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Mar. Drugs 2015, 13(4), 1726-1738; doi:10.3390/md13041726

Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model

1
Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago 8320000, Chile
2
Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile
3
Escuela de Tecnología Médica, Facultad de Medicina, Universidad Andrés Bello, Santiago 8370186, Chile
4
Facultad de Ciencias de la Salud, Universidad Autónoma de Chile, Santiago 8910132, Chile
5
Facultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 Calle 67, Ibagué 730001, Colombia
6
Laboratorio de Productos Naturales, Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Antofagasta 1240000, Chile
7
Departmento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Quillota 980, Viña del Mar 2520000, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Valeria Costantino
Received: 22 January 2015 / Revised: 1 March 2015 / Accepted: 20 March 2015 / Published: 30 March 2015
(This article belongs to the Special Issue Marine Secondary Metabolites)
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Abstract

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. View Full-Text
Keywords: Stypopodium flabelliforme; meroditerpenoids; gastroprotective; gastric ulcer; seaweed Stypopodium flabelliforme; meroditerpenoids; gastroprotective; gastric ulcer; seaweed
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Areche, C.; Benites, J.; Cornejo, A.; Ruiz, L.M.; García-Beltrán, O.; Simirgiotis, M.J.; Sepúlveda, B. Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model. Mar. Drugs 2015, 13, 1726-1738.

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