Cucumin S, a new phenylethyl chromone from Cucumis melo var. reticulatus seeds

Abstract

A new phenylethyl chromenone, cucumin S [(R)-5, 7-dihydroxy-2-[1-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]chromone] (1), along with five known compounds: 5, 7-dihydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (2), 5, 7-dihydroxy-2-[2-(3, 4-dihydroxyphenyl)ethyl]chromone (3), luteolin (4), quercetin (5), and 7-glucosyloxy-5-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (6) were isolated from the EtOAc fraction of Cucumis melo var. reticulatus Ser., Cucurbitaceae, seeds. Their structures were determined by spectroscopic means (1D and 2D NMR), as well as HRESIMS, optical rotation measurement, and comparison with literature data. The isolated compounds 1-6 were assessed for their antioxidant activity using DPPH assay. Compounds 3, 4, and 5 showed potent activities compared to propyl gallate at concentration 100 uM.

References

  1. Adams, C.F., Richardson, M., 1981. Nutritive value of foods. USDA Home and Garden Bul. 72. Government Printing Office, Washington DC, USA, pp. A2–A35.

    Google Scholar 

  2. Al-Musayeib, N.M., Mohamed, G.A., Ibrahim, S.R.M., Ross, S.A., 2014. Newthiophene and flavonoid from Tagetes minuta leaves growing in Saudi Arabia. Molecules 19, 2819–2828.

    Article  Google Scholar 

  3. Bernhardt, M., Shaker, K.H., Elgamal, M.H.A., Seifert, K., 2000. The new bishomoflavone ononin and its glucoside from Ononis vaginalis. Z. Naturforsch. C 55, 516–519.

    CAS  Article  Google Scholar 

  4. Dugas, A.J.J., Castañeda-Acosta, J., Bonin, G.C., Price, K.L., Fischer, N.H., Winston, G.W., 2000. Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships. J. Nat. Prod. 63, 327–331.

    CAS  Article  Google Scholar 

  5. Fleshman, M.K., Lester, G.E., Riedl, K.M., Kopec, R.E., Narayanasamy, S., Curley Jr., R.W., Schwartz, S.J., Harrison, E.H., 2011. Carotene and novel apocarotenoid concentrations in orange-fleshed Cucumis melo melons: determinations of ß-carotene bioaccessibility and bioavailability. J. Agric. Food Chem. 59, 4448–4454.

    CAS  Article  Google Scholar 

  6. Harborne, J.B., 1988. The Flavonoids. Advances in Research Since 1980. Chapman & Hall, New York.

    Google Scholar 

  7. Ibrahim, S.R.M., Fouad, M.A., Abdel-Lateff, A., Okino, T., Mohamed, G.A., 2014. Alnuheptanoid A: a new diarylheptanoid derivative from Alnus japonica. Nat. Prod. Res. 28, 1765–1771.

    CAS  Article  Google Scholar 

  8. Ibrahim, S.R.M., 2010. New 2-(2-phenylethyl)chromone derivatives from the seeds of Cucumis melo L var. reticulatus. Nat. Prod. Commun. 5, 403–406.

    CAS  PubMed  Google Scholar 

  9. Ibrahim, S.R.M., 2014. New chromone and triglyceride from Cucumis melo seeds. Nat. Prod. Commun. 9, 205–208.

    CAS  PubMed  Google Scholar 

  10. Ibrahim, S.R.M., Mohamed, G.A., 2014. Natural occurring 2-(2-phenylethyl) chromones, structure elucidation and biological activities. Nat. Prod. Res., https://doi.org/10.1080/14786419.2014.991323.

    Google Scholar 

  11. Kim, J.M., Ko, R.K., Jung, D.S., Kim, S.S., Lee, N.H., 2010. Tyrosinase inhibitory constituents from the stems of Maackia fauriei. Phytother. Res. 24, 70–75.

    CAS  Article  Google Scholar 

  12. Lester, G., 1997. Melon (Cucumis meio L.) fruit nutritional quality and health functionality. HortTechnology 7, 222–227.

    Article  Google Scholar 

  13. Lewinsohn, E., Portnoy, V., Benyamini, Y., Bar, E., Harel-Beza, R., Gepstein, S., Giovannoni, J.J., Schaffer, A.A., Burger, Y., Tadmor, Y., Katzir, N., 2008. Sesquiterpene biosynthesis in melon (Cucumis meio L.) rinds. In: Pitrat, M. (Ed.), Cucurbitaceae Proceedings of the IXth EUCARPIA Meeting on Genetics and Breeding of Cucurbitaceae. INRA, Avignon, France, pp. 249–255.

    Google Scholar 

  14. Mohamed, A.G., 2008. Alliuocide G., a new flavonoid with potent α-amylase inhibitory activity from Allium cepa L. ARKIVOC xi, 202–209.

    Google Scholar 

  15. 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.

    CAS  Article  Google Scholar 

  16. Mohamed, G.A., Ibrahim, S.R.M., Al-Musayeib, N.M., Ross, S.A., 2014. New antiinflammatory flavonoids from Cadaba glandulosa Forssk. Arch. Pharm. Res. 37, 459–466.

    CAS  Article  Google Scholar 

  17. Park, D., Kim, H.J., Jung, S.Y., Yook, C., Jin, C., Lee, Y.S., 2010. A new diarylheptanoid glycoside from the stem bark of Alnus hirsuta and protective effects of diarylheptanoid derivatives in human HepG2 cells. Chem. Pharm. Bull. 58, 238–241.

    CAS  Article  Google Scholar 

  18. Portnoy, V., Benyamini, Y., Bar, E., Harel-Beza, R., Gepstein, S., Giovannoni, J.J., Schaffer, A.A., Burger, Y., Tadmor, Y., Lewinsohn, E., Katzir, N., 2008. The molecular and biochemical basis for varietal variation in sesquiterpene content in melon (Cucumis melo L) rinds. Plant Mol. Biol. 66, 647–661.

    CAS  Article  Google Scholar 

  19. Ribeiro, S.F.F., Agizzio, A.P., Machado, O.L.T., Neves-Ferreira, A.G.C., Oliveira, M.A., Fernandes, K.V.S., Carvalho, A.O., Perales, J., Gomes, V.M.A., 2007. A new peptide of melon seeds which shows sequence homology with vicilin: partial characterization and antifungal activity. Sci. Hortic. 111, 399–405.

    CAS  Article  Google Scholar 

  20. Velcheva, M.P., Donchev, C., 1997. Isoprenoid hydrocarbons from the fruit of extant plants. Phytochemistry 45, 637–639.

    CAS  Article  Google Scholar 

  21. Vouldoukis, L., 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.

    Article  Google Scholar 

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Authors

Contributions

SRMI and GAM contributed in collecting the plant sample, running the laboratory work, analysis of the spectroscopic data, and writing the manuscript. GAM carried out the antioxidant activity measurement. SRMI has revised and approved the submission.

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Correspondence to Sabrin R. M. Ibrahim.

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Ibrahim, S.R.M., Mohamed, G.A. Cucumin S, a new phenylethyl chromone from Cucumis melo var. reticulatus seeds. Rev. Bras. Farmacogn. 25, 462–464 (2015). https://doi.org/10.1016/j.bjp.2015.06.006

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Keywords

  • Cucumis melo
  • Cucurbitaceae
  • Chromone
  • Flavonoid
  • Antioxidant