Phenolics of Achillea fragrantissima growing in Egypt and its cytotoxic activity
Loading...
Date
2014
Journal Title
Journal ISSN
Volume Title
Type
Article
Publisher
Journal of Medicinal Plant Research
Series Info
Journal of Medicinal Plant Research;Volume: 8 Issue: 21 Pages: 763-771
Scientific Journal Rankings
Abstract
Achillea fragrantissima Sch. Bip. (Asteraceae) has been reputed in folk medicine of the Arabia region
and Egypt for the treatment of many diseases. Air dried aerial parts of A. fragrantissima were extracted
with 70% aqueous ethanol and fractionated with petroleum ether, dichloromethane, n-butanol and ethyl
acetate fractions. Among them, dichloromethane showed the highest activity and was subjected to
separation and purification by various chromatographic techniques. Five flavones and one phenolic
acid were isolated and identified as acerosin (1), cirsimaritin (2), cirsiliol (3), luteolin (4), apigenin (5)
and caffeic acid (6), respectively. Acerosin, the flavone of higher concentration isolated for the first time
in genus Achillea, showed promising cytotoxic and radical scavenging activity. Molecular modeling of
acerosin indicated its ability to bind in a co-crystallized ligand-like manner with kinase enzyme (FAK),
namely with Cys502, alongside extra binding interactions with Glu430, Lys454 and Asp564. Total
protein profiling of A. fragrantissima DNA was performed using polyacrylamide gel electrophoresis
(PAGE) for characterization of plant where the total number of bands recovered was 4.
Description
MSA Google Scholar
Keywords
University of Acerosin, hepatocellular carcinoma, molecular modeling, DPPH, kinase enzyme (FAK)
Citation
Ahmed AA, Elsayed NH, Mabry TJ (1989). Flavonoids of Achillea santolina andA. fragrantissima. Rev. Latinoam. Quim. 20:5-7. Ahmed AA, Jakupovk J, Seif El-din AA, Melek FR (1990).Irregular oxygenated monoterpenes from Achillea fragrantissima. Phytochemistry 29:1322-1324. Ahmed AA, Shalaby AM, Melek FR, Mabry TJ (1988). Swertisin 2ʹʹarabinoside, a new c-glycosylflavone fromAchillea fragrantissima. J. Nat. Prod.51:971-972. Al-Abd AM, Lee JH, Kim SY, Kun N, Kuh HJ (2008). Novel application of multicellular layers culture forin situevaluation of cytotoxicity and penetration of paclitaxel. Cancer Sci. 99:423-431. Alenad AM, Al-Jaber NA, Krishnaswamy S, Yakout SM, Al-Daghri NM, Alokail MS (2013). Achillea fragrantissimaextract exerts its anticancer effect via induction of differentiation, cell cycle arrest and apoptosis in chronic myeloid leukemia (CML) cell line K562. J. Med. Plants Res. 7 (21):1561-1567. Amić D, Davidović D, Bešlo, D, Trinajstić N (2003). Structure- radical scavenging activity relationships of flavonoids.Croat.Chem. Acta 76(1):55-61. Bai N, He K, Roller M, Lai C, Shao X, Pan M, Bily A, Ho C (2011). Flavonoid glycosides from Microteadebilis and their cytotoxic and anti-inflammatory effects. Fitoterapia 82:168-172. Cao G, Sofic E, Prior RL (1997). Antioxidant and pro-oxidant behavior of flavonoids: Structure-activity relationships. Free Radic. Biol. Med. 22:749-760. Chang CC, Yang MH, Wen HM, Chern JC (2002). Estimation of total flavonoid content in propolis by two complementary colorimetric methods. J. Food Drug Anal. 10:178-182. Elmann A, Mordechay S, Erlank H, Telerman A, Rindner M, Ofir R (2011a). Anti-neuroinflammatory effects of the extract of Achillea fragrantissima. BMC Compl. Altern. Med. 11:98-124. Elmann A, Telerman A, Mordechay S, Erlank H, Rindner M, Ofir R, BeitYannai E (2011b). Extract ofAchillea fragrantissima downregulates ROS production and protects astrocytes from oxidative-stressinduced cell death. In: Chang, R.C., ed. Neurodegenerative Diseases-Processes, Prevention, Protection, and Monitoring, 435- 452 [online]. Available at: http://www.intechopen.com/books/neurodegenerative-diseasesprocesses-prevention-protection-and-monitoring/extract-of-achilleafragrantissima-downregulates-ros-production-and-protectsastrocytes-from-oxidati. Last accessed on January 8th, 2012. ElSayed EE (2010). Chemistry and biology of Achillea fragrantissima present in Sinai. Master dissertation, Suez Canal University, Egypt. El-Zanaty F, Way A (2009). Egypt demographic and health survey 2008, Egyptian Ministry of Health, Cairo: El-Zanaty and associates and macro international. Ezzat SM, Salama MM (2014). A new α-glucosidase inhibitor fromAchillea fragrantissima (Forssk.) Sch. Bip. growing in Egypt. Nat. Prod. Res. 28:812-818. Ghantous A, Nasser N, Saab I, Darwiche N, Saliba NA (2009). Structure-activity relationship of seco-tanapartholides isolated fromAchillea falcatafor inhibition of HaCaT cell growth. Eur. J. Med. Chem. 44:3794-3797. Huang YT, Lee LT, Lee PP, Lin YS, Lee MT (2005). Targeting of focal adhesion kinase by flavonoids and small-interfering RNAs reduces tumor cell migration ability. Anticancer Res. 25: 2017-2025. Karihaloo JL, Kaur M, Singh S (2002). Seed protein diversity inSolanummelongena L. and its wild and weedy relatives. Genet. Res. Crop Eval. 49:533-539. Keepers YP, Pizao PE, Peters GJ, Van Ar-Otte J, Winograd B, Pinedo HM (1991). Comparison of sulforhodamine B protein and tetrazolium (MTT) assays for in vitro chemosensitivity testing. Eur. J. Cancer 27:897-900. Khaled AT, Fawzi I, Adnan SJ, Magda E, Khaled MK (2010). Evaluation of antibacterial and antioxidant activities of methanolic extracts of some medicinal plants in Northern Part of Jordan. J. Biol. Sci. 10(4):325-332. Kosalec H, Bakmaz M, Pepeljnjak S, Vladimir-kne S (2004). Quantitative analysis of the flavonoids in raw propolis from Northern Croatia. Acta Pharm. 54:65-72. Kundaković T, Stanojković T, Juranić Z, Kovacević N (2005). Cytotoxic and antioxidant activity of Achillea alexandri-regis. Pharmazie 60:319-320. Laemmli UK (1970). Cleavage of structural protein during the assembly of the head of Bacteriophage T4. Nature 227:680-685. Lin C, Huang Y, Cheng L, Sheu S, Chen C (2006). Bioactive flavonoids from Ruellia tuberose. J. Chin. Med. 17:103-109. Lin Y, Shi R, Wang X, Shen H M (2008). Luteolin, a flavonoid with potentials for cancer prevention and therapy. Curr. Cancer Drug Targets 8:634-646. Lioi L, Sparvoli F, Bollini R (1999). Variation and genomic polymorphism of lectin related proteins inLima bean (Phaseoluslunatus L.) seeds. Genet. Resour. Crop Evol. 46:175-182. Marder M, Viola H, Wasowski C, Wolfman C, Waterman PG, Medina JH, Paladini AC (1996). Cirsiliol and caffeic acid ethyl ester, isolated from Salvia guaranitica, are competitive ligands for the central benzodiazepine receptors. Phytomedicine 3:29-31. Mesquita AAL, Correa DDB, De Padua AP, Guedes MLO, Gottlieb O (1986). Flavonoids from four compositae species. Phytochemistry 25:1255-1256. Middleton E Jr, Kandaswami C, Theoharides TC (2000). The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease and cancer. Pharmacol. Rev. 52:673-751. Mosmann T (1983). Rapid colorimetric assays for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 65:55-63. Mustafa EH, Abu Zarga M, Abdalla S (1992). Effects of cirsiliol, a flavone isolated fromAchillea fragrantissima, on rat isolated ileum. Gen. Pharmacol.23:555-560. Nagao T, Abe F, Kinjo J, Okabe H (2002). Antiproliferative constituents in plants: 10 Flavones from the leaves of Lantana montevidensis BRIQ and consideration of structure–activity relationship. Biol. Pharm. Bull. 25:875-879. Oktay M, Gulcin I, Kufrevioglu OI (2003). Determination of in vitro antioxidant activity of fennel (Foeniculumvulgare) seed extracts. LWT Food Sci. Technol.36:263-271. Paradies I, Ohms JP (1987). Identification of triticale cultivars by electrophoresis of seed proteins. Landwirtschaftlich Forschung. 40:251-257. Rice-Evans CA, Miller NJ, Paganga G (1996). Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20:933-956. Rubinstein LV, Shoemaker RH, Paull KD, Simon RM, Tosini S, Skehan P, Scudiero DA, Monks A, Boyd MR (1990). Comparison of in vitro anticancer drug screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J. Natl. Cancer Inst. 82:1113-1117. Saeidnia S, Gohari AR, Mokhber-Dezfuli N, Kiuchi F (2011). A review on phytochemistry and medicinal properties of the genus Achillea. Daru. 19(3):173-186. Saeidnia S, Moradi-Afrapoli F, Gohari AR, Malmir M (2009). Cytotoxic flavonoid fromAchillea talagonica Bioss. J. Med. Plants 8:52-56. Saleh NAM (2003). Global phytochemistry: The Egyptian experience. Phytochemistry 63:239-241. Sathiyamoorthy P, Lugasi-Evgi H, Van-Damme P, Abu-Rabia A, Gopas J, Golan-Goldhirsh A (1997). Larvicidal activity in desert plants of the Negev and Bedouin market plant products. Pharm. Biol. 35:265-273. Bakr et al. 771 Segal RA, Duddeck DH, Kajtar M (1987). The sesquiterpene lactones from A. fragrantissima. Tetrahedron 43:4125-4132. Sellappan S, Akoh CC (2002). Flavonoids and antioxidant capacity of Georgia-grown Vidalia onions. J. Agric. Food Chem. 50:5338-5342. Shimada K, Fujikawa K, Yahara K, Nakamura T (1992). Antioxidative properties of xanthan on the autooxidation of soybean in cyclodextrin emulsion. J. Agric. Food Chem. 40:945-948. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990). New colorimetric cytotoxicity assay for anticancer-drug screening. Natl. J. Cancer Inst. 82:1107-1112. Soltan MM, Zaki AK (2009). Antiviral screening of forty-two Egyptian medicinal plants. J. Ethnopharmacol. 126:102-107. Stegmann H, Burgermeister W, Shah AA, Francksen HE, Krogerrecklenfort E (1988). PANTA-PHOR and MONO-PHOR Manual. (Institut fur Biochemie, Biologische Bundesanstlt, Messeweg 11, D-3300 Braunschweig West Germany). Thabrew MI, Hughes RD, McFarlane IG (1997). Screening of hepatoprotective plant components using a HepG2 cell cytotoxicity assay. J. Pharm. Pharmacol. 49:1132-1135. Trifunovic S, Vajs V, Juranic Z, Zizak Z, Tesevic V, Macura S, Milosavljevic S (2006). Cytotoxic constituents of Achillea clavennaefrom Montenegro. Phytochemistry 68:887-893. Vichai V, Kirtikara K (2006). Sulforhodamine B colorimetric assay for cytotoxicity screening. Nature protocols 1:1112-1116. Vicker N, Sharland CM, Heaton WB, Gonzalez AM, Bailey HV, Smith A, Springall JS, Day JM, Tutill HJ, Reed MJ, Purohit A, Potter BV (2009). The design of novel 17-hydroxysteroid dehydrogenase type 3 inhibitors. Mol. Cell Endocrinol. 301:259-265. Wallage JW (1971). Cirsimaritin-4ʹ-O-rutinoside, a new flavone glycoside from Cirsiumbrevistylum. Phytochemistry 10:452-454. Wollenweber E, Dörra M, Riverab D, Roitmanc JN (2003). Externally accumulated flavonoids in three Mediterranean Ononis species. Z. Naturforsch. 58c:771-775. Yaniv Z, Dafni A, Friedman J, Palevitch D (1987). Plants used for the treatment of diabetes in Israel. J. Ethnopharmacol. 19:145-151.