Stigmasterol Tetracosanoate, a New Stigmasterol Ester from the Egyptian Blepharis ciliaris

Abstract

A new stigmasterol ester: stigmasterol tetracosanoate (3), along with 7 compounds: β-sitosterol (1), stigmasterol (2), (2S,3S,4R)-2[(2′R)-2′-(hydroxyeicosanoyl amino) octadecane-1,3,4-triol (4), apigenin (5), β-sitosterol-3-O-β-D-glucopyranoside (6), stigmasterol-3-O-β-D-glucopyranose (7), and apigenin-7-O-β-D-glucopyranoside (8) were isolated from Blepharis ciliaris aerial parts. Compounds 1, 2, and 5–7 are reported here for the first time from the plant and 4 for the first time from the family. GCMS analysis revealed the presence of 45 fatty acids, 53 hydrocarbons, and 24 sterols. The different fractions exhibited mild cytotoxic in brine shrimp assay and anti-hyperglycaemic activities. The EtOAc fraction and TME (total MeOH extract) showed weak anti-malarial activity against P. falciparum. The CHCl₃ fraction gave potent ­anti-inflammatory activity compared with indomethacin.

Key words

Blepharis ciliaris - stigmasterol tetracosanoate - GCMS - cytotoxic - anti-malarial - anti-inflammatory - anti-hyperglycaemic

• References

• 1 Mahboubi M, Haghi G, Kazempour N et al. Total phenolic content, antioxidant and antimicrobial activities of Blepharis edulis extracts. Songklanakarin J Sci Technol 2013; 35: 11-16
• 2 Mundla KK, Sitaram B. Comparative study of phytochemical, antimicrobial, cytotoxic and antioxidant activities in Blepharis genus plant seeds. Int J Sci Invent Today 2013; 2: 7-20
• 3 Maregesi SM, Ngassapa OD, Pieters L et al. Ethnopharmacological survey of the Bunda district, Tanzania: Plants used to treat infectious diseases. J Ethnopharmacol 2007; 113: 457-470
• 4 El-Shanawany MA, Sayed HM, Ibrahim SRM et al. A new isoflavone from Blepharis ciliaris of an Egyptian origin. Med Chem Res 2012; 19: 2346-2350
• 5 El-Shanawany MA, Sayed HM, Ibrahim SRM et al. Chemical constituents, anti-inflammatory, and antioxidant activities of Anisotes trisulcus. Bull Fac Pharm Cairo University 2014; http://dx.doi.org/10.1016/j.bfopcu.2014.02.004
• 6 Ali AA, Sayed HM, Ibrahim SRM et al. Chemical constituents, antimicrobial, analgesic, antipyretic, and anti-inflammatory activities of Euphorbia peplus L. Phytopharmacol 2013; 4: 69-80
• 7 El-Shanawany MA, Sayed HM, Ibrahim SRM et al. New nitrogenous compounds from Anisotes trisulcus. Z Naturforsch 2014; 69c http://dx.doi.org/10.5560/ZNC.2013-0116
• 8 Al-Musayeib NM, Mohamed GA, Ibrahim SRM et al. Lupeol-3-O-decanoate a new triterpene ester from Cadaba farinosa Forsk. growing in Saudi Arabia. Med Chem Res 2013; 22: 5297-5302
• 9 Ibrahim SRM, Badr JM, El Sayed KA et al. A new cytotoxic sesquiterpene and three anti-inflammatory flavonoids of the Egyptian Tanacetum santolinoides. Nat Prod Commun 2007; 2: 1071-1074
• 10 El-Shanawany MA, Mohamed GA, Nafady AM et al. A new xanthone from the roots of Centaurium spicatum L. Phytochemistry Lett 2011; 4: 126-128
• 11 Makler MT, Hinrichs DJ. Measurement of the lactate dehydrogenase activity of Plasmodium falciparum as an assessment of parasitemia. Am J Trop Med Hyg 1993; 48: 205-210
• 12 Ibrahim SRM, Mohamed GA, Al-Musayeib NM. New Constituents from the Rhizomes of Egyptian Iris germanica L. Molecules 2012; 17: 2587-2598
• 13 Al-Awadi FM, Khattar MA, Gumaa KA. On the mechanism of the hypoglycaemic effect of a plant extract. Diabetologia 1985; 28: 432-434
• 14 Schmidt J. Organic Chemistry. 8^th ed. Edinburgh and London: Oliver and Boyd; 1964: 318 673
• 15 Elkhayat ES, Mohamed GA, Ibrahim SRM. Ceramides, activity and structure elucidation. Curr Bioactive Compds 2013; 8: 370-409
• 16 Bara JS, Kaiya T, Fukuda H et al. 6β-Hydroxyursolic acid and other triterpenoids of Enkianthus cernuus. Phytochemistry 1983; 22: 2553-2555
• 17 Fontana G, Savona G, Rodriguez B et al. Unusual 6′-fatty acid esters of (24S)-24-ethylcholesta-5,25-dien-3β-yl-β-D-glucopyranoside from Teucrium fruticans. Phytochemistry 1999; 50: 283-285
• 18 Sayed HM, Mohamed MH, Farag SF et al. A new steroid glycoside and furochromones from Cyperus rotundus L. Nat Prod Res 2007; 21: 343-350
• 19 Jia-yuan C, Xiao T, Wen-jie L et al. A new stigmasterol ester from Aeschynomene indica. Chinese Herbal Med 2011; 3: 248-250
• 20 Bagri P, Ali M, Sultana S et al. New sterol esters from the flowers of Punica granatum Linn. J Asian Nat Prod Res 2009; 11: 710-715
• 21 Mohamed GA, Ibrahim SRM. Eucalyptone G, a new phloroglucinol derivative and other constituents from Eucalyptus globulus Labill. ARKIVOC 2007; xv: 281-291
• 22 Feng Z, Yu-min P, Guang-ying C et al. Sphingolipid metabolites of mangrove endophytic fungus (No. 2534) from the South China Sea. Foshan Kexue Jishu Xueyuan Xuebao, Ziran Kexueban 2007; 25: 55-57
• 23 Mabry TJ, Markham KR, Thomas MB. The Systematic Identification of Flavonoids. NewYork, Heidelberg and Berlin: Springer-Verlage; 1970
• 24 Ibrahim SRM. New 2-(2-phenylethyl)chromone derivatives from the seeds of Cucumis melo L var. reticulates. Nat Prod Commun 2010; 5: 403-407
• 25 Palermo JA, Seldes AM, Gros EG. Free sterols of the red alga Gigartina skottsbergii. Phytochemistry 1984; 23: 2688-2689