance 2695) and mass spectrometry (Waters 3100)] according to the methods of Hussein et al. (2018). Known peaks were identified by comparing their retention time and mass spectrum with the flavonoid standards (95% purity; UV, Nuclear Magnetic Resonance) which were obtained from our research group (Phytochemical and Plant Systematic Department, NRC) (El-Shabrawy et al., 2016; El-Sherei et al., 2018; Hussein et al., 2017, 2018; Ibrahim et al., 2013; Marzouk et al., 2010). Other peaks were tentatively identified by comparing the mass spectrum with the literature.

Cell culture and sample treatment

The investigated human carcinoma cell lines were breast (MCF7), hepatocellular (HEPG2), lung (A549), and colon (HCT116). They were purchased from American Tissue Culture Collection. HEPG2, MCF7, and HCT116 cells lines were cultured in RPMI 1640 medium, while A549 cell line was cultured in DMEM media. Media and cell culture preparations and treatments in addition to the in vitro cytotoxic activity of the plant extract were measured and followed the same method of Ibrahim et al. (2013).


RESULTS AND DISCUSSION

Identification of phenolics using LC-ESI-MS analysis

Twenty-two compounds were identified in the bulbs extract of D. erythraeum (Fig. 1, Table 1), all of them were characterized for the first time in the studied species.

Peak 2 (m/z 195) was characterized as gluconic acid. Its spectrum showed a fragment ion at m/z 129 which corresponds to the loss of H2O and CO2 molecules [M-H-CO2-H2O] (Felipe et al., 2014). Peak (3) at m/z 335 showed a fragment ion at m/z 173 [M-162-H], after the loss of hexose unit, indicative for shikimic acid which showed other two fragments after the loss of H2O molecules; m/z155 [M-162-H-H2O] and 137 [M-162-H-2H2O]. Accordingly, compound 3 was tentatively identified as shikimic acid hexoside (Spínola et al., 2015). Peak (4) showed [M-H] ion at m/z 487 and produced fragments at m/z 325 [M-H-hexose] (coumaric acid hexoside), 163 [M-H-2hexose] (coumaric acid), and m/z 119 [M-H-2hexose-COOH] (decarboxylated coumaric acid). Thus, compound 4 was tentatively identified as coumaric acid dihexoside (Simirgiotis et al., 2015). Peak (5) showed a molecular ion at m/z 503 and revealed fragments at m/z 341 [M-H-hexose], 179 [M-H-2 hexose], and 135 [M-H-2 hexose-COOH], indicating the presence of caffeic acid di-hexoside (Simirgiotis et al., 2015). Compound (8) at m/z 191 was existing as quinic acid, confirmed by the presence of the fragment ion at m/z 127 [M-H-CO-2H2O] (Taamalli et al., 2015).

Figure 1. LC-ESI-MS chromatogram of D. erythraeum bulbs.

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Table 1. Tentative identificatiotn of chemical compounds in D. erythraeum bulbs.



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Peak (9) at m/z 421 revealed the fragmentation pattern of coumaroyl quinic acid (m/z 337, 191, 173, 163, and 119) (Marzouk et al., 2018) with an extra 84 amu, suggestive for a malonyl group. Therefore, compound 9 was considered as malonylcoumaroyl quinic acid. Peak (10) showed a molecular ion at m/z 355 and revealed fragments at m/z 193 [M-H-hexose] and 149 [M-H-hexose-COOH], indicating the presence of ferulic acid hexoside (Simirgiotis et al., 2015). Peak (11) with a molecular anion at m/z 609 showed a fragment ion at m/z 447 after the loss of a dehydrated hexose unit [M-162-H], attached as O-substitution of the C-glycosyl flavone structure. The fragment ions at m/z 327 [447-120-H] and at m/z 357 [447-90-H] confirmed the characteristic isoorientin ion. Therefore, peak 11 assigned as isoorientin-7-O-hexoside. In comparison with standards, compound 11 was identified as isoorientin-7-O-β-glucopyranoside (lutonarin) (El-Sherei et al., 2018).

Compound (12) showed a molecular anion at m/z 562 and exhibited losses of (−90) which appeared at m/z 472. It was readily assigned as apigenin-6, 8-di-C-rhamnoside, in comparison with a standard. Likewise, apigenin-6, 8-di-C-glucoside was identified for peak (13) at m/z 593 and confirmed by its losses of (−90 amu) and (−120 amu) appearing at m/z 503 and 473.

Peak (15) showed typical fragments of isoorientin (m/z 327 [M-120-H] and m/z 357 [M-90-H])with an extra 42 amu, suggestive for an acetyl group connected to a glucose moiety and identified as isoorientin X″-O-acetyl. Moreover, peak (16) has a molecular ion at m/z 605 and showed fragmentation pattern of apigenin 6-C-pentoside-8-C-hexoside with an extra 42 amu indicative for an acetyl group connected to either hexose or pentose moieties as revealed from its −120 amu and −90 amu losses appearing at m/z 443 and 473, respectively, in addition to−60 amu loss for a C-pentoside appearing at m/z 503 [M-60-H] corresponding to a C-linked pentose. Pentose moiety is suggested to attach at the C-6 position as evident from m/z 503 [M-60-H] appearing at higher intensity relative to m/z 443 [M-120-H] and 473 [M-90-H] (Geiger and Markham, 1986). Therefore, peak 16 was identified as apigenin-6-C-pentoside-8-C-hexoside X″-O-acetyl. Di-C-glycosyl apigenin acetate derivatives were reported previously from some monocotyledon members (Williams, 1975).

Peak (17) with m/z 638 showed a fragment ion at m/z 506 [M-132-H], after the loss of pentose unit and indicative for delphinidin-O-hexoside with an extra 42 amu indicative for an acetyl group connected to the hexose moiety. Another fragment was observed at m/z 302 for delphinidin aglycone, thus compounds 17 was tentatively identified as delphinidin-O-hexoside X″-O-acetyl-O-pentoside. Delphinidin di-acetyl di-glycoside was reported before from the bulbs of other member of family Hyacinthaceae (Dias et al., 2003).

On the bases of retention time and fragmentation pattern of standards, compound 18 with m/z 579 is identified as luteolin 6-C-β-glucopyranoside-8-C-α-arabinopyranoside (carlinoside) (El-Sherei et al., 2018), confirmed by three fragment ions at m/z 519 [M-60-H], m/z 489 [M-90-H], and m/z 459 [M-120-H].

Isomer peaks (19) and (25) showed the same molecular ion peak at m/z 577 and displayed the same fragment ions at m/z 487 [M-90-H] and m/z 457 [M-120-H] indicative for a C-hexose unit. Isomers difference was founded on the intensity of m/z 457 [M-120-H] fragment for compound 19, it appeared as a base peak suggesting the attachment of the deoxyhexosyl moiety at the C-6 (Farag et al., 2016). In comparison with standards, compounds 19 and 25 were identified as apigenin 6-C-β-glucopyranoside-8-C-α-rhamnopyranoside (violanthin) and apigenin 6-C-α-rhamnopyranoside-8-C-β-glucopyranoside (isoviolanthin), respectively (El-Sherei et al., 2018).

Peak (20) at m/z 677 showed a fragment ion at m/z 533, after the loss of a dehydrated rhamnose unit [M-146-H], attached as O-substitution of the flavone di C-glycoside structure (m/z 533). Further fragmentation pattern of m/z 533 was revealed as m/z 473 [M-60-H] and 443 [M-90-H], indicating the loss for C-pentoside. Therefore, compound 20 was identified as apigenin 6, 8-di-C-pentoside-O-rhamnoside.

Peak (21) at m/z 563 showed fragmentation pattern of flavone-C-hexoside as revealed from its (−120 amu) and (−90 amu) losses appearing at m/z 443 and 473, respectively, in addition to (−60 amu) loss for a C-pentoside appearing at m/z 503 [M-60-H] corresponding to a C-linked pentose. Hexose moiety is suggested to attach at the C-6 position as evident from m/z 443 [M-120-H] appearing as base peak relative to pentose (Geiger and Markham, 1986) and was identified as apigenin-6-C-hexoside-8-C-pentoside.

Peak (23) at m/z 547 revealed a fragment ion at m/z 487 after the loss of −60 amu corresponding to a C-linked pentose; therefore, compound 23 was identified as apigenin-6-C-pentoside-8-C-rhamnoside.

Peak (22) and (24) at 679 and m/z 693 revealed the same fragment ion at m/z 547, after the loss of pentose unit [M-132-H] or rhamnose unit [M-146-H], respectively. Both pentose and rhamnose are suggested to be attached as O-substitution of the flavone di C-glycoside structure (m/z 547). Further fragmentation pattern of m/z 547 indicates the same structure of compound 23. Therefore, compounds 22 and 24 were similar to peak (23) with an extra mass difference of 132 amu (pentose moiety) and 146 amu (rhamnose moiety) in molecular ions, respectively. Therefore, compounds (22) and (24) were identified as apigenin 6-C-pentoside-8-C-rhamnose-O-pentoside and apigenin 6-C-pentoside-8-C-rhamnose-O-rhamnoside, respectively.

Peak (26) m/z 753 showed a fragment ion at m/z 591, after the loss of a dehydrated hexose unit [M-162-H], attached as O-substitution of the flavone di C-glycoside structure (m/z 591). Further fragmentation pattern of m/z 591 was similar to that of the peak (25) with an extra mass difference of 14 amu in molecular ions and its fragment masses assigned as apigenin 6-C-rhamnoside-8-C-hexoside-methyl ether (Farag et al., 2016). C-glycosyl apigenin methyl ether derivatives were reported previously from some monocotyledon member; Iris species (Iridaceae) (Kawase and Yagishita, 1968).

In vitro cytotoxic activity

The results indicated that the bulbs aqueous methanol extract of D. erythraeum showed moderate activity against MCF7 and HCT116 at 100 μg/ml with cell viability of 43.6% and 48.4%, respectively. However, it exhibited no evident cytotoxicity against A549 and HEPG2 cell lines.


CONCLUSION

Total 22 compounds including 14 C-glycosyl flavonoids, 6 phenolic acid derivatives (coumaric and caffeic acids derivatives), one organic acid, and one anthocyanin (delphinine derivative) were identified or tentatively characterized, all of them were detected for the first time from D. erythraeum. The presence of C-glycosyl flavonoids supported the suggestion achieved by El-Shabrawy et al. (2016), which indicate that D. erythraeum has a similar biosynthetic pathway and, therefore, a closer relationship with the species of Asparagaceae family than Liliaceae. Moreover, the studied extract showed moderate activity against MCF7 and HCT116 at 100 μg/ml with cell viability of 43.6% and 48.4%, respectively.


ACKNOWLEDGMENTS

This research is funded by the National Research Centre, Cairo, Egypt; Project number 11010328. The authors also thanks Dr. El-Shabrawy M. for collecting and authenticating the plant material of the present study.


CONFLICT OF INTERESTS

Author declares that there are no conflicts of interest.


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Reference

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Adly F, Moussaid M, Berhal C, Razik A, Elamrani AA, Moussaid H, Bourhim N, Loutfi M. Phytochemical screening and biological study of ethanol extractives of Dipcadi serotinum (L.) Medik. EJARBLS, 2015; 3(3):17-23.

Ali SI. Flora of Pakistan: hyacinthaceae. Department of Botany, University of Karachi, Karachi, Pakistan, no. 214, 2005.

Bhandari MM. Flora of the Indian Desert. Scientific Publishers, Jodhpur, India, 1990.

Boulos L. Flora of Egypt, revised annotated edition. Al Hadara Publishing, Egypt, 2009.

Dias C, Dias M, Borges C, Almoster FMA, Paulo A, Nascimento J. Structural elucidation of natural 2-Hydroxy Di- and Tricarboxilic Esters, Phenylpropanoid Esters, and Flavonoids extracted from the bulbs of Autonoë madeirensis using GC-EIMS, ESIMS and MS/MS techniques. Proceeding of 21st Informal Meeting on Mass Spectrometry, Antwerp, Belgium, 11-15 May 2003, P22:118.

El-Shabrawy MO, Marzouk MM, Hosni HA, El Garf IA, Kawashty SA, Saleh NAM. Flavonoid constituents of Dipcadi erythraeum Webb. & Berthel. Asian Pac J Trop Dis, 2016; 6(5):404-5. https://doi.org/10.1016/S2222-1808(15)61056-8

El-Sherei MM, Ragheb AY, Mosharrafa SA, Marzouk MM, Kassem MES, Saleh NAM. Pterygota alata (Roxb.) R. Br. leaves and stems: chemical constituents, anti-hyperglycemic effect and anti-oxidative stress in alloxan-induced diabetic rats. J Mater Environ Sci, 2018; 9(1):245-55. https://doi.org/10.26872/jmes.2018.9.1.28

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Hussein SR, Abdel Latif RR, Marzouk MM, Elkhateeb A, Mohammed RS, Soliman AAF, Abdel-Hameed ES. Spectrometric analysis, phenolics isolation and cytotoxic activity of Stipagrostis plumosa (Family Poaceae). Chem Pap, 2018; 72:29-37. https://doi.org/10.1007/s11696-017-0254-0

Ibrahim LF, Marzouk MM, Hussein SR, Kawashty SA, Mahmoud K, Saleh NAM. Flavonoid constituents and biological screening of Astragalus bombycinus Boiss. Nat Prod Res, 2013; 27:386-93. https://doi.org/10.1080/14786419.2012.701213

Jongbloed M, Western AR, Böer B. Annotated check-list for plants in the U.A.E. Zodiac Publishing, Dubai, UAE, 2000.

Kawase A, Yagishita K. On the structure of a new C-Glycosyl Flavone Embinin, isolated from the petals of Iris germanica Linnaeous. Agric Biol Chem, 1968; 32(4):537-8. https://doi.org/10.1271/bbb1961.32.537

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Mandaville JP. Flora of Eastern Saudi Arabia. Kegan Paul Int, London, UK, 1990.

Marzouk MM, Hussein SR, Elkhateeb A, El-shabrawy M, Abdel- Hameed ESS, Kawashty SA. Comparative study of Mentha species growing wild in Egypt: LC-ESI-MS analysis and chemosystematic significance. J Appl Pharm Sci, 2018; 8(8):116-22. https://doi.org/10.7324/JAPS.2018.8816

Marzouk MM, Al-Nowaihi ASM, Kawashty SA, Saleh NA. Chemosystematic studies on certain species of the family Brassicaceae (Cruciferae) in Egypt. Biochem Syst Ecol, 2010; 38:680-5. https://doi.org/10.1016/j.bse.2010.04.004

Moussaid M, Elamrani A, Bourhim N, Benaissa M. Contribution to the study of the essential oil of Dipcadi serotinum (L.) Medik du Maroc. Afrique Sci, 2013; 9(1):34-42.

Simirgiotis MJ, Benites J, Areche C, Sepúlveda B. Antioxidant capacities and analysis of Phenolic Compounds in three endemic Nolana species by HPLC-PDA-ESI-MS. Molecules, 2015; 20:11490-507. https://doi.org/10.3390/molecules200611490

Spínola V, Pinto J, Castilho PC. Identification and quantification of phenolic compounds of selected fruits from Madeira Island by HPLC-DAD-ESI-MSn and screening for their antioxidant activity. Food Chem, 2015; 173:14-30. https://doi.org/10.1016/j.foodchem.2014.09.163

Taamalli A, Arráez-Román D, Abaza L, Iswaldi I, Fernández- Gutiérrez A, Zarrouk M, Segura-Carretero A. LC-MS-based metabolite profiling of methanolic extracts from the medicinal and aromatic species Mentha pulegium and Origanum majorana. Phytochem Anal, 2015; 26:320-30. https://doi.org/10.1002/pca.2566

Williams CA. Biosystematics of the monocotyledoneae flavonoid patterns in leaves of the liliaceae. Biochem Syst Ecol, 1975; 3(4):229-44. https://doi.org/10.1016/0305-1978(75)90007-1

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