Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model
Ten known meroterpenoids and the new meroterpenoid 7 were isolated from the Chilean seaweed Stypopodium flabelliforme as their acetylated derivatives. Furthermore, the known metabolite taondiol has been isolated for the first time from this species. The molecular structure of the new metabolite was...
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| Format: | Article |
| Language: | English |
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MDPI AG
2015-03-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/13/4/1726 |
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| author | Carlos Areche Julio Benites Alberto Cornejo Lina M. Ruiz Olimpo García-Beltrán Mario J. Simirgiotis Beatriz Sepúlveda |
| author_facet | Carlos Areche Julio Benites Alberto Cornejo Lina M. Ruiz Olimpo García-Beltrán Mario J. Simirgiotis Beatriz Sepúlveda |
| author_sort | Carlos Areche |
| collection | DOAJ |
| description | Ten known meroterpenoids and the new meroterpenoid 7 were isolated from the Chilean seaweed Stypopodium flabelliforme as their acetylated derivatives. Furthermore, the known metabolite taondiol has been isolated for the first time from this species. The molecular structure of the new metabolite was determined by spectroscopic methods based on 1D- and 2D-NMR. Isolation of 7 represents a key step toward a better understanding of the biogenesis of this class of meroterpenoids. Among the meroditerpenoids isolated, stypodiol, isoepitaondiol, epitaondiol and sargaol exhibited gastroprotective activity on the HCl/Ethanol-induced gastric lesions model in mice. Regarding the mode of gastroprotective action, the activity of epitaondiol was reversed significantly when animals were pretreated with indomethacin, N-ethylmaleimide and N-nitro-l-arginine methyl ester (L-NAME) suggesting that prostaglandins, sulfhydryl groups and nitric oxide are involved in their mode of gastroprotective action. In the case of sargaol the gastroprotective activity was attenuated with indomethacin and N-ethylmaleimide, which suggests that prostaglandins and sulfhydryl groups are also involved in the mode of action using this model. |
| first_indexed | 2024-04-13T08:47:12Z |
| format | Article |
| id | doaj.art-f3cac24bb5b4457c95e1f311815503d6 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-13T08:47:12Z |
| publishDate | 2015-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-f3cac24bb5b4457c95e1f311815503d62022-12-22T02:53:38ZengMDPI AGMarine Drugs1660-33972015-03-011341726173810.3390/md13041726md13041726Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse ModelCarlos Areche0Julio Benites1Alberto Cornejo2Lina M. Ruiz3Olimpo García-Beltrán4Mario J. Simirgiotis5Beatriz Sepúlveda6Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago 8320000, ChileFacultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, ChileEscuela de Tecnología Médica, Facultad de Medicina, Universidad Andrés Bello, Santiago 8370186, ChileFacultad de Ciencias de la Salud, Universidad Autónoma de Chile, Santiago 8910132, ChileFacultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 Calle 67, Ibagué 730001, ColombiaLaboratorio de Productos Naturales, Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Antofagasta 1240000, ChileDepartmento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Quillota 980, Viña del Mar 2520000, ChileTen known meroterpenoids and the new meroterpenoid 7 were isolated from the Chilean seaweed Stypopodium flabelliforme as their acetylated derivatives. Furthermore, the known metabolite taondiol has been isolated for the first time from this species. The molecular structure of the new metabolite was determined by spectroscopic methods based on 1D- and 2D-NMR. Isolation of 7 represents a key step toward a better understanding of the biogenesis of this class of meroterpenoids. Among the meroditerpenoids isolated, stypodiol, isoepitaondiol, epitaondiol and sargaol exhibited gastroprotective activity on the HCl/Ethanol-induced gastric lesions model in mice. Regarding the mode of gastroprotective action, the activity of epitaondiol was reversed significantly when animals were pretreated with indomethacin, N-ethylmaleimide and N-nitro-l-arginine methyl ester (L-NAME) suggesting that prostaglandins, sulfhydryl groups and nitric oxide are involved in their mode of gastroprotective action. In the case of sargaol the gastroprotective activity was attenuated with indomethacin and N-ethylmaleimide, which suggests that prostaglandins and sulfhydryl groups are also involved in the mode of action using this model.http://www.mdpi.com/1660-3397/13/4/1726Stypopodium flabelliformemeroditerpenoidsgastroprotectivegastric ulcerseaweed |
| spellingShingle | Carlos Areche Julio Benites Alberto Cornejo Lina M. Ruiz Olimpo García-Beltrán Mario J. Simirgiotis Beatriz Sepúlveda Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model Marine Drugs Stypopodium flabelliforme meroditerpenoids gastroprotective gastric ulcer seaweed |
| title | Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model |
| title_full | Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model |
| title_fullStr | Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model |
| title_full_unstemmed | Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model |
| title_short | Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model |
| title_sort | seco taondiol an unusual meroterpenoid from the chilean seaweed stypopodium flabelliforme and its gastroprotective effect in mouse model |
| topic | Stypopodium flabelliforme meroditerpenoids gastroprotective gastric ulcer seaweed |
| url | http://www.mdpi.com/1660-3397/13/4/1726 |
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