Abstract
Phytochemical investigation of the MeOH extract of Cucumis melo L. var. reticulates, Cucurbitaceae, seeds led to the isolation of a new triterpenoid: cucumol A (27-hydroxy taraxerol-3β-ol), along with three known compounds: α-spinasterol and D:B-friedoolean-5-ene-3-β-ol. Their structures were established by extensive 1D (1H, 13C, and DEPT) and 2D (1H-1H COSY, HMQC, and HMBC) NMR, as well as IR and HRESIMS spectral analyses. Compound 3 displayed cytotoxic activity against L5178Y and Hela cancer cell lines with ED50 of 1.30 and 5.40 μg/ml, respectively compared to paclitaxel (0.07 and 0.92 μg/ml, respectively).
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Al Muqarrabun, L.M.R., Ahmat, N., Aris, S.R.S., Norizan, N., Shamsulrijal, N., Yusof, F.Z.M., Suratman, M.N., Yusof, M.I.M., Salim, F., 2014. A new triterpenoid from Sapium baccatum (Euphorbiaceae). Nat. Prod. Res. 28, 1003–1009.
Al Musayeib, N.M., Mothana, R.A., Ibrahim, S.R.M., El Gamal, A.A., Al-Massarani, S.M., 2014. KlodoroneAandklodorol A: newtriterpenes fromKleiniaodora. Nat. Prod. Res. 28, 1142–1146.
Baghaei, H., Shahidi, F., Varidi, M.J., Mahallati, M.N., 2008. Orange-cantaloupe seed beverage: nutritive value, effect of storage time and condition on chemical, sensory and microbial properties. World Appl. Sci. J. 3, 753–758.
Baitar, I.E., 2003. Aljamaiul Mufradatul Advia Wal Aghzia. CCRUM, New Delhi, pp. 248.
De Marino, S., Festa, C., Zollo, F., Iorizzi, M., 2009. Phenolic glycosides from Cucumis melovar. inodorus seeds. Phytochem. Lett. 2, 130–133.
Duke, J.A., Ayensu, E.S., 1985. Medicinal Plants of China, ISBN 0-9177256-20-4.
Gill, N.S., Bajwa, J., Dhiman, K., Sharma, P., Sood, S., Sharma, P.D., Singh, B., Bali, M., 2011. Therapeutic potential oftraditionally consumed Cucumis melo seeds. Asian J. Plant Sci. 10, 86–91.
Ibrahim, S.R.M., 2010. New 2-(2-phenylethyl)chromone derivatives from the seeds of Cucumis melo L var. reticulates. Nat. Prod. Commun. 5, 403–407.
Ibrahim, S.R.M., Mohamed, G.A., 2015a. Cucumin S., a new phenylethyl chromone from Cucumis melo var. reticulatus seeds. Rev. Bras. Farmacogn. 25, 462–464.
Ibrahim, S.R.M., Mohamed, G.A., 2015b. Natural occurring 2(2- phenylethyl)chromones, structure elucidation and biological activities. Nat. Prod. Res. 29, 1489–1520.
Ibrahim, S.R.M., 2014. New chromone and triglyceride from Cucumis melo seeds. Nat. Prod. Commun. 9, 205–208.
Ibrahim, S.R.M., Mohamed, G.A., Zayed, M.F., Sayed, H.M., 2015c. Ingenines A and B., two new alkaloids from the Indonesian sponge Acanthostrongylophora ingens. Drug Res. 65, 361–365.
Ibrahim, S.R.M., Mohamed, G.A., Shaala, L.A., Banuls, L.M.Y., Van Goietsenoven, G., Kiss, R., Youssef, D.T.A., 2012. New ursane-type triterpenes from the root bark of Calotropis procera. Phytochem. Lett. 5, 490–495.
Lal, S.D., Lata, K., 1980. Plants used by Bhat community for regulating fertility. Econ. Bot. 34, 273–275.
Laphookhieo, S., Karalai, C., Ponglimanont, C., 2004. New sesquiterpenoid and triterpenoids from the fruits of Rhizophora mucronata. Chem. Pharm. Bull. 52, 883–885.
Mahato, S.B., Kundu, A.P., 1994. 13C NMR spectra of pentacyclic triterpenoids A compilation and some salient features. Phytochemistry 37, 1517–1575.
Mariod, A., Matthaus, B., 2008. Investigations on fatty acids, tocopherols, sterols, phenolic profiles and oxidative stability of Cucumis melovar. agrestis oil.J. Food Lipids 15, 56–67.
Melo, M.L.S., Narain, N., Bora, P.S., 2000. Characterisation of some nutritional constituents of melon (Cucumis melo hybrid AF-522) seeds. Food Chem. 68, 411–414.
Milind, P., Kulwant, S., 2011. Musk melon is eat-must melon. Int. Res. J. Pharm. 2, 52–57.
Mohamed, G.A., 2014. New cytotoxic cycloartane triterpene from Cassia italica aerial parts. Nat. Prod. Res. 28, 976–983.
Mohamed, G.A., Ibrahim, S.R.M., Ross, S.A., 2013. New ceramides and isoflavone from the Egyptian Iris germanica L. rhizomes. Phytochem. Lett. 6, 340–344.
Nayar, N.M., Singh, R., 1998. In: Nayar, N.M., More, T.A. (Eds.), Taxonomy, Distribution and Ethnobotanical Uses in Cucurbits. Science Publishers, Inc., USA, pp. 1–18.
Reinhold, J.G., 1935. Liebermann-Burchard reaction velocities of sterols: I. Differences between free and ester cholesterol applied to the determination of cholesterol esters, II. A test for the presence of coprostenol in plasma. Am. J. Med. Sci. 189, 302.
Sayed, H.M., Mohamed, M.H., Farag, S.F., Mohamed, G.A., Proksch, P., 2007. A new steroid glycoside and furochromones from Cyperus rotundus L. Nat. Prod. Res. 21, 343–350.
Silverstein, R.M., Webster, F.X., 1998. Spectrometric Identification of Organic Compounds, 6th ed. New York, John Wiley.
Teotia, M.S., Ramakrishna, P., 1984. Chemistry and technology of melon seeds. J. Food Sci. Technol. 21, 332–340.
Ullah, N., Khan, S., Khan, A., Ahmad, W., Shah, Y., Ahmad, L., Ullah, I., 2015. Aprospective pharmacological review of medicinal herbs, Cucumis melo and Berberis vulgaris, commonly used in the treatment of renal diseases in Pakistan. Acta Poloniae Pharm. Drug Res. 72, 651–654.
Vouldoukis, I., Lacan, D., Kamate, C., Coste, P., Calenda, A., Mazier, D., Conti, M., Dugas, B., 2004. Antioxidant and anti-inflammatory properties of Cucumis melo LC. extract rich in superoxide dismutase activity. J. Ethnopharmacol. 94, 67–75.
Yasar, F., Kusvuran, S., Ellialtioglu, S., 2006. Determination of antioxidant activities in some melon (Cucumis melo L.) varieties and cultivarsundersalt stress.J. Hortic. Sci.
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GAM collected the plant sample. SRMI, RAA, MAAM, and GAM contributed in running the laboratory work, analysis of the spectroscopic data, and writing the manuscript. SRMI and ESE have revised and approved the submission.
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Ibrahim, S., Al Haidari, R., Mohamed, G. et al. Cucumol A: a cytotoxic triterpenoid from Cucumis melo seeds. Rev. Bras. Farmacogn. 26, 701–704 (2016). https://doi.org/10.1016/j.bjp.2016.03.012
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DOI: https://doi.org/10.1016/j.bjp.2016.03.012