Studies in Natural Products Chemistry

,

• Publisher: Elsevier
• Year: 2018
• Print ISBN:
  9780444641793
• eBook ISBN:
  9780444641809
• Topic: Physical Sciences
• Subtopic: Organic Chemistry

Studies in Natural Products Chemistry, Volume 59, the latest in the series, covers the synthesis, or testing and recording, of the medicinal properties of natural products, providing cutting-edge accounts of fascinating developments in the isolation, structure elucidation, synthesis, biosynthesis and pharmacology of a diverse array of bioactive natural products. Natural products in the plant and animal kingdom offer a huge diversity of chemical structures that are the result of biosynthetic processes that have been modulated over the millennia through genetic effects. With the rapid developments in spectroscopic techniques and accompanying advances in high-throughput screening techniques, this book is a welcomed resource. - Focuses on the chemistry of bioactive natural products - Contains contributions by leading authorities in the field - Presents sources of new pharmacophores

Chapter 1

Metabolic Screening of Wine (Grapevine) Resveratrol

Tomáš Řezanka*^,1; Irena Kolouchová^†; Lucia Gharwalová^†; Karel Sigler* ^* Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague, Czech Republic
^† Department of Biotechnology, Institute of Chemical Technology Prague, Prague, Czech Republic
¹ Corresponding author: email address: [email protected]

Abstract

Resveratrol (3,4,5-trihydroxystilbene) is a naturally occurring phytoalexin produced by some plants classified as spermatophytes in response to biotic and abiotic stress, e.g., pathogenesis, UV radiation, ozone exposure, or mechanical damage. Resveratrol and its natural glycoside derivatives have been found in over 72 plants, including grapevine, peanuts, cranberries, strawberries, teas, mulberries, peanuts, and many of which are used in human nutrition.

In this chapter, we focus on various approaches to mass spectrometry (MS) useful in the detection of stilbene derivatives, predominantly resveratrol, both in conjunction with chromatography, i.e., the use of GC/MS, HPLC/MS, and the shotgun analysis. In the case of MS, soft ionization techniques such as electrospray ionization, atmospheric pressure chemical ionization, or matrix-assisted laser desorption are often used, especially in combination with high-resolution MS and also single ion monitoring, neutral loss scan, ion scan precursor, etc. The chapter also includes illustrative examples of some applications. It should be noted that the use of MS in metabolomics aids in the discovery of both new stilbenes of biomedical importance and for clarifying the mechanisms of their action in complex matrices, though it is only at the very beginning of its development.

Keywords

Resveratrol; Polyphenols; Grapevine; Mass spectrometry; Metabolomics

Abbreviations

3-O-GT 3-O-β-glycosyltransferase

4CL 4-coumarate-CoA ligase

APCI atmospheric pressure chemical ionization

API atmospheric pressure ionization

APPI atmospheric pressure photoionization

BTH benzothiadiazole

C4H cinnamate-4-hydroxylase

CE capillary electrophoresis

CZE capillary zone electrophoresis

DAD diode array detector

DMSO dimethyl sulfoxide

ECD electrochemical detector

EI electron impact

ESI electrospray ionization

FLD fluorescence detector

FT Fourier transform

GC gas chromatography

HIV human immunodeficiency virus

HPLC high-performance liquid chromatography

HR high resolution

ICR ion cyclotron resonance

iNOS inducible nitric oxide synthase

LDL low density lipoproteins

LOD limit of detection

LOQ limit of quantification

MALDI matrix-assisted laser desorption-ionization

MeJA methyl jasmonate

MEKC micellar electrokinetic chromatography

MISPE molecular imprinted solid-phase extraction

MRM multiple reaction monitoring

MS mass spectrometry

PAL phenylalanine ammonia-lyase

PER peroxidase

PGE2 prostaglandin E2

QTOF quadrupole time-of-flight

RP reverse phase

SIM selective ion monitoring

SPE solid-phase extraction

STS stilbene synthase

TAL tyrosine ammonia-lyase

TLC thin-layer chromatography

UHPLC ultra-high-performance liquid chromatography

UV ultraviolet

Vis visible

Introduction

Plants produce millions of low molecular compounds, most of which are products of secondary metab...

Table of contents

• Cover image
• Title page
• Table of Contents
• Copyright
• Contributors
• Preface
• Chapter 1: Metabolic Screening of Wine (Grapevine) Resveratrol
• Chapter 2: Sweet Cherry Phenolic Compounds: Identification, Characterization, and Health Benefits
• Chapter 3: Phenolic Compounds: A Good Choice Against Chronic Degenerative Diseases
• Chapter 4: Recent Developments in the Quest for Novel Microbial Natural Products
• Chapter 5: Mycosporine-Like Amino Acids as Multifunctional Secondary Metabolites in Cyanobacteria: From Biochemical to Application Aspects
• Chapter 6: Basic and Clinical Studies With Marine LipoFishins and Vegetal Favalins in Neurodegeneration and Age-Related Disorders
• Chapter 7: Terpenoids as Emerging Therapeutic Agents: Cellular Targets and Mechanisms of Action against Protozoan Parasites
• Chapter 8: Bioactive Sesquiterpene Coumarins From Plants
• Chapter 9: Assessing Herb–Drug Interactions of Herbal Products With Therapeutic Agents for Metabolic Diseases: Analytical and Regulatory Perspectives
• Chapter 10: Natural Products for the Management of Diabetes
• Chapter 11: Limonoids: Structure–Activity Relationship Studies and Anticancer Properties
• Chapter 12: Anticancer Potential of Flavonoids: Chemistry, Biological Activities, and Future Perspectives
• Chapter 13: Chemistry and Biology of Salicyl-Capped Siderophores
• Chapter 14: Southern Brazilian Hypericum Species, Promising Sources of Bioactive Metabolites
• Chapter 15: Citrus Polymethoxyflavones: Biofunctional Molecules of Therapeutic Interest
• Index