Exploring the molecular mechanism of karrikins and strigolactones

Adrian Scaffidi; Mark T Waters; Charles S Bond; Kingsley W Dixon; Steven M Smith; Emilio L Ghisalberti; Gavin R Flematti

doi:10.1016/j.bmcl.2012.04.016

Exploring the molecular mechanism of karrikins and strigolactones

Bioorg Med Chem Lett. 2012 Jun 1;22(11):3743-6. doi: 10.1016/j.bmcl.2012.04.016. Epub 2012 Apr 10.

Authors

Adrian Scaffidi¹, Mark T Waters, Charles S Bond, Kingsley W Dixon, Steven M Smith, Emilio L Ghisalberti, Gavin R Flematti

Affiliation

¹ School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009, Australia. adrian.scaffidi@uwa.edu.au

PMID: 22542018
DOI: 10.1016/j.bmcl.2012.04.016

Abstract

Karrikins and strigolactones are novel plant growth regulators that contain similar molecular features, but very little is known about how they elicit responses in plants. A tentative molecular mechanism has previously been proposed involving a Michael-type addition for both compounds. Through structure-activity studies with karrikins, we now propose an alternative mechanism for karrikin and strigolactone mode of action that involves hydrolysis of the butenolide ring.

Publication types

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

MeSH terms

Binding Sites
Computer Simulation
Furans / chemistry
Furans / pharmacology*
Germination / drug effects
Lactones / chemistry
Lactones / metabolism*
Plant Growth Regulators / chemistry
Plant Growth Regulators / pharmacology*
Plant Proteins / chemistry
Plant Proteins / metabolism
Protein Structure, Tertiary
Pyrans / chemistry
Pyrans / pharmacology*
Seeds / metabolism
Solanum / growth & development
Solanum / metabolism
Structure-Activity Relationship

Substances

3-methyl-2H-furo(2,3-c)pyran-2-one
Furans
GR24 compound
Lactones
Plant Growth Regulators
Plant Proteins
Pyrans