Antitumoral potential of carbamidocyclophanes and carbamidocylindrofridin A isolated from the cyanobacterium Cylindrospermum stagnale BEA 0605B

Víctor Tena Pérez; Luis Apaza Ticona; Alfredo H Cabanillas; Santiago Maderuelo Corral; Josefina Perles; Diego Fernando Rosero Valencia; Antera Martel Quintana; Montserrat Ortega Domenech; Ángel Rumbero Sánchez

doi:10.1016/j.phytochem.2020.112529

Antitumoral potential of carbamidocyclophanes and carbamidocylindrofridin A isolated from the cyanobacterium Cylindrospermum stagnale BEA 0605B

Phytochemistry. 2020 Dec:180:112529. doi: 10.1016/j.phytochem.2020.112529. Epub 2020 Oct 5.

Authors

Víctor Tena Pérez¹, Luis Apaza Ticona², Alfredo H Cabanillas¹, Santiago Maderuelo Corral³, Josefina Perles⁴, Diego Fernando Rosero Valencia³, Antera Martel Quintana⁵, Montserrat Ortega Domenech⁶, Ángel Rumbero Sánchez¹

Affiliations

¹ Department of Organic Chemistry, Faculty of Sciences, University Autónoma of Madrid, Cantoblanco, 28049, Madrid, Spain.
² Department of Organic Chemistry, Faculty of Sciences, University Autónoma of Madrid, Cantoblanco, 28049, Madrid, Spain; Department of Pharmacology, Pharmacognosy and Botany, Faculty of Pharmacy, University Complutense of Madrid, Ciudad Universitaria s/n, 28040, Madrid, Spain. Electronic address: luis.apaza@uam.es.
³ Valoralia I más D SLU, Tres Cantos, 28760, Madrid, Spain.
⁴ Single Crystal X-ray Diffraction Laboratory, Interdepartmental Research Service (SIdI), University Autónoma of Madrid, Cantoblanco, 28049, Madrid, Spain.
⁵ Spanish Algae Bank, University of Las Palmas of Gran Canaria, 35214, Telde, Las Palmas, Canary Islands, Spain.
⁶ Valoralia I más D SLU, Tres Cantos, 28760, Madrid, Spain. Electronic address: montsetaod@gmail.com.

PMID: 33032099
DOI: 10.1016/j.phytochem.2020.112529

Abstract

Three carbamidocyclophanes, A, F and V, and carbamidocylindrofridin A were isolated from the cultured freshwater cyanobacterium Cylindrospermum stagnale, collected in the Canary Islands. The chemical structures of these compounds were elucidated through NMR, HRMS and ECD spectroscopy. The absolute configuration of carbamidocyclophane A was confirmed using X-ray-diffraction. All compounds showed apoptotic capacity against the SK-MEL-1, SK-MEL-28 and SK-MEL-31 tumour cells. Carbamidocylindrofridin A had the highest anti-tumour potential, with an IC₅₀ of 1 ± 0.3 μM in the SK-MEL-1 cell line.

Keywords: Anti-tumour; Carbamidocyclophane; Carbamidocylindrofridin; Cyanobacterium; Cylindrospermum stagnale; Nostocaceae.

MeSH terms

Cell Line, Tumor
Cyanobacteria*
Magnetic Resonance Spectroscopy
Spain

Supplementary concepts

Cylindrospermum stagnale