Table Of ContentTerpenoids
This unique volume covers specific aspects of the biological chemistry of terpenoids. It provides extensive information related
to classification, general methods of extraction and isolation of terpenoids, synthesis and pharmacological activities of monoter-
penoids, synthesis and medicinal uses of diterpenoids, biogenesis of terpenoids, synthesis and medicinal uses of sesqui terpe-
noids and sesterpenoids. Some terpenes are also classified as diterpene alkaloids. Most of the terpenoids with diverse molecular
structures are biologically active and are used for the treatment of various diseases such as cancer, malaria, inflammation,
tuberculosis and infection, and this is discussed.
Features
• Activities and biological relationships of terpenes.
• An accurate assessment of where and what terpenes can lead to.
• Discusses how microbes, in particular the actinomycetales, have well over 400 different gene clusters that produce terpenes.
• Arranged by biological activities and usage.
• Provides information on eukaryotic enzymes that have been shown to be a source of “ethnobotanical” terpenes.
Terpenoids
Chemistry, Biochemistry, Medical Effects,
Ethno-pharmacology
Bimal Krishna Banik
Prince Mohammad Bin Fahd University, Kingdom of Saudi Arabia
Biswa Mohan Sahoo
Roland Institute of Pharmaceutical Sciences, India
Abhishek Tiwari
Pharmacy Academy, IFTM University, Moradabad, India
Cover image: PowerUp/Shutterstock
First edition published 2023
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ISBN: 978-0-367-44031-2 (HB)
ISBN: 978-1-032-41640-3 (PB)
ISBN: 978-1-003-00868-2 (EB)
DOI: 10.1201/9781003008682
Typeset in Times
by codeMantra
Contents
Preface ...........................................................................................................................................................................................vii
Acknowledgement ...........................................................................................................................................................................ix
Authors ............................................................................................................................................................................................xi
1. Classification, General Methods of Extraction and Isolation of Terpenoids ...........................................................................1
Biswa Mohan Sahoo, Bimal Krishna Banik, and Abhishek Tiwari
2. Synthesis and Pharmacological Activities of Monoterpenoids .............................................................................................29
Biswa Mohan Sahoo, Bimal Krishna Banik, and Abhishek Tiwari
3. Synthesis, and Medicinal Uses of Diterpenoids ....................................................................................................................87
Biswa Mohan Sahoo, Bimal Krishna Banik, and Abhishek Tiwari
4. Name Reactions in Terpenoid Chemistry ............................................................................................................................153
Bimal Krishna Banik, Biswa Mohan Sahoo, and Abhishek Tiwari
5. Biogenesis of Terpenoids .......................................................................................................................................................181
Bimal Krishna Banik, Biswa Mohan Sahoo, and Abhishek Tiwari
6. Anticancer Natural Terpenoids ............................................................................................................................................197
Bimal Krishna Banik, Biswa Mohan Sahoo, and Abhishek Tiwari
7. Terpene Glycosides ..............................................................................................................................................................229
Bimal Krishna Banik, Biswa Mohan Sahoo, and Abhishek Tiwari
8. Terpenes as Starting Compounds for Other Types of Molecules Including Alkaloids .......................................................255
Bimal Krishna Banik, Biswa Mohan Sahoo, and Abhishek Tiwari
9. Synthesis and Medicinal Uses of Triterpenoids ...................................................................................................................285
Biswa Mohan Sahoo, Bimal Krishna Banik, and Abhishek Tiwari
10. Synthesis and Medicinal Uses of Sesquiterpenoids and Sesterpenoids................................................................................331
Biswa Mohan Sahoo, Bimal Krishna Banik, and Abhishek Tiwari
11. Terpenes as Useful Drugs ....................................................................................................................................................361
Biswa Mohan Sahoo, Bimal Krishna Banik, and Abhishek Tiwari
12. Terpenoids: A Brief Survey of Naturally Occurring Terpenes Molecules ..........................................................................399
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
13. A Brief Account on Plant and Marine-Derived Terpenoids ................................................................................................453
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
14. A Synthetic Overview of Terpenes and Nor Diterpenes ......................................................................................................467
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
15. Sesquiterpenes: A Chemical Synthesis and Biological Activity .........................................................................................487
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
16. Sesquiterpenes Lactone: Biogenesis and Chemical Synthesis ..............................................................................................517
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
v
vi Contents
17. An Overview of Lactarane: A New Class of Bio-Active Molecules ...................................................................................547
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
18. Terpenes: A Potential Chiral Pool for the Synthesis of Medicinally Privileged Bioactive Molecules ...............................557
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
19. Terpenes: A Unique Source of Oil and Fragrance in Industry ............................................................................................589
Bimal Krishna Banik, Abhishek Tiwari, and Biswa Mohan Sahoo
Index .............................................................................................................................................................................................611
Preface
Terpenoids are natural products and isolated from different diterpenoids are focused. In Chapter 4, name reactions in
natural sources such as plants, animals, microbes, insects terpenoid chemistry are discussed; in Chapter 5, biogenesis
and marine. Terpenoids are categorized into monoterpenes, of terpenoids is discussed; in Chapter 6, anticancer natural
sesquiterpenes, diterpenes, sesterpenes, and triterpenes terpenoids are discussed; in Chapter 7, terpene glycosides is
depending on the presence of their carbon units. Most of the discussed; in Chapter 8, terpenes as starting compounds for
terpenoids with diverse molecular structures are biologically other types of molecules including alkaloids; in Chapter 9,
active and are used for the treatment of various diseases such synthesis and medicinal uses of triterpenoids are discussed;
as cancer, malaria, inflammation, tuberculosis and infection. in Chapter 10, synthesis and medicinal uses of sesquiterpe-
This book provides extensive information related to classifica- noids and sesterpenoids are discussed; in Chapter 11, terpenes
tion, general methods of extraction and isolation of terpenoids, as useful drugs are described; in Chapter 12, a brief survey
synthesis and pharmacological activities of monoterpenoids, of naturally occurring terpenes molecules is presented; in
synthesis and medicinal uses of diterpenoids, biogenesis of Chapter 13, a brief account on plant and marine-derived terpe-
terpenoids, synthesis and medicinal uses of sesqui terpenoids noids is given; in Chapter 14, a synthetic overview of terpenes
and sesterpenoids. Some terpenes are also classified as diter- and nor diterpenes; in Chapter 15, sesquiterpenes: A chemical
pene alkaloids. synthesis and biological activity; in Chapter 16, sesquiterpenes
This book will be beneficial for undergraduate, postgradu- lactone: biogenesis and chemical synthesis; in Chapter 17, An
ate and research scholars in chemistry and biological science, overview of lactarane: a new class of bio-active molecules; in
plant physiologists, pharmacists, pharmacologists, clinicians, Chapter 18, terpenes: A potential chiral pool for the synthesis
industrialists and biochemists. This will enable the readers to of medicinally privileged bio-active molecules; in Chapter 19,
get thorough knowledge about terpenoids. terpenes: A unique source of oil & fragrance in industry are
This book has 19 chapters targeting the above subjects. discussed in detail.
Banik, Sahoo and Tiwari have written these chapters. The authors will be pleased if this book activates the
In Chapter 1, classification, general methods of extraction research and education lives of students, scientists and aca-
and isolation of terpenoids are documented. Synthesis and demic professionals along with creating business potential.
pharmacological activities of monoterpenoids are described Information provided in this book will also serve the curiosity
in Chapter 2. In Chapter 3, synthesis and medicinal uses of of general people about terpenoids and natural products.
vii
Acknowledgement
This book could not have been published without the assis- Ms. Sukirti Singh for their knowledge in science, helping atti-
tance of CRC, Taylor & Francis Publisher. In particular, the tude and encouragement.
authors are tremendously grateful to Ms. Hilary Lafoe and
ix
Authors
Professor Bimal Krishna Banik Dr. Sahoo received his Ph.D. degree from the School
Bimal Krishna Banik con- of Pharmaceutical Education and Research, Berhampur
ducted his Ph. D. degree work University. He has also completed his Post Graduate
in Chemistry at the Indian Diploma in Pharmaceutical Regulatory Affairs from Dept.
Association for the Cultivation Of Pharmaceutics, Hamdard University, New Delhi. He has
of Science, Calcutta. Then, he published more than 60 research and review articles in peer-
pursued postdoctoral research at reviewed national and international journals of repute. His
Case Western Reserve University, h-index is 16.
Ohio and Stevens Institute of He has filed and published four patents in India and
Technology, New Jersey. Dr. Australia and authored several book chapters in various text-
Banik is a FRSC and CChem of books published by known authors. He is an editorial board
the Royal Society of Chemistry, UK. Dr. Banik was a Tenured and advisory board member of various international jour-
Full Professor in Chemistry and First President’s Endowed nals. He is recognized as a Ph.D. Supervisor under Jawaharlal
Professor in Science & Engineering at the University of Texas- Nehru Technological University (JNTU) Kakinada, Mewar
Pan American (UTPA). He was also the Vice President of University, Rajsthan and BPUT, Odisha.
Research & Education Development at the Community Health
Systems of Texas. At present, he is a Full Professor and Senior Professor Abhishek Tiwari
Researcher of Natural Sciences & Human Studies at Prince Dr. Abhishek Tiwari is working
Mohammad Bin Fahd University, Kingdom of Saudi Arabia. as Professor in the Department
Professor Banik has been conducting synthetic chemis- of Pharmaceutical Chemistry,
try and medicinal research on diverse cancers, antibiotics, Pharmacy Academy, IFTM
hormones, carbohydrates, metals and salts, natural prod- University, Lodhipur-Rajput,
ucts, catalysis and environmentally benign methods. As the Moradabad (U.P.), India. Dr.
Principal Investigator, he has been awarded $7.25 million Tiwari obtained his B.Pharm.
grants from US NIH, US NCI and US Private Foundations. degree from Jiwaji University
At present, he has 578 publications, 513 presentation abstracts Gwalior (M.P.), M.Pharm.
and 8,017 journal citations with 47 h-index. Due to his con- from M.S. Ramaiah College
tributions to research, Professor Banik is designated as a of Pharmacy, Bengaluru
“Distinguished Researcher” and a “Distinguished Scientist” (Karnataka) and Ph.D. from Uttarakhand Technical University,
by Scientific Organizations. Dehradun (Uttarakhand). Dr. Tiwari has received grants of
more than 15 lakhs from the Department of Biotechnology,
Dr. Biswa Mohan Sahoo Uttarakhand; All India Council of Technical Education,
Dr. Biswa Mohan Sahoo is cur- India; Oil and Natural Gas Corporation and Power Finance
rently working as Professor at Corporation. Dr. Tiwari has been granted 3 Indian and 7 over-
Roland Institute of Pharmaceutical seas patents. In addition, he has submitted a number of pat-
Sciences, Berhampur, Odisha. ents for approval. Dr. Tiwari is an editorial member of various
He is also serving as Research national and international journals. He received “Outstanding
Coordinator of Biju Patnaik Academic and Research Award” in 2021, “Best Author Award”
University of Technology Nodal in 2019, “Best Teacher Award” in 2019 and “Outstanding
Centre of Research, Odisha. Teacher Award” in 2014 and 2015. He has published 48
Dr. Sahoo obtained his B. research papers in international journals. Remarkably, he has
Pharm. Degree from Berhampur published more than 17 Indian books and a few chapters. He
University, Odisha, and a Master’s degree from the Department is a recognized Ph.D. supervisor of Uttarakhand Technical
of Medicinal Chemistry, L.M College of Pharmacy, Gujarat. University, Dehradun, and IFTM University, Moradabad.
xi
1
Classification, General Methods of Extraction
and Isolation of Terpenoids
Biswa Mohan Sahoo*, Bimal Krishna Banik†, and Abhishek Tiwari‡
CONTENTS
1.1 Introduction ............................................................................................................................................................................2
1.1.1 Properties of Terpenoids ............................................................................................................................................2
1.1.1.1 Physical Properties .....................................................................................................................................2
1.1.1.2 Chemical Properties ...................................................................................................................................2
1.1.1.3 Phytochemical Properties ..........................................................................................................................2
1.1.1.4 Pharmacological Properties .......................................................................................................................2
1.1.2 Isoprene Rule .............................................................................................................................................................2
1.1.3 Violations of Isoprene Rule .......................................................................................................................................3
1.1.4 Special Isoprene Rule ................................................................................................................................................3
1.1.5 Exception to Special Isoprene Rule ...........................................................................................................................4
1.2 Classification of Terpenoids ...................................................................................................................................................4
1.3 Nomenclature of Terpenoids ..................................................................................................................................................7
1.4 General Methods of Extraction of Terpenoids .......................................................................................................................9
1.4.1 Maceration ...............................................................................................................................................................10
1.4.1.1 Types of Maceration ................................................................................................................................10
1.4.1.2 S teps Involved in Maceration...................................................................................................................10
1.4.2 Digestion ..................................................................................................................................................................10
1.4.3 Infusion ....................................................................................................................................................................11
1.4.4 Decoction .................................................................................................................................................................11
1.4.5 Percolation ...............................................................................................................................................................11
1.4.5.1 Types of Percolation .................................................................................................................................11
1.4.5.2 S teps Involved in Percolation ...................................................................................................................11
1.4.6 Soxhlet Extraction ...................................................................................................................................................12
1.4.7 A utomated Soxhlet Extraction ................................................................................................................................12
1.4.8 S upercritical Fluid Extraction (SFE) .......................................................................................................................12
1.4.9 P ressurized Liquid Extraction (PLE) ......................................................................................................................12
1.4.10 P ressurized Hot Water Extraction (PHWE) ............................................................................................................12
1.4.11 M icrowave-Assisted Extraction (MAE) ..................................................................................................................12
1.4.12 U ltrasound Extraction (Sonication) .........................................................................................................................13
1.5 Solvents Used for Extraction ................................................................................................................................................15
1.5.1 Properties of Solvents Used in Extractions .............................................................................................................16
1.5.2 Factors to Be Considered for Selecting Solvents during Extraction .......................................................................16
1.6 Isolation of Terpenoids .........................................................................................................................................................16
1.6.1 Isolation of Essential Oils from Plant Parts ............................................................................................................17
1.6.2 Separation of Terpenoids from Essential Oils .........................................................................................................17
1.6.2.1 C hemical Methods ...................................................................................................................................17
1.6.2.2 P hysical Methods .....................................................................................................................................17
* Roland Institute of Pharmaceutical Sciences, Berhampur affiliated to Biju Patnaik University of Technology (BPUT), Rourkela, Odisha, India.
[email protected].
† Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Prince Mohammad Bin Fahd University, Al Khobar,
Kingdom of Saudi Arabia. [email protected] and [email protected]
‡ Pharmacy Academy, IFTM University, Lodhipur Rajput, Moradabad, U.P. 244102.
DOI: 10.1201/9781003008682-1 1
