{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,8]],"date-time":"2026-05-08T15:36:35Z","timestamp":1778254595286,"version":"3.51.4"},"reference-count":37,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2026,3,9]],"date-time":"2026-03-09T00:00:00Z","timestamp":1773014400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Acad\u00e9mie de Recherche et d\u2019Enseignement Sup\u00e9rieur, Commission de la Coop\u00e9ration au D\u00e9veloppementARES CCD","award":["ARES-PRD"],"award-info":[{"award-number":["ARES-PRD"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Reproductive management in goats remains challenging due to seasonal breeding and the use of hormones that raise concerns about immunogenicity, cost, sustainability, and animal welfare. In this study, we evaluated date palm pollen (Phoenix dactylifera L.) (DPP) as a natural source of estrogenic compounds capable of modulating reproductive function. DPP was extracted using methanol, ethanol, acetone, and hexane, and the extracts were analyzed by ultra-performance liquid chromatography. Quercetin and coumestrol were detected in the methanolic and ethanolic extracts at comparable levels (quercetin 0.043\u20130.044 mg\/g; coumestrol 0.987\u20131.015 mg\/g of extract) (p &gt; 0.05). The acetone extract contained significantly lower concentrations (quercetin 0.017 mg\/g; coumestrol 0.033 mg\/g of extract), while the hexane extract showed no detectable amounts. Molecular docking using the crystallographic structure of estrogen receptor alpha (PDB:6PIT) showed that both compounds interact with key residues of the receptor\u2019s ligand-binding domain. Coumestrol exhibited the highest affinity (\u22129.3 kcal\/mol), surpassing 17-\u03b2 estradiol (\u22128.9 kcal\/mol), forming several hydrogen bonds and hydrophobic contacts. Quercetin showed a lower affinity (\u22127.2 kcal\/mol) but maintained stabilizing interactions compatible with partial agonist activity. Overall, methanol and ethanol were the most effective solvents for extracting phytoestrogens from DPP, and the findings support their potential as natural alternatives to hormones for estrus induction in goats.<\/jats:p>","DOI":"10.3390\/molecules31050898","type":"journal-article","created":{"date-parts":[[2026,3,9]],"date-time":"2026-03-09T15:49:42Z","timestamp":1773071382000},"page":"898","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Date Palm Pollen (Phoenix dactylifera L.) Phytoestrogens as Natural Modulators of Estrus in Goats: A Molecular and Phytochemical Insight"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8847-4881","authenticated-orcid":false,"given":"Amr","family":"Kchikich","sequence":"first","affiliation":[{"name":"Department of Biology, Abdelmalek Essa\u00e2di University, Tangier 90000, Morocco"},{"name":"Regional Center of Agricultural Research of Tangier, National Institute of Agricultural Research, Rabat 10090, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2878-2377","authenticated-orcid":false,"given":"Anass Ben","family":"Moula","sequence":"additional","affiliation":[{"name":"Laboratory of Natural and Economic Resources for Sustainable Development, Department of Life Sciences, Polydisciplinary Faculty of Larache (FPL), Abdelmalek Essa\u00e2di University, 745 BP, Larache 92004, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ayoub","family":"Kounnoun","sequence":"additional","affiliation":[{"name":"Regional Laboratory for Analysis and Research, National Office for Food Safety, Tangier 90000, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Said","family":"Barrijal","sequence":"additional","affiliation":[{"name":"Department of Biology, Abdelmalek Essa\u00e2di University, Tangier 90000, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8646-2043","authenticated-orcid":false,"given":"Mohammed","family":"El Maadoudi","sequence":"additional","affiliation":[{"name":"Regional Laboratory for Analysis and Research, National Office for Food Safety, Tangier 90000, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1788-4212","authenticated-orcid":false,"given":"Nathalie","family":"Kirschvink","sequence":"additional","affiliation":[{"name":"Department of Medicine, Namur Research Institute for Life Sciences (NARILIS), University of Namur, 5000 Namur, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7023-7439","authenticated-orcid":false,"given":"Youssef","family":"Chebli","sequence":"additional","affiliation":[{"name":"Regional Center of Agricultural Research of Tangier, National Institute of Agricultural Research, Rabat 10090, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0320-0123","authenticated-orcid":false,"given":"Samira","family":"El Otmani","sequence":"additional","affiliation":[{"name":"Regional Center of Agricultural Research of Tangier, National Institute of Agricultural Research, Rabat 10090, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3443-5988","authenticated-orcid":false,"given":"Bouchra","family":"El Amiri","sequence":"additional","affiliation":[{"name":"Animal Production Unit, Regional Center Agricultural Research of Settat, National Institute for Agricultural Research (INRA), Avenue Ennasr, P.O. Box 415 Rabat Principal, Rabat 10090, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoual","family":"Alahlah","sequence":"additional","affiliation":[{"name":"Regional Laboratory for Analysis and Research, National Office for Food Safety, Tangier 90000, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6802-9350","authenticated-orcid":false,"given":"Mouad","family":"Chentouf","sequence":"additional","affiliation":[{"name":"Regional Center of Agricultural Research of Tangier, National Institute of Agricultural Research, Rabat 10090, Morocco"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2026,3,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"39","DOI":"10.5513\/JCEA01\/22.1.2939","article-title":"Induction and Synchronization of Oestrus in Sheep and Goats","volume":"22","author":"Skliarov","year":"2021","journal-title":"J. Cent. Eur. Agric."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"47","DOI":"10.2527\/jas2000.00218812007700ES0040x","article-title":"Current Concepts in Synchronization of Estrus: Sheep and Goats","volume":"77","author":"Wildeus","year":"2000","journal-title":"J. Anim. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Saleh, M., Kokoszy\u0144ski, D., Mousa, M.A.-A., and Abuoghaba, A.A.-K. (2021). Effect of Date Palm Pollen Supplementation on the Egg Production, Ovarian Follicles Development, Hematological Variables and Hormonal Profile of Laying Hens. Animals, 11.","DOI":"10.3390\/ani11010069"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"320","DOI":"10.1177\/2156587215609851","article-title":"The Role of Date Palm (Phoenix dactylifera L.) Pollen in Fertility: A Comprehensive Review of Current Evidence","volume":"21","author":"Tahvilzadeh","year":"2016","journal-title":"J. Evid.-Based Complement. Altern. Med."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Tang, Z.-R., Zhang, R., Lian, Z.-X., Deng, S.-L., and Yu, K. (2019). Estrogen-Receptor Expression and Function in Female Reproductive Disease. Cells, 8.","DOI":"10.3390\/cells8101123"},{"key":"ref_6","first-page":"75","article-title":"The Effect of Palm Pollen and Black Seed Pollen on Male Sex Hormones and Sperm Quality: A Single-Blind, Placebo-Controlled Clinical Trial Study","volume":"17","author":"Hajb","year":"2022","journal-title":"Int. J. Fertil. Steril."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"109","DOI":"10.36326\/kjvs\/2015\/v6i23992","article-title":"Effect of Different Doses of Ethanolic Extract of Date Palm Pollen Grains on Serum Gonadotropin and Total Glutathione in Mature Female Rats","volume":"6","author":"Jiheel","year":"2015","journal-title":"Kufa J. Vet. Med. Sci."},{"key":"ref_8","first-page":"83","article-title":"The Health-Related Biological Effects of Date Palm Pollen (DPP) along with Physical Activity: A Narrative Mini-Review","volume":"10","author":"Abdollahi","year":"2022","journal-title":"Jorjani Biomed. J."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Salhi, S., Rahim, A., Chentouf, M., Harrak, H., Bister, J.L., Hamidallah, N., and El Amiri, B. (2024). Reproductive Enhancement through Phytochemical Characteristics and Biological Activities of Date Palm Pollen: A Comprehensive Review on Potential Mechanism Pathways. Metabolites, 14.","DOI":"10.3390\/metabo14030166"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1177\/10820132231168914","article-title":"Assessment of Physicochemical Parameters, Bioactive Compounds, Biological Activities, and Nutritional Value of the Most Two Commercialized Pollen Types of Date Palm (Phoenix dactylifera L.) in Morocco","volume":"30","author":"Salhi","year":"2024","journal-title":"Food Sci. Technol. Int."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1080\/12538078.2012.758496","article-title":"D\u00e9tection et Identification de Saponines St\u00e9ro\u00efdes de Type Spirostane Chez Le Palmier Dattier Ph\u0153nix Dactylifera L. (Arecaceae)","volume":"159","author":"Rahmania","year":"2012","journal-title":"Acta Bot. Gallica"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3075","DOI":"10.1016\/j.arabjc.2015.07.014","article-title":"Assessment of Polyphenol Composition, Antioxidant and Antimicrobial Properties of Various Extracts of Date Palm Pollen (DPP) from Two Tunisian Cultivars","volume":"12","author":"Daoud","year":"2019","journal-title":"Arab. J. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Chaves, J.O., De Souza, M.C., Da Silva, L.C., Lachos-Perez, D., Torres-Mayanga, P.C., Machado, A.P.D.F., Forster-Carneiro, T., V\u00e1zquez-Espinosa, M., Gonz\u00e1lez-de-Peredo, A.V., and Barbero, G.F. (2020). Extraction of Flavonoids from Natural Sources Using Modern Techniques. Front. Chem., 8.","DOI":"10.3389\/fchem.2020.507887"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Lee, J.-E., Jayakody, J., Kim, J.-I., Jeong, J.-W., Choi, K.-M., Kim, T.-S., Seo, C., Azimi, I., Hyun, J., and Ryu, B. (2024). The Influence of Solvent Choice on the Extraction of Bioactive Compounds from Asteraceae: A Comparative Review. Foods, 13.","DOI":"10.3390\/foods13193151"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"27192","DOI":"10.1021\/acsomega.4c01321","article-title":"Solvent Effects on the Phenolic Compounds and Antioxidant Activity Associated with Camellia Polyodonta Flower Extracts","volume":"9","author":"Xiang","year":"2024","journal-title":"ACS Omega"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"16374","DOI":"10.1021\/jacs.9b07578","article-title":"Versatile Peptide Macrocyclization with Diels\u2013Alder Cycloadditions","volume":"141","author":"Montgomery","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Pool, K.R., Chazal, F., Smith, J.T., and Blache, D. (2022). Estrogenic Pastures: A Source of Endocrine Disruption in Sheep Reproduction. Front. Endocrinol., 13.","DOI":"10.3389\/fendo.2022.880861"},{"key":"ref_18","first-page":"S129","article-title":"Effects of Phytoestrogens on Mammalian Reproductive Physiology","volume":"15","author":"Hernandez","year":"2012","journal-title":"Trop. Subtrop. Agroecosyst."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/j.steroids.2013.11.019","article-title":"3D Models of Human ER\u03b1 and ER\u03b2 Complexed with Coumestrol","volume":"80","author":"Chandsawangbhuwana","year":"2014","journal-title":"Steroids"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"81295","DOI":"10.1039\/C5RA14745J","article-title":"Insight into the Structural Stability of Coumestrol with Human Estrogen Receptor \u03b1 and \u03b2 Subtypes: A Combined Approach Involving Docking and Molecular Dynamics Simulation Studies","volume":"5","author":"Zafar","year":"2015","journal-title":"RSC Adv."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Daviter, T., Johnson, C.M., McLaughlin, S.H., and Williams, M.A. (2021). Protein-Ligand Interactions: Methods and Applications, Springer. Methods in Molecular Biology.","DOI":"10.1007\/978-1-0716-1197-5"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"5061","DOI":"10.1021\/jm100112j","article-title":"A Medicinal Chemist\u2019s Guide to Molecular Interactions","volume":"53","author":"Bissantz","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"15458","DOI":"10.1074\/jbc.273.25.15458","article-title":"\u03c0-Stacking Interactions","volume":"273","author":"McGaughey","year":"1998","journal-title":"J. Biol. Chem."},{"key":"ref_24","unstructured":"de Brevern, A.G. (2022). Recent Developments on Protein-Ligand Interactions: From Structure, Function to Applications, MDPI-Multidisciplinary Digital Publishing Institute."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Slighoua, M., Amrati, F.E.-Z., Chebaibi, M., Mahdi, I., Al Kamaly, O., El Ouahdani, K., Drioiche, A., Saleh, A., and Bousta, D. (2023). Quercetin and Ferulic Acid Elicit Estrogenic Activities in Vivo and in Silico. Molecules, 28.","DOI":"10.3390\/molecules28135112"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Ma, C., Xiang, Q., Song, G., and Wang, X. (2022). Quercetin and Polycystic Ovary Syndrome. Front. Pharmacol., 13.","DOI":"10.3389\/fphar.2022.1006678"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1016\/j.compbiolchem.2014.04.002","article-title":"Gene Cloning, Homology Comparison and Analysis of the Main Functional Structure Domains of Beta Estrogen Receptor in Jining Gray Goat","volume":"51","author":"Liu","year":"2014","journal-title":"Comput. Biol. Chem."},{"key":"ref_28","first-page":"1056","article-title":"Vers une optimisation de la modulation du r\u00e9cepteur des \u0153strog\u00e8nes dans le traitement hormonal de la m\u00e9nopause","volume":"34","author":"Fontaine","year":"2018","journal-title":"M\u00e9d.\/Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6040149","DOI":"10.1155\/2018\/6040149","article-title":"Identification of Estrogen Receptor \u03b1 Antagonists from Natural Products via in Vitro and in Silico Approaches","volume":"2018","author":"Pang","year":"2018","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"e20210112","DOI":"10.1590\/1984-3143-ar2021-0112","article-title":"Influence of eCG and Reproductive Management in the Resynchronization of Ovulation in Dairy Goats","volume":"19","author":"Cosentino","year":"2022","journal-title":"Anim. Reprod."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Kara, E., Dupuy, L., Bouillon, C., Casteret, S., and Maurel, M.-C. (2019). Modulation of Gonadotropins Activity by Antibodies. Front. Endocrinol., 10.","DOI":"10.3389\/fendo.2019.00015"},{"key":"ref_32","unstructured":"Schr\u00f6dinger, LLC (The PyMOL Molecular Graphics System, 2015). The PyMOL Molecular Graphics System, Version 2.0."},{"key":"ref_33","unstructured":"BIOVIA (Dassault Syst\u00e8mes Discovery Studio Visualizer, 2025). Dassault Syst\u00e8mes Discovery Studio Visualizer, Version 2025."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading","volume":"31","author":"Trott","year":"2010","journal-title":"J. Comput. Chem."},{"key":"ref_35","first-page":"20763","article-title":"Interaction of Protein-Ligand: Molecular Docking, A Novel Computational Biology Tool","volume":"25","author":"Avinash","year":"2021","journal-title":"Ann. Rom. Soc. Cell Biol."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Haideri, M.H., Phanjaroen, T., Khiaolaongam, W., Boonchalaem, T., Laoung-on, J., Chaipoot, S., Hongsibsong, S., Boonyapranai, K., and Ounjaijean, S. (2024). Effect of Different Extraction Techniques on Phenolic Profile and Phytochemical Potential of Gymnema Inodorum Leaf Extract. Molecules, 29.","DOI":"10.3390\/molecules29225475"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"142024","DOI":"10.25259\/JKSUS_14_2024","article-title":"The Improved Preconditioned Iterative Integration-Exponential Method for Linear Ill-Conditioned Problems","volume":"37","author":"Sun","year":"2025","journal-title":"J. King Saud Univ.\u2013Sci."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/5\/898\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,3,9]],"date-time":"2026-03-09T15:52:23Z","timestamp":1773071543000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/5\/898"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,3,9]]},"references-count":37,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2026,3]]}},"alternative-id":["molecules31050898"],"URL":"https:\/\/doi.org\/10.3390\/molecules31050898","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,3,9]]}}}