Stachyonic Acid: A Dengue Virus Inhibitor from Basilicum polystachyon

Yuen P Tan; Sevan D Houston; Naphak Modhiran; Andrei I Savchenko; Glen M Boyle; Paul R Young; Daniel Watterson; Craig M Williams

doi:10.1002/chem.201900591

Stachyonic Acid: A Dengue Virus Inhibitor from Basilicum polystachyon

Chemistry. 2019 Apr 17;25(22):5664-5667. doi: 10.1002/chem.201900591. Epub 2019 Mar 29.

Authors

Yuen P Tan¹, Sevan D Houston¹, Naphak Modhiran², Andrei I Savchenko¹, Glen M Boyle³, Paul R Young^{1

2}, Daniel Watterson^{1

2}, Craig M Williams¹

Affiliations

¹ School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia.
² Australian Infectious Diseases Research Centre, School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia.
³ QIMR Berghofer Medical Research Institute, PO Royal Brisbane Hospital, Brisbane, 4029, Queensland, Australia.

PMID: 30924209
DOI: 10.1002/chem.201900591

Abstract

Stachyonic acid A, arising from the first in-depth phytochemical investigation of the herb Basilicum polystachyon, was found to display potent inhibitory activity against dengue virus, with limited cytotoxicity. Andrographolide, a known dengue virus inhibitor and closely related labdane-type diterpene, is structurally more complex but displayed poor antiviral activity in the PRNT assay, and increased cytotoxicity in comparison. Furthermore, a Diels-Alder reaction with PTAD identified the active pharmacophore of stachyonic acid to be the conjugated diene.

Keywords: basilicum; dengue; labdane; natural products; viruses.

MeSH terms

Antiviral Agents / chemistry*
Antiviral Agents / pharmacology*
Dengue / drug therapy*
Dengue Virus / drug effects*
Diterpenes / chemistry*
Diterpenes / pharmacology*
Drug Discovery
Humans
Lamiaceae / chemistry
Models, Molecular
Virus Replication / drug effects

Substances

Antiviral Agents
Diterpenes
labdane
stachyonic acid A
andrographolide