Isolation and identification of hyperin and naringenin from guava cultivated in Iraq and evaluation of cytotoxic activity of hyperin

Authors

DOI:

https://doi.org/10.14719/pst.3460

Keywords:

Ultrasonic-assisted extraction, Hyperin, Naringenin, Guava, NMR spectroscopy

Abstract

The guava plant, Psidium guajava L., serves as proof of the abundant donations of nature, providing a delicious guava fruit; this plant is rich in groups of medicinal and nutritional benefits. Guava belonging to the Myrtaceae family, many previous studies reported many phytochemical constituents in its leaves that have many pharmacological activities and medicinal properties; this study focuses on the isolation, structural elucidation and calculation concentration of flavonoids, assessment of the cytotoxic activityof hyperin from Psidium guajava leaves newly cultivated in Iraq. The isolation process involved the use of thin-layer chromatography (TLC) and preparative high-performance liquid chromatography (PHPLC) and structural elucidation involved NMR (nuclear magnetic resonance spectroscopy) and FTIR (Fourier transform infrared spectrometer) for detailed structural insights into 2 isolated flavonoids. The isolation techniques proved effective in obtaining pure samples of hyperin and naringenin from the ethyl acetate and n.butanol fractions and structural elucidation techniques gives a good explanation for 2 isolated flavonoids. Evaluate cytotoxic activity of hyperin flavonoid against prostate cancer cell line (PC-3), human breast cancer cell line (MCF-7) and normal dermal fibroblast neonatal (HdFn), hyperin flavonoid exhibited a decrease in cell viability (%) with IC50 58.9 ?g /mL against the prostate cancer cell and IC50 90.58 ?g /mL against human breast cancer and noncytotoxic to HDFn, with an IC50 value substantially surpassing concentrations of 100 ?g/mL. These analytical approaches provided a comprehensive understanding of the chemical composition of the isolated flavonoids and interpreted that guava has cytotoxic activity against some cancers, depending on a concentration-dependent mode.

Downloads

Download data is not yet available.

References

Kumar M, Tomar M, Amarowicz R, Saurabh V, Nair MS, Maheshwari C et al. Guava (Psidium guajava L.) leaves: Nutritional composition, phytochemical profile and health-promoting bioactivities. Foods. 2021;10(4):752. https://doi.org/10.3390/foods10040752

Thuaytong W, Anprung P. Bioactive compounds and prebiotic activity in Thailand-grown red and white guava fruit (Psidium guajava L.). Food Science and Technology International. 2011;17(3):205-12. https://doi.org/10.1177/1082013210382066

Naseer S, Hussain S, Naeem N, Pervaiz M, Rahman M. The phytochemistry and medicinal value of Psidium guajava (guava). Clinical Phytoscience. 2018;4(1):1-8. https://doi.org/10.1186/s40816-018-0093-8

Díaz-de-Cerio E, Verardo V, Gómez-Caravaca AM, Fernández-Gutiérrez A, Segura-Carretero A. Health effects of Psidium guajava L. leaves: An overview of the last decade. International Journal of Molecular Sciences. 2017;18(4):897. https://doi.org/10.3390/ijms18040897

Gutierrez-Montiel D, Guerrero-Barrera AL, Chávez-Vela NA, Avelar-Gonzalez FJ, Ornelas-García IG. Psidium guajava L.: From byproduct and use in traditional Mexican medicine to antimicrobial agent. Frontiers in Nutrition. 2023;10:1108306. https://doi.org/10.3389/fnut.2023.1108306

Díaz-de-Cerio E, Gómez-Caravaca AM, Verardo V, Fernández-Gutiérrez A, Segura-Carretero A. Determination of guava (Psidium guajava L.) leaf phenolic compounds using HPLC-DAD-QTOF-MS. Journal of Functional Foods. 2016;22:376-88. https://doi.org/10.1016/j.jff.2016.01.040

Prakoso NI, Nita MT. Exploring anticancer activity of the Indonesian guava leaf (Psidium guajava L.) fraction on various human cancer cell lines in an in vitro cell-based approach. Open Chemistry. 2023;21(1):20230101. https://doi.org/10.1515/chem-2023-0101

Vijayakumar K, Arumugam VA, Ramasamy M, Natesan M, Palanisamy S, Thajuddin NB et al. Hepatoprotective effects of Psidium guajava on mitochondrial enzymes and inflammatory markers in carbon tetrachloride-induced hepatotoxicity. Drug Development and Industrial Pharmacy. 2020;46(12):2041-50. https://doi.org/10.1080/03639045.2020.1843474

Abdlkareem SK. Isolation, identification and quantification of two compounds from Cassia glauca cultivated in Iraq. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2023;32(3):95-104. https://doi.org/10.31351/vol32iss3pp95-104

Ghalib SA, Kadhim EJ. The investigation of some phytochemical compounds found in Anchusa strigosa L. grown naturally in Iraq. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2021;30(1):179-88. https://doi.org/10.31351/vol30iss1pp179-188

Tawfeeq AA, Ali SH. 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. 2022;31:121-30. https://doi.org/10.31351/vol31isssuppl.pp121-130

Atiyah KH, Kadhum EJ. Isolation and identification of phenolic compounds from Dianthus orientalis wildly grown in Iraq. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2021;30(2):122-34. https://doi.org/10.31351/vol30iss2pp122-134

Jewely HM, Zuhair T. Evaluation of anti-leishmanial activity of Osteospermum ecklonis extract of aerial parts against Leishmania donovani: in vitro (Conference Paper). Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2022;31(Suppl.):45-53. https://doi.org/10.31351/vol31isssuppl.pp45-53

Khamees AH. Isolation, characterization and quantification of a pentacyclic triterpinoid compound ursolic acid in Scabiosa palaestina L. distributed in the north of Iraq. Plant Science Today. 2022;9(1):178-82. https://doi.org/10.14719/pst.1398

Ibrahem NM, Khadum EJ, Mutlag SH. Isolation of catchin and epigallocatchin from Iraqi Rhus coriaria by preparative high-performance liquid chromatography (PHPLC). Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2022;31(2):271-82. https://doi.org/10.31351/vol31iss2pp271-282

Shah SM, Abdul-Jalil TZ. Qualitative and quantitative estimation or chemical constituents from leaves and roots of Iraqi Agave attenuata by GC-MS and RP-HPLC (Conference Paper). Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2022;31(Suppl.):75-85. https://doi.org/10.31351/vol31isssuppl.pp75-85

Zahra'a SN, Khadem EJ. Phytochemical investigations of Iraqi Abrus precatorius Linn. plant. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2018;27(1):30-38. https://doi.org/10.31351/vol27iss1pp30-38

Freshney RI. Culture of animal cells: A manual of basic technique and specialized applications. John Wiley & Sons; 2015. https://doi.org/10.1002/9780470649367.

Ryu NH, Park KR, Kim SM, Yun HM, Nam D, Lee SG et al. A hexane fraction of guava leaves (Psidium guajava L.) induces anticancer activity by suppressing AKT/mammalian target of rapamycin/ribosomal p70 S6 kinase in human prostate cancer cells. Journal of Medicinal Food. 2012;15(3):231-41. https://doi.org/10.1089/jmf.2011.1701

Ashraf A, Sarfraz RA, Rashid MA, Mahmood A, Shahid M, Noor N. Chemical composition, antioxidant, antitumor, anticancer and cytotoxic effects of Psidium guajava leaf extracts. Pharmaceutical Biology. 2016 ; 2;54(10):1971-81. https://doi.org/10.3109/13880209.2015.1137604

Buqui GA, Gouvea DR, Sy SK, Voelkner A, Singh RS, da Silva DB et al. Pharmacokinetic evaluation of avicularin using a model-based development approach. Planta Medica. 2015;81(05):373-81. https://doi.org/10.1055/s-0035-1545728

Gahlaut A, Chhillar AK. Evaluation of antibacterial potential of plant extracts using resazurin based microtiter dilution assay. International Journal of Pharmacy and Pharmaceutical Sciences. 2013;5(2):372-76. https://doi.org/10.1186/s12866-014-0259-6

Nassir ZS. Detection of epicatechin in Camellia sinensis leaves by thin layer chromatography and high performance liquid chromatography techniques. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2022;31(2):304-12. https://doi.org/10.31351/vol31iss2pp304-312

Hu HB, Zheng XD, Hu HS. Analysis of flavonoids from leaves of Acanthopanax brachypus harms. Journal of the Chilean Chemical Society. 2013;58(1):1549-52. https://doi.org/10.4067/s0717-97072013000100011

Latos-Brozio M, Masek A, Piotrowska M. Novel polymeric biomaterial based on naringenin. Materials. 2021;14(9):2142. https://doi.org/10.3390/ma14092142

Huang HM, Ho CY, Chang GR, Shia WY, Lai CH, Chao CH, Wang CM. HPLC/ESI-MS and NMR analysis of chemical constitutes in bioactive extract from the root nodule of Vaccinium emarginatum. Pharmaceuticals. 2021;14(11):1098. https://doi.org/10.3390/ph14111098

Quintanilla-Licea R, Vargas-Villarreal J, Verde-Star MJ, Rivas-Galindo VM, Torres-Hernández ÁD. Antiprotozoal activity against Entamoeba histolytica of flavonoids isolated from Lippia graveolens Kunth. Molecules. 2020;25(11):2464. https://doi.org/10.3390/molecules25112464

Ping MH. Hyperin controls the development and therapy of gastric cancer via regulating wnt/?-catenin signaling. Cancer Management and Research. 2020:11773-82. https://doi.org/10.2147/CMAR.S270544

Ma SN, Mao ZX, Wu Y, Liang MX, Wang DD, Chen X et al. The anti-cancer properties of heparin and its derivatives: A review and prospect. Cell Adhesion and Migration. 2020;14(1):118-28. https://doi.org/10.1080/19336918.2020.1767489

Mohammed AH, Muthanna FM, Hassan BA, Karuppannan M, Wayyes AM. Impact and association of anaemia severity and its treatment with quality of life of breast cancer patients in Malaysia. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2022;31(2):62-70. https://doi.org/10.21203/rs.3.rs-205318/v1

Mahde S, Haishm S. Carvone exerts lung anti-inflammatory effect through hampering NF-KB pathway in lipopolysaccharide-induced acute lung injury in mice. Iraqi Journal of Pharmaceutical Sciences (P-ISSN 1683-3597 E-ISSN 2521-3512). 2023;32(1):125-32. https://doi.org/10.31351/vol32iss1pp125-132

Published

28-05-2024 — Updated on 01-06-2024

Versions

How to Cite

1.
T. Kareem A, J. Kadhim E. Isolation and identification of hyperin and naringenin from guava cultivated in Iraq and evaluation of cytotoxic activity of hyperin. Plant Sci. Today [Internet]. 2024 Jun. 1 [cited 2024 Dec. 25];11(2). Available from: https://horizonepublishing.com/journals/index.php/PST/article/view/3460

Issue

Section

Research Articles