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Antioxidant Activity of Mayodendron Igneum Kurz and the Cytotoxicity of the Isolated Terpenoids

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Antioxidant Activity of Mayodendron Igneum Kurz and the Cytotoxicity of the Isolated Terpenoids Journal of Medicinally Active Plants Volume 1 Issue 3 January 2012 Antioxidant activity of Mayodendron igneum Kurz and the cytotoxicity of the isolated terpenoids Follow this and additional works at: https://scholarworks.umass.edu/jmap Part of the Plant Sciences Commons Recommended Citation Hashem, F.A; A.E Sengab; M.H. Shabana; and S. Khaled. 2012. "Antioxidant activity of Mayodendron igneum Kurz and the cytotoxicity of the isolated terpenoids." Journal of Medicinally Active Plants 1, (3):88-97. DOI: https://doi.org/10.7275/R53B5X3B https://scholarworks.umass.edu/jmap/vol1/iss3/3 This Article is brought to you for free and open access by ScholarWorks@UMass Amherst. It has been accepted for inclusion in Journal of Medicinally Active Plants by an authorized editor of ScholarWorks@UMass Amherst. For more information, please contact [email protected]. Hashem et al.: Antioxidant activity of Mayodendron igneum Kurz and the cytotoxic Journal of Medicinally Active Plants Volume 1 | Issue 3 October 2012 Antioxidant activity of Mayodendron igneum Kurz and the cytotoxicity of the isolated terpenoids F.A Hashem Pharmacognosy depart. NRC. Cairo, Egypt, [email protected] A.E Sengab Pharmacognosy depart. Ain Shams University, Cairo, Egypt M.H. Shabana Phytochemistry and Plant Systematics depart. NRC. Cairo, Egypt S. Khaled Pharmacognosy depart. NRC. Cairo, Egypt Follow this and additional works at: http://scholarworks.umass.edu/jmap Recommended Citation Hashem, F.A, A.E Sengab, M.H. Shabana, S. Khaled. 2012. "Antioxidant activity of Mayodendron igneum Kurz and the cytotoxicity of the isolated terpenoids," Journal of Medicinally Active Plants 1(3):88-97. DOI: https://doi.org/10.7275/R53B5X3B Available at: http://scholarworks.umass.edu/jmap/vol1/iss3/3 This Article is brought to you for free and open access by ScholarWorks@UMass Amherst. It has been accepted for inclusion in Journal of Medicinally Active Plants by an authorized administrator of ScholarWorks@UMass Amherst. For more information, please contact [email protected]. Hashem et al.: Antioxidant activity of Mayodendron igneum Kurz and the cytotoxic Antioxidant Activity of Mayodendron igneum Kurz and Cytotoxicity of Isolated Terpenoids F.A. Hashem,1* A.E. Sengab,2 M.H. Shabana,3and S. Khaled1 1Pharmacognosy Department, NRC. Cairo, Egypt. 2 Pharmacognosy Department, Ain Shams University, Cairo, Egypt. 3Phytochemistry and Plant Systematics Department, NRC. Cairo, Egypt. *Corresponding author: [email protected] Date Received: January 16, 2012 Keywords: Bignoniaceae, cytotoxic, erythrodiol, norigeumone, oleanolic acid, sitosterol, trumpet creeper, ursolic acid. ABSTRACT INTRODUCTION A petroleum ether extract of Mayodendron The Trumpet Creeper family (Bignoniaceae), igneum Kurz, (Family Bignoniaceae) yielded five which includes approximately 750 species of plants compounds identified as sitosterol, erythrodiol, in 120 genera within 8 tribes, is distributed through- oleanolic acid, ursolic acid and 5', 6' norigeumone. out tropical and subtropical regions of South Antioxidant activity of total ethanol extracts of the America, Africa, and India, growing as both a wild plant was equal to 77.02% of the antioxidant activity plant and a cultivated ornamental (Von Poser et al., of ascorbic acid (100%) as measured by electron spin 2000). Plants in the Bignoniaceae family are notably resonance (ESR) and using DPPH as the stable free rich in terpenoids and flavonoids and are used medi- radical. The antioxidant activity of successive frac- cinally in traditional medicine and pharmaceutical tions of M. igneum leaves were tested with the preparations. strongest inhibition of DPPH stable free radicals Species within the Bignoniaceae, have yielded exhibited by the successive ethanol fraction (equal to a number of phytochemicals. Sitosterol and other 100% of free radical scavenging activity relative to compounds have been isolated from the bark of ascorbic acid). The ethyl acetate fraction had 64.96% Tecomella undulata, and the heartwood of of the antioxidant activity of ascorbic acid, and the Heterophragma adenophylum and Millingtonia petroleum ether and chloroform fractions had 12.46% hortensis (Singh, et al., 1972) and β-sitosterol has and 0%, respectively, of the antioxidant activity of been isolated from the trunkwood of Tabebuia ascorbic acid. An examination of isolated oleanolic ochracea (Zani et al., 1991) and the roots of acid demonstrated moderate cytotoxic activity against Incarvillea arguta (Luo et al., 2004). In addition to four tested cancer cell lines (liver, cervix, breast, and β-sitosterol, an aqueous extract of Jacaranda colon). The highest activity level was against the caucana has yielded the triterpene jacarandic acid, cervix cancer cell line (HELA) (IC50= 32 µg/mL), ursolic acid, 2 α-hydroxyursolic acid and 2 α,3 α- followed by the liver cancer cell line (HEPG2) (IC50= dihydroxyurs-12-en-28-oic acid (Ogura et al., 1977). 33 µg/mL), the colon cancer cell line (HCT-116) The diterpene, 2-α-hydroxy-12 β-hydroxy-isopimara- (IC50= 35 µg/mL), and the breast cancer cell line 8(14), 15-diene, along with six known triterpenes, (MCF7) (IC50= 37 µg/mL). sterol. and fatty acids, has been isolated from the 88 Hashem et al.: Antioxidant activity of Mayodendron igneum Kurz and the cytotoxic stem bark of Tanaecium jaroba, a Bolivian plant used phlogacantholide B, lup-20(29)-ene-3α, 27β-diol, in traditional medicine (Mitaine-Offer et al., 2002). paederoside, nemoroside, picroside, 2-hydroxy-3- Jin et al. (2004) has isolated five pentacyclic tri- hydroxymethyl-9,10 anthraquinone, 1-methoxy-3- terpenoids from leaves of Campsis grandiflora that hydroxy-2-carbon-methoxy-9,10-anthraquinone, have characterized as oleanolic acid, hederagenin, lucidin primeveroside, β-daucosterol, β-sitosterol, and ursolic acid, tormentic acid, and myrianthic acid auranamide (Guo et al., 2007). using spectroscopic methods. Work by Ogura et al. In a study of a total alcohol and successive (1977) and Hashem and Sleem (2006) led, extracts of M. igneum leaves against human cancer respectively, to the isolation of the triterpenoid cell lines Hashem, et al. (2011), the total ethanol ursolic acid from the petroleum ether extract of extract demonstrated strong cytotoxic activity against Jacranda caucana and Tecoma radicans. the cervix cancer cell line (IC50= 0.60 µg/mL), breast The biological activities of phytochemicals cancer cell line (IC50=0.54 µg/mL) and liver cancer extracted from plants in the Bignoniaceae family cell line (IC50=0.87 µg/mL) when compared with the have been demonstrated in a number of studies. For anticancer drug doxorubicin. A petroleum ether ex- example, ursolic acid is known to have cytotoxic tract showed cytotoxic activity against a liver cancer activity in vitro (El-Hossary et al., 2000). Biological cell line (IC50= 0.37 µg/mL) and breast cancer cell investigations on Tecoma stans fruit extract indicates line (IC50= 2.15 µg/mL). Therefore, in this study, the a strong scavenging activity to DPPH, peroxyl, and petroleum ether extract was subjected to a phyto- hydroxyl radicals plus cytotoxic effects on human chemical investigation to determine the active hepatocarcinoma cells and growth inhibition of constituents that contribute to the observed cytotoxic human breast carcinoma cells (Marzouk et al., 2006). activity. In a study on the coumarin fraction of Macfadyena unguis–cati by Hashem et al. (2007), demonstrated MATERIALS AND METHODS 93.9% inhibition of the stable DPPH free radical, Plant material. Fresh leaves from plants of level similar to that of vitamin C at 95.5% inhibition. Mayodendron igneum Kurz. (Bignoniaceae) growing Additional studies by Hashem (2007a) demonstrated in the Giza Zoo, Giza, Egypt, were used in this study. the coumarin fraction of Tecoma radicans and The plants were identified by Dr. M. El-Gibaly, a peucenin had active antioxidant activity. A later study plant taxonomist, and Mrs. Trease Labib, Consultant by Hashem (2007b) showed that the most potent free of Plant Taxonomy at the Ministry of Agriculture and radical scavenger of the five identified flavonoids in Director of Orman Botanical Garden, Giza, Egypt. A Teocoma radicans was quercetin 3-methyl ether. voucher specimen of the plant material (Voucher Of special interest in the current study are the number M.20) has been placed in the herbarium at phytochemical constituents of Mayodendron igneum the Orman Botanical Garden, Giza Egypt. Kurz. (also known as Radermachera ignea), a mem- Plant extracts. A total ethanol extract was ber of the Bignoniaceae family used in traditional prepared from 400 g of air-dried, powdered leaves of medicine. M. igneum grows wild in Northern M. igneum by repeatedly extracting in a Soxhlet ap- Myanmar, Northern Thailand, Laos, Vietnam, and paratus with 80% ethanol until exhaustion. The South China (Chun-Lin, 1990). The plant, which is extract was recovered and filtered to remove debris frequently grown in gardens as an ornamental and before concentrating under reduced pressure to vegetable, is known to contain a number of minerals, dryness at 55°C, yielding 95 g of crude extract. vitamins, and amino acids (Youkai et al., 2005). Successive fractions of the 80% ethanol extract were Earlier studies have shown the plant bark of M. made using 90 g of the crude extract suspended in igneum to contain a number of phytochemicals, water and partitioned successively with petroleum including the meroditerpenoid igeumone and 18 other ether (60-80oC), chloroform, and ethyl acetate. The chemical compounds: quercetin, naringenin, naringin, solvents were evaporated to dryness under reduced vanillic acid, ethyl caffeate, eugenin, syringaldehyde, pressure at 55°C yielding fractions of 25 g of 89 Hashem et al.: Antioxidant activity of Mayodendron igneum Kurz and the cytotoxic petroleum ether extract, 19 g of chloroform extract, Compound I: 10 g of ethyl acetate extract, and 30 g of remaining IR Spectrum: The IR spectrum shows the following -1 residue that was considered the ethanol extract. signals, IR υmax (KBr) cm : 3423.9 (OH), 2925.2, Phytoconstituent isolation and identification. 2854.3 both for aliphatic C-H, 1612.3 (C=C), 1421.8 The petroleum ether fraction from the leaves of M.
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