Presentation Title

The structure determination of rhamnocrocin, a novel metabolite from Rhamnus crocea, the spiny redberry plant

Faculty Mentor

Jacqueline Trischman

Start Date

23-11-2019 10:45 AM

End Date

23-11-2019 11:30 AM

Location

240

Session

poster 4

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

The Hermes Copper butterfly (Lycaena hermes), a native to Southern California and Mexico, lays its eggs on a plant known as the spiny redberry plant (Rhamnus crocea). However, the butterfly does not lay eggs on all spiny redberry plants inside of its known habitat, rather it lays them on a selective stretch of plants. Unfortunately, due to the recent California wildfires and the selectivity of where they lay their eggs, the species is considered vulnerable. In this study, we hoped to determine a connection between regions of redberry plants where eggs are laid and the chemistry of the plants in that region. We collected 60 samples from regions where they lay eggs and where they don’t, then analyzed the samples using Liquid Chromatography-Mass Spectrometry (LC-MS). A large amount of spiny redberry leaves from several plants was dried and extracted to help discover which compounds might be produced at differing levels between the two groups. A High-Performance Liquid Chromatography (HPLC) method was developed, due to the species never being studied for secondary metabolite production, to fractionate the samples and to identify compounds from the spiny redberry plant. In performing the separations, there was one major component seen, later found through Nuclear Magnetic Resonance (NMR), to be a novel compound that we named rhamnocrocin. The proposed structure includes kaempferol aglycone and three sugar moieties. The structure elucidation of this new compound will be presented and the strategy for the establishment of the stereochemistry of the glycosides will be discussed.

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Nov 23rd, 10:45 AM Nov 23rd, 11:30 AM

The structure determination of rhamnocrocin, a novel metabolite from Rhamnus crocea, the spiny redberry plant

240

The Hermes Copper butterfly (Lycaena hermes), a native to Southern California and Mexico, lays its eggs on a plant known as the spiny redberry plant (Rhamnus crocea). However, the butterfly does not lay eggs on all spiny redberry plants inside of its known habitat, rather it lays them on a selective stretch of plants. Unfortunately, due to the recent California wildfires and the selectivity of where they lay their eggs, the species is considered vulnerable. In this study, we hoped to determine a connection between regions of redberry plants where eggs are laid and the chemistry of the plants in that region. We collected 60 samples from regions where they lay eggs and where they don’t, then analyzed the samples using Liquid Chromatography-Mass Spectrometry (LC-MS). A large amount of spiny redberry leaves from several plants was dried and extracted to help discover which compounds might be produced at differing levels between the two groups. A High-Performance Liquid Chromatography (HPLC) method was developed, due to the species never being studied for secondary metabolite production, to fractionate the samples and to identify compounds from the spiny redberry plant. In performing the separations, there was one major component seen, later found through Nuclear Magnetic Resonance (NMR), to be a novel compound that we named rhamnocrocin. The proposed structure includes kaempferol aglycone and three sugar moieties. The structure elucidation of this new compound will be presented and the strategy for the establishment of the stereochemistry of the glycosides will be discussed.