Bioassay-Guided Isolation and Structure Elucidation of Fungicidal and Herbicidal Compounds from Ambrosia salsola (Asteraceae)

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Wilmer H PereraStephen O Duke

Abstract

The discovery of potent natural and ecofriendly pesticides is one of the focuses of the agrochemical industry, and plant species are a source of many potentially active compounds. We describe the bioassay-guided isolation of antifungal and phytotoxic compounds from the ethyl acetate extract of Ambrosia salsola twigs and leaves. With this methodology, we isolated and identified twelve compounds (four chalcones, six flavonols and two pseudoguaianolide sesquiterpene lactones). Three new chalcones were elucidated as (S)-β-Hydroxy-2',3,4,6'-tetrahydroxy-5-methoxydihydrochalcone (salsolol A), (S)-β-Hydroxy-2',4,4',6'-tetrahydroxy-3-methoxydihydrochalcone (salsolol B), and (R)-α, (R)-β-Dihydroxy-2',3,4,4',6'- pentahydroxydihydrochalcone (salsolol C) together with nine known compounds: balanochalcone, six quercetin derivatives, confertin, and neoambrosin. Chemical structures were determined based on comprehensive direct analysis in real time-high resolution mass spectrometry (HR-DART-MS), as well as 1D and 2D NMR experiments: Cosy Double Quantum Filter (DQFCOSY), Heteronuclear Multiple Quantum Coherence (HMQC) and Heteronuclear Multiple Bond Coherence (HMBC), and the absolute configurations of the chalcones were confirmed by CD spectra...Continue Reading

References

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Citations

Aug 29, 2019·Chemistry & Biodiversity·Wenjun WeiKun Gao

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Methods Mentioned

BETA
NMR
circular dichroism
X-ray

Software Mentioned

SHELXS
LemnaMiner
Lemnatec Scanalyzer
SHELXL
97
LemnaLauncher
R Studio
DQFCOSY

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