Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum
Two pairs of meroterpenoid enantiomers, (±)-fissisternoids A (1) and B (2), along with their putative biogenetic precursor 3 were isolated from the branches and leaves of Fissistigma bracteolatum . Compound 1 represents an unprecedented meroterpenoid featuring a unique tricyclo [3,3,1,0 1′,5′ ] deca...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2021-12, Vol.9 (1), p.190-196 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Xue, Gui-Min Zhao, Chen-Guang Xue, Jin-Feng Chen, Hui Zhao, Zhen-Zhu Si, Ying-Ying Du, Kun Zhi, Yan-Le Feng, Wei-Sheng |
| description | Two pairs of meroterpenoid enantiomers, (±)-fissisternoids A (1) and B (2), along with their putative biogenetic precursor 3 were isolated from the branches and leaves of
Fissistigma bracteolatum
. Compound 1 represents an unprecedented meroterpenoid featuring a unique tricyclo [3,3,1,0
1′,5′
] decane central framework, and compound 2 possesses a rare 6/6/5/4 tetracyclic carbon skeleton, both of which were derived from quinodihydrochalcone and monoterpenoid
via
a key [4 + 2] Diels–Alder cyclization and Prins reaction. Their structures and absolute configurations were established using spectroscopic data, X-ray diffraction, and electronic circular dichroism calculations. Compounds 1 and 2 exhibit anti-inflammatory activity (IC
50
: 13.2 μM, 1; 9.8 μM, 2)
via
suppression of inflammatory cytokines IL-1β, IL-6, and iNOS. |
| doi_str_mv | 10.1039/D1QO01404H |
| format | Article |
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Fissistigma bracteolatum
. Compound 1 represents an unprecedented meroterpenoid featuring a unique tricyclo [3,3,1,0
1′,5′
] decane central framework, and compound 2 possesses a rare 6/6/5/4 tetracyclic carbon skeleton, both of which were derived from quinodihydrochalcone and monoterpenoid
via
a key [4 + 2] Diels–Alder cyclization and Prins reaction. Their structures and absolute configurations were established using spectroscopic data, X-ray diffraction, and electronic circular dichroism calculations. Compounds 1 and 2 exhibit anti-inflammatory activity (IC
50
: 13.2 μM, 1; 9.8 μM, 2)
via
suppression of inflammatory cytokines IL-1β, IL-6, and iNOS.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D1QO01404H</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Anti-inflammatory agents ; Carbon ; Circular dichroism ; Cytokines ; Dichroism ; Enantiomers ; IL-1β ; Inflammation ; Interleukin 6 ; Nitric-oxide synthase ; Organic chemistry ; X-ray diffraction</subject><ispartof>Organic Chemistry Frontiers, 2021-12, Vol.9 (1), p.190-196</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c218t-2abfd5b5a69371dd4b9a78ed5c2c0b19c305f9267ddbe42a198e3041f8a018523</cites><orcidid>0000-0001-7961-4694 ; 0000-0002-5919-524X ; 0000-0002-4631-6882 ; 0000-0002-5987-412X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Xue, Gui-Min</creatorcontrib><creatorcontrib>Zhao, Chen-Guang</creatorcontrib><creatorcontrib>Xue, Jin-Feng</creatorcontrib><creatorcontrib>Chen, Hui</creatorcontrib><creatorcontrib>Zhao, Zhen-Zhu</creatorcontrib><creatorcontrib>Si, Ying-Ying</creatorcontrib><creatorcontrib>Du, Kun</creatorcontrib><creatorcontrib>Zhi, Yan-Le</creatorcontrib><creatorcontrib>Feng, Wei-Sheng</creatorcontrib><title>Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum</title><title>Organic Chemistry Frontiers</title><description>Two pairs of meroterpenoid enantiomers, (±)-fissisternoids A (1) and B (2), along with their putative biogenetic precursor 3 were isolated from the branches and leaves of
Fissistigma bracteolatum
. Compound 1 represents an unprecedented meroterpenoid featuring a unique tricyclo [3,3,1,0
1′,5′
] decane central framework, and compound 2 possesses a rare 6/6/5/4 tetracyclic carbon skeleton, both of which were derived from quinodihydrochalcone and monoterpenoid
via
a key [4 + 2] Diels–Alder cyclization and Prins reaction. Their structures and absolute configurations were established using spectroscopic data, X-ray diffraction, and electronic circular dichroism calculations. Compounds 1 and 2 exhibit anti-inflammatory activity (IC
50
: 13.2 μM, 1; 9.8 μM, 2)
via
suppression of inflammatory cytokines IL-1β, IL-6, and iNOS.</description><subject>Anti-inflammatory agents</subject><subject>Carbon</subject><subject>Circular dichroism</subject><subject>Cytokines</subject><subject>Dichroism</subject><subject>Enantiomers</subject><subject>IL-1β</subject><subject>Inflammation</subject><subject>Interleukin 6</subject><subject>Nitric-oxide synthase</subject><subject>Organic chemistry</subject><subject>X-ray diffraction</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpNUMtKAzEUDaJgqd34BQF30tEkM5nHslZrhYIIuh7uJBmbOpO0SYbSnV_hh_hJfolTWtDNPZfDecBB6JKSG0ri4vaevjwTmpBkfoIGjHAWJZQVp__-czTyfkUIoYynhGcD9DXT3msflDNWS48nGIzEd2Mcthazn8_vMe9PtOm0sVIvd9JZsYRGWKOiCrySuFXO9va12gdgZcAEbXvS460OS9yZznfQYAGusgb7D9WoYI3HtbMtPrbr9xZw5UAEZRsIXXuBzmpovBodcYjeZg-v03m0eH58mk4WkWA0DxGDqpa84pAWcUalTKoCslxJLpggFS1ETHhdsDSTslIJA1rkKiYJrXMgNOcsHqKrQ-7a2U2nfChXtnOmryxZShlhWZrkver6oBLOeu9UXa6dbsHtSkrK_fTl3_TxL7bmezo</recordid><startdate>20211221</startdate><enddate>20211221</enddate><creator>Xue, Gui-Min</creator><creator>Zhao, Chen-Guang</creator><creator>Xue, Jin-Feng</creator><creator>Chen, Hui</creator><creator>Zhao, Zhen-Zhu</creator><creator>Si, Ying-Ying</creator><creator>Du, Kun</creator><creator>Zhi, Yan-Le</creator><creator>Feng, Wei-Sheng</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-7961-4694</orcidid><orcidid>https://orcid.org/0000-0002-5919-524X</orcidid><orcidid>https://orcid.org/0000-0002-4631-6882</orcidid><orcidid>https://orcid.org/0000-0002-5987-412X</orcidid></search><sort><creationdate>20211221</creationdate><title>Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum</title><author>Xue, Gui-Min ; Zhao, Chen-Guang ; Xue, Jin-Feng ; Chen, Hui ; Zhao, Zhen-Zhu ; Si, Ying-Ying ; Du, Kun ; Zhi, Yan-Le ; Feng, Wei-Sheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c218t-2abfd5b5a69371dd4b9a78ed5c2c0b19c305f9267ddbe42a198e3041f8a018523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Anti-inflammatory agents</topic><topic>Carbon</topic><topic>Circular dichroism</topic><topic>Cytokines</topic><topic>Dichroism</topic><topic>Enantiomers</topic><topic>IL-1β</topic><topic>Inflammation</topic><topic>Interleukin 6</topic><topic>Nitric-oxide synthase</topic><topic>Organic chemistry</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xue, Gui-Min</creatorcontrib><creatorcontrib>Zhao, Chen-Guang</creatorcontrib><creatorcontrib>Xue, Jin-Feng</creatorcontrib><creatorcontrib>Chen, Hui</creatorcontrib><creatorcontrib>Zhao, Zhen-Zhu</creatorcontrib><creatorcontrib>Si, Ying-Ying</creatorcontrib><creatorcontrib>Du, Kun</creatorcontrib><creatorcontrib>Zhi, Yan-Le</creatorcontrib><creatorcontrib>Feng, Wei-Sheng</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xue, Gui-Min</au><au>Zhao, Chen-Guang</au><au>Xue, Jin-Feng</au><au>Chen, Hui</au><au>Zhao, Zhen-Zhu</au><au>Si, Ying-Ying</au><au>Du, Kun</au><au>Zhi, Yan-Le</au><au>Feng, Wei-Sheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-12-21</date><risdate>2021</risdate><volume>9</volume><issue>1</issue><spage>190</spage><epage>196</epage><pages>190-196</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Two pairs of meroterpenoid enantiomers, (±)-fissisternoids A (1) and B (2), along with their putative biogenetic precursor 3 were isolated from the branches and leaves of
Fissistigma bracteolatum
. Compound 1 represents an unprecedented meroterpenoid featuring a unique tricyclo [3,3,1,0
1′,5′
] decane central framework, and compound 2 possesses a rare 6/6/5/4 tetracyclic carbon skeleton, both of which were derived from quinodihydrochalcone and monoterpenoid
via
a key [4 + 2] Diels–Alder cyclization and Prins reaction. Their structures and absolute configurations were established using spectroscopic data, X-ray diffraction, and electronic circular dichroism calculations. Compounds 1 and 2 exhibit anti-inflammatory activity (IC
50
: 13.2 μM, 1; 9.8 μM, 2)
via
suppression of inflammatory cytokines IL-1β, IL-6, and iNOS.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1QO01404H</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7961-4694</orcidid><orcidid>https://orcid.org/0000-0002-5919-524X</orcidid><orcidid>https://orcid.org/0000-0002-4631-6882</orcidid><orcidid>https://orcid.org/0000-0002-5987-412X</orcidid></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Anti-inflammatory agents Carbon Circular dichroism Cytokines Dichroism Enantiomers IL-1β Inflammation Interleukin 6 Nitric-oxide synthase Organic chemistry X-ray diffraction |
| title | Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum |
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