EXTRACTION, ISOLATION, AND CHARACTERIZATION OF BIOACTIVE COMPOUNDS AND ESSENTIAL OIL FROM SYZYGIUM JAMBOS

Mosad Ahmed Ghareeb; Manal Mortady Hamed; Abdel-aleem Hassan Abdel-aleem; Amal Mohamed Saad; Mohamed Sayed Abdel-aziz; Asmaa Hadad Hadad

doi:10.22159/ajpcr.2017.v10i8.18849

Authors

Mosad Ahmed Ghareeb Department of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt. 2Department of Organic Chemistry, Faculty of Science, Menoufia University, Shebin El-Kom, Egypt
Manal Mortady Hamed Department of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt. 2Department of Organic Chemistry, Faculty of Science, Menoufia University, Shebin El-Kom, Egypt
Abdel-aleem Hassan Abdel-aleem Department of Organic Chemistry, Faculty of Science, Menoufia University, Shebin El-Kom, Egypt
Amal Mohamed Saad Department of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt.
Mohamed Sayed Abdel-aziz Department of Microbial Chemistry, Genetic Engineering and Biotechnology Division, National Research Center, Dokki, Giza, Egypt
Asmaa Hadad Hadad Department of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt.

DOI:

https://doi.org/10.22159/ajpcr.2017.v10i8.18849

Keywords:

Syzygium jambos, Antioxidant compounds, Flavonoids, Natural products, Phenols

Abstract

Objectives: Over the past few decades, phenolic compounds become important due to it has been associated with protection against different diseasesand sensory point of vision. Hence, at the present study, there has been a growing interest to carry out structural elucidation and characterization ofthe pure isolates from Syzygium jambos.

Methods: S. jambos dried powder leaves were extracted by soaking in 85% methanol solvent at room temperature 25Â±2Â°C. The antioxidative activityof the isolates was assessed according to 2,2'-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and phosphomolybdenum assays.

Results: A total of 8 compounds were isolated from the n-butanol extract of S. jambos (Family Myrtaceae) plant, they were identified as quercetin-3-O-rutinoside (1), prenylbenzoic acid 4-Î²-D-glucoside (2), morolic acid 3-O-caffeate (3), 5,4'-dihydroxy, 7-methoxy, 6-methyl-flavone (4),3,4,5-trihydroxybenzoic acid (5), quercetin (6), isoetin-7-O-Î²-D-glucopyranoside (7), and (4'-hydroxy-3'-methoxyphenol-Î²-D-[6-O-(4â€-hydroxy-3â€,5â€-dimethoxylbenzoate)] glucopyranoside) (8). Compounds 5 and 6 showed the most radical scavengers among the tested compounds with SC50 values of5.50 and 4.30 Î¼g/ml, respectively, compared to ascorbic acid as standard and the total antioxidant capacity (TAC) values of 605.0 and 680.59 mg ascorbicacid equivalent/g compound, respectively. In vitro antimicrobial activities of the isolated compounds were tested using disc agar plate method againstfour pathogenic microbial strains including Gram-positive, Gram-negative bacteria and yeast with inhibition zones from 9 to 19 mm. Gas chromatographymassspectrometry analysis for the essential oil provides twenty four identified components representing 92% of its total oil composition.

Conclusion: The results supported that S. jambos could be attributed to sources of natural antioxidant and antimicrobial applications.

Downloads

Download data is not yet available.

References

Wijesekera RO. In: Roca R, editor. The Medicinal Plant Industry. USA: Taylor & Francis Inc., CRC Press Inc.; 1991.

Hassanein H, El-Ahwany E, Salah F, Hammam O, Refai L, Hamed M.Extracts of five medicinal herbs induced cytotoxicity in both hepatoma and myloma cell lines. Cancer Sci Ther 2010;3(10):239-43.

Mukherjee S. Diarrhea associated with lansoprazole. J Gastrol Hepatol 2003;18(5):602-3.

Marja PK, Anu IH, Heikki JV, Jussi-Pekka R, Kalevi P, Tytti SK, et al. Antioxidant activity of plant extracts containing phenolic compounds. J Agric Food Chem 1999;47:3954-62.

Mohamed MA, Hamed MM, Ahmed WS, Abdou AM. Antioxidant and cytotoxic flavonols from Calotropis procera. Z Naturforsch

;66C:547-54.

Garzon GA, NarvÃ¡ez CE, Riedl KM, Schwartz SJ. Chemical composition, anthocyanins, non-anthocyanin phenolics and antioxidant

activity of wild bilberry (Vaccinium meridionale Swartz) from Colombia. Food Chem 2010;122:980-6.

Shylaja P, Gothandam KM, Karthikeyan S. Phytochemical and antimicrobial properties of Syzygium cumini an ethanomedicinal plant

of Javadhu hills. Res Pharm 2011;1:22-32.

Sharma R, Navneet K, Ahmed H, Namrita L. Antibacterial and anti-inflammatory effects of Syzygium jambos L. (Alston) and isolated

compounds on acne vulgaris. BMC Complement Altern Med 2013;13(292):1-10.

Hossain H, Rahman SE, Akbar PN, Khan TA, Rahman MM, Jahan IA. HPLC profiling, antioxidant and in vivo anti-inflammatory activity of the ethanol extract of Syzygium jambos available in Bangladesh. BMC

Res Notes 2016;9:191.

Kuiate J, Simplice M, Hypolyte KW, Pierre T. Antidermatophytic triterpenoids from Syzygium jambos (L.) Alston (Myrtaceae). Phytother Res 2007;21:149-52.

Islam MR, Shahnaj MP, Ekramul MI. Antioxidant and hepatoprotective activity of an ethanol extract of Syzygium jambos (L.) leaves. Drug Discov Ther 2012;6(4):205-11.

Slowing K, Carretero E, Villar A. Anti-inflammatory activity of leaf extracts of Eugenia jambos in rats. J Ethnopharmacol 1994;43:9-11.

Murugan S, Devi PU, Parameswari NK, Mani KR. Antimicrobial activity of Syzygium jambos against selected human pathogens. Int J

Pharm Pharm Sci 2011;3(2):44-7.

Marwah RG, Fatope MO, Mahrooqi RA, Varma GB, Abadi HA, Al-Burtamani SK. Antioxidant capacity of some edible and wound healing plants in Oman. Food Chem 2007;101:465-70.

Prieto P, Pineda M, Aguilar M. Spectrophotometric quantation of ntioxidant capacity through the formation of a phosphomolybdenum

complex: Specific application to the determination of vitamin E. Anal Biochem 1999;269:337-41.

Hamed MM, Refahy LA, Abdel-Aziz MS. Evaluation of antimicrobial activity of some compounds isolated from Rhamnus cathartica L.Orient J Chem 2015;31:1133-40.

Mabry TJ, Markham KR, Thomas MB. The systematic identification of flavonoids. In: The Ultraviolet Spectra of Flavones and Flavonols Part II. Ch. V. Berlin, Germany: Springer-Verlag; 1970. p. 41-164.

Harborne JB, Mabry TJ. The Flavonoids Advances in Research. London, New York: Chapman and Hall; 1982.

Annegowda HV, Nee CW, Mordi MN, Ramanathan S, Mansor SM.Evaluation of phenolic content and antioxidant property of hydrolysed extracts of Terminalia catappa (L.) leaf. Asian J Plant Sci 2010;9:479â€‘85.

Hamed MM. Volatile oils from Pelargonium zonale and its cytotoxic

effect on tumor cells. Bull Fac Pharm Cairo Univ 2007;45(3):297-300.

Adams RP. Identification of Essential oils by Gas Chromatography Quadrupole Mass Spectrometry. Carol Stream, Illinois, USA: Allured Publishing Co.; 2001.

Harborne JB, Mabry TJ, Mabry H. The Flavonoids. London: Chapman and Hall; 1975.

Agrawal PK. Carbon-13 NMR of Flavonoids. Ch. 6. New York: Elsevier; 1989.

Qin X, Lunga P, Zhao Y, Li J, Yang X, Liu Y, et al. Antibacteria prenylbenzoic acid derivatives from Anodendron formicinum.

Fitoterapia 2014;92:238-43.

Jeong W, Hong SS, Kim N, Yang YT, Shin YS, Lee C, et al. Bioactive triterpenoids from Callistemon lanceolatus. Arch Pharmacol Res 2009;32:845-9.

Wollenweber E, Kohorst G. Epicuticular leaf flavonoids from Eucalyptus Species and from Kalmia latifolia. Z Naturforsch 1981;36c:913-5.

Shi S, Zhang Y, Zhao Y, Huang K. Preparative isolation and purification of three flavonoid glycosides from Taraxacum mongolicum by highspeed counter-current chromatography. J Sep Sci 2008;31:683-8.

Gawronska-Grzywacz M, Krzaczek T. Flavonoids and coumarins from Hieracium pilosella L. (Asteraceae). Acta Soc Bot Pol

;78(3):189â€‘95.

Hongzhou J, Yanbo S, Eri Y, Motoi C, Minoru T. Phenolic glucosides from inner bark of Shirakamba birch, Betula platyphyla Sukatchev var. Japonica hara. Eurasian J Forest Res 2001;3:49-54. 30. Rezende WP, Borges LL, Alves NM, Ferri PH, Paula JR. Chemical

variability in the essential oils from leaves of Syzygium jambos. Rev Bras Farmacogn 2013;23(3):433-40.

Rice-Evans CA, Miller NJ, Paganga G. Structure - Antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Sci 1996;20:933-56. 32. Hamed MM, Mohamed MA, Ahmed WS. Antioxidant potential, antitumor activity and phenolic profile of Phoenix dactylifera Linn. Int J Pharm Pharm Sci 2017;9(5):130-6.

Hamed MM, Refahy LA, Abdel-Aziz MS. Assessing the bioactivity and antioxidative properties of some compounds isolated from Abutilon hirtum (Lam.). Asian J Pharm Clin Res 2017;10(3):333-40.