Squamins C-F, four cyclopeptides from the seeds of Annona globiflora

Javier Sosa-Rueda; Vanihamin Domínguez-Meléndez; Araceli Ortiz-Celiseo; Fernando C López-Fentanes; Cristina Cuadrado; José J Fernández; Antonio Hernández Daranas; Francisco Cen-Pacheco

doi:10.1016/j.phytochem.2021.112839

Squamins C-F, four cyclopeptides from the seeds of Annona globiflora

Phytochemistry. 2022 Feb:194:112839. doi: 10.1016/j.phytochem.2021.112839. Epub 2021 Jul 28.

Authors

Javier Sosa-Rueda¹, Vanihamin Domínguez-Meléndez², Araceli Ortiz-Celiseo³, Fernando C López-Fentanes¹, Cristina Cuadrado⁴, José J Fernández⁵, Antonio Hernández Daranas⁴, Francisco Cen-Pacheco⁶

Affiliations

¹ Facultad de Bioanálisis, Veracruz University, Iturbide s/n, 91700, Veracruz, Ver., Mexico.
² Centro de Estudios y Servicios en Salud, Veracruz University, Iturbide s/n, 91700, Veracruz, Ver., Mexico.
³ Facultad de Bioanálisis, Veracruz University, Iturbide s/n, 91700, Veracruz, Ver., Mexico; Instituto Tecnológico de Orizaba, Tecnológico Nacional de México Oriente 9, Emiliano Zapata, 94320, Orizaba, Ver., Mexico.
⁴ Instituto de Productos Naturales y Agrobiología del CSIC (IPNA-CSIC), La Laguna, 38206, Tenerife, Spain.
⁵ Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Departamento de Química Orgánica, University of La Laguna, Av. Astrofísico Francisco Sánchez 2, 38206, Tenerife, Spain.
⁶ Facultad de Bioanálisis, Veracruz University, Iturbide s/n, 91700, Veracruz, Ver., Mexico; Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Departamento de Química Orgánica, University of La Laguna, Av. Astrofísico Francisco Sánchez 2, 38206, Tenerife, Spain. Electronic address: [email protected].

PMID: 34332784
DOI: 10.1016/j.phytochem.2021.112839

Abstract

Four cyclic octapeptides, squamins C-F, were isolated from the seeds of Annona globiflora Schltdl. These compounds share part of their amino acid sequence, -Pro-Met(O)-Tyr-Gly-Thr-, with previously reported squamins A and B. Their structures were determined using NMR spectroscopic techniques together with quantum mechanical calculations (QM-NMR), ESI-HRMS data and a modified version of Marfey's chromatographic method. All compounds showed cytotoxic activity against DU-145 (human prostate cancer) and HeLa (human cervical carcinoma) cell lines. Clearly, A. globiflora is an important source of bioactive molecules, which could promote the sustainable exploitation of this undervalued specie.

Keywords: Annona globiflora Schltdl.; Annonaceae; Cyclopeptides; Cytotoxic activity.

MeSH terms

Amino Acid Sequence
Annona* / chemistry
Antineoplastic Agents, Phytogenic / pharmacology*
HeLa Cells
Humans
Peptides, Cyclic / pharmacology*
Phytochemicals / pharmacology
Seeds / chemistry

Substances

Antineoplastic Agents, Phytogenic
Peptides, Cyclic
Phytochemicals