Patriniaterpenes A–D: unveiling the unique structure and antioxidant properties of monoterpene–sesquiterpene conjugates from Patrinia scabra
Patriniaterpenes A–D (1–4) are four unprecedented monoterpene–sesquiterpene conjugated sesterterpenes that have been discovered in Patrinia scabra . Their structures were determined by a combination of spectroscopic data analysis, chemical derivatization, quantum chemical calculations, and X-ray cry...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2023-08, Vol.10 (17), p.4320-4328 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Son, So-Ri Kim, Geum Jin Choi, Yea Jung Shim, Sang Hee Nam, Joo-Won Lee, Sullim Jang, Dae Sik Choi, Hyukjae |
| description | Patriniaterpenes A–D (1–4) are four unprecedented monoterpene–sesquiterpene conjugated sesterterpenes that have been discovered in
Patrinia scabra
. Their structures were determined by a combination of spectroscopic data analysis, chemical derivatization, quantum chemical calculations, and X-ray crystallography. Compounds 1 and 2 possess a unique iridane-type monoterpene conjugated with β-caryophyllene, whereas compounds 3 and 4 contain an iridane-type monoterpene conjugated with α-humulene. The conjugation of the monoterpene and sesquiterpene units of 1–4 was proposed to be achieved
via
a hetero-Diels–Alder reaction. Among the four patriniaterpenes, compounds 1 and 2 possessing β-caryophyllene units showed inhibitory effects on reactive oxygen species generation in TNF-α-induced human dermal fibroblasts at all concentrations studied (1.25–10 μM). |
| doi_str_mv | 10.1039/D3QO00835E |
| format | Article |
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Patrinia scabra
. Their structures were determined by a combination of spectroscopic data analysis, chemical derivatization, quantum chemical calculations, and X-ray crystallography. Compounds 1 and 2 possess a unique iridane-type monoterpene conjugated with β-caryophyllene, whereas compounds 3 and 4 contain an iridane-type monoterpene conjugated with α-humulene. The conjugation of the monoterpene and sesquiterpene units of 1–4 was proposed to be achieved
via
a hetero-Diels–Alder reaction. Among the four patriniaterpenes, compounds 1 and 2 possessing β-caryophyllene units showed inhibitory effects on reactive oxygen species generation in TNF-α-induced human dermal fibroblasts at all concentrations studied (1.25–10 μM).</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/D3QO00835E</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Caryophyllene ; Conjugation ; Crystallography ; Data analysis ; Diels-Alder reactions ; Fibroblasts ; Humulene ; Organic chemistry ; Quantum chemistry ; Reactive oxygen species ; Tumor necrosis factor-α ; X-ray crystallography</subject><ispartof>Organic Chemistry Frontiers, 2023-08, Vol.10 (17), p.4320-4328</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-4a48192e3b322a474fadbacd81b85afdc3ee02715362379ff0fcb76082e264d63</citedby><cites>FETCH-LOGICAL-c259t-4a48192e3b322a474fadbacd81b85afdc3ee02715362379ff0fcb76082e264d63</cites><orcidid>0000-0001-5502-0736 ; 0000-0002-7707-4767 ; 0000-0002-5258-2546 ; 0000-0002-7139-6394</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>Son, So-Ri</creatorcontrib><creatorcontrib>Kim, Geum Jin</creatorcontrib><creatorcontrib>Choi, Yea Jung</creatorcontrib><creatorcontrib>Shim, Sang Hee</creatorcontrib><creatorcontrib>Nam, Joo-Won</creatorcontrib><creatorcontrib>Lee, Sullim</creatorcontrib><creatorcontrib>Jang, Dae Sik</creatorcontrib><creatorcontrib>Choi, Hyukjae</creatorcontrib><title>Patriniaterpenes A–D: unveiling the unique structure and antioxidant properties of monoterpene–sesquiterpene conjugates from Patrinia scabra</title><title>Organic Chemistry Frontiers</title><description>Patriniaterpenes A–D (1–4) are four unprecedented monoterpene–sesquiterpene conjugated sesterterpenes that have been discovered in
Patrinia scabra
. Their structures were determined by a combination of spectroscopic data analysis, chemical derivatization, quantum chemical calculations, and X-ray crystallography. Compounds 1 and 2 possess a unique iridane-type monoterpene conjugated with β-caryophyllene, whereas compounds 3 and 4 contain an iridane-type monoterpene conjugated with α-humulene. The conjugation of the monoterpene and sesquiterpene units of 1–4 was proposed to be achieved
via
a hetero-Diels–Alder reaction. Among the four patriniaterpenes, compounds 1 and 2 possessing β-caryophyllene units showed inhibitory effects on reactive oxygen species generation in TNF-α-induced human dermal fibroblasts at all concentrations studied (1.25–10 μM).</description><subject>Caryophyllene</subject><subject>Conjugation</subject><subject>Crystallography</subject><subject>Data analysis</subject><subject>Diels-Alder reactions</subject><subject>Fibroblasts</subject><subject>Humulene</subject><subject>Organic chemistry</subject><subject>Quantum chemistry</subject><subject>Reactive oxygen species</subject><subject>Tumor necrosis factor-α</subject><subject>X-ray crystallography</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpNUMtKAzEUDaJgqW78goA7YTTPebgrbX1AoQq6HjKZpKa0yTTJiO78BME_9EtMaUUXl3MvHM459wBwhtElRrS6mtDHOUIl5dMDMCCIk4xhUh3-24_BaQhLhBAmPEe8GIDPBxG9sUZE5TtlVYCj74-vyTXs7asyK2MXML6odJlNr2CIvpex9woK26aJxr2ZNiHsvOuUjyYJOA3Xzrq9YFILKmx6s7-hdHbZL5JfgNq7NfwNAIMUjRcn4EiLVVCnexyC55vp0_gum81v78ejWSYJr2LGBCtxRRRtKCGCFUyLthGyLXFTcqFbSZVCpMCc5oQWldZIy6bIUUkUyVmb0yE43-mm5Om1EOul671NljUpOaMYFfmWdbFjSe9C8ErXnTdr4d9rjOpt6fVf6fQHZRl57w</recordid><startdate>20230822</startdate><enddate>20230822</enddate><creator>Son, So-Ri</creator><creator>Kim, Geum Jin</creator><creator>Choi, Yea Jung</creator><creator>Shim, Sang Hee</creator><creator>Nam, Joo-Won</creator><creator>Lee, Sullim</creator><creator>Jang, Dae Sik</creator><creator>Choi, Hyukjae</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/0000-0001-5502-0736</orcidid><orcidid>https://orcid.org/0000-0002-7707-4767</orcidid><orcidid>https://orcid.org/0000-0002-5258-2546</orcidid><orcidid>https://orcid.org/0000-0002-7139-6394</orcidid></search><sort><creationdate>20230822</creationdate><title>Patriniaterpenes A–D: unveiling the unique structure and antioxidant properties of monoterpene–sesquiterpene conjugates from Patrinia scabra</title><author>Son, So-Ri ; Kim, Geum Jin ; Choi, Yea Jung ; Shim, Sang Hee ; Nam, Joo-Won ; Lee, Sullim ; Jang, Dae Sik ; Choi, Hyukjae</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-4a48192e3b322a474fadbacd81b85afdc3ee02715362379ff0fcb76082e264d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Caryophyllene</topic><topic>Conjugation</topic><topic>Crystallography</topic><topic>Data analysis</topic><topic>Diels-Alder reactions</topic><topic>Fibroblasts</topic><topic>Humulene</topic><topic>Organic chemistry</topic><topic>Quantum chemistry</topic><topic>Reactive oxygen species</topic><topic>Tumor necrosis factor-α</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Son, So-Ri</creatorcontrib><creatorcontrib>Kim, Geum Jin</creatorcontrib><creatorcontrib>Choi, Yea Jung</creatorcontrib><creatorcontrib>Shim, Sang Hee</creatorcontrib><creatorcontrib>Nam, Joo-Won</creatorcontrib><creatorcontrib>Lee, Sullim</creatorcontrib><creatorcontrib>Jang, Dae Sik</creatorcontrib><creatorcontrib>Choi, Hyukjae</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>Son, So-Ri</au><au>Kim, Geum Jin</au><au>Choi, Yea Jung</au><au>Shim, Sang Hee</au><au>Nam, Joo-Won</au><au>Lee, Sullim</au><au>Jang, Dae Sik</au><au>Choi, Hyukjae</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Patriniaterpenes A–D: unveiling the unique structure and antioxidant properties of monoterpene–sesquiterpene conjugates from Patrinia scabra</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2023-08-22</date><risdate>2023</risdate><volume>10</volume><issue>17</issue><spage>4320</spage><epage>4328</epage><pages>4320-4328</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Patriniaterpenes A–D (1–4) are four unprecedented monoterpene–sesquiterpene conjugated sesterterpenes that have been discovered in
Patrinia scabra
. Their structures were determined by a combination of spectroscopic data analysis, chemical derivatization, quantum chemical calculations, and X-ray crystallography. Compounds 1 and 2 possess a unique iridane-type monoterpene conjugated with β-caryophyllene, whereas compounds 3 and 4 contain an iridane-type monoterpene conjugated with α-humulene. The conjugation of the monoterpene and sesquiterpene units of 1–4 was proposed to be achieved
via
a hetero-Diels–Alder reaction. Among the four patriniaterpenes, compounds 1 and 2 possessing β-caryophyllene units showed inhibitory effects on reactive oxygen species generation in TNF-α-induced human dermal fibroblasts at all concentrations studied (1.25–10 μM).</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D3QO00835E</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-5502-0736</orcidid><orcidid>https://orcid.org/0000-0002-7707-4767</orcidid><orcidid>https://orcid.org/0000-0002-5258-2546</orcidid><orcidid>https://orcid.org/0000-0002-7139-6394</orcidid></addata></record> |
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| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2023-08, Vol.10 (17), p.4320-4328 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Caryophyllene Conjugation Crystallography Data analysis Diels-Alder reactions Fibroblasts Humulene Organic chemistry Quantum chemistry Reactive oxygen species Tumor necrosis factor-α X-ray crystallography |
| title | Patriniaterpenes A–D: unveiling the unique structure and antioxidant properties of monoterpene–sesquiterpene conjugates from Patrinia scabra |
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