Phytotoxic cis-cinnamoyl glucosides from Spiraea thunbergii

Syuntaro Hiradate; Sayaka Morita; Hajime Sugie; Yoshiharu Fujii; Jiro Harada

doi:10.1016/j.phytochem.2004.01.010

Phytotoxic cis-cinnamoyl glucosides from Spiraea thunbergii

Phytochemistry. 2004 Mar;65(6):731-9. doi: 10.1016/j.phytochem.2004.01.010.

Authors

Syuntaro Hiradate¹, Sayaka Morita, Hajime Sugie, Yoshiharu Fujii, Jiro Harada

Affiliation

¹ Department of Biological Safety Science, National Institute for Agro-Environmental Sciences, 3-1-3 Kan-nondai, Tsukuba, Ibaraki 305-8604, Japan. hiradate@affrc.go.jp

PMID: 15016569
DOI: 10.1016/j.phytochem.2004.01.010

Abstract

Spiraea thunbergii Sieb. was found to contain 1-O-cis-cinnamoyl-beta-D-glucopyranose and 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-cis-cinnamoyl-beta-D-glucopyranose as major plant growth inhibitory constituents along with related compounds of lower phytotoxicity including 6-O-(trans-cinnamoyl)-1-O-(4"-hydroxy-3"-methyl-furan-2"-one)-beta-D-glucopyranose, 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-trans-cinnamoyl-beta-D-glucopyranose, and 1-O-trans-cinnamoyl-beta-D-glucopyranose. The former three compounds were cinnamoyl glucosides.

MeSH terms

Biological Assay
Cinnamates / chemistry*
Cinnamates / pharmacology*
Glucosides / chemistry*
Glucosides / pharmacology*
Lactuca / drug effects
Lactuca / growth & development
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Extracts / chemistry
Plant Growth Regulators / chemistry*
Plant Growth Regulators / pharmacology*
Plant Leaves / chemistry
Plant Roots / drug effects
Plant Roots / growth & development
Spiraea / chemistry*
Stereoisomerism

Substances

Cinnamates
Glucosides
Plant Extracts
Plant Growth Regulators