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Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.

Identifieur interne : 000743 ( Main/Exploration ); précédent : 000742; suivant : 000744

Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.

Auteurs : Wael M. Abdel-Mageed [Égypte] ; Soad A H. Bayoumi [Égypte] ; Caixia Chen [République populaire de Chine] ; Christopher J. Vavricka [République populaire de Chine] ; Li Li [République populaire de Chine] ; Ajamaluddin Malik [Arabie saoudite] ; Huanqin Dai [République populaire de Chine] ; Fuhang Song [République populaire de Chine] ; Luoqiang Wang [République populaire de Chine] ; Jingyu Zhang [République populaire de Chine] ; George F. Gao [République populaire de Chine] ; Yali Lv [République populaire de Chine] ; Lihong Liu [République populaire de Chine] ; Xueting Liu [République populaire de Chine] ; Hanaa M. Sayed [Égypte] ; Lixin Zhang [République populaire de Chine]

Source :

RBID : pubmed:24613627

Descripteurs français

English descriptors

Abstract

The high mutation rate of RNA viruses has resulted in limitation of vaccine effectiveness and increased emergence of drug-resistant viruses. New effective antivirals are therefore needed to control of the highly mutative RNA viruses. The n-butanol fraction of the stem bark of Mangifera indica exhibited inhibitory activity against influenza neuraminidase (NA) and coxsackie virus 3C protease. Bioassay guided phytochemical study of M. indica stem bark afforded two new compounds including one benzophenone C-glycoside (4) and one xanthone dimer (7), together with eleven known compounds. The structures of these isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Anti-influenza and anti-coxsackie virus activities were evaluated by determining the inhibition of anti-influenza neuraminidase (NA) from pandemic A/RI/5+/1957 H2N2 influenza A virus and inhibition of coxsackie B3 virus 3C protease, respectively. The highest anti-influenza activity was observed for compounds 8 and 9 with IC50 values of 11.9 and 9.2μM, respectively. Compounds 8 and 9 were even more potent against coxsackie B3 virus 3C protease, with IC50 values of 1.1 and 2.0μM, respectively. Compounds 8 and 9 showed weak cytotoxic effect against human hepatocellular carcinoma and human epithelial carcinoma cell lines through MTT assay.

DOI: 10.1016/j.bmc.2014.02.014
PubMed: 24613627


Affiliations:


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<nlm:affiliation>Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt. Electronic address: hanaa.sayed@gmail.com.</nlm:affiliation>
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<name sortKey="Zhang, Lixin" sort="Zhang, Lixin" uniqKey="Zhang L" first="Lixin" last="Zhang">Lixin Zhang</name>
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<name sortKey="Abdel Mageed, Wael M" sort="Abdel Mageed, Wael M" uniqKey="Abdel Mageed W" first="Wael M" last="Abdel-Mageed">Wael M. Abdel-Mageed</name>
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<nlm:affiliation>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China; Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
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<nlm:affiliation>Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.</nlm:affiliation>
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<name sortKey="Chen, Caixia" sort="Chen, Caixia" uniqKey="Chen C" first="Caixia" last="Chen">Caixia Chen</name>
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<nlm:affiliation>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
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<name sortKey="Vavricka, Christopher J" sort="Vavricka, Christopher J" uniqKey="Vavricka C" first="Christopher J" last="Vavricka">Christopher J. Vavricka</name>
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<nlm:affiliation>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.</nlm:affiliation>
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<name sortKey="Li, Li" sort="Li, Li" uniqKey="Li L" first="Li" last="Li">Li Li</name>
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<nlm:affiliation>Department of Medicinal Chemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, PR China.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>Department of Medicinal Chemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050</wicri:regionArea>
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<settlement type="city">Pékin</settlement>
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<name sortKey="Malik, Ajamaluddin" sort="Malik, Ajamaluddin" uniqKey="Malik A" first="Ajamaluddin" last="Malik">Ajamaluddin Malik</name>
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<nlm:affiliation>Protein Research Chair, Department of Biochemistry, College of Sciences, King Saud University, Riyadh 11451, Saudi Arabia.</nlm:affiliation>
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<wicri:regionArea>Protein Research Chair, Department of Biochemistry, College of Sciences, King Saud University, Riyadh 11451</wicri:regionArea>
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<name sortKey="Dai, Huanqin" sort="Dai, Huanqin" uniqKey="Dai H" first="Huanqin" last="Dai">Huanqin Dai</name>
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<name sortKey="Song, Fuhang" sort="Song, Fuhang" uniqKey="Song F" first="Fuhang" last="Song">Fuhang Song</name>
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<name sortKey="Wang, Luoqiang" sort="Wang, Luoqiang" uniqKey="Wang L" first="Luoqiang" last="Wang">Luoqiang Wang</name>
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<name sortKey="Zhang, Jingyu" sort="Zhang, Jingyu" uniqKey="Zhang J" first="Jingyu" last="Zhang">Jingyu Zhang</name>
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<nlm:affiliation>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.</nlm:affiliation>
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<name sortKey="Gao, George F" sort="Gao, George F" uniqKey="Gao G" first="George F" last="Gao">George F. Gao</name>
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<name sortKey="Lv, Yali" sort="Lv, Yali" uniqKey="Lv Y" first="Yali" last="Lv">Yali Lv</name>
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<nlm:affiliation>Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, PR China.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020</wicri:regionArea>
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<settlement type="city">Pékin</settlement>
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<name sortKey="Liu, Lihong" sort="Liu, Lihong" uniqKey="Liu L" first="Lihong" last="Liu">Lihong Liu</name>
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<nlm:affiliation>Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, PR China.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020</wicri:regionArea>
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<settlement type="city">Pékin</settlement>
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<name sortKey="Liu, Xueting" sort="Liu, Xueting" uniqKey="Liu X" first="Xueting" last="Liu">Xueting Liu</name>
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<nlm:affiliation>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China. Electronic address: liuxueting_cn@hotmail.com.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190</wicri:regionArea>
<placeName>
<settlement type="city">Pékin</settlement>
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<name sortKey="Sayed, Hanaa M" sort="Sayed, Hanaa M" uniqKey="Sayed H" first="Hanaa M" last="Sayed">Hanaa M. Sayed</name>
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<nlm:affiliation>Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt. Electronic address: hanaa.sayed@gmail.com.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526</wicri:regionArea>
<wicri:noRegion>Assiut 71526</wicri:noRegion>
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<name sortKey="Zhang, Lixin" sort="Zhang, Lixin" uniqKey="Zhang L" first="Lixin" last="Zhang">Lixin Zhang</name>
<affiliation wicri:level="1">
<nlm:affiliation>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China. Electronic address: zhanglixin@im.ac.cn.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190</wicri:regionArea>
<placeName>
<settlement type="city">Pékin</settlement>
</placeName>
</affiliation>
</author>
</analytic>
<series>
<title level="j">Bioorganic & medicinal chemistry</title>
<idno type="eISSN">1464-3391</idno>
<imprint>
<date when="2014" type="published">2014</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc>
<textClass>
<keywords scheme="KwdEn" xml:lang="en">
<term>Antineoplastic Agents, Phytogenic (chemistry)</term>
<term>Antineoplastic Agents, Phytogenic (isolation & purification)</term>
<term>Antineoplastic Agents, Phytogenic (pharmacology)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (isolation & purification)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Benzophenones (chemistry)</term>
<term>Benzophenones (isolation & purification)</term>
<term>Benzophenones (pharmacology)</term>
<term>Cell Proliferation (drug effects)</term>
<term>Cysteine Endopeptidases (metabolism)</term>
<term>Dose-Response Relationship, Drug</term>
<term>Drug Screening Assays, Antitumor</term>
<term>Enterovirus B, Human (enzymology)</term>
<term>HeLa Cells</term>
<term>Hep G2 Cells</term>
<term>Humans</term>
<term>Hydrolyzable Tannins (chemistry)</term>
<term>Hydrolyzable Tannins (isolation & purification)</term>
<term>Hydrolyzable Tannins (pharmacology)</term>
<term>Influenza A virus (drug effects)</term>
<term>Mangifera (chemistry)</term>
<term>Molecular Structure</term>
<term>Plant Bark (chemistry)</term>
<term>Plant Stems (chemistry)</term>
<term>Protease Inhibitors (chemistry)</term>
<term>Protease Inhibitors (isolation & purification)</term>
<term>Protease Inhibitors (pharmacology)</term>
<term>Structure-Activity Relationship</term>
<term>Tumor Cells, Cultured</term>
<term>Viral Proteins (antagonists & inhibitors)</term>
<term>Viral Proteins (metabolism)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr">
<term>Antinéoplasiques d'origine végétale ()</term>
<term>Antinéoplasiques d'origine végétale (isolement et purification)</term>
<term>Antinéoplasiques d'origine végétale (pharmacologie)</term>
<term>Antiviraux ()</term>
<term>Antiviraux (isolement et purification)</term>
<term>Antiviraux (pharmacologie)</term>
<term>Benzophénones ()</term>
<term>Benzophénones (isolement et purification)</term>
<term>Benzophénones (pharmacologie)</term>
<term>Cellules HeLa</term>
<term>Cellules HepG2</term>
<term>Cellules cancéreuses en culture</term>
<term>Cysteine endopeptidases (métabolisme)</term>
<term>Entérovirus humain B (enzymologie)</term>
<term>Humains</term>
<term>Inhibiteurs de protéases ()</term>
<term>Inhibiteurs de protéases (isolement et purification)</term>
<term>Inhibiteurs de protéases (pharmacologie)</term>
<term>Mangifera ()</term>
<term>Prolifération cellulaire ()</term>
<term>Protéines virales (antagonistes et inhibiteurs)</term>
<term>Protéines virales (métabolisme)</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Structure moléculaire</term>
<term>Tanins hydrolysables ()</term>
<term>Tanins hydrolysables (isolement et purification)</term>
<term>Tanins hydrolysables (pharmacologie)</term>
<term>Tests de criblage d'agents antitumoraux</term>
<term>Tiges de plante ()</term>
<term>Virus de la grippe A ()</term>
<term>Écorce ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en">
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en">
<term>Antineoplastic Agents, Phytogenic</term>
<term>Antiviral Agents</term>
<term>Benzophenones</term>
<term>Hydrolyzable Tannins</term>
<term>Protease Inhibitors</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en">
<term>Antineoplastic Agents, Phytogenic</term>
<term>Antiviral Agents</term>
<term>Benzophenones</term>
<term>Hydrolyzable Tannins</term>
<term>Protease Inhibitors</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en">
<term>Cysteine Endopeptidases</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en">
<term>Antineoplastic Agents, Phytogenic</term>
<term>Antiviral Agents</term>
<term>Benzophenones</term>
<term>Hydrolyzable Tannins</term>
<term>Protease Inhibitors</term>
</keywords>
<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr">
<term>Protéines virales</term>
</keywords>
<keywords scheme="MESH" qualifier="chemistry" xml:lang="en">
<term>Mangifera</term>
<term>Plant Bark</term>
<term>Plant Stems</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en">
<term>Cell Proliferation</term>
<term>Influenza A virus</term>
</keywords>
<keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr">
<term>Entérovirus humain B</term>
</keywords>
<keywords scheme="MESH" qualifier="enzymology" xml:lang="en">
<term>Enterovirus B, Human</term>
</keywords>
<keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr">
<term>Antinéoplasiques d'origine végétale</term>
<term>Antiviraux</term>
<term>Benzophénones</term>
<term>Inhibiteurs de protéases</term>
<term>Tanins hydrolysables</term>
</keywords>
<keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr">
<term>Cysteine endopeptidases</term>
<term>Protéines virales</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr">
<term>Antinéoplasiques d'origine végétale</term>
<term>Antiviraux</term>
<term>Benzophénones</term>
<term>Inhibiteurs de protéases</term>
<term>Tanins hydrolysables</term>
</keywords>
<keywords scheme="MESH" xml:lang="en">
<term>Dose-Response Relationship, Drug</term>
<term>Drug Screening Assays, Antitumor</term>
<term>HeLa Cells</term>
<term>Hep G2 Cells</term>
<term>Humans</term>
<term>Molecular Structure</term>
<term>Structure-Activity Relationship</term>
<term>Tumor Cells, Cultured</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr">
<term>Antinéoplasiques d'origine végétale</term>
<term>Antiviraux</term>
<term>Benzophénones</term>
<term>Cellules HeLa</term>
<term>Cellules HepG2</term>
<term>Cellules cancéreuses en culture</term>
<term>Humains</term>
<term>Inhibiteurs de protéases</term>
<term>Mangifera</term>
<term>Prolifération cellulaire</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Structure moléculaire</term>
<term>Tanins hydrolysables</term>
<term>Tests de criblage d'agents antitumoraux</term>
<term>Tiges de plante</term>
<term>Virus de la grippe A</term>
<term>Écorce</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front>
<div type="abstract" xml:lang="en">The high mutation rate of RNA viruses has resulted in limitation of vaccine effectiveness and increased emergence of drug-resistant viruses. New effective antivirals are therefore needed to control of the highly mutative RNA viruses. The n-butanol fraction of the stem bark of Mangifera indica exhibited inhibitory activity against influenza neuraminidase (NA) and coxsackie virus 3C protease. Bioassay guided phytochemical study of M. indica stem bark afforded two new compounds including one benzophenone C-glycoside (4) and one xanthone dimer (7), together with eleven known compounds. The structures of these isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Anti-influenza and anti-coxsackie virus activities were evaluated by determining the inhibition of anti-influenza neuraminidase (NA) from pandemic A/RI/5+/1957 H2N2 influenza A virus and inhibition of coxsackie B3 virus 3C protease, respectively. The highest anti-influenza activity was observed for compounds 8 and 9 with IC50 values of 11.9 and 9.2μM, respectively. Compounds 8 and 9 were even more potent against coxsackie B3 virus 3C protease, with IC50 values of 1.1 and 2.0μM, respectively. Compounds 8 and 9 showed weak cytotoxic effect against human hepatocellular carcinoma and human epithelial carcinoma cell lines through MTT assay.</div>
</front>
</TEI>
<affiliations>
<list>
<country>
<li>Arabie saoudite</li>
<li>République populaire de Chine</li>
<li>Égypte</li>
</country>
<region>
<li>Anhui</li>
</region>
<settlement>
<li>Hefei</li>
<li>Pékin</li>
</settlement>
</list>
<tree>
<country name="Égypte">
<noRegion>
<name sortKey="Abdel Mageed, Wael M" sort="Abdel Mageed, Wael M" uniqKey="Abdel Mageed W" first="Wael M" last="Abdel-Mageed">Wael M. Abdel-Mageed</name>
</noRegion>
<name sortKey="Bayoumi, Soad A H" sort="Bayoumi, Soad A H" uniqKey="Bayoumi S" first="Soad A H" last="Bayoumi">Soad A H. Bayoumi</name>
<name sortKey="Sayed, Hanaa M" sort="Sayed, Hanaa M" uniqKey="Sayed H" first="Hanaa M" last="Sayed">Hanaa M. Sayed</name>
</country>
<country name="République populaire de Chine">
<noRegion>
<name sortKey="Chen, Caixia" sort="Chen, Caixia" uniqKey="Chen C" first="Caixia" last="Chen">Caixia Chen</name>
</noRegion>
<name sortKey="Dai, Huanqin" sort="Dai, Huanqin" uniqKey="Dai H" first="Huanqin" last="Dai">Huanqin Dai</name>
<name sortKey="Gao, George F" sort="Gao, George F" uniqKey="Gao G" first="George F" last="Gao">George F. Gao</name>
<name sortKey="Li, Li" sort="Li, Li" uniqKey="Li L" first="Li" last="Li">Li Li</name>
<name sortKey="Liu, Lihong" sort="Liu, Lihong" uniqKey="Liu L" first="Lihong" last="Liu">Lihong Liu</name>
<name sortKey="Liu, Xueting" sort="Liu, Xueting" uniqKey="Liu X" first="Xueting" last="Liu">Xueting Liu</name>
<name sortKey="Lv, Yali" sort="Lv, Yali" uniqKey="Lv Y" first="Yali" last="Lv">Yali Lv</name>
<name sortKey="Song, Fuhang" sort="Song, Fuhang" uniqKey="Song F" first="Fuhang" last="Song">Fuhang Song</name>
<name sortKey="Vavricka, Christopher J" sort="Vavricka, Christopher J" uniqKey="Vavricka C" first="Christopher J" last="Vavricka">Christopher J. Vavricka</name>
<name sortKey="Wang, Luoqiang" sort="Wang, Luoqiang" uniqKey="Wang L" first="Luoqiang" last="Wang">Luoqiang Wang</name>
<name sortKey="Zhang, Jingyu" sort="Zhang, Jingyu" uniqKey="Zhang J" first="Jingyu" last="Zhang">Jingyu Zhang</name>
<name sortKey="Zhang, Lixin" sort="Zhang, Lixin" uniqKey="Zhang L" first="Lixin" last="Zhang">Lixin Zhang</name>
</country>
<country name="Arabie saoudite">
<noRegion>
<name sortKey="Malik, Ajamaluddin" sort="Malik, Ajamaluddin" uniqKey="Malik A" first="Ajamaluddin" last="Malik">Ajamaluddin Malik</name>
</noRegion>
</country>
</tree>
</affiliations>
</record>

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