Re-investigation of the MeOH extract of the seeds of Cucumis melo L. var. reticulatus (Cucurbitaceae) led to the isolation of a new chromone derivative (5,7-dihydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromone (5) and a triglyceride (1,3-di-(6Z,9Z)-docosa-6,9-dienoyl-2-(6Z) hexacos-6-enoylglycerol (1), together with three known compounds; α-spinasterol (2), stigmasta-7,22,25-trien-3-ol (3), and D:B-friedoolean-5-ene-3-β-ol (4), are reported from this species for the first time. Their structures were determined by extensive 1D (1H, 13C, and DEPT) and 2D (1H-1H COSY, HMQC, and HMBC) NMR and mass spectral measurements. Compound 5 displayed significant cytotoxic activity against L5178Y cells, with an ED50 of 5 μM. The MeOH extract and 5 showed antioxidant activity using the DPPH assay.
YasarF., KusvuranS., EllialtiogluS. (2006) Determination of antioxidant activities in some melon (Cucumis melo L.) varieties and cultivars under salt stress. Journal of Horticultural Science & Biotechnology, 81, 627–630.
2.
MeloM.L.S., NarainN., BoraP.S. (2000) Characterisation of some nutritional constituents of melon (Cucumis melo hybrid AF-522) seeds. Food Chemistry, 68, 411–414.
3.
BaghaeiH., ShahidiF., VaridiM.J., MahallatiM.N. (2008) Orange-cantaloupe seed beverage: Nutritive value, effect of storage time and condition on chemical, sensory and microbial properties. World Applied Sciences Journal, 3, 753–758.
4.
GillN.S., BajwaJ., DhimanK., SharmaP., SoodS., SharmaP.D., SinghB., BaliM. (2011) Therapeutic potential of traditionally consumed Cucumis melo seeds. Asian Journal of Plant Sciences, 10, 86–91.
5.
MirzaM., KalhoroM.A., YaqeenZ., SarfarazT.B., QadriR.B. (2003) Physico-chemical studies of indigenous diuretic medicinal plants Citrullus vulgaris Schrad, Cucumis melo Linn, Cymbopogon citratus (DC) Stapf, Moringa oleifera Lam, Raphanus sativus Linn and Zea mays Linn. Pakistan Journal of Pharmacology, 20, 9–16.
6.
MariodA., MatthausB. (2008) Investigations on fatty acids, tocopherols, sterols, phenolic profiles and oxidative stability of Cucumis melo var. agrestis oil. Journal of Food Lipids, 15, 56–67.
7.
VouldoukisI., LacanD., KamateC., CosteP., CalendaA., MazierD., ContiM., DugasB. (2004) Antioxidant and anti-inflammatory properties of Cucumis melo LC. extract rich in superoxide dismutase activity. Journal of Ethnopharmacology, 94, 67–75.
8.
IbrahimS.R. (2010) New 2-(2-phenylethyl)chromone derivatives from the seeds of Cucumis melo L var. reticulatus. Natural Product Communications, 5, 403–406.
9.
SwaroopA., SinhaA.K., ChawlaR., AroraR., SharmaR.K., KumarJ.K. (2005) Isolation and characterization of 1,3-dicapryloyl-2-linoleoylglycerol: A novel triglyceride from berries of Hippophae rhamnoides. Chemical & Pharmaceutical Bulletin, 53, 1021–1024.
10.
VlahovG. (1999) Application of NMR to the study of olive oils. Progress in Nuclear Magnetic Resonance Spectroscopy, 35, 341–357.
11.
VlahovG. (2009) 13C nuclear magnetic resonance spectroscopy to determine fatty acid distribution in triacylglycerols of vegetable oils with “high -low oleic acid” and “high linolenic acid”. The Open Magnetic Resonance Journal, 2, 8–19.
12.
ShiaoT., ShiaoM. (1989) Determination of fatty acid composition of triacylglycerols by high resolution NMR spectroscopy. Botanical Bulletin-Academia Sinica, 30, 191–199.
13.
WangW., TianS., StarkR.E. (2010) Isolation and identification of triglycerides and ester oligomers from potential degradation of potato suberin. Journal of Agricultural and Food Chemistry, 58, 1040–1045.
14.
HsuF., TurkJ. (2008) Elucidation of the double-bond position of long-chain unsaturated fatty acids by multiple-stage linear ion-trap mass spectrometry with electrospray ionization. Journal of the American Society for Mass Spectrometry, 19, 1673–1680.
15.
FellenbergA.J., JohnsonD.W., PoulosA., SharpP. (1987) Simple mass spectrometric differentiation of the n–3, n–6 and n–9 series of methylene interrupted polyenoic acids. Biomedical and Environmental Mass Spectrometry, 14, 127–130.
16.
PlattnerR.D., SpencerG.F., KleimanR. (1976) Double bond location in polyenoic fatty esters through partial oxymercuration. Lipids, 11, 222–227.
17.
KonishiT., KonoshimaT., ShimadaY., KiyosawaS. (2002) Six new 2-(2-phenylethyl)chromones from Agarwood. Chemical & Pharmaceutical Bulletin, 50, 419–422.
18.
YaguraT., ItoM., KiuchiF., HondaG., ShimadaY. (2003) Four new 2-(2-phenylethyl)chromones derivatives from withered wood of Aquiliaria sinensis. Chemical & Pharmaceutical Bulletin, 51, 560–564.
19.
YoonJ.S., LeeM.K., SungS.H., KimY.C. (2006) Neuroprotective 2-(2-phenylethyl)chromones of Imperata cylindrica. Journal of Natural Products, 69, 290–291.
20.
IshiiH., NakamuraM., SeoS., ToriK., TozyoT., YoshimuraY. (1980) Isolation, characterization, and nuclear magnetic resonance spectra of new saponins from the roots of Bupleurum falcatum L. Chemical & Pharmaceutical Bulletin, 28, 2367–2383.
21.
ThuyT.T., SungT.V., FrankK., WessjohannL. (2008) Triterpenes from the roots of Codonopsis pilosula. Journal of Chemistry, 46, 515–520.
22.
LiuW.Y., ZhangW.D., ChenH.S., GuZ.B., LiT.Z., ChenW.S. (2003) Two new sterols from Bolbostemma paniculatum. Chinese Chemical Letters, 14, 1037–1040.
23.
MohamedG.A. (2013) Alliuocide A: a new antioxidant flavonoid from Allium cepa L. Phytopharmacology, 4, 220–227.
24.
IbrahimS.R.M., Edrada-EbelR., MohamedG.A., YoussefD.T.A., WrayV., ProkschP. (2008) Callyaerin G, a new cytotoxic cyclic peptide from the marine sponge Callyspongia aerizusa, ARKIVOC, xii, 164–171.
