[en] The aim of this study is first to identify the major phenolic compound of a crude ethanol extract of Psidium guajava leaves collected in Vietnam and to develop validated methods for quantification of phenolic and triterpenic components by HPLC-PDA-HRMS. The major phenolic compound was determined as quercetin-3-O-sulfate which is isolated and quantified for the first time in P. guajava. Validated HPLC-DAD quantification methods were developed to quantify the major triterpenic and phenolic derivatives of this extract and found to be accurate in the concentration range of 2–50 μg/mL for phenolic, and 5–100 μg/mL for triterpenic compounds. Four crude ethanol extracts of guava leaves collected at different periods of the year were analyzed using the developed methods and were found to be richer in triterpenic than phenolic derivatives. We also observed that the weather or rainfall influenced the richness in bioactive compounds in guava leaves.
Research Center/Unit :
FARAH. Santé publique vétérinaire - ULiège
Disciplines :
Food science
Author, co-author :
Nguyen, Phuc-Dam; Department of Chemistry Education, School of Education, Can Tho University, Can Tho, Viet Nam ; Louvain Drug research Institute (LDRI), Pharmacognosy Research group, Université catholique de Louvain (UCLouvain), Brussels, Belgium
Hérent, Marie-France; Louvain Drug research Institute (LDRI), Pharmacognosy Research group, Université catholique de Louvain (UCLouvain), Brussels, Belgium
Le, Thi-Bach; Department of Chemistry, College of Natural Sciences, Can Tho University, Can Tho, Viet Nam
Bui, Thi-Buu-Hue; Department of Chemistry, College of Natural Sciences, Can Tho University, Can Tho, Viet Nam
Bui, Thi-Bich-Hang; Department of Aquatic Pathology, College of Aquaculture and Fisheries, Can Tho University, Can Tho, Viet Nam
Do, Thi-Thanh-Huong; Department of Aquatic Nutrition and Products Processing, College of Aquaculture and Fisheries, Can Tho University, Can Tho, Viet Nam
Nguyen, Thanh-Phuong; Department of Coastal Aquaculture, College of Aquaculture and Fisheries, Can Tho University, Can Tho, Viet Nam
Scippo, Marie-Louise ; Université de Liège - ULiège > Département de sciences des denrées alimentaires (DDA) > Analyse des denrées alimentaires
Kestemont, Patrick; Research Unit in Environmental and Evolutionary Biology (URBE), Institute of Life, Earth and Environment (ILEE), University of Namur, Namur, Belgium
Quetin-Leclercq, Joëlle; Louvain Drug research Institute (LDRI), Pharmacognosy Research group, Université catholique de Louvain (UCLouvain), Brussels, Belgium
Language :
English
Title :
Isolation of quercetin-3-O-sulfate and quantification of major compounds from Psidium guajava L. from Vietnam
The authors are grateful for the financial support from the Commission of Cooperation and Development of the Académie de Recherche et d′Enseignement Supérieur (ARES-CCD) and the General Directorate for Cooperation and Development (DGD) in Belgium for financial support through the AquaBioActive Research Project for Development between the University of Namur, the University of Liège and the Université catholique de Louvain in Belgium, and Can Tho University in Vietnam , and an additional post-doc grant for Phuc-Dam Nguyen . The authors wish to thank Doctor Minh-Quan DANG (School of Education, Can Tho University, Vietnam) for the plant identification, Lucy Catteau (LDRI, UCLouvain, Belgium) for the standard supply of 4TTE, Claire Beaufay, and Kelly Dujardin (LDRI, UCLouvain, Belgium) for skillful technical assistance.The authors are grateful for the financial support from the Commission of Cooperation and Development of the Académie de Recherche et d′Enseignement Supérieur (ARES-CCD) and the General Directorate for Cooperation and Development (DGD) in Belgium for financial support through the AquaBioActive Research Project for Development between the University of Namur, the University of Liège and the Université catholique de Louvain in Belgium, and Can Tho University in Vietnam, and an additional post-doc grant for Phuc-Dam Nguyen. The authors wish to thank Doctor Minh-Quan DANG (School of Education, Can Tho University, Vietnam) for the plant identification, Lucy Catteau (LDRI, UCLouvain, Belgium) for the standard supply of 4TTE, Claire Beaufay, and Kelly Dujardin (LDRI, UCLouvain, Belgium) for skillful technical assistance.
Agency, E.M. ( 21 July 2011). Guideline on Bioanalytical Method Validation EMEA/CHMP/EWP/192217/2009 Rev 1 Corr 2**. In.
Altendorf, S. (2018). Minor Tropical Fruits (Mainstreaming a Niche Market). FAO Food Outlook 1, 67–75.
Barron, D., Colebrook, L.D., Ibrahim, R.K., An equimolar mixture of quercetin 3-sulphate and patuletin 3-sulphate from Flaveria chloraefolia. Phytochemistry 25:7 (1986), 1719–1721, 10.1016/S0031-9422(00)81243-1.
Beaufay, C., Henry, G., Streel, C., Bony, E., Hérent, M.F., Bero, J., Quetin-Leclercq, J., Optimization and validation of extraction and quantification methods of antimalarial triterpenic esters in Keetia leucantha plant and plasma. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 1104 (2019), 109–118.
Begum, S., Hassan, S., Ali, S., Siddiqui, B., Chemical constituents of the leaves of Psidium guajava. Nat. Prod. Res. 18 (2004), 135–140, 10.1080/14786410310001608019.
Begum, S., Hassan, S.I., Siddiqui, B.S., Shaheen, F., Nabeel Ghayur, M., Gilani, A.H., Triterpenoids from the leaves of Psidium guajava. Phytochemistry 61:4 (2002), 399–403, 10.1016/S0031-9422(02)00190-5.
Bezerra, C.F., Rocha, J.E., Nascimento Silva, M.K.D., de Freitas, T.S., de Sousa, A.K., Dos Santos, A.T.L., da Cruz, R.P., Ferreira, M.H., da Silva, J.C.P., Machado, A.J.T., Carneiro, J.N.P., Sales, D.L., Coutinho, H.D.M., Ribeiro, P.R.V., de Brito, E.S., Morais-Braga, M.F.B., ). Analysis by UPLC-MS-QTOF and antifungal activity of guava (Psidium guajava L.). Food Chem. Toxicol. 119 (2018), 122–132, 10.1016/j.fct.2018.05.021.
Bylka, W., Stobiecki, M., Frański, R., Sulphated flavonoid glycosides from leaves of Atriplex hortensis. Acta Physiol. Plant. 23:3 (2001), 285–290, 10.1007/s11738-001-0035-8.
Catteau, L., Schioppa, L., Beaufay, C., Girardi, C., Hérent, M.F., Frédérich, M., Quetin-Leclercq, J., Antiprotozoal activities of Triterpenic Acids and Ester Derivatives Isolated from the Leaves of Vitellaria paradoxa. Planta Med 87:10/11 (2021), 860–867.
Chao, C.L., Hou, Y.C., Chao, P.D., Weng, C.S., Ho, F.M., The antioxidant effects of quercetin metabolites on the prevention of high glucose-induced apoptosis of human umbilical vein endothelial cells. Br. J. Nutr. 101:8 (2009), 1165–1170, 10.1017/s0007114508073637.
Chao, I.C., Chen, Y., Gao, M.H., Lin, L.G., Zhang, X.Q., Ye, W.C., Zhang, Q.W., Simultaneous determination of α-glucosidase inhibitory triterpenoids in Psidium guajava using HPLC-DAD-ELSD and pressurized liquid extraction. Molecules, 25(6), 2020, 1278, 10.3390/molecules25061278.
Chen, Y., Zhang, Q.W., Li, S.L., Yi, Y., Zhao, J., Wang, Y., Ye, W.C., Psidium guajava, a potential resource rich in corosolic acid revealed by high performance liquid chromatography. J. Med. Plants Res. 5 (2011), 4261–4266.
Correia-da-Silva, M., Sousa, E., Pinto, M.M.M., Emerging sulfated flavonoids and other polyphenols as drugs: nature as an inspiration. Med. Res. Rev. 34:2 (2014), 223–279, 10.1002/med.21282.
David, M., Abraham, T.J., Talagunda Srinivasan, N., Adikesavalu, H., Immunomodulatory effect of Guavarine®, Aqueous Guava leaf extract, on Ornamental Koi Carp Cyprinus carpio var. koi L. 1758. J. Appl. Aquac. 29 (2017), 322–330, 10.1080/10454438.2017.1363680.
Deguchi, Y., Miyazaki, K., Anti-hyperglycemic and anti-hyperlipidemic effects of guava leaf extract. Nutr. Metab. (Lond. ), 7, 2010, 9, 10.1186/1743-7075-7-9.
Díaz-de-Cerio, E., Gómez-Caravaca, A.M., Verardo, V., Fernández-Gutiérrez, A., Segura-Carretero, A., Determination of guava (Psidium guajava L.) leaf phenolic compounds using HPLC-DAD-QTOF-MS. J. Funct. Foods 22 (2016), 376–388, 10.1016/j.jff.2016.01.040.
Díaz-de-Cerio, E., Verardo, V., Gómez-Caravaca, A.M., Fernández-Gutiérrez, A., Segura-Carretero, A., Exploratory characterization of phenolic compounds with demonstrated anti-diabetic activity in guava leaves at different oxidation states. Int. J. Mol. Sci., 17(5), 2016, 699, 10.3390/ijms17050699.
Díaz-de-Cerio, E., Verardo, V., Gómez-Caravaca, A.M., Fernández-Gutiérrez, A., Segura-Carretero, A., Health effects of Psidium guajava L. leaves: an overview of the last decade. Int. J. Mol. Sci., 18(4), 2017, 897, 10.3390/ijms18040897.
Dueñas, M., González-Manzano, S., Surco-Laos, F., González-Paramas, A., Santos-Buelga, C., Characterization of sulfated quercetin and epicatechin metabolites. J. Agric. Food Chem. 60:14 (2012), 3592–3598, 10.1021/jf2050203.
EDQM. (2011). European Pharmacopoeia, 6th edition. Strasbourg: European Directorate for the Quality of Medicines and Health Care (EDQM) of Council of Europe.
Giri, S.S., Sen, S.S., Chi, C., Kim, H.J., Yun, S., Park, S.C., Sukumaran, V., Effect of guava leaves on the growth performance and cytokine gene expression of Labeo rohita and its susceptibility to Aeromonas hydrophila infection. Fish. Shellfish Immunol. 46:2 (2015), 217–224, 10.1016/j.fsi.2015.05.051.
Gobi, N., Ramya, C., Vaseeharan, B., Malaikozhundan, B., Vijayakumar, S., Murugan, K., Benelli, G., Oreochromis mossambicus diet supplementation with Psidium guajava leaf extracts enhance growth, immune, antioxidant response and resistance to Aeromonas hydrophila. Fish. Shellfish Immunol. 58 (2016), 572–583, 10.1016/j.fsi.2016.09.062.
Hubert, P., Nguyen-Huu, J.J., Boulanger, B., Chapuzet, E., Chiap, P., Cohen, N., Valat, L., Harmonization of strategies for the validation of quantitative analytical procedures. A SFSTP proposal–Part I. J. Pharm. Biomed. Anal. 36:3 (2004), 579–586, 10.1016/j.jpba.2004.07.027.
Irondi, E.A., Agboola, S.O., Oboh, G., Boligon, A.A., Athayde, M.L., Shode, F.O., Guava leaves polyphenolics-rich extract inhibits vital enzymes implicated in gout and hypertension in vitro. J. Intercult. Ethnopharmacol. 5:2 (2016), 122–130, 10.5455/jice.20160321115402.
ISO-5725–1. (1994(en)). Accuracy (trueness and precision) of measurement methods and results — Part 1: General principles and definitions. In.
ISO/IEC-GUIDE-98–3. (2008). Uncertainty of measurement —. Part 3: Guide to the expression of uncertainty in measurement. (GUM:1995). In.
Lorena, C., Ressaissi, A., Serralheiro, M.L., Bioactives from Psidium guajava leaf decoction: LC-HRMS-MS-Qtof identification, bioactivities and bioavailability evaluation. Food Chem. Adv., 1, 2022, 100003, 10.1016/j.focha.2021.100003.
Nguyen, T.N.H., Vietnam - Scaling-Up Urban Upgrading Project: Environmental Assessment (Vol. 7): Environmental and Social Impact Assessment: Vinh Long Province (English). 2017, World Bank Group, Washington, D.C.
Nguyen, V.H., Le, Q.D., Dang, T.K. U., & Nguyen, T.N. H. (2017). Overview on guava, pineapple, wax apple, sugar apple research and production in Vietnam, International Society for Horticultural Science (ISHS), Leuven, Belgium.
Omitoyin, B.O., Ajani, E.K., Orisasona, O., Bassey, H.E., Kareem, K.O., Osho, F.E., Effect of guava Psidium guajava (L.) aqueous extract diet on growth performance, intestinal morphology, immune response and survival of Oreochromis niloticus challenged with Aeromonas hydrophila. Aquac. Res. 2019 (2019), 1–11.
Park, C., Lee, J.S., Mini Review: Natural ingredients for diabetes which are approved by Korean FDA. Biomed. Res. (India) 24 (2013), 164–169.
Park, C., Lee, J.S., Review on corosolic acid:based on various pharmaceutical effects. Asian J. Pharm. Res. Dev. 7 (2019), 104–107, 10.22270/ajprd.v7i3.516.
Rafamantanana, M.H., Rozet, E., Raoelison, G.E., Cheuk, K., Ratsimamanga, S.U., Hubert, P., Quetin-Leclercq, J., An improved HPLC-UV method for the simultaneous quantification of triterpenic glycosides and aglycones in leaves of Centella asiatica (L.) Urb (APIACEAE). J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 877:23 (2009), 2396–2402, 10.1016/j.jchromb.2009.03.018.
Rahman, M., Zaman, S., Mamun, F., Gias, Z., Alam, M., Ulla, A., Alam, M., Phenolic content analysis in Psidium guajava leaves powder by HPLC‐DAD system and in vivo renoprotective and antioxidant activities in fludrocortisone acetate‐induced rats. J. Food Biochem., 42, 2018, e12687, 10.1111/jfbc.12687.
Sak, K., Chapter 6 - anticancer action of sulfated flavonoids as phase II metabolites. Grumezescu, A.M., Holban, A.M., (eds.) Food Bioconversion, 2017, Academic Press, 207–236.
Santos, W., Sauthier, M., Santos, A., Santana, D., Azevedo, R., Caldas, J., Simultaneous determination of 13 phenolic bioactive compounds in guava (Psidium guajava L.) by HPLC-PAD with evaluation using PCA and Neural Network Analysis (NNA). Microchem. J. 133 (2017), 583–592, 10.1016/j.microc.2017.04.029.
Sasmaz, H.K., Uzlasir, T., Kelebek, H., Effect of infusion time on the phenolic profile and some physicochemical properties of Lavandula x intermedia cv. 'SUPER'. J. Raw Mater. Process. Foods 1:2 (2020), 55–71.
Stevigny, C., Wautier, M.C., Jiwan, J.L., Chiap, P., Hubert, P., Quetin-Leclercq, J., Development and validation of a high performance liquid chromatographic method for quantitative determination of aporphine alkaloids from different samples of Cassytha filiformis. Planta Med. 70 (2004), 764–770, 10.1055/s-2004-827209.
Truong, Q.N., Nguyen, P.D., Bui, T.B.H., Le, T.B., Do, T.T.H., Bui, T.B.H., Kestemont, P., Immunomodulatory potential of extracts, fractions and pure compounds from Phyllanthus amarus and Psidium guajava on striped catfish (Pangasianodon hypophthalmus) head kidney leukocytes. Fish. Shellfish Immunol. 104 (2020), 289–303, 10.1016/j.fsi.2020.05.051.
Valentová, K., Káňová, K., Di Meo, F., Pelantová, H., Chambers, C.S., Rydlová, L., Křen, V., Chemoenzymatic preparation and biophysical properties of sulfated quercetin metabolites. Int. J. Mol. Sci., 18(11), 2017, 10.3390/ijms18112231.
Wang, H., Du, Y.J., Song, H.C., α-Glucosidase and α-amylase inhibitory activities of guava leaves. Food Chem. 123:1 (2010), 6–13, 10.1016/j.foodchem.2010.03.088.
Wang, H.J., Chiang, B.H., Anti-diabetic effect of a traditional Chinese medicine formula. Food Funct. 3:11 (2012), 1161–1169, 10.1039/c2fo30139c.
Wang, L., Wu, Y., Bei, Q., Shi, K., Wu, Z., Fingerprint profiles of flavonoid compounds from different Psidium guajava leaves and their antioxidant activities. J. Sep Sci. 40:19 (2017), 3817–3829, 10.1002/jssc.201700477.
