Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i>
Further chemical investigation of the EtOAc extract of the soft coral <i>Lobophytum varium</i> resulted in the discovery of eleven new diterpenoids lobovarols F–P (<b>1</b>–<b>11</b>) of lobane– and prenyleudesmane–types, along with two known metabolites (<b>...
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MDPI AG
2020-04-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/4/223 |
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| author | Chuan-Hsiang Chang Atallah F. Ahmed Tian-Sheng Yang You-Cheng Lin Chiung-Yao Huang Tsong-Long Hwang Jyh-Horng Sheu |
| author_facet | Chuan-Hsiang Chang Atallah F. Ahmed Tian-Sheng Yang You-Cheng Lin Chiung-Yao Huang Tsong-Long Hwang Jyh-Horng Sheu |
| author_sort | Chuan-Hsiang Chang |
| collection | DOAJ |
| description | Further chemical investigation of the EtOAc extract of the soft coral <i>Lobophytum varium</i> resulted in the discovery of eleven new diterpenoids lobovarols F–P (<b>1</b>–<b>11</b>) of lobane– and prenyleudesmane–types, along with two known metabolites (<b>12</b> and <b>13</b>). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of <b>1</b> was determined using Mosher’s method. The complete assignment of <sup>1</sup>H and <sup>13</sup>C NMR spectroscopic data of <b>12</b> and <b>13</b> and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for <b>1</b>, <b>2</b>, <b>4</b>, <b>12</b>, and <b>13</b>. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in <i>L. varium</i>. |
| first_indexed | 2024-03-10T20:18:01Z |
| format | Article |
| id | doaj.art-1416b567923b4864afac2ef5f537c074 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T20:18:01Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-1416b567923b4864afac2ef5f537c0742023-11-19T22:23:47ZengMDPI AGMarine Drugs1660-33972020-04-0118422310.3390/md18040223Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i>Chuan-Hsiang Chang0Atallah F. Ahmed1Tian-Sheng Yang2You-Cheng Lin3Chiung-Yao Huang4Tsong-Long Hwang5Jyh-Horng Sheu6Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, TaiwanDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, TaiwanDoctoral Degree Program in Marine Biotechnology, National Sun Yat-sen University, Kaohsiung 804, TaiwanDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, TaiwanGraduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, TaiwanDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, TaiwanFurther chemical investigation of the EtOAc extract of the soft coral <i>Lobophytum varium</i> resulted in the discovery of eleven new diterpenoids lobovarols F–P (<b>1</b>–<b>11</b>) of lobane– and prenyleudesmane–types, along with two known metabolites (<b>12</b> and <b>13</b>). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of <b>1</b> was determined using Mosher’s method. The complete assignment of <sup>1</sup>H and <sup>13</sup>C NMR spectroscopic data of <b>12</b> and <b>13</b> and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for <b>1</b>, <b>2</b>, <b>4</b>, <b>12</b>, and <b>13</b>. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in <i>L. varium</i>.https://www.mdpi.com/1660-3397/18/4/223lobaneprenyleudesmaneanti-inflammatory activity<i>Lobophytum varium</i> |
| spellingShingle | Chuan-Hsiang Chang Atallah F. Ahmed Tian-Sheng Yang You-Cheng Lin Chiung-Yao Huang Tsong-Long Hwang Jyh-Horng Sheu Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i> Marine Drugs lobane prenyleudesmane anti-inflammatory activity <i>Lobophytum varium</i> |
| title | Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i> |
| title_full | Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i> |
| title_fullStr | Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i> |
| title_full_unstemmed | Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i> |
| title_short | Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral <i>Lobophytum varium</i> |
| title_sort | isolation of lobane and prenyleudesmane diterpenoids from the soft coral i lobophytum varium i |
| topic | lobane prenyleudesmane anti-inflammatory activity <i>Lobophytum varium</i> |
| url | https://www.mdpi.com/1660-3397/18/4/223 |
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