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Effect of guaianolides in the meiosis reinitiation of amphibian oocytes

Published online by Cambridge University Press:  03 November 2016

J. Zapata-Martínez ,
G. Sánchez-Toranzo ,
F. Chaín ,
C.A.N. Catalán  and
M.I. Bühler
J. Zapata-Martínez*
Affiliation:
Departamento de Biología del Desarrollo, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Chacabuco 461, San Miguel de Tucumán, Argentina.
G. Sánchez-Toranzo
Affiliation:
Departamento de Biología del Desarrollo, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Chacabuco 461, San Miguel de Tucumán, Argentina.
F. Chaín
Affiliation:
INSIBIO-CONICET, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Chacabuco 461, San Miguel de Tucumán, Tucumán, Argentina.
C.A.N. Catalán
Affiliation:
INQUINOA-CONICET, Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, San Miguel de Tucumán, Argentina.
M.I. Bühler
Affiliation:
Departamento de Biología del Desarrollo, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Chacabuco 461, San Miguel de Tucumán, Argentina.
*
All correspondence to: José Zapata-Martínez. Departamento de Biología del Desarrollo, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Chacabuco 461, San Miguel de Tucumán (T4000INI), Argentina. Fax: +54 381 4248025. E-mail: [email protected]
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Summary

Sesquiterpene lactones (STLs) are a large and structurally diverse group of plant metabolites generally found in the Asteraceae family. STLs exhibit a wide spectrum of biological activities and it is generally accepted that their major mechanism of action is the alkylation of the thiol groups of biological molecules. The guaianolides is one of various groups of STLs. Anti-tumour and anti-migraine effects, an allergenic agent, an inhibitor of smooth muscle cells and of meristematic cell proliferation are only a few of the most commonly reported activities of STLs. In amphibians, fully grown ovarian oocytes are arrested at the beginning of meiosis I. Under stimulus with progesterone, this meiotic arrest is released and meiosis progresses to metaphase II, a process known as oocyte maturation. There are previous records of the inhibitory effect of dehydroleucodin (DhL), a guaianolide lactone, on the progression of meiosis. It has been also shown that DhL and its 11,13-dihydroderivative (2H-DhL; a mixture of epimers at C-11) act as blockers of the resumption of meiosis in fully grown ovarian oocytes from the amphibian Rhinella arenarum (formerly classified as Bufo arenarum). The aim of this study was to analyze the effect of four closely related guaianolides, i.e., DhL, achillin, desacetoxymatricarin and estafietin as possible inhibitors of meiosis in oocytes of amphibians in vitro and discuss some structure–activity relationships. It was found that the inhibitory effect on meiosis resumption is greater when the lactone has two potentially reactive centres, either a α,β–α′,β′-diunsaturated cyclopentanone moiety or an epoxide group plus an exo-methylene-γ-lactone function.

Keywords

AmphibianGuaianolidesMeiosisOocyte maturationSesquiterpene lactones
Type
Research Article
Information
Zygote , Volume 25 , Issue 1 , February 2017 , pp. 10 - 16
Copyright
Copyright © Cambridge University Press 2016 

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