Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i>
Five new oxygenated sesquiterpenes, molestins A⁻D (<b>1</b>, <b>3</b>⁻<b>5</b>) and <i>epi</i>-gibberodione (<b>2</b>), three new cyclopentenone derivatives, <i>ent</i>-sinulolides C, D, and F ((+)-<b>9...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/16/12/517 |
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| author | Mei-Jun Chu Xu-Li Tang Xiao Han Tao Li Xiang-Chao Luo Ming-Ming Jiang Leen van Ofwegen Lian-Zhong Luo Gang Zhang Ping-Lin Li Guo-Qiang Li |
| author_facet | Mei-Jun Chu Xu-Li Tang Xiao Han Tao Li Xiang-Chao Luo Ming-Ming Jiang Leen van Ofwegen Lian-Zhong Luo Gang Zhang Ping-Lin Li Guo-Qiang Li |
| author_sort | Mei-Jun Chu |
| collection | DOAJ |
| description | Five new oxygenated sesquiterpenes, molestins A⁻D (<b>1</b>, <b>3</b>⁻<b>5</b>) and <i>epi</i>-gibberodione (<b>2</b>), three new cyclopentenone derivatives, <i>ent</i>-sinulolides C, D, and F ((+)-<b>9</b>⁻(+)-<b>11</b>), one new butenolide derivative, <i>ent</i>-sinulolide H ((+)-<b>13</b>), and one new cembranolide, molestin E (<b>14</b>), together with 14 known related metabolites (<b>6</b>⁻<b>8</b>, (⁻)-<b>9</b>⁻(⁻)-<b>11</b>, (±)-<b>12</b>, (⁻)-<b>13</b>, <b>15</b>⁻<b>19</b>) were isolated from the Paracel Islands soft coral <i>Sinularia</i> cf. <i>molesta</i>. The structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, quantum chemical calculations, and comparison with the literature data. Compound <b>5</b> is the first example of a norsesquiterpene with a de-isopropyl guaiane skeleton isolated from the genus <i>Sinularia</i>. Molestin E (<b>14</b>) exhibited cytotoxicities against HeLa and HCT-116 cell lines with IC<sub>50</sub> values of 5.26 and 8.37 μM, respectively. Compounds <b>4</b>, <b>5</b>, and <b>8</b> showed significant inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC<sub>50</sub> values of 218, 344, and 1.24 μM, respectively. |
| first_indexed | 2024-04-11T13:40:08Z |
| format | Article |
| id | doaj.art-c59c05af572f40e79976c8bd67e36515 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T13:40:08Z |
| publishDate | 2018-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-c59c05af572f40e79976c8bd67e365152022-12-22T04:21:17ZengMDPI AGMarine Drugs1660-33972018-12-01161251710.3390/md16120517md16120517Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i>Mei-Jun Chu0Xu-Li Tang1Xiao Han2Tao Li3Xiang-Chao Luo4Ming-Ming Jiang5Leen van Ofwegen6Lian-Zhong Luo7Gang Zhang8Ping-Lin Li9Guo-Qiang Li10Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaCollege of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaNationaal Natuurhistorisch Museum, 2300 RA Leiden, The NetherlandsXiamen Key Laboratory of Marine Medicinal Natural Products Resources, Xiamen Medical College, Xiamen 361023, ChinaXiamen Key Laboratory of Marine Medicinal Natural Products Resources, Xiamen Medical College, Xiamen 361023, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaFive new oxygenated sesquiterpenes, molestins A⁻D (<b>1</b>, <b>3</b>⁻<b>5</b>) and <i>epi</i>-gibberodione (<b>2</b>), three new cyclopentenone derivatives, <i>ent</i>-sinulolides C, D, and F ((+)-<b>9</b>⁻(+)-<b>11</b>), one new butenolide derivative, <i>ent</i>-sinulolide H ((+)-<b>13</b>), and one new cembranolide, molestin E (<b>14</b>), together with 14 known related metabolites (<b>6</b>⁻<b>8</b>, (⁻)-<b>9</b>⁻(⁻)-<b>11</b>, (±)-<b>12</b>, (⁻)-<b>13</b>, <b>15</b>⁻<b>19</b>) were isolated from the Paracel Islands soft coral <i>Sinularia</i> cf. <i>molesta</i>. The structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, quantum chemical calculations, and comparison with the literature data. Compound <b>5</b> is the first example of a norsesquiterpene with a de-isopropyl guaiane skeleton isolated from the genus <i>Sinularia</i>. Molestin E (<b>14</b>) exhibited cytotoxicities against HeLa and HCT-116 cell lines with IC<sub>50</sub> values of 5.26 and 8.37 μM, respectively. Compounds <b>4</b>, <b>5</b>, and <b>8</b> showed significant inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC<sub>50</sub> values of 218, 344, and 1.24 μM, respectively.https://www.mdpi.com/1660-3397/16/12/517Marine soft coral<i>Sinularia</i>terpenoids |
| spellingShingle | Mei-Jun Chu Xu-Li Tang Xiao Han Tao Li Xiang-Chao Luo Ming-Ming Jiang Leen van Ofwegen Lian-Zhong Luo Gang Zhang Ping-Lin Li Guo-Qiang Li Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i> Marine Drugs Marine soft coral <i>Sinularia</i> terpenoids |
| title | Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i> |
| title_full | Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i> |
| title_fullStr | Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i> |
| title_full_unstemmed | Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i> |
| title_short | Metabolites from the Paracel Islands Soft Coral <i>Sinularia</i> cf. <i>molesta</i> |
| title_sort | metabolites from the paracel islands soft coral i sinularia i cf i molesta i |
| topic | Marine soft coral <i>Sinularia</i> terpenoids |
| url | https://www.mdpi.com/1660-3397/16/12/517 |
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