Halichonic Acid B, a Rearranged Nitrogenous Bisabolene-Type Sesquiterpene from a Marine Sponge Axinyssa sp
A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unpre...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2021/08/01, Vol.69(8), pp.802-805 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Hitora, Yuki Ogura, Kenta El-Desoky, Ahmed H. H. Ise, Yuji Angkouw, Esther D. Mangindaan, Remy E. P. Tsukamoto, Sachiko |
| description | A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unprecedented carbon framework, and its absolute configuration was elucidated by time-dependent density-functional theory (TDDFT)-based electronic circular dichroism (ECD) spectrum calculation. We propose that 1 and 2 may be biosynthesized in the same pathway, involving the reaction between farnesyl pyrophosphate and glycine, followed by cyclization. |
| doi_str_mv | 10.1248/cpb.c21-00392 |
| format | Article |
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H. ; Ise, Yuji ; Angkouw, Esther D. ; Mangindaan, Remy E. P. ; Tsukamoto, Sachiko</creator><creatorcontrib>Hitora, Yuki ; Ogura, Kenta ; El-Desoky, Ahmed H. H. ; Ise, Yuji ; Angkouw, Esther D. ; Mangindaan, Remy E. P. ; Tsukamoto, Sachiko ; National Research Centre ; University of the Ryukyus ; aGraduate School of Pharmaceutical Sciences ; cSesoko Station ; Kumamoto University ; Pharmacognosy Department ; dFaculty of Fisheries and Marine Science ; bPharmaceutical Industries Research Division ; Tropical Biosphere Research Center ; Sam Ratulangi University</creatorcontrib><description>A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unprecedented carbon framework, and its absolute configuration was elucidated by time-dependent density-functional theory (TDDFT)-based electronic circular dichroism (ECD) spectrum calculation. We propose that 1 and 2 may be biosynthesized in the same pathway, involving the reaction between farnesyl pyrophosphate and glycine, followed by cyclization.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c21-00392</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Absolute configuration ; Axinyssa ; Axinyssa species ; Bisabolene ; Circular dichroism ; Density functional theory ; Dichroism ; Glycine ; marine sponge ; nitrogenous bisabolone-type sesquiterpene ; NMR ; Nuclear magnetic resonance</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2021/08/01, Vol.69(8), pp.802-805</ispartof><rights>2021 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c723t-c113a390add2eceba381b7d9f88a27d77bfbcadac641adac64e057d85fa9aa133</citedby><cites>FETCH-LOGICAL-c723t-c113a390add2eceba381b7d9f88a27d77bfbcadac641adac64e057d85fa9aa133</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids></links><search><creatorcontrib>Hitora, Yuki</creatorcontrib><creatorcontrib>Ogura, Kenta</creatorcontrib><creatorcontrib>El-Desoky, Ahmed H. 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Bull.</addtitle><description>A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unprecedented carbon framework, and its absolute configuration was elucidated by time-dependent density-functional theory (TDDFT)-based electronic circular dichroism (ECD) spectrum calculation. We propose that 1 and 2 may be biosynthesized in the same pathway, involving the reaction between farnesyl pyrophosphate and glycine, followed by cyclization.</description><subject>Absolute configuration</subject><subject>Axinyssa</subject><subject>Axinyssa species</subject><subject>Bisabolene</subject><subject>Circular dichroism</subject><subject>Density functional theory</subject><subject>Dichroism</subject><subject>Glycine</subject><subject>marine sponge</subject><subject>nitrogenous bisabolone-type sesquiterpene</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkM1r3DAQxU1podu0x94FvfRQp_qwLPm4WZqkkA9I0rMYy-NdLbblSF7o_vfR2iWBXmbQ6DfvSS_LvjJ6znihf9qxPrec5ZSKir_LVkwUKpeci_fZilJa5VyU4mP2KcY9pVxSJVbZ_ho6Z3d-cJasrWvIxQ8C5AEhBBi22JA7NwW_xcEfIrlwEWrf4YD503FE8ojx-eAmDGMakTb4Pu3eQnDp9Dj6tE_Wf91wjBFIHD9nH1roIn7518-yP5e_njbX-c391e_N-ia3iospt4wJEBWFpuFosQahWa2aqtUauGqUqtvaQgO2LNjSkErVaNlCBcCEOMu-L7pj8M8HjJPpXbTYdTBg-oXhUipZUCFoQr_9h-79IQzpdTPFZSlnKl8oG3yMAVszBtdDOBpGzSl5k5I3KXkzJ5_4q4XvsXEWOj90KZE3aRuV3WHvDKfzTllRbSgrDNWUn4oUWoqy1Elpsyjt4wRbfPWFMDnb4exbVkafyqv_2-0OgsFBvACD_6YZ</recordid><startdate>20210801</startdate><enddate>20210801</enddate><creator>Hitora, Yuki</creator><creator>Ogura, Kenta</creator><creator>El-Desoky, Ahmed H. H.</creator><creator>Ise, Yuji</creator><creator>Angkouw, Esther D.</creator><creator>Mangindaan, Remy E. P.</creator><creator>Tsukamoto, Sachiko</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20210801</creationdate><title>Halichonic Acid B, a Rearranged Nitrogenous Bisabolene-Type Sesquiterpene from a Marine Sponge Axinyssa sp</title><author>Hitora, Yuki ; Ogura, Kenta ; El-Desoky, Ahmed H. H. ; Ise, Yuji ; Angkouw, Esther D. ; Mangindaan, Remy E. P. ; Tsukamoto, Sachiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c723t-c113a390add2eceba381b7d9f88a27d77bfbcadac641adac64e057d85fa9aa133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Absolute configuration</topic><topic>Axinyssa</topic><topic>Axinyssa species</topic><topic>Bisabolene</topic><topic>Circular dichroism</topic><topic>Density functional theory</topic><topic>Dichroism</topic><topic>Glycine</topic><topic>marine sponge</topic><topic>nitrogenous bisabolone-type sesquiterpene</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hitora, Yuki</creatorcontrib><creatorcontrib>Ogura, Kenta</creatorcontrib><creatorcontrib>El-Desoky, Ahmed H. 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H.</au><au>Ise, Yuji</au><au>Angkouw, Esther D.</au><au>Mangindaan, Remy E. P.</au><au>Tsukamoto, Sachiko</au><aucorp>National Research Centre</aucorp><aucorp>University of the Ryukyus</aucorp><aucorp>aGraduate School of Pharmaceutical Sciences</aucorp><aucorp>cSesoko Station</aucorp><aucorp>Kumamoto University</aucorp><aucorp>Pharmacognosy Department</aucorp><aucorp>dFaculty of Fisheries and Marine Science</aucorp><aucorp>bPharmaceutical Industries Research Division</aucorp><aucorp>Tropical Biosphere Research Center</aucorp><aucorp>Sam Ratulangi University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Halichonic Acid B, a Rearranged Nitrogenous Bisabolene-Type Sesquiterpene from a Marine Sponge Axinyssa sp</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2021-08-01</date><risdate>2021</risdate><volume>69</volume><issue>8</issue><spage>802</spage><epage>805</epage><pages>802-805</pages><artnum>c21-00392</artnum><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unprecedented carbon framework, and its absolute configuration was elucidated by time-dependent density-functional theory (TDDFT)-based electronic circular dichroism (ECD) spectrum calculation. We propose that 1 and 2 may be biosynthesized in the same pathway, involving the reaction between farnesyl pyrophosphate and glycine, followed by cyclization.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.c21-00392</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Absolute configuration Axinyssa Axinyssa species Bisabolene Circular dichroism Density functional theory Dichroism Glycine marine sponge nitrogenous bisabolone-type sesquiterpene NMR Nuclear magnetic resonance |
| title | Halichonic Acid B, a Rearranged Nitrogenous Bisabolene-Type Sesquiterpene from a Marine Sponge Axinyssa sp |
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