Hygroline derivatives from Schizanthus tricolor and their anti-trypanosomatid and antiplasmodial activities

Sylvian Cretton; Grégory Genta-Jouve; Marcel Kaiser; Pascal Mäser; Orlando Muñoz; Thomas Bürgi; Muriel Cuendet; Philippe Christen

doi:10.1016/j.phytochem.2021.112957

Hygroline derivatives from Schizanthus tricolor and their anti-trypanosomatid and antiplasmodial activities

Phytochemistry. 2021 Dec:192:112957. doi: 10.1016/j.phytochem.2021.112957. Epub 2021 Sep 23.

Authors

Sylvian Cretton¹, Grégory Genta-Jouve², Marcel Kaiser³, Pascal Mäser³, Orlando Muñoz⁴, Thomas Bürgi⁵, Muriel Cuendet⁶, Philippe Christen⁶

Affiliations

¹ School of Pharmaceutical Sciences, University of Geneva, 1211, Geneva, 4, Switzerland; Institute of Pharmaceutical Sciences of Western Switzerland, University of Geneva, 1211, Geneva, 4, Switzerland. Electronic address: sylvian.cretton@unige.ch.
² Laboratoire Ecologie, Evolution, Interactions des Systèmes Amazoniens (LEEISA), USR 3456, Université De Guyane, CNRS Guyane, 97300, Cayenne, French Guyana, France.
³ Swiss Tropical and Public Health Institute, 4002, Basel, Switzerland; University of Basel, 4003, Basel, Switzerland.
⁴ Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile.
⁵ Department of Physical Chemistry, University of Geneva, 1211, Geneva, 4, Switzerland.
⁶ School of Pharmaceutical Sciences, University of Geneva, 1211, Geneva, 4, Switzerland; Institute of Pharmaceutical Sciences of Western Switzerland, University of Geneva, 1211, Geneva, 4, Switzerland.

PMID: 34563977
DOI: 10.1016/j.phytochem.2021.112957

Abstract

Chemical investigation of the alkaloid extract of the aerial parts of Schizanthus tricolor led to the targeted isolation of 26 hygroline derivatives of which 20 were fully characterized. They have not yet been described in the literature and their structures were established by 1D and 2D NMR, UV and IR spectroscopy, and HRESIMS. The configuration was determined by Gauge-Independent Atomic Orbital NMR chemical shift calculations supported by the advanced statistical method DP4 plus, vibrational circular dichroism, and measurement of optical rotation. Their anti-trypanosomatid, antiplasmodial and cytotoxic activities were measured. Several compounds exhibited low micromolar activity against Plasmodium falciparum. None of the identified molecules was cytotoxic.

Keywords: Antiparasitic activity; Hygroline derivatives; Pyrrolidine alkaloids; Schizanthus tricolor; Solanaceae.

MeSH terms

Alkaloids*
Antimalarials* / pharmacology
Molecular Structure
Plasmodium falciparum
Pyrrolidines
Solanaceae*

Substances

Alkaloids
Antimalarials
Pyrrolidines
pseudohygroline