Isolation and Structural Characterization of Quercetin 3-O-Rhamnoside and Essential oil Estimation from Leaves of Iraqi Cupressus sempervirens L (Conference Paper )#

Authors

  • Amani Amer Tawfeeq PHD STUDENT,College of Pharmacy, University of Baghdad
  • Shatha H Ali

DOI:

https://doi.org/10.31351/vol31issSuppl.pp121-130

Keywords:

Cupressus, Conifers, al Sarw, Mass, Pinene, Quercitrin, Spectroscopy

Abstract

     Cupressus sempervirens L., Cupressaceae, that is known as evergreen cypress, Mediterranean cypress and in Arabic called “al -Sarw. It is an evergreen, medium sized, longevity, and wide distributed over all the world. The plant represents an important member of conifer plants which characterized with aromatic leaves and cones. Cupressus sempervirens have been ethnobotanical uses as an antiseptic, relief of cough, astringent, antispasmodic, wound healing and anti-inflammatory. Aims of this work are phytochemical analysis, isolation and structural identification of Quercitroside (quercitrin) and essential oil in Iraqi C. sempervirens. Isolation of quercitrin was performed by preparative HPLC from n-butanol fraction that prepared and extracted from Cupressus sempervirens leaves using ultrasound probe extraction, the structural identification of isolated quercitrin done by FT-IR characterized by bands at varies of frequency ranges. Moreover, LCMSMS; molecular ion at 448 m/z and base peak m/z 301. Furthermore, isolation of essential oil using hydro-distillation and estimated by GC-MS, the results show a good essential oil yield 0.9% with an interesting concentration of alpha-pinene 44%, carene10%, cedrol 4.86%, and β- myrcene 3.67%. A new Quercetin-glycoside in Cupressus Semperviren species in addition, 0.9% essential oil yield considered important phytochemicals with good concentration in Iraqi cypress plant.

References

Mujeeb F., P. Bajpai, and N. Pathak. Phytochemical evaluation, antimicrobial activity , and determination of bioactive components from leaves of Aegle marmelos. BioMed Res. Intl. 2014; 6 (1): 1–11.

Nedhal A. Al-douri.A survey of medicinal plants and their traditional uses in Iraq. Pharmaceut. Biol. 2000; 38(1): 74-79.

Neale, D.B., Wheeler, N.C. The conifers in the conifers: genomes. In chapter one of variation and evolution. Cham, Springer Nature Switzerland .2019: 1-21.

Bhardwaj K, Islam MT, Jayasena V, Sharma B, Sharma S, Sharma P, et al. Review on essential oils, chemical composition, extraction, and utilization of some conifers in Northwestern Himalayas. Phyto. Res., Wiley. 2020 ;34(11):2889–910.

Farahmand, H. et al. Characterization and evaluation of genetic diversity of some old cypress genotypes (Cupressus sempervirens L.) in Iran using leaf mineral concentration, biochemical characteristics and SSR markers. Pl. Syst. Evol. 2014;301(2):761–772.

Eldalawy R, Naser NM, Naqqash ZA. Antimicrobial and antioxidant activity of Iraqi Cupressus empervirens cones. AIP. 2020 ;. 2213(1): 020006.

Goetz, P. & Ghedira, K. Cupressus sempervirens L. (Cupressaceae): Cyprès. Phytothérapie anti-infectieuse. 2012: 253–257

D’Auria A, Vingiani S, Marzaioli F, Teobaldelli M, Di Pasquale G. Recent history, use and forgetfulness of the cypress forest of Fontegreca (Southern Italy). Diver., MDPI.2020; 12(12):461-7.

Thukral SK, Singh S, Sharma SK. Pharmacognostical standardization of leaves of Cupressus macrocarpa Hartweg. ex Gordon. J.App. Pharm.Sci. 2014 May ;4(5):071-4.

Kuiate, Jules-Roger, Jean Marie Bessière, Paul Henri Amvam Zollo, and Serge Philibert Kuate. Chemical composition and antidermatophytic properties of volatile fractions of hexanic extract from leaves of Cupressus Lusitanica Mill. from Cameroon. J.Eth.pharma. 2006;103 (2): 160–165.

Sharma, Hitender, and Munish Garg. A Review of traditional use, phytoconstituents and biological activities of himalayan yew, Taxus Wallichiana. J. Integ. Med. 2015;13 (2): 80–90.

Kunwar RM, Shrestha KP, Bussmann RW. Traditional herbal medicine in Far-west Nepal: a pharmacological appraisal. Journal of ethnobiology and ethnomedicine. 2010 ;6(1):1-8.

N, Heimler DH. HPLC quantification of flavonoids and biflavonoids in Cupressaceae leaves. J. Chromatog.. 2002;56(7):469-74.

Romani A, Galardi C, Pinelli P, Mulinacci N, Heimler DH. HPLC quantification of flavonoids and biflavonoids in Cupressaceae leaves. Chromatographia. 2002;56(7):469-74.

Elmongy EI, Negm WA, Elekhnawy E, El-Masry TA, Attallah NG, Altwaijry N, Batiha GE, El-Sherbeni SA. Antidiarrheal and antibacterial activities of Monterey cypress phytochemicals: in vivo and in vitro approach. Molecules. 2022;27(2):346-20.

YÜKSEL TN, Bozgeyik E, Yayla M. The effect of quercetin and quercetin-3-d-xyloside on breast cancer proliferation and migration. J.Basic Clin. Heal. Sci. 2021;6(2):235-44.

Luo J, Si H, Jia Z, Liu D. Dietary anti-aging polyphenols and potential mechanisms, antioxidant, MDPI AG; 2021;10(2):283-87.

Abdulrazzaq MH, Khadeem EJ, Al-Muhammadi SS, Hepatoprotective Effect of Echinops tenuisectus (Compositae) on CCl4 Induced Hepatic Damage in Rats. IJPS, 2008;17(1):16-24.

Pandey A, Kumar R, Mishra A, Pandey A, Pandey AK., A systematic review on synthetic drugs and phytopharmaceuticals used to manage diabetes. Current Nutr., 2020; 16(4):340-356.

Yang D, Wang T, Long M, Li P., Oxidative medicine and cellular longevity, Hindawi Limited; 2020 Dec;2020:1–13.

Gonzalez - Burgos E, Gomez-Serranillos MP. Terpene compounds in nature: A review of their potential antioxidant activity. C.Med.Chem., Bentham Science Publishers Ltd. 2012 Nov;19(31):5319–41.

Karkabounas S, KoRTsIs DN, Zelovitis J, Skafida P, DEMETzos CO, Malamas M, Elisaf M, Ev.angelou A. Effects of Cupressus Sempervirens cone extract on lipid parameters. in vivo. 2003; 17:101-4.

Al-Sayed E, Gad HA, El-Shazly M, Abdel-Daim MM, Nasser Singab A. Anti-inflammatory and analgesic activities of cupressuflavone from Cupressus macrocarpa: Impact on pro-inflammatory mediators. D. Dev. Res., Wiley. 2017;79(1):22–8.

Ulusal BG, Arikan S, Durusoy C. Anticoagulant effect of Cupressus sempervirens. Phytotherapy Research. Wiley.2007;21(11):1116–16.

Ibrahim NA, El-Seedi HR, Mohammed MMD. Phytochemical investigation and hepatoprotective activity of Cupressus sempervirens L. leaves growing in Egypt. Nat.Prod. Res. 2007;21(10):857–66.

Degenhardt RT, Farias IV, Grassi LT, Franchi GC, Nowill AE, da S. Bittencourt CM, et al. Characterization and evaluation of the cytotoxic potential of the essential oil of Chenopodium ambrosioides. Revista Bras. de Farm. . Springer. 2016;26(1):56–61

Zahari NAAR, Chong GH, Abdullah LC, Chua BL. Ultrasonic-Assisted Extraction (UAE) Process on Thymol Concentration from Plectranthus Amboinicus Leaves: K. Mod. and Opt. MDPI; 2020 9;8(3):322.

Altemimi A, Lakhssassi N, Baharlouei A, Watson D, Lightfoot D. Phytochemicals: extraction, isolation, and identification of bioactive compounds from plant extracts. Plants, MDPI. 2017 ;6(4):42

Ibrahim NM, Kadhim EJ. Phytochemical investigation and antioxidant activity of Iraqi Tribulus terrestris. IJPS. Sci.2015;24(1):68-73.

Sahagun G, Pobre RF. Sahagun G, Pobre RF. Effects of ultrasonic waves on breast cancer cell line (MCF-7) coupled with Zinger officinale (GINGER) extract using cell viability and comet assay tests. In International Conference on Photonics and Imaging in Biology and Medicine 2017 ; 7(1):18.

M’barek K. Chemical composition and phytotoxicity of Cupressus sempervirens leaves against crops. J.Ess. Oil.Plants. 2016;19(7):1582-99.

Trineeva OV, Safonova II, Safonova EF, Slivkin AI. Quantitative determination of rutin by thin-layer chromatography. Pharmaceutical Chemistry Journal. Springer Science and Business Media. 2014 ;48(2):134–8.

Karapandzova M, Stefkov G, Cvetkovikj I, Stanoeva JP, Stefova M, Kulevanova S. Flavonoids and other phenolic compounds in needles of Pinus peuce and other pine species from the macedonian flora. Nat.Prod. Comm. 2015 ;10(6): 1934578X1501000

Yang B., Kortesniemi M., P. Liu, et al., Analysis of hydrolyzable tannins and other phenolic compounds in Emblic leaf flower (Phyllanthus emblica L.) fruits by high-performance liquid chromatography-electrospray ionization mass spectrometry, J. Agric. Food Chem. 60 (2012) 8672–8683.

Corradini E, Foglia P, Giansanti P, Gubbiotti R, Samperi R, Laganà A. Flavonoids: chemical properties and analytical methodologies of identification and quantitation in foods and plants. Natural Product Research. 2011 ;25(5):469–95.

Azzaz NA, Hamed SS, Kenawy TA. Chemical studies on cypress leaves (Cupressus sempervirens) and their activity as antimicrobial agents. Al-Azhar J.Agricul.Res. 2019 ;44(2):100-9.

Ulukanli Z, Karabörklü S, Ates B, Erdogan S, Cenet M, Karaaslan MG. Chemical composition of the essential oil from Cupressus sempervirens L. Horizontalis Resin in conjunction with its biological assessment. J. E.Oil-Bearing Plants. 2014;17(2):277–87.

Milos M, Radonic A, Mastelic J. Seasonal variation in essential oil compositions of Cupressus sempervirens L. J. E. Oil Res .2002 ;14(3):222–3.

Ben Nouri A, Dhifi W, Bellili S, Ghazghazi H, Aouadhi C, Chérif A, et al. Chemical composition, antioxidant potential, and antibacterial activity of essential oil cones of tunisian Cupressus sempervirens. J. Chemist. 2015; 2015:1–8.

Tawfeeq AA, Mahdi MF, Abaas IS, Alwan AH. Isolation, quantification, and identification of rosmarinic acid, gas chromatography-mass spectrometry analysis of essential oil, cytotoxic effect, and antimicrobial investigation of Rosmarinus officinalis leaves. AJPCR2018 ;11(6):126.

Glavnik V, Simonovska B, Albreht A, Vovk I. TLC and HPLC screening of p-coumaric acid, trans-resveratrol, and pterostilbene in bacterial cultures, food supplements, and wine. JPC-J. of Planar Chromatog.Modern TLC. 2012 ;25(3):251-8.

Karakurt S. Modulatory effects of rutin on the expression of cytochrome P450s and antioxidant enzymes in human hepatoma cells. Acta Pharmaceutica. 2016;66(4):491-502.

Gopi K, Anbarasu K, Renu K, Jayanthi S, Vishwanath BS, Jayaraman G. Quercetin-3-O-rhamnoside from Euphorbia hirta protects against snake Venom induced toxicity. Biochimica et Biophysica Acta (BBA).2016 ;1860(7):1528-40.

Kumar S, Singh A, Kumar B. Identification and characterization of phenolics and terpenoids from ethanolic extracts of Phyllanthus species by HPLC-ESI-QTOF-MS/MS. J. pharmac. anal. 2017 ;7(4):214-22.

Romani A, Galardi C, Pinelli P, Mulinacci N, Heimler DH. HPLC quantification of flavonoids and biflavonoids in Cupressaceae leaves. Chromatographia. 2002 ;56(7):469-74.

Attallah NG, Negm WA, Elekhnawy E, Elmongy EI, Altwaijry N, El-Haroun H, El-Masry TA, El-Sherbeni SA. Elucidation of phytochemical content of Cupressus macrocarpa leaves: in vitro and in vivo antibacterial effect against methicillin-resistant Staphylococcus aureus clinical isolates. Antibiotics. 2021;10(8):890.

Downloads

Published

2023-02-16

How to Cite

1.
Tawfeeq AA, Shatha H Ali. Isolation and Structural Characterization of Quercetin 3-O-Rhamnoside and Essential oil Estimation from Leaves of Iraqi Cupressus sempervirens L (Conference Paper )#. Iraqi Journal of Pharmaceutical Sciences [Internet]. 2023 Feb. 16 [cited 2024 Nov. 19];31(Suppl.):121-30. Available from: https://bijps.uobaghdad.edu.iq/index.php/bijps/article/view/2009

Publication Dates