Neolignans from Aristolochia elegans as antagonists of the neurotropic effect of scorpion venom

Alejandro Zamilpa, Rodolfo Abarca-Vargas, Elsa Ventura-Zapata, Lidia Osuna-Torres, Miguel A. Zavala, Maribel Herrera-Ruiz, Enrique Jiménez-Ferrer, Manasés González-Cortazar

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Ethnopharmacological relevance: The high frequency of poisoning by sting or bite from venomous animals has begun to be a serious public health problem in Mexico where scorpion sting is the most common. Because of this, there is the need to seek active substances in plant species with an antagonistic effect against neurotropic activity of scorpion venom. The aim of this work was to demonstrate which of the compounds contained in the n-hexane extract from Aristolochia elegans roots display activity against scorpion venom.

Material and methods: Antagonist activity displayed by extract, fractions and isolated compounds obtained from Aristolochia elegans was guided by the inhibition of smooth muscle contraction induced by scorpion venom (Centruroides limpidus limpidus) in a model of isolated guinea pig ileum. The neolignans obtained from this extract were isolated and analyzed by chromatographic methods including 1-IPLC. The chemical characterization of these compounds was performed by the analysis of 1f4 and 13C NMR spectra.

Results: The bio-guided chromatographic fractionation allowed us to isolate 4 known neolignans: Eupomatenoid-7 (1), licarin A (2), licarin B (3), eupomatenoid-1 (4) and other new neolignan which was characterized as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-al1-7-methoxy- benzo FbI furan (5). This compound was named as eleganal. Compounds 1 and 2 were purified from the most active fraction AeF3 (EC50 of 149.9 ig!mL Em of 65.66%). A dosesresponse analysis of eupomatenoid-7(1) and licarin A(2) allowed us to establish EC50 values (65.96 ig!mL and 51.96 ig!mL) respectively.

Conclusions: The antagonistic effect against Centuroides limpidus limpidus scorpion venom displayed by the n-hexane extract fromAristolochia elegans roots is due to the presence of neolignans 12 contained in the fraction AeF3. Chemical analysis of fraction AeF2 allowed the isolation of a new compound which was identified as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-ali-7-methoxy-benzoFbi furan (5), denominated as eleganal. 2014 Elsevier Ireland Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)156-160
Number of pages5
JournalJournal of Ethnopharmacology
Volume157
DOIs
StatePublished - 18 Nov 2014

Fingerprint

Aristolochia
Scorpion Venoms
Lignans
Scorpion Stings
Bites and Stings
Muscle Contraction
Mexico
Ileum
Ireland
Poisoning
Smooth Muscle
Guinea Pigs
Public Health

Keywords

  • Aristolochia elegans
  • Aristolochiaceae
  • Centruroides limpidus limpidus
  • neolignans
  • scorpion venom

Cite this

Zamilpa, A., Abarca-Vargas, R., Ventura-Zapata, E., Osuna-Torres, L., Zavala, M. A., Herrera-Ruiz, M., ... González-Cortazar, M. (2014). Neolignans from Aristolochia elegans as antagonists of the neurotropic effect of scorpion venom. Journal of Ethnopharmacology, 157, 156-160. https://doi.org/10.1016/j.jep.2014.08.045
Zamilpa, Alejandro ; Abarca-Vargas, Rodolfo ; Ventura-Zapata, Elsa ; Osuna-Torres, Lidia ; Zavala, Miguel A. ; Herrera-Ruiz, Maribel ; Jiménez-Ferrer, Enrique ; González-Cortazar, Manasés. / Neolignans from Aristolochia elegans as antagonists of the neurotropic effect of scorpion venom. In: Journal of Ethnopharmacology. 2014 ; Vol. 157. pp. 156-160.
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title = "Neolignans from Aristolochia elegans as antagonists of the neurotropic effect of scorpion venom",
abstract = "Ethnopharmacological relevance: The high frequency of poisoning by sting or bite from venomous animals has begun to be a serious public health problem in Mexico where scorpion sting is the most common. Because of this, there is the need to seek active substances in plant species with an antagonistic effect against neurotropic activity of scorpion venom. The aim of this work was to demonstrate which of the compounds contained in the n-hexane extract from Aristolochia elegans roots display activity against scorpion venom.Material and methods: Antagonist activity displayed by extract, fractions and isolated compounds obtained from Aristolochia elegans was guided by the inhibition of smooth muscle contraction induced by scorpion venom (Centruroides limpidus limpidus) in a model of isolated guinea pig ileum. The neolignans obtained from this extract were isolated and analyzed by chromatographic methods including 1-IPLC. The chemical characterization of these compounds was performed by the analysis of 1f4 and 13C NMR spectra.Results: The bio-guided chromatographic fractionation allowed us to isolate 4 known neolignans: Eupomatenoid-7 (1), licarin A (2), licarin B (3), eupomatenoid-1 (4) and other new neolignan which was characterized as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-al1-7-methoxy- benzo FbI furan (5). This compound was named as eleganal. Compounds 1 and 2 were purified from the most active fraction AeF3 (EC50 of 149.9 ig!mL Em of 65.66{\%}). A dosesresponse analysis of eupomatenoid-7(1) and licarin A(2) allowed us to establish EC50 values (65.96 ig!mL and 51.96 ig!mL) respectively.Conclusions: The antagonistic effect against Centuroides limpidus limpidus scorpion venom displayed by the n-hexane extract fromAristolochia elegans roots is due to the presence of neolignans 12 contained in the fraction AeF3. Chemical analysis of fraction AeF2 allowed the isolation of a new compound which was identified as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-ali-7-methoxy-benzoFbi furan (5), denominated as eleganal. 2014 Elsevier Ireland Ltd. All rights reserved.",
keywords = "Aristolochia elegans, Aristolochiaceae, Centruroides limpidus limpidus, neolignans, scorpion venom",
author = "Alejandro Zamilpa and Rodolfo Abarca-Vargas and Elsa Ventura-Zapata and Lidia Osuna-Torres and Zavala, {Miguel A.} and Maribel Herrera-Ruiz and Enrique Jim{\'e}nez-Ferrer and Manas{\'e}s Gonz{\'a}lez-Cortazar",
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Zamilpa, A, Abarca-Vargas, R, Ventura-Zapata, E, Osuna-Torres, L, Zavala, MA, Herrera-Ruiz, M, Jiménez-Ferrer, E & González-Cortazar, M 2014, 'Neolignans from Aristolochia elegans as antagonists of the neurotropic effect of scorpion venom', Journal of Ethnopharmacology, vol. 157, pp. 156-160. https://doi.org/10.1016/j.jep.2014.08.045

Neolignans from Aristolochia elegans as antagonists of the neurotropic effect of scorpion venom. / Zamilpa, Alejandro; Abarca-Vargas, Rodolfo; Ventura-Zapata, Elsa; Osuna-Torres, Lidia; Zavala, Miguel A.; Herrera-Ruiz, Maribel; Jiménez-Ferrer, Enrique; González-Cortazar, Manasés.

In: Journal of Ethnopharmacology, Vol. 157, 18.11.2014, p. 156-160.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Neolignans from Aristolochia elegans as antagonists of the neurotropic effect of scorpion venom

AU - Zamilpa, Alejandro

AU - Abarca-Vargas, Rodolfo

AU - Ventura-Zapata, Elsa

AU - Osuna-Torres, Lidia

AU - Zavala, Miguel A.

AU - Herrera-Ruiz, Maribel

AU - Jiménez-Ferrer, Enrique

AU - González-Cortazar, Manasés

PY - 2014/11/18

Y1 - 2014/11/18

N2 - Ethnopharmacological relevance: The high frequency of poisoning by sting or bite from venomous animals has begun to be a serious public health problem in Mexico where scorpion sting is the most common. Because of this, there is the need to seek active substances in plant species with an antagonistic effect against neurotropic activity of scorpion venom. The aim of this work was to demonstrate which of the compounds contained in the n-hexane extract from Aristolochia elegans roots display activity against scorpion venom.Material and methods: Antagonist activity displayed by extract, fractions and isolated compounds obtained from Aristolochia elegans was guided by the inhibition of smooth muscle contraction induced by scorpion venom (Centruroides limpidus limpidus) in a model of isolated guinea pig ileum. The neolignans obtained from this extract were isolated and analyzed by chromatographic methods including 1-IPLC. The chemical characterization of these compounds was performed by the analysis of 1f4 and 13C NMR spectra.Results: The bio-guided chromatographic fractionation allowed us to isolate 4 known neolignans: Eupomatenoid-7 (1), licarin A (2), licarin B (3), eupomatenoid-1 (4) and other new neolignan which was characterized as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-al1-7-methoxy- benzo FbI furan (5). This compound was named as eleganal. Compounds 1 and 2 were purified from the most active fraction AeF3 (EC50 of 149.9 ig!mL Em of 65.66%). A dosesresponse analysis of eupomatenoid-7(1) and licarin A(2) allowed us to establish EC50 values (65.96 ig!mL and 51.96 ig!mL) respectively.Conclusions: The antagonistic effect against Centuroides limpidus limpidus scorpion venom displayed by the n-hexane extract fromAristolochia elegans roots is due to the presence of neolignans 12 contained in the fraction AeF3. Chemical analysis of fraction AeF2 allowed the isolation of a new compound which was identified as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-ali-7-methoxy-benzoFbi furan (5), denominated as eleganal. 2014 Elsevier Ireland Ltd. All rights reserved.

AB - Ethnopharmacological relevance: The high frequency of poisoning by sting or bite from venomous animals has begun to be a serious public health problem in Mexico where scorpion sting is the most common. Because of this, there is the need to seek active substances in plant species with an antagonistic effect against neurotropic activity of scorpion venom. The aim of this work was to demonstrate which of the compounds contained in the n-hexane extract from Aristolochia elegans roots display activity against scorpion venom.Material and methods: Antagonist activity displayed by extract, fractions and isolated compounds obtained from Aristolochia elegans was guided by the inhibition of smooth muscle contraction induced by scorpion venom (Centruroides limpidus limpidus) in a model of isolated guinea pig ileum. The neolignans obtained from this extract were isolated and analyzed by chromatographic methods including 1-IPLC. The chemical characterization of these compounds was performed by the analysis of 1f4 and 13C NMR spectra.Results: The bio-guided chromatographic fractionation allowed us to isolate 4 known neolignans: Eupomatenoid-7 (1), licarin A (2), licarin B (3), eupomatenoid-1 (4) and other new neolignan which was characterized as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-al1-7-methoxy- benzo FbI furan (5). This compound was named as eleganal. Compounds 1 and 2 were purified from the most active fraction AeF3 (EC50 of 149.9 ig!mL Em of 65.66%). A dosesresponse analysis of eupomatenoid-7(1) and licarin A(2) allowed us to establish EC50 values (65.96 ig!mL and 51.96 ig!mL) respectively.Conclusions: The antagonistic effect against Centuroides limpidus limpidus scorpion venom displayed by the n-hexane extract fromAristolochia elegans roots is due to the presence of neolignans 12 contained in the fraction AeF3. Chemical analysis of fraction AeF2 allowed the isolation of a new compound which was identified as 2-(3-hydroxy-4-methoxyphenyl)-3-methyl-5-F(E)-c-propen-y-ali-7-methoxy-benzoFbi furan (5), denominated as eleganal. 2014 Elsevier Ireland Ltd. All rights reserved.

KW - Aristolochia elegans

KW - Aristolochiaceae

KW - Centruroides limpidus limpidus

KW - neolignans

KW - scorpion venom

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JO - Journal of Ethnopharmacology

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SN - 0378-8741

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