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Research ArticleOriginal Article
Open Access

Ajwa date extract (Phoenix dactylifera L.)

Phytochemical analysis, antiviral activity against herpes simplex virus-I and coxsackie B4 virus, and in silico study

Ahmad K. Aljohani, Nader A. Maghrabi, Osama M. Alrehili, Abdulaziz S. Alharbi, Rawad S. Alsihli, Abdulrahman M. Alharthe, Rayan S. Albladi, Khalid A. Alosaimi, Bader M. Albadrani, Samar F. Miski, Hossein M. Elbadawy, Bandar D. Alrehaili, Fahd A. Abdelkarem and Modather F. Hussein
Saudi Medical Journal January 2025, 46 (1) 26-35; DOI: https://doi.org/10.15537/smj.2025.46.1.20240780
Ahmad K. Aljohani
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
MSc, PhD
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  • For correspondence: [email protected]
Nader A. Maghrabi
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Osama M. Alrehili
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Abdulaziz S. Alharbi
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Rawad S. Alsihli
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Abdulrahman M. Alharthe
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Rayan S. Albladi
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Khalid A. Alosaimi
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Bader M. Albadrani
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
BSc
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Samar F. Miski
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
MSc, PhD
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Hossein M. Elbadawy
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
MSc, PhD
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Bandar D. Alrehaili
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
MSc, PhD
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Fahd A. Abdelkarem
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
MSc, PhD
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Modather F. Hussein
From the Department of Pharmacognosy and Pharmaceutical Chemistry (Aljohani), College of Pharmacy; from the College of Pharmacy (Maghrabi, Alrehili, Alharbi, Alsihli, Alharthe, Albladi, Alosaimi, Albadrani); from the Department of Pharmacology and Toxicology (Miski, Elbadawy, Alrehaili), College of Pharmacy, Taibah University, Al-Medinah Al-Munawarah, from the Departmet of Chemistry (Hussein), Collage of Science, Jouf University, Aljouf, Kingdom of Saudi Arabia; from the Graduate School of Bioresource and Bioenvironmental Science (Abdelkarem), Kyushu University, Kyushu, Japan; from the Department of Pharmacognosy (Abdelkarem), Faculty of Pharmacy; and from the Department of Chemistry (Hussein), Faculty of Science, Al-Azhar University, Assiut, Egypt.
MSc, PhD
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    Figure 1

    - Chemical structures of the identified secondary metabolites of the crude extract of Ajwa and their quantities (gallic acid 3.56 Rt.min. 60.05% area under the peak, chlorogenic acid 4.17 Rt.min. 9.55% area under the peak, caffeic acid 5.83 Rt.min. 12.49% area under the peak, coumaric acid 8.57 Rt.min. 4.86% area under the peak, ferulic acid 9.61 Rt.min. 10.36% area under the peak, and quercetin 17.47 Rt.min. 2.67% area under the peak) using high performance liquid chromatography.

  • Figure 2
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    Figure 2

    - The cytotoxic activity of crude extract of Ajwa dates at different concentrations; A) 1000 μg/mL, B) 500 μg/mL, C) 250g/mL, D) 125 μg/mL, E) 62.5 μg/mL, F) 31.25 μμg/mL on VERO cell lines.

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    Figure 3

    - Virucidal activity of Ajwa date crude extract at different concentrations using the MTT assay.

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    Figure 4

    - The chlorogenic acid moiety substrate binding channel formed by several important bonds against 3 different glycoproteins D. A) The 2D structure of the formed interaction, B) the 3D structure, and C) the surface structure.

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    Figure 5

    - The energy gaps of the complexes followed an ascending order: A) quercetin, B) caffeic acid, C) chlorogenic acid, D) coumaric acid, E) ferulic acid, and F) gallic acid.

Tables

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    Table 1

    - Liquid chromatography-electrospray ionization-quadrupole time-of-flight-mass spectrometry data of Ajwa extract in negative ionization modes.

    CompoundsMolecular formulaRt. (min)m/zIon speciesError ppm
    Flavonoid and their derivatives
    Chrysoeriol hexosyl sulfateC22 H22 O14 S13.896541.065[M-H]--0.72
    Chrysoeriol rhamnosyl hexosideC28 H32 O1514.25607.1658[M-H]--1.1
    Dihydrokaempferol hexosideC21 H22 O114.243449.1083[M-H]--0.62
    Isorhamnetin hexosideC22 H22 O1213.781477.1028[M-H]--1.17
    Luteolin rhamnosyl hexosideC27H30O1512.656593.15032[M-H]-0.50
    OrientinC21 H20 O1112.14447.0924[M-H]--0.91
    TectoridinC22 H22 O1114.205461.1084[M-H]--0.52
    Phenolic acid and their derivatives
    Caffeoyl shikimic acidC16 H16 O83.488335.0771[M-H]--0.11
    Caffeoyl shikimic acid hexosideC22 H26 O132.564497.1304[M-H]-0.35
    Ferulic acidC10 H10 O47.61193.0501[M-H]--0.52
    Fatty acid and their derivatives
    Hydroxy octadecenoic acidC18 H34 O334.024297.2425[M-H]--1.12
    Hydroxy octadecatrienoic acidC18 H30 O334.058293.2108[M-H]--1.36
    Dihydroxy octadecanoic acidC18 H36 O441.476375.2738[M-H]--1.5
    Dihydroxy octadecenoic acidC18 H34 O426.968313.2369[M-H]--1.6
    Trihydroxy octadecenoic acidC18 H34 O520.303329.2329[M-H]--0.51
    Sugar derivatives
    GlucoseC6 H12 O60.697179.0558[M-H]--0.32
    Gluconic acidC6 H12 O70.821195.0507[M-H]--0.17
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Ajwa date extract (Phoenix dactylifera L.)
Ahmad K. Aljohani, Nader A. Maghrabi, Osama M. Alrehili, Abdulaziz S. Alharbi, Rawad S. Alsihli, Abdulrahman M. Alharthe, Rayan S. Albladi, Khalid A. Alosaimi, Bader M. Albadrani, Samar F. Miski, Hossein M. Elbadawy, Bandar D. Alrehaili, Fahd A. Abdelkarem, Modather F. Hussein
Saudi Medical Journal Jan 2025, 46 (1) 26-35; DOI: 10.15537/smj.2025.46.1.20240780

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Ajwa date extract (Phoenix dactylifera L.)
Ahmad K. Aljohani, Nader A. Maghrabi, Osama M. Alrehili, Abdulaziz S. Alharbi, Rawad S. Alsihli, Abdulrahman M. Alharthe, Rayan S. Albladi, Khalid A. Alosaimi, Bader M. Albadrani, Samar F. Miski, Hossein M. Elbadawy, Bandar D. Alrehaili, Fahd A. Abdelkarem, Modather F. Hussein
Saudi Medical Journal Jan 2025, 46 (1) 26-35; DOI: 10.15537/smj.2025.46.1.20240780
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Keywords

  • Ajwa dates
  • antiviral activity
  • high-performance liquid chromatography
  • gas chromatography-mass spectrometry
  • molecular docking

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