Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i>
Three pairs of racemic honokiol-derived dimeric neolignans, named honolignols A–C (<b>1</b>–<b>3</b>), featuring unique carbon skeletons, were isolated from the barks of <i>Magnolia officinalis</i> var. <i>biloba</i>. Honolignol A (<b>1</b>...
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2025
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| _version_ | 1851480969441181696 |
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| author | Wei-Ming Huang (7134713) |
| author2 | Ping Ying (20876752) Han-fei Gong (22651991) Yue-You Yang (20403221) Chuan-Lu Fu (22428605) Ze Liu (130881) Zi-wei Jia (22651994) Zhen-Zhen Zhang (5042102) Ling-Yi Kong (1344264) Wen-Jun Xu (1596799) |
| author2_role | author author author author author author author author author |
| author_facet | Wei-Ming Huang (7134713) Ping Ying (20876752) Han-fei Gong (22651991) Yue-You Yang (20403221) Chuan-Lu Fu (22428605) Ze Liu (130881) Zi-wei Jia (22651994) Zhen-Zhen Zhang (5042102) Ling-Yi Kong (1344264) Wen-Jun Xu (1596799) |
| author_role | author |
| dc.creator.none.fl_str_mv | Wei-Ming Huang (7134713) Ping Ying (20876752) Han-fei Gong (22651991) Yue-You Yang (20403221) Chuan-Lu Fu (22428605) Ze Liu (130881) Zi-wei Jia (22651994) Zhen-Zhen Zhang (5042102) Ling-Yi Kong (1344264) Wen-Jun Xu (1596799) |
| dc.date.none.fl_str_mv | 2025-11-20T06:47:38Z |
| dc.identifier.none.fl_str_mv | 10.1021/acs.joc.5c02184.s003 |
| dc.relation.none.fl_str_mv | https://figshare.com/articles/dataset/Honolignols_A_C_Three_Racemic_Forms_of_Honokiol-Derived_Dimeric_Neolignans_from_i_Magnolia_Officinalis_i_Var_i_Biloba_i_/30664175 |
| dc.rights.none.fl_str_mv | CC BY-NC 4.0 info:eu-repo/semantics/openAccess |
| dc.subject.none.fl_str_mv | Biophysics Biochemistry Microbiology Molecular Biology Environmental Sciences not elsewhere classified Chemical Sciences not elsewhere classified proposed biosynthetic pathway involving key radical exhibited antinonalcoholic steatohepatitis dioxapentacyclo [ 10 chiral hplc resolution bioactivity evaluation showed 2d nmr data magnolia officinalis </ compounds (+)/(−)-< b compound (−)-< b derived dimeric neolignans 9 ′– c 8 ′– c three racemic forms connecting two honokiol 4 ′′ linkages 3 </ b c (< b 2 </ b 1 </ b (< b biloba </ (+)-< b unprecedented 3 three pairs racemic honokiol derived units – c spectral comparisons relative configurations planar structures honokiol precursors comprehensive analysis absolute configurations 5 μm 4 ″ 20 μm |
| dc.title.none.fl_str_mv | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> |
| dc.type.none.fl_str_mv | Dataset info:eu-repo/semantics/publishedVersion dataset |
| description | Three pairs of racemic honokiol-derived dimeric neolignans, named honolignols A–C (<b>1</b>–<b>3</b>), featuring unique carbon skeletons, were isolated from the barks of <i>Magnolia officinalis</i> var. <i>biloba</i>. Honolignol A (<b>1</b>) represents a novel polycyclic neolignan characterized by an unprecedented 3,13-dioxapentacyclo[10.4.1.0<sup>2,10</sup>.0<sup>4,9</sup>.0<sup>11,15</sup>]heptadecane framework. Honolignols B (<b>2</b>) and C (<b>3</b>) were identified as dimers formed via previously unreported C-8′–C-4″ and C-9′–C-4′′ linkages, respectively, connecting two honokiol-derived units. The planar structures and relative configurations of <b>1</b>–<b>3</b> were established through comprehensive analysis of HRMS (ESI) and 1D/2D NMR data. Chiral HPLC resolution of <b>1</b>–<b>3</b> afforded three enantiomeric pairs. Their absolute configurations were assigned by experimental and time-dependent density functional theory (TDDFT)-calculated electronic circular dichroism (ECD) spectral comparisons. A proposed biosynthetic pathway of <b>1</b>–<b>3</b> involving key radical-mediated cascade cyclization steps of honokiol precursors was postulated. The bioactivity evaluation showed that compound (−)-<b>1</b> displayed notable antimycoplasma pneumoniae (MP) activity at a concentration of 5 μM; and compounds (+)/(−)-<b>2</b> and (+)-<b>3</b> exhibited antinonalcoholic steatohepatitis (NASH) activities at a concentration of 20 μM. |
| eu_rights_str_mv | openAccess |
| id | Manara_ba7780300c62bcdb2cbb01e3e2b71812 |
| identifier_str_mv | 10.1021/acs.joc.5c02184.s003 |
| network_acronym_str | Manara |
| network_name_str | ManaraRepo |
| oai_identifier_str | oai:figshare.com:article/30664175 |
| 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 | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i>Wei-Ming Huang (7134713)Ping Ying (20876752)Han-fei Gong (22651991)Yue-You Yang (20403221)Chuan-Lu Fu (22428605)Ze Liu (130881)Zi-wei Jia (22651994)Zhen-Zhen Zhang (5042102)Ling-Yi Kong (1344264)Wen-Jun Xu (1596799)BiophysicsBiochemistryMicrobiologyMolecular BiologyEnvironmental Sciences not elsewhere classifiedChemical Sciences not elsewhere classifiedproposed biosynthetic pathwayinvolving key radicalexhibited antinonalcoholic steatohepatitisdioxapentacyclo [ 10chiral hplc resolutionbioactivity evaluation showed2d nmr datamagnolia officinalis </compounds (+)/(−)-< bcompound (−)-< bderived dimeric neolignans9 ′– c8 ′– cthree racemic formsconnecting two honokiol4 ′′ linkages3 </ bc (< b2 </ b1 </ b(< bbiloba </(+)-< bunprecedented 3three pairsracemic honokiolderived units– cspectral comparisonsrelative configurationsplanar structureshonokiol precursorscomprehensive analysisabsolute configurations5 μm4 ″20 μmThree pairs of racemic honokiol-derived dimeric neolignans, named honolignols A–C (<b>1</b>–<b>3</b>), featuring unique carbon skeletons, were isolated from the barks of <i>Magnolia officinalis</i> var. <i>biloba</i>. Honolignol A (<b>1</b>) represents a novel polycyclic neolignan characterized by an unprecedented 3,13-dioxapentacyclo[10.4.1.0<sup>2,10</sup>.0<sup>4,9</sup>.0<sup>11,15</sup>]heptadecane framework. Honolignols B (<b>2</b>) and C (<b>3</b>) were identified as dimers formed via previously unreported C-8′–C-4″ and C-9′–C-4′′ linkages, respectively, connecting two honokiol-derived units. The planar structures and relative configurations of <b>1</b>–<b>3</b> were established through comprehensive analysis of HRMS (ESI) and 1D/2D NMR data. Chiral HPLC resolution of <b>1</b>–<b>3</b> afforded three enantiomeric pairs. Their absolute configurations were assigned by experimental and time-dependent density functional theory (TDDFT)-calculated electronic circular dichroism (ECD) spectral comparisons. A proposed biosynthetic pathway of <b>1</b>–<b>3</b> involving key radical-mediated cascade cyclization steps of honokiol precursors was postulated. The bioactivity evaluation showed that compound (−)-<b>1</b> displayed notable antimycoplasma pneumoniae (MP) activity at a concentration of 5 μM; and compounds (+)/(−)-<b>2</b> and (+)-<b>3</b> exhibited antinonalcoholic steatohepatitis (NASH) activities at a concentration of 20 μM.2025-11-20T06:47:38ZDatasetinfo:eu-repo/semantics/publishedVersiondataset10.1021/acs.joc.5c02184.s003https://figshare.com/articles/dataset/Honolignols_A_C_Three_Racemic_Forms_of_Honokiol-Derived_Dimeric_Neolignans_from_i_Magnolia_Officinalis_i_Var_i_Biloba_i_/30664175CC BY-NC 4.0info:eu-repo/semantics/openAccessoai:figshare.com:article/306641752025-11-20T06:47:38Z |
| spellingShingle | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> Wei-Ming Huang (7134713) Biophysics Biochemistry Microbiology Molecular Biology Environmental Sciences not elsewhere classified Chemical Sciences not elsewhere classified proposed biosynthetic pathway involving key radical exhibited antinonalcoholic steatohepatitis dioxapentacyclo [ 10 chiral hplc resolution bioactivity evaluation showed 2d nmr data magnolia officinalis </ compounds (+)/(−)-< b compound (−)-< b derived dimeric neolignans 9 ′– c 8 ′– c three racemic forms connecting two honokiol 4 ′′ linkages 3 </ b c (< b 2 </ b 1 </ b (< b biloba </ (+)-< b unprecedented 3 three pairs racemic honokiol derived units – c spectral comparisons relative configurations planar structures honokiol precursors comprehensive analysis absolute configurations 5 μm 4 ″ 20 μm |
| status_str | publishedVersion |
| title | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> |
| title_full | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> |
| title_fullStr | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> |
| title_full_unstemmed | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> |
| title_short | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> |
| title_sort | Honolignols A–C, Three Racemic Forms of Honokiol-Derived Dimeric Neolignans from <i>Magnolia Officinalis</i> Var. <i>Biloba</i> |
| topic | Biophysics Biochemistry Microbiology Molecular Biology Environmental Sciences not elsewhere classified Chemical Sciences not elsewhere classified proposed biosynthetic pathway involving key radical exhibited antinonalcoholic steatohepatitis dioxapentacyclo [ 10 chiral hplc resolution bioactivity evaluation showed 2d nmr data magnolia officinalis </ compounds (+)/(−)-< b compound (−)-< b derived dimeric neolignans 9 ′– c 8 ′– c three racemic forms connecting two honokiol 4 ′′ linkages 3 </ b c (< b 2 </ b 1 </ b (< b biloba </ (+)-< b unprecedented 3 three pairs racemic honokiol derived units – c spectral comparisons relative configurations planar structures honokiol precursors comprehensive analysis absolute configurations 5 μm 4 ″ 20 μm |