Total synthesis and antiplasmodial activity of pohlianin C and analogues

Aggie Lawer; Jonathan Tai; Katrina A Jolliffe; Sabine Fletcher; Vicky M Avery; Luke Hunter

doi:10.1016/j.bmcl.2014.04.071

Total synthesis and antiplasmodial activity of pohlianin C and analogues

Bioorg Med Chem Lett. 2014 Jun 15;24(12):2645-7. doi: 10.1016/j.bmcl.2014.04.071. Epub 2014 Apr 29.

Authors

Aggie Lawer¹, Jonathan Tai², Katrina A Jolliffe², Sabine Fletcher³, Vicky M Avery³, Luke Hunter⁴

Affiliations

¹ School of Chemistry, UNSW Australia, Sydney, NSW 2052, Australia.
² School of Chemistry, The University of Sydney, NSW 2006, Australia.
³ Eskitis Institute for Drug Discovery, Griffith University, Nathan, QLD 4111, Australia.
⁴ School of Chemistry, UNSW Australia, Sydney, NSW 2052, Australia; School of Chemistry, The University of Sydney, NSW 2006, Australia. Electronic address: l.hunter@unsw.edu.au.

PMID: 24813731
DOI: 10.1016/j.bmcl.2014.04.071

Abstract

The first synthesis of the glycine-rich cyclic octapeptide pohlianin C is reported, confirming the structure of this natural product. Screening against Plasmodium falciparum reveals moderate antiplasmodial activity, consistent with data obtained from the natural sample. In addition, the synthesis of three analogues reveals that the antiplasmodial activity of pohlianin C can be preserved or increased with simplified structures.

Keywords: Cyclic peptide; Jatropha; Malaria; Natural product; Pohlianin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antimalarials / chemical synthesis*
Antimalarials / pharmacology*
Inhibitory Concentration 50
Molecular Structure
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Peptides, Cyclic / pharmacology*
Plasmodium falciparum / drug effects*

Substances

Antimalarials
Peptides, Cyclic
pohlianin C