Unveiling the power of nature: Investigating the chemical composition of a medicinal plant Restricted; Files Only

Xu, Yixin (Spring 2019)

Permanent URL: https://etd.library.emory.edu/concern/etds/4t64gp08q?locale=en
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Abstract

The fruit part of Carya tomentosa has a rich history as an important medicine to many Native American tribes. The Quave Research Group has found that the methanolic extract of immature fruits of Carya tomentosa (CQ-640) has a half maximal effective concentration (EC50) =5.5±2.2 μg/mL for growth inhibition of the Zika virus Puerto Rico strain PRVABC59 and a cytotoxicity concentration 50% (CC50) >20 μg/mL. This study focuses on the development of separation and analytical methods for investigating the chemical composition of the immature fruit part of Carya tomentosa. An efficient fractionation process was developed using the Amberlite XAD-2 resin packing and a gradient mobile phase of deionized (DI) H2O and methanol, generating five fractions in total and giving a total recovery yield of 93.41%. A High-Performance Liquid Chromatography (HPLC) method was developed using a 4.6*150mm Agilent ZORBAX SB-Phenyl column and a solvent system of 0.1% formic acid in H2O and 0.1% formic acid in methanol. This method was applied to Liquid Chromatography- Mass Spectroscopy (LC-MS) runs and several putative structural matches were found under the negative mode FTMS spectrums: peak 1 detected in 640D-F1 with a retention time of 27.49 minutes has a mass to charge (m/z) ratio of 577.1379 and the generated molecular formula is C30 H25O12 -( Δ ppm =1.8), which matches up with the mass of procyanidin B1, B2, B3, B4, B6, B8 and proanthocyanidin B5, B7; peak 3 detected in the spectrum of 640D-F2 with a retention time of 18.81 minutes has a m/z ratio of 575.1216 and the generated molecular formula is C30H23O12 - (Δ ppm =3.6), which matches up with the mass of (+)-proanthocyanidin A2; peak 6 detected in the spectrum of 640D-F5 with a retention time of 41.61 minutes has a m/z ratio of 865.1988 and the generated molecular formula is C45 H37 O18 - (Δ ppm =0.27), which matches up with the mass of procyanidin C1 and C2; peak7 detected in the spectrum of 640D-F5 with a retention time of 26.27 minutes has a m/z ratio of 447.0953 and the generated molecular formula is C21 H19 O11 - (Δ ppm =2.0), which matches up with the mass of kaempferol 3-galactoside.

Table of Contents

1) Introduction

1.1) Prevailing Worldwide Zika Virus Infection……………………………………………………………………….1

1.2) Plant Second Metabolites as Source of Finding Novel Bioactive Chemicals…………………….2

1.3) Ethnobotanical Approach to Drug Discovery against ZIKV Infection………………………………..3

1.4) Project Aims and Research Questions…………………………………………………………………………..…4

2) Literature Review

2.1) Chemical Profile Investigation on Carya tomentosa and its Relative Species……………………5

2.2) Bioactivity of Phytochemicals Found in Related Species of Carya tomentosa………………….5

2.3) Biological Assessment of the Anti-ZIKV Potential of Carya tomentosa……………………………..6

3) Materials and Methods

3.1) Experimental Overview……………………………………………………………………………………………………8

3.2) Fractionation Method Development……………………………………………………………………………..10

3.3) HPLC Method Development………………………………………………………………………………………….13

3.4) LC-MS Method Development………………………………………………………………………………………..18

4) Results and Discussion

4.1) Fractionation Method Development Results………………………………………………………………...19

4.2) HPLC Method Development Results………………………………………………………………………………24

4.3) LC-MS Results and Putative Structure Analysis………………………………………………………………29

5) Conclusion………………………………………………………………………………………………………………….……….41

References………………………………………………………………………………………………………………….…………..43

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