Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates
The first asymmetric total synthesis of the bisbenzylisoquinoline alkaloids berbamine (<b>1a</b>) and oxyacanthine (<b>1b</b>) has been accomplished by employing Noyori asymmetric hydrogenation for chirality installation and leveraging copper-mediated Ullmann coupling for mac...
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2025
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| _version_ | 1849927621881626624 |
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| author | Li Xiang (586649) |
| author2 | Jishan Qin (20535872) Temur Kushatov (22687969) Firdavsi Tursunov (22687972) Ozod Farmonov (22687975) Xiangrui Jiang (1601968) Feipu Yang (2937366) Jingshan Shen (1601962) Khurshed Bozorov (5517845) Haji Akber Aisa (7312430) |
| author2_role | author author author author author author author author author |
| author_facet | Li Xiang (586649) Jishan Qin (20535872) Temur Kushatov (22687969) Firdavsi Tursunov (22687972) Ozod Farmonov (22687975) Xiangrui Jiang (1601968) Feipu Yang (2937366) Jingshan Shen (1601962) Khurshed Bozorov (5517845) Haji Akber Aisa (7312430) |
| author_role | author |
| dc.creator.none.fl_str_mv | Li Xiang (586649) Jishan Qin (20535872) Temur Kushatov (22687969) Firdavsi Tursunov (22687972) Ozod Farmonov (22687975) Xiangrui Jiang (1601968) Feipu Yang (2937366) Jingshan Shen (1601962) Khurshed Bozorov (5517845) Haji Akber Aisa (7312430) |
| dc.date.none.fl_str_mv | 2025-11-26T08:03:35Z |
| dc.identifier.none.fl_str_mv | 10.1021/acs.jnatprod.5c01211.s002 |
| dc.relation.none.fl_str_mv | https://figshare.com/articles/dataset/Asymmetric_Total_Synthesis_and_Anti-Inflammatory_Activity_of_Berbamine_Oxyacanthine_and_Related_Intermediates/30719371 |
| dc.rights.none.fl_str_mv | CC BY-NC 4.0 info:eu-repo/semantics/openAccess |
| dc.subject.none.fl_str_mv | Biochemistry Microbiology Physiology Biotechnology Ecology Immunology Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified synthesis unequivocally confirmed stimulated raw 264 promising lead candidate mediated ullmann coupling asymmetric total synthesis inflammatory activities revealed 15a </ b inflammatory activity coupled displayed potent anti inflammatory cytokines il oxyacanthine (< b inflammatory activity inflammatory agents sample misidentification related intermediates previous work novel anti minimal cytotoxicity macrocycle formation leveraging copper chirality installation 7 macrophages |
| dc.title.none.fl_str_mv | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates |
| dc.type.none.fl_str_mv | Dataset info:eu-repo/semantics/publishedVersion dataset |
| description | The first asymmetric total synthesis of the bisbenzylisoquinoline alkaloids berbamine (<b>1a</b>) and oxyacanthine (<b>1b</b>) has been accomplished by employing Noyori asymmetric hydrogenation for chirality installation and leveraging copper-mediated Ullmann coupling for macrocycle formation. Our synthesis unequivocally confirmed the sample misidentification of <b>1a</b>, as indicated in our previous work. Evaluation of anti-inflammatory activities revealed that both synthetic and natural berbamine or oxyacanthine comparably suppressed gene expression of pro-inflammatory cytokines IL-6 and IL-1β in LPS-stimulated RAW 264.7 macrophages. Notably, intermediate <b>15a</b> displayed potent anti-inflammatory activity coupled with minimal cytotoxicity, emerging as a promising lead candidate for the development of novel anti-inflammatory agents. |
| eu_rights_str_mv | openAccess |
| id | Manara_7b1a347c607efde4f3b191b8a8d903aa |
| identifier_str_mv | 10.1021/acs.jnatprod.5c01211.s002 |
| network_acronym_str | Manara |
| network_name_str | ManaraRepo |
| oai_identifier_str | oai:figshare.com:article/30719371 |
| publishDate | 2025 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| rights_invalid_str_mv | CC BY-NC 4.0 |
| spelling | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related IntermediatesLi Xiang (586649)Jishan Qin (20535872)Temur Kushatov (22687969)Firdavsi Tursunov (22687972)Ozod Farmonov (22687975)Xiangrui Jiang (1601968)Feipu Yang (2937366)Jingshan Shen (1601962)Khurshed Bozorov (5517845)Haji Akber Aisa (7312430)BiochemistryMicrobiologyPhysiologyBiotechnologyEcologyImmunologyBiological Sciences not elsewhere classifiedChemical Sciences not elsewhere classifiedsynthesis unequivocally confirmedstimulated raw 264promising lead candidatemediated ullmann couplingasymmetric total synthesisinflammatory activities revealed15a </ binflammatory activity coupleddisplayed potent antiinflammatory cytokines iloxyacanthine (< binflammatory activityinflammatory agentssample misidentificationrelated intermediatesprevious worknovel antiminimal cytotoxicitymacrocycle formationleveraging copperchirality installation7 macrophagesThe first asymmetric total synthesis of the bisbenzylisoquinoline alkaloids berbamine (<b>1a</b>) and oxyacanthine (<b>1b</b>) has been accomplished by employing Noyori asymmetric hydrogenation for chirality installation and leveraging copper-mediated Ullmann coupling for macrocycle formation. Our synthesis unequivocally confirmed the sample misidentification of <b>1a</b>, as indicated in our previous work. Evaluation of anti-inflammatory activities revealed that both synthetic and natural berbamine or oxyacanthine comparably suppressed gene expression of pro-inflammatory cytokines IL-6 and IL-1β in LPS-stimulated RAW 264.7 macrophages. Notably, intermediate <b>15a</b> displayed potent anti-inflammatory activity coupled with minimal cytotoxicity, emerging as a promising lead candidate for the development of novel anti-inflammatory agents.2025-11-26T08:03:35ZDatasetinfo:eu-repo/semantics/publishedVersiondataset10.1021/acs.jnatprod.5c01211.s002https://figshare.com/articles/dataset/Asymmetric_Total_Synthesis_and_Anti-Inflammatory_Activity_of_Berbamine_Oxyacanthine_and_Related_Intermediates/30719371CC BY-NC 4.0info:eu-repo/semantics/openAccessoai:figshare.com:article/307193712025-11-26T08:03:35Z |
| spellingShingle | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates Li Xiang (586649) Biochemistry Microbiology Physiology Biotechnology Ecology Immunology Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified synthesis unequivocally confirmed stimulated raw 264 promising lead candidate mediated ullmann coupling asymmetric total synthesis inflammatory activities revealed 15a </ b inflammatory activity coupled displayed potent anti inflammatory cytokines il oxyacanthine (< b inflammatory activity inflammatory agents sample misidentification related intermediates previous work novel anti minimal cytotoxicity macrocycle formation leveraging copper chirality installation 7 macrophages |
| status_str | publishedVersion |
| title | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates |
| title_full | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates |
| title_fullStr | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates |
| title_full_unstemmed | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates |
| title_short | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates |
| title_sort | Asymmetric Total Synthesis and Anti-Inflammatory Activity of Berbamine, Oxyacanthine, and Related Intermediates |
| topic | Biochemistry Microbiology Physiology Biotechnology Ecology Immunology Biological Sciences not elsewhere classified Chemical Sciences not elsewhere classified synthesis unequivocally confirmed stimulated raw 264 promising lead candidate mediated ullmann coupling asymmetric total synthesis inflammatory activities revealed 15a </ b inflammatory activity coupled displayed potent anti inflammatory cytokines il oxyacanthine (< b inflammatory activity inflammatory agents sample misidentification related intermediates previous work novel anti minimal cytotoxicity macrocycle formation leveraging copper chirality installation 7 macrophages |