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Flavonoids from Neurada Procumbens L. (Neuradaceae) in Egypt

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Flavonoids from Neurada Procumbens L. (Neuradaceae) in Egypt See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/264624475 Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt Article in Biochemical Systematics and Ecology · December 2014 DOI: 10.1016/j.bse.2014.07.001 CITATIONS READS 3 777 6 authors, including: Mona Marzouk Sameh Hussein National Research Center, Egypt National Research Center, Egypt 62 PUBLICATIONS 406 CITATIONS 48 PUBLICATIONS 346 CITATIONS SEE PROFILE SEE PROFILE Lamyaa F. Ibrahim Ahmed Elkhateeb National Research Center, Egypt National Research Center, Egypt 24 PUBLICATIONS 339 CITATIONS 47 PUBLICATIONS 344 CITATIONS SEE PROFILE SEE PROFILE Some of the authors of this publication are also working on these related projects: Chemosystimatic and biological studies of some Egyptian flora View project Anti-oxidative stress phytochemicals View project All content following this page was uploaded by Ahmed Elkhateeb on 12 November 2018. The user has requested enhancement of the downloaded file. Biochemical Systematics and Ecology 57 (2014) 67e68 Contents lists available at ScienceDirect Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt Mona M. Marzouk a, Sameh R. Hussein a, Lamyaa F. Ibrahim a, * Ahmed Elkhateeb a, Salwa A. Kawashty a, b, Nabiel A.M. Saleh a, a Department of Phytochemistry and Plant Systematics, National Research Centre, Dokki, 12311 Giza, Egypt b Department of Biology, Faculty of Sciences, Taibah University, Al Madinah Al Munawwarah, P.O. Box: 344, Saudi Arabia article info Article history: Received 3 March 2014 Accepted 4 July 2014 Available online Keywords: Neurada procumbens L. Neuradaceae Flavonoids Chemosystematics 1. Subject and source Neuradaceae is a small family with three genera and ten species distributed within North Africa, the East Mediterranean, Sinai, Sudan, Ethiopia, and Saudi Arabia to the Indian desert (Boulos, 1999). In Egypt it is represented by a monotypic genus Neurada (Neurada procumbens L.) (Tackholm,€ 1974; El Hadidi and Fayed, 1994e95 and Boulos, 1999). N. procumbens, commonly known as ''Als'dan'', is a desert plant considered edible by Bedouin and has been used traditionally as a medicinal herb to treat diarrhea and dysentery, as well as being used as a tonic to increase heart and respiration function (James, 1990). The plant material was collected 4 km along El-Arish-Rafah Road, Egypt in March 2009 by Dr. Sameh R. Hussein and indentified by Dr. Mona M. Marzouk. A voucher specimen (no. 988) was deposited in the herbarium of the National Research Centre (CAIRC). 2. Previous work Only a single publication on N. procumbens reported the isolation of three acidic mucilages and two flavonoids; taxifolin 3- O-a-rhamnopyranoside (astilbin) and a second tentatively identified as a taxifolin glycoside (Afifi et al., 2008). 3. Present study The whole plant of N. procumbens was dried in the shade and ground. The powder (140 g) was successively fractioned by Soxhlet using solvents with increasing polarity; petroleum ether (1 g), ethyl acetate (1.5 g), butanol (12.5 g), then methanol * Corresponding author. E-mail address: [email protected] (N.A.M. Saleh). http://dx.doi.org/10.1016/j.bse.2014.07.001 0305-1978/© 2014 Elsevier Ltd. All rights reserved. 68 M.M. Marzouk et al. / Biochemical Systematics and Ecology 57 (2014) 67e68 (15 g). The butanol extract was filtered and concentrated then subjected to column chromatography (CC) using Silica gel 60 (Merck, 0.063e0.2 mm) and eluted with a mixture of CH2Cl2/MeOH (2:3). Similar fractions were combined to give three main fractions. Each was subjected to PC fractionation using BAW and 15% AcOH which led to the isolation of compounds (1&2). The methanol extract was chromatographed on PC (Whatman No. 1 and 3 MM) and eluted with BAW, three times. The obtained fractions were chromatographed on Sephadex LH-20 column using MeOH/H2O (1:1) as eluent to yield compounds (3e6). All compounds were further purified on a Sephadex LH-20 column using methanol as solvent (Mabry et al., 1970). The present work deals with the isolation and characterization of six flavonoids from the aerial parts of N. procumbens. They were identified as; taxifolin (1), taxifolin 3-O-a-rhamnopyranoside (2), vitexin (3), vitexin 200-O-a-rhamnopyranoside (4), orientin 200-O-a-rhamnopyranoside (5) and isoorientin 200-O-a-rhamnopyranoside (6). Except for compound (2), all compounds were isolated for the first time from N. procumbens. They were elucidated on the basis of detailed chemical and spectral analysis. Their spectral data were in agreement with those published in previous studies (Mabry et al., 1970; Agrawal and Bansal, 1989; Markham and Geiger, 1994; El- Mousallamy, 1998; Shahat et al., 1998; Afifi et al., 2008). 4. Chemosystematic significance The systematic placement of Neurada on morphological and anatomical ground has been somewhat controversial. Originally the genus was included in a subfamily or tribe of the Rosaceae and later placed in a distinct family Neuradaceae in the order Rosales (Takhtajan, 1980; Cronquist, 1981; Dahlgren, 1983). Ronse and Smets (1995) suggested a relationship with Rosaceae based on floral development. However, Huber (1993) suggested that Neurada has an affinity with the Malvales on the basis of the exotegmic seed coat with a palisade layer and the presence of cyclopropanoid fatty acids in the seed. Neurada also shares other common characters, but not unique to malvalean taxa, including valvate sepals, lysigenous mucilage canals, stellate hair and epicalyx (Solereder, 1908; Murbeck, 1916; Huber, 1993). A recent review by Alverson et al. (1998) using rbcL sequence data reported the placement of Neurada at or near the base of the expanded Malvales and supported the idea that the true affinities of Neurada are within Malvales rather than Rosales. Finally several authors placed Neurada in the order Malvales together with Malvaceae, Bombacaceae, Sterculiaceae, Tiliaceae (core Malvales), Bixaceae, Cistaceae, Cochlo- spermaceae, Dipterocarpaceae, Mutingiaceae, Sarcolaenaceae, Sphaerosepalaceae and Thymelaeaceae (expanded Malvales), on the bases of phylogenetic characters (APG, 2003; Judd and Olmstead, 2004; Takhtajan, 2009). Neurada is characterized by flavone C-glycosides, flavone O-C-diglycosides, dihydroflavonols and their glycosides. Some species of the families Malvaceae, Bombacaceae, Sterculiaceae and Thymelaeaceae are also characterized by flavone C-gly- cosides and flavone O-C-diglycosides similar to Neurada (Giannasi, 1988; Seetharaman, 1990; Faizi and Ali, 1996; Joshi et al., 2013). Within the expanded Malvales, genus Momobtes (family Dipterocarpaceae) and genus Cochlospermum (family Bix- aceae) show a similarity to Neurada in the presence of dihydroflavonols and their glycosides (Meragelman et al., 2001; Solon et al., 2012). Finally, also both genera Neurada and Momobtes are characterized by oblate pollen in a recent study (Polevova et al., 2010). This represents a strong link between Neurada and the expanded Malvales taking into account the morphological arguments, the cyclopropanoid fatty acids in their seeds and the rbcL sequence data (Huber, 1993; Alverson et al., 1998). References Afifi, M.S., Salama, O.M., Gohar, A., Marzouk, A.M., 2008. J. Pharm. Sci. 24, 124. Agrawal, P.K., Bansal, M.C., 1989. Flavonoid glycosides. In: Agrawal, P.K. (Ed.), Carbon-13-NMR of Flavonoids. Elsevier, New York, p. 283. Alverson, W.S., Karol, K.G., Baum, D.A., Chase, M.W., Swensen, S.M., Mccourt, R., Sytsma, K., 1998. Am. J. Bot. 876. Angiosperm Phylogeny Group, 2003. Bot. J. Linn. Soc. 141, 399. Boulos, L., 1999. Flora of Egypt, vol. 1. Al Hadara Publishing, Cairo, Egypt (Azollaceae-Oxalidaceae). Cronquist, A., 1981. An Integrated System of Classification of Flowering Plants. New York. Dahlgren, R.M.T., 1983. J. Bot. 3, 119. El Hadidi, M.N., Fayed, A.A., 1994e95. Taeckholmia 15, 57. El-Mousallamy, A.M.D., 1998. Nat. Prod. Sci. 4 (2), 53. Faizi, S., Ali, M., 1996. Planta Med. 65, 383. Giannasi, D.E., 1988. Flavonoids and evolution in the dicotyledons. In: Harborne, J.B. (Ed.), The Flavonoids, Advances in Research since 1980. Chapman & Hall, p. 479. Huber, H., 1993. Neurada: Eine Gattung der Malvales. Sendtnera 1, 7. James, P.M., 1990. Flora of Eastern Saudi Arabia. Kegan Paul International Limited, England, p. 29. Joshi, K.R., Devkota, H.P., Yahara, S., 2013. Nat. Prod. Commun. 8, 583. Judd, W.S., Olmstead, R.G., 2004. Amer. J. Bot. 91, 1627. Mabry, T.J., Markham, K.R., Thomas, M.B., 1970. The Systematic Identification of Flavonoids. Springer, Heidelberg. Markham, K.R., Geiger, H., 1994. 1H-NMR spectroscopy of flavonoids and their glycosides in hexadeutero dimethylsulfoxide. In: Harborne, J.B. (Ed.), The Flavonoids, Advances in Research since 1986. Chapman and Hall, London, p. 441. Meragelman, K.M., McKee, T.C., Boyd, M.R., 2001. J. Nat. Prod. 64, 546. Murbeck, S., 1916. Uber die Organisation, Biologie und Verwandtschaftlichen Beziehungen der Neuradoideen. Acta Univ. Lund. 12 (2), 1. Polevova, S., Tekleva, M., Neumann, F.H., Scott, L., Stager, J.C., 2010. Rev. Palaeobot. Palynol. 160, 163. Ronse, D.L.P., Smets, E.F., 1995. Acta Bot. Neerl. 44, 439. Seetharaman, T.R., 1990. Fitoterapia 61, 373. Shahat, A.A., Ismail, S., Hammouda, F.M., Azzam, S.A., Lerniere, G., De Bruyne, T., De Swaef, S., Pieters, L., Vlietinck, A., 1998. Phytomed 5 (2), 133. Solereder, H., 1908. Systematic Anatomy of the Dicotyledons: a Handbook for Laboratories of Pure and Applied Botany. Clarendon Press, Oxford. Solon, S., Carollo, C.A., Brandao,~ L.F.G., Macedo, C.D.S., Klein, A., Dias-Junior, C.A., Siqueira, J.M., 2012. Quim. Nova 35, 1169. Tackholm,€ V., 1974. Students, Flora of Egypt, second ed. Cairo University, Cairo. Takhtajan, A.L., 1980. Bot. Rev. 46 (3), 225. Takhtajan, A.L., 2009. Flowering Plants. Springer Verlag, Heidelberg. View publication stats.
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