A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf

Fitoterapia

Volume 106, October 2015, Pages 7–11

• Gustavo da Silva^a,
• Ana Martinho^c,
• Raquel González Soengas^b,
• Ana Paula Duarte^c,
• Rita Serrano^a,
• Elsa Teixeira Gomes^a,
• Olga Silva^{a, ,}

doi:10.1016/j.fitote.2015.07.020

Get rights and content

---

Abstract

The isolation and structural elucidation of a macrocyclic alkaloid, characterized by the presence of a 13-membered macrolactam ring containing a spermidine unit N-linked to a benzoyl group is hereby reported. The structure of this previously unknown spermidine alkaloid isolated from Gymnosporia arenicola (Celastraceae) leaves has been elucidated by ¹H and ¹³C NMR spectroscopy (including bidimensional analysis) and further characterized by high-resolution mass spectrometry and polarimetry. A route for the biosynthesis of this new bioactive macrocycle is proposed and the cytotoxicity of the compound was evaluated against two ATCC cell lines – one normal-derived (MCF10A) and one cancer-derived cell line (MCF7) – using the MTT assay. The alkaloid revealed to be non-cytotoxic against both cell lines. The IC₅₀ values from the cells were also determined.

---

Graphical abstract

Keywords

• Gymnosporia arenicola;
• Celastraceae;
• Macrolactam ring;
• Spermidine alkaloid;
• Structural characterization

Corresponding author.

Copyright © 2015 Elsevier B.V. All rights reserved.