Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma

Cen-Pacheco, Francisco; Valerio-Alfaro, Gerardo; Santos-Luna, Dalia; Fernández, José Javier

doi:10.3390/molecules24030554

Open AccessArticle

Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma

by

Francisco Cen-Pacheco

^1,*

,

Gerardo Valerio-Alfaro

²,

Dalia Santos-Luna

^1,2

and

José Javier Fernández

^3,*

¹

Faculty of Bioanalysis, Veracruz University, Iturbide s/n, Veracruz 91700, Mexico

²

Food Research and Development Unit, Tecnológico Nacional de México-I T Veracruz-UNIDA. M.A. de Quevedo 2779, Col. Formando Hogar Veracruz Ver. C.P., Mexico 91860, Mexico

³

Institute of Bio-Organic Chemistry Antonio González, Department of Organic Chemistry, University of La Laguna, Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain

^*

Authors to whom correspondence should be addressed.

Molecules 2019, 24(3), 554; https://doi.org/10.3390/molecules24030554

Submission received: 10 January 2019 / Revised: 28 January 2019 / Accepted: 31 January 2019 / Published: 3 February 2019

(This article belongs to the Collection Bioactive Compounds)

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Abstract

A new cytotoxic cyclononapeptide, sclerin, cyclo(–Dab¹–Ser²–Tyr³–Gly⁴–Thr⁵–Val⁶–Ala⁷– Ile⁸–Pro⁹–) (1), was isolated from the methanol extract of the seeds of Annona scleroderma, together with the known metabolite, cyclosenegalin A, cyclo(–Pro¹–Gly²–Leu³–Ser⁴–Ala⁵–Val⁶–Thr⁷–) (2). The planar structures for the two compounds were established by comprehensive analysis of NMR and ESI-HRMS data, and the absolute stereochemistry was stablished by Marfey’s method. Compound 1 showed moderate cytotoxic activity against the human prostate carcinoma cell line DU-145 at µM concentration.

Keywords: cyclopeptide; cyclononapeptide; cytotoxic compound; Annona

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MDPI and ACS Style

Cen-Pacheco, F.; Valerio-Alfaro, G.; Santos-Luna, D.; Fernández, J.J. Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma. Molecules 2019, 24, 554. https://doi.org/10.3390/molecules24030554

AMA Style

Cen-Pacheco F, Valerio-Alfaro G, Santos-Luna D, Fernández JJ. Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma. Molecules. 2019; 24(3):554. https://doi.org/10.3390/molecules24030554

Chicago/Turabian Style

Cen-Pacheco, Francisco, Gerardo Valerio-Alfaro, Dalia Santos-Luna, and José Javier Fernández. 2019. "Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma" Molecules 24, no. 3: 554. https://doi.org/10.3390/molecules24030554

APA Style

Cen-Pacheco, F., Valerio-Alfaro, G., Santos-Luna, D., & Fernández, J. J. (2019). Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma. Molecules, 24(3), 554. https://doi.org/10.3390/molecules24030554

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Sclerin, a New Cytotoxic Cyclononapeptide from Annona scleroderma

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