Recent Advances in Medicinal Chemistry

Volume 2

by

Atta-ur-Rahman, FRS, Muhammad Iqbal Choudhary, George Perry

DOI: 10.2174/97816810817171150201
eISBN: 978-1-68108-171-7, 2015
ISBN: 978-1-68108-172-4
ISSN: 2452-3682 (Print)
ISSN: 2215-0722 (Online)



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Recent advances in Medicinal Chemistry is a book series focused on leading-edge...[view complete introduction]

Table of Contents

Preface

- Pp. i-ii (2)

Atta-ur-Rahman, Muhammad Iqbal Choudhary and George Perry

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List of Contributors

- Pp. iii-iv (2)

Atta-ur-Rahman, Muhammad Iqbal Choudhary and George Perry

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Brief Introduction to Polyphenols, Bioactive Phytochemicals for Human Health

- Pp. 3-9 (7)

Marcello Iriti and Elena M. Varoni

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Analysis and Occurrence of Flavonoids in Foods and Biological Samples

- Pp. 10-58 (49)

Celestino Santos-Buelga, Ana M. González-Paramás, Susana González- Manzano and Montserrat Dueñas

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Therapeutic Potential of Cannabinoids in the Treatment of Neuroinflammation Associated with Parkinson’s Disease

- Pp. 59-75 (17)

Erika B. Villanueva, Jonathan P. Little and Andis Klegeris

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Epipolythiodioxopiperazines from Fungi: Chemistry and Bioactivities

- Pp. 76-106 (31)



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Updated Report on Synthesis and Biological Properties of Oxadiazine-Based Heterocyclic Derivatives

- Pp. 107-143 (37)

Xiufang Cao and Shaoyong Ke

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The Emerging Role of Sunitinib in the Treatment of Advanced Epithelial Thyroid Cancer

- Pp. 144-155 (12)

Giuseppe Pasqualetti, Sergio Ricci, Valeria Calsolaro, Sara Tognini, Antonio Polini and Fabio Monzani

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Considerations about Oxidative Damage on the Electron Transport Chain and the Quality Control of Mitochondrial Function for the Design of Mitochondria-Targeted Antioxidants

- Pp. 156-179 (24)

C. Cortés-Rojo and A.R. Rodríguez-Orozco

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Subject Index

- Pp. 180-185 (6)

Atta-ur-Rahman, Muhammad Iqbal Choudhary and George Perry

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Preface

Vol. 2 of the eBook series “Recent Advances in the Medicinal Chemistry” comprises seven chapters written by the leading experts in the field that provide state-of-the art information about the developments in important selected areas of medicinal chemistry.

Polyphenols, such as carotenoids, glucosinolates, phytosterols, lignins, and flavonoids, are secondary metabolites of plants, abundantly found in fruits, vegetables, cereals, and beverages. Grapes, apple, pear, cherries, berries, dry legumes, tea, and cocoa, and products manufactured from them contain various classes of polyphenols in substantial quantities. Polyphenols have attracted tremendous scientific interest as antioxidants, which can provide protection against the on-set of cancers, cardiovascular diseases, diabetes, osteoporosis, and neurodegenerative disorders. Iriti and Vironi review the current state of knowledge about the biological effects of plant polyphenols relevant to human health in chapter 1.

Among plant polyphenols, flavonoids have special significance because of their anti-oxidant, anti-inflammatory, anti-cancer and neuroprotective properties. Flavonoids are the most common polyphenols in the human diet. Diverse classes of flavonoids are found in natural sources such as parsley, onions, blueberries and other berries, tea, bananas, citrus fruits, Ginkgo biloba, red wine, sea-buckthorns, cocoa extracts, and dark chocolate. In chapter 2, Santos-Bulega et al. have reviewed the various classes of flavonoids, their role in plants, and their health benefits. They have also discussed the various techniques used for optimal extraction and analysis of flavonoids in various biological fluids, and dietary and medicinal plants.

Klegeris et al. have contributed a comprehensive review in chapter 3 on cannabinoids, a class of diverse chemical compounds, which bind to cannabinoid receptors (CB1 and CB2) in the nervous system. Cannabinoids are produced endogenously and obtained from plant sources. The most important cannabinoid is the tetrahydrocannabinol (THC), which is the primary psychoactive compound of Cannabis. Cannabinoids exhibit various biological properties. This chapter is largely focused on neuroprotective properties of cannabinoids, such as inhibition of neuroinflammatory cascades contributing to Parkinson’s diseases and other neurodegenerative disorders. The mechanism of action of synthetic and natural cannabinoids as well as their adverse effects at molecular levels is presented.

In chapter 4 Guo et al. present various aspects of medicinal chemistry related to epipolythiodioxopiperazines (ETPs) which are unique bridged disulfide or polysulfide dioxopiperazine six-membered heterocyclic compounds, found in many fungi. ETPs are known to possess a broad spectrum of biological activities, and have attracted major scientific interest in recent years. This review covers the diverse bacterial sources that produce ETPs, their synthesis, bioactivities and biosynthetic pathways.

Oxadiazines are an important class of heterocyclic derivatives with diverse bioactivities. The Recent advances in the chemistry and biological activities of oxadiazine-based heterocyclic derivatives have been reviewed in chapter 5 by Cao & Ke.

Sunitinib is an anticancer drug, which functions by inhibiting the cellular signalling by targeting multiple receptor tyrosine kinases (RTKs). The drug targets receptors for platelet-derived growth factor(PDGF-Rs) and vascular endothelial growth factor receptors (VEGFRs), which play a crucial role in tumour angiogenesis and tumour cell proliferation. In chapter 6 by Monzani et al. the recent literature on effects of sunitinib in the treatment of metastatic and radioiodine refractory thyroid cancers is reviewed.

Mitochondria perform vital functions such as production of the energy for the cell, ATP (i.e., phosphorylation of ADP), through respiration, and to regulate cellular metabolism. In certain pathological conditions, the overproduction of reactive oxygen species (ROS), impairment in electron transport chain (ETC) and disturbance in mitochondrial quality control can occur. These mitochondrial dysfunctions can lead to a large number of diseases such as diabetes, hypertension, neurodegeneration, etc. In the final chapter by Cortes-Rojo and Rodriguez-Orozco an overview is provided of mitochondrial functions, consequences of mitochondrial damage, and the role of mitochondria in ROS generation. Efforts to develop new therapies, particularly mitochondria-targeted antioxidants, to manage the mitochondrial related disorders are also presented.

We would like to express our gratitude to all the authors for their excellent contributions. We would also like to thank the entire team of Bentham Science Publishers, particularly Mr. Omer Shafi (Assistant Manager Publications), Mr. Shehzad Naqvi (Senior Manager Publications) and team leader Mr. Mahmood Alam (Director Publications) for their excellent efforts. We are confident that this volume will receive wide appreciation from students and researchers.

Prof. Atta-ur-Rahman, FRS
Honorary Life Fellow
Kings College
University of Cambridge
UK

Prof. M. Iqbal Choudhary
H.E.J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi
Pakistan

&

George Perry
Department of Biology
University of Texas
San Antonio
Texas
USA

List of Contributors

Editor(s):
Atta-ur-Rahman, FRS
Honorary Life Fellow
Kings College
University of Cambridge
UK


Muhammad Iqbal Choudhary
H.E.J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi
Karachi
Pakistan


George Perry
Department of Biology
University of Texas
San Antonio
Texas
USA




Contributor(s):
A.R. Rodríguez-Orozco
Facultad de Ciencias Médicas y Biológicas “Dr. Ignacio Chávez”
Universidad Michoacana de San Nicolás de Hidalgo. 58020
Morelia
Mich. México
/
Instituto de Investigación Científica en temas de Familia
Alergia e Inmunología
Morelia
Mich. México


Ana M. González-Paramás
Grupo de Investigación en Polifenoles (GIP/USAL), Universidad de Salamanca
Unidad de Nutrición y Bromatología, Facultad de Farmacia
Campus Miguel de Unamuno, E-37007
Salamanca
Spain


Andis Klegeris
Department of Biology
University of British Columbia Okanagan
Kelowna
BC
Canada


Antonio Polini
Geriatrics Unit, Department of Clinical and Experimental Medicine
University Hospital of Pisa
Via Paradisa 2, 56100 –
Pisa
Italy
/
Oncology Unit, Department of Oncology and Transplantation
University Hospital of Pisa
Via Roma 67, 56126
Pisa
Italy


C. Cortés-Rojo
Facultad de Ciencias Médicas y Biológicas “Dr. Ignacio Chávez”
Universidad Michoacana de San Nicolás de Hidalgo. 58020
Morelia
Mich. México
/
nstituto de Investigación Científica en temas de Familia
Alergia e Inmunología
Morelia
Mich. México


Celestino Santos-Buelga
Grupo de Investigación en Polifenoles (GIP/USAL), Universidad de Salamanca
Unidad de Nutrición y Bromatología, Facultad de Farmacia
Campus Miguel de Unamuno, E-37007
Salamanca
Spain


Cheng-Shi Jiang
School of Biological Science and Technology
University of Jinan
Shandong
PR China


Elena M. Varoni
Department of Biomedical, Surgical and Dental Sciences
Milan State University
Milan
Italy


Erika B. Villanueva
Department of Biology
University of British Columbia Okanagan
Kelowna
BC
Canada


Fabio Monzani
Geriatrics Unit, Department of Clinical and Experimental Medicine
University Hospital of Pisa
Via Paradisa 2, 56100 –
Pisa
Italy
/
Oncology Unit, Department of Oncology and Transplantation
University Hospital of Pisa
Via Roma 67, 56126
Pisa
Italy


Giuseppe Pasqualetti
Geriatrics Unit, Department of Clinical and Experimental Medicine
University Hospital of Pisa
Via Paradisa 2, 56100 –
Pisa
Italy
/
Oncology Unit, Department of Oncology and Transplantation
University Hospital of Pisa
Via Roma 67, 56126
Pisa
Italy


Jonathan P. Little
Department of Biology
University of British Columbia Okanagan
Kelowna
BC
Canada


Li Wang
Division of Nephrology
Shanghai Ninth Peoples' Hospital Affiliated to Shanghai Jiaotong University School of Medicine
PR China


Marcello Iriti
Department of Agricultural and Environmental Sciences
Milan State University
Milan
Italy


Montserrat Dueñas
Grupo de Investigación en Polifenoles (GIP/USAL), Universidad de Salamanca
Unidad de Nutrición y Bromatología, Facultad de Farmacia
Campus Miguel de Unamuno, E-37007
Salamanca
Spain


Sara Tognini
Geriatrics Unit, Department of Clinical and Experimental Medicine
University Hospital of Pisa
Via Paradisa 2, 56100 –
Pisa
Italy
/
Oncology Unit, Department of Oncology and Transplantation
University Hospital of Pisa
Via Roma 67, 56126
Pisa
Italy


Sergio Ricci
Geriatrics Unit, Department of Clinical and Experimental Medicine
University Hospital of Pisa
Via Paradisa 2, 56100 –
Pisa
Italy
/
Oncology Unit, Department of Oncology and Transplantation
University Hospital of Pisa
Via Roma 67, 56126
Pisa
Italy


Shaoyong Ke
National Biopesticide Engineering Research Center
Hubei Academy of Agricultural Sciences
Wuhan 430064
People′s Republic of China


Susana González-Manzano
Grupo de Investigación en Polifenoles (GIP/USAL), Universidad de Salamanca
Unidad de Nutrición y Bromatología, Facultad de Farmacia
Campus Miguel de Unamuno, E-37007
Salamanca
Spain


Valeria Calsolaro
Geriatrics Unit, Department of Clinical and Experimental Medicine
University Hospital of Pisa
Via Paradisa 2, 56100 –
Pisa
Italy
/
Oncology Unit, Department of Oncology and Transplantation
University Hospital of Pisa
Via Roma 67, 56126
Pisa
Italy


Xiufang Cao
College of Science
Huazhong Agricultural University
Wuhan 430070
People′s Republic of China


Yue-Wei Guo
School of Biological Science and Technology
University of Jinan
Shandong
PR China
/
State Key Laboratory of Drug Research
Shanghai Institute of Materia Medica, China Academy of Science
Shanghai
PR China




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