Seco-taondiol, an unusual meroterpenoid from the Chilean seaweed Stypopodium flabelliforme and its gastroprotective effect in mouse model

Carlos Areche, Julio Benites, Alberto Cornejo, Lina M. Ruiz, Olimpo García-Beltrán, Mario J. Simirgiotis, Beatriz Sepúlveda

Resultado de la investigación: Article

7 Citas (Scopus)

Resumen

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.

Idioma originalEnglish
Páginas (desde-hasta)1726-1738
Número de páginas13
PublicaciónMarine Drugs
Volumen13
N.º4
DOI
EstadoPublished - 1 abr 2015

Huella dactilar

Seaweed
Ethylmaleimide
Indomethacin
Prostaglandins
Molecular Structure
Stomach
Nitric Oxide
Ethanol
sargaol
epitaondiol
taondiol
isoepitaondiol
arginine methyl ester

ASJC Scopus subject areas

  • Drug Discovery
  • Medicine(all)

Citar esto

Areche, Carlos ; Benites, Julio ; Cornejo, Alberto ; Ruiz, Lina M. ; García-Beltrán, Olimpo ; Simirgiotis, Mario J. ; Sepúlveda, Beatriz. / Seco-taondiol, an unusual meroterpenoid from the Chilean seaweed Stypopodium flabelliforme and its gastroprotective effect in mouse model. En: Marine Drugs. 2015 ; Vol. 13, N.º 4. pp. 1726-1738.
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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.",
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author = "Carlos Areche and Julio Benites and Alberto Cornejo and Ruiz, {Lina M.} and Olimpo Garc{\'i}a-Beltr{\'a}n and Simirgiotis, {Mario J.} and Beatriz Sep{\'u}lveda",
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Areche, C, Benites, J, Cornejo, A, Ruiz, LM, García-Beltrán, O, Simirgiotis, MJ & Sepúlveda, B 2015, 'Seco-taondiol, an unusual meroterpenoid from the Chilean seaweed Stypopodium flabelliforme and its gastroprotective effect in mouse model', Marine Drugs, vol. 13, n.º 4, pp. 1726-1738. https://doi.org/10.3390/md13041726

Seco-taondiol, an unusual meroterpenoid from the Chilean seaweed Stypopodium flabelliforme and its gastroprotective effect in mouse model. / Areche, Carlos; Benites, Julio; Cornejo, Alberto; Ruiz, Lina M.; García-Beltrán, Olimpo; Simirgiotis, Mario J.; Sepúlveda, Beatriz.

En: Marine Drugs, Vol. 13, N.º 4, 01.04.2015, p. 1726-1738.

Resultado de la investigación: Article

TY - JOUR

T1 - Seco-taondiol, an unusual meroterpenoid from the Chilean seaweed Stypopodium flabelliforme and its gastroprotective effect in mouse model

AU - Areche, Carlos

AU - Benites, Julio

AU - Cornejo, Alberto

AU - Ruiz, Lina M.

AU - García-Beltrán, Olimpo

AU - Simirgiotis, Mario J.

AU - Sepúlveda, Beatriz

PY - 2015/4/1

Y1 - 2015/4/1

N2 - 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.

AB - 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.

KW - Gastric ulcer

KW - Gastroprotective

KW - Meroditerpenoids

KW - Seaweed

KW - Stypopodium flabelliforme

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U2 - 10.3390/md13041726

DO - 10.3390/md13041726

M3 - Article

VL - 13

SP - 1726

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JO - Marine Drugs

JF - Marine Drugs

SN - 1660-3397

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