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Page 1: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Joginder SinghVineet MeshramMahiti Gupta   Editors

Bioactive Natural Products in Drug Discovery

Page 2: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Bioactive Natural Products in Drug Discovery

Page 3: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Joginder Singh • Vineet Meshram •Mahiti GuptaEditors

Bioactive Natural Productsin Drug Discovery

Page 4: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

EditorsJoginder SinghDepartment of MicrobiologyLovely Professional UniversityPhagwara, Punjab, India

Vineet MeshramDepartment of Plant Pathologyand Weed ResearchAgricultural Research Organization,The Volcani CentreRishon Lezion, Israel

Mahiti GuptaDepartment of BiotechnologyLovely Professional UniversityPhagwara, Punjab, India

ISBN 978-981-15-1393-0 ISBN 978-981-15-1394-7 (eBook)https://doi.org/10.1007/978-981-15-1394-7

# Springer Nature Singapore Pte Ltd. 2020This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of thematerial is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation,broadcasting, reproduction on microfilms or in any other physical way, and transmission or informationstorage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodologynow known or hereafter developed.The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoes not imply, even in the absence of a specific statement, that such names are exempt from the relevantprotective laws and regulations and therefore free for general use.The publisher, the authors, and the editors are safe to assume that the advice and information in thisbook are believed to be true and accurate at the date of publication. Neither the publisher nor the authors orthe editors give a warranty, expressed or implied, with respect to the material contained herein or for anyerrors or omissions that may have been made. The publisher remains neutral with regard to jurisdictionalclaims in published maps and institutional affiliations.

This Springer imprint is published by the registered company Springer Nature Singapore Pte Ltd.The registered company address is: 152 Beach Road, #21-01/04 Gateway East, Singapore 189721,Singapore

Page 5: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Preface

Natural products are small organic molecules produced naturally by any organismincluding primary and secondary metabolites. Natural products offer colossal struc-tural diversity and unique biological activities which are the result of biosyntheticprocesses that have been modulated over millions of years due to natural selectionsand evolutionary process substantiating their superiority over chemicallysynthesized compounds. Thus, natural products have been used in both traditionaland modern medicines as a panacea for various diseases. Furthermore, naturalproducts also provide template for the synthesis of various drugs followed bysynthetic modifications to increase the bioavailability and reduce the side effectsof the drugs. Traditional methods used for screening and isolation of natural productswere ineffective, cost-intensive, and cumbersome; however, with the advent ofmodern analytical and high-throughput techniques, isolation and characterizationof the natural products can be done rapidly which open up exciting opportunities forthe pharmaceutical industries in the field of drug discovery and development.

The endeavor of the book entitled Bioactive Natural Products in Drug Discoveryis to present details of cutting-edge research in the field of drug discovery anddevelopment from bioactive natural products and helps its reader to understandhow natural product research continues to make significant contributions in thediscovery and development of novel medicinal entities. With 27 chapters contributedby an elite group of researchers working in the forefront of bioprospecting naturalproducts, the book is divided into three modules; the first two modules respectivelyelaborates the significance and applications of plant and microbial natural products,whereas the third module highlights the important biotechnological applications ofthe natural products with an intention to unravel their pharmaceutical applicability inmodern drug discovery processes. The book covers the biosynthesis, bioactivities,pharmacology, chemical profiling, and structure–activity relationships of variousbioactive natural products. Modern emerging areas such as metabolomics, proteo-mics, nutraceuticals, and drug targeting are also covered. It also includes interestingchapter that deals with the economics, consumers’ attitudes, and intentions in

v

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purchasing natural products. It therefore serves as a useful reference book forstudents and researchers in a wide variety of research fields, including analyticalchemistry, biochemistry, biotechnology, ethnobotany, microbiology, pharmacy, andphytochemistry.

Phagwara, India Joginder SinghRishon LeZion, Israel Vineet MeshramPhagwara, India Mahiti Gupta2020

vi Preface

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Contents

Part I Plants Natural Products: Fountainheads for Drug Discoveryand Development

1 The Artemisia Genus: Panacea to Several Maladies . . . . . . . . . . . . . 3Bhupendra Koul and Taslimahemad Khatri

2 Bacopa monnieri: The Neuroprotective Elixir fromthe East—Phytochemistry, Pharmacology, and BiotechnologicalImprovement . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97Samapika Nandy, Anuradha Mukherjee, Devendra Kumar Pandey,and Abhijit Dey

3 Current Knowledge of Cinnamomum Species: A Reviewon the Bioactive Components, Pharmacological Properties,Analytical and Biotechnological Studies . . . . . . . . . . . . . . . . . . . . . 127Devendra Kumar Pandey, Ronni Chaudhary, Abhijit Dey,Samapika Nandy, R. M. Banik, Tabarak Malik,and Padmanabh Dwivedi

4 Swertia spp.: A Potential Source of High-Value BioactiveComponents, Pharmacology, and Analytical Techniques . . . . . . . . . 165Prabhjot Kaur, Devendra Kumar Pandey, Abhijit Dey,Padmanabh Dwivedi, Tabarak Malik, and R. C. Gupta

5 The Genus Calophyllum: Review of Ethnomedicinal Uses,Phytochemistry and Pharmacology . . . . . . . . . . . . . . . . . . . . . . . . . 215Shiv Gupta and Pawan Gupta

Part II Plant Derived Natural Products as Leads for Drug Discovery

6 Plant-Derived Quinones as a Source of Antibacterialand Anticancer Agents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 245Surbhi Goel, Preeti Singh Parihar, and Vineet Meshram

7 Drugging Protein-Protein Interaction Interfacewith Natural Products: A Computational Approach . . . . . . . . . . . . 281Ria Biswas and Angshuman Bagchi

vii

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8 CQDs Derived from Natural Sources: ExcellentBioimaging Agents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 303Ranjana Singh, Jyoti Goutam, and Ranjan K. Singh

Part III Microbial Natural Products: A Quintessential Sourcefor Drug Discovery and Development

9 Microbial Natural Products: Recent Insightsinto Novel Applications . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 315Rajnish Kumar Verma and Amita Sharma

10 Bioactive Peptides and Carbohydrates from Natural Products:A Source of Functional Foods and Nutraceuticals . . . . . . . . . . . . . . 335Gurseen Rakhra, Sumit Kumar Jaiswal, and Gurmeen Rakhra

11 Metabolites of Fluorescent Pseudomonadsand Their Antimicrobial and Anticancer Potentials . . . . . . . . . . . . . 355Kranti Tanguturu, Moumita Mondal, Ankit Banik, Gurusamy Raman,and Natarajan Sakthivel

12 Ganoderma: A Propitious Medicinal Poroid Mushroom . . . . . . . . . 379Ranjeet Singh, Avneet Pal Singh, Gurpaul Singh Dhingra,and Richa Shri

13 Pharmaceutically Important Metabolites from Marine Fungi . . . . . 411Vijayalakshmi Selvakumar, Satyender Singh, Karthik Kannan,and Panneerselvam Annamalai

14 Endophytic Fungi: A Treasure Trove of NovelBioactive Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 427Mahiti Gupta and Kamlesh Kumar Shukla

15 Novel Products from Microalgae . . . . . . . . . . . . . . . . . . . . . . . . . . . 451G. Subashini and S. Bhuvaneswari

16 Lactic Acid Production and Its Application in Pharmaceuticals . . . 467Ajay Kumar, Joginder Singh, and Chinnappan Baskar

17 Microbial Clot Busters: An Overview of Source, Production,Properties and Fibrinolytic Activity . . . . . . . . . . . . . . . . . . . . . . . . 485Mahiti Gupta, Sanjai Saxena, and Vineet Meshram

18 Carbohydrate Biopolymers: Diversity, Applications,and Challenges . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 517Taranpreet Kaur and Raman Preet Singh

viii Contents

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Part IV Important Biotechnological Applications of Natural Products

19 Biotechnological Aspects of Nanoparticles Driven from NaturalProducts for Drug Delivery System and Other Applications . . . . . . 549Simranjeet Singh, Vijay Kumar, Satyender Singh, Shivika Datta,Sanjay Kumar, Pooja Bhadrecha, Daljeet Singh Dhanjal,and Joginder Singh

20 Methods and Techniques for the Chemical Profilingand Quality Control of Natural Products and NaturalProduct-Derived Drugs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 585Vijay Kumar, Simranjeet Singh, Satyender Singh, Shivika Datta,Daljeet Singh Dhanjal, and Joginder Singh

21 Characterization of Bioactive Secondary Metabolites of FungalEndophytes from Melghat Forest in Maharashtra, India . . . . . . . . 599Kishor Suradkar and Dillip Hande

22 Modulation of Cellular Protein Quality Control PathwaysUsing Small Natural Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . 609Rahul Badhwar and Arun Upadhyay

23 Elaborating on the Potential for Mushroom-Based ProductMarket Expansion: Consumers’ Attitudes and PurchasingIntentions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 643Sonja Veljović and Jelena Krstić

24 The Role of Algae in Nutraceutical and PharmaceuticalProduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 665Shristy Gautam and M. Amin-ul Mannan

25 Microbial Interventions to Induce Secondary MetaboliteBiosynthesis in Medicinal and Aromatic Plants . . . . . . . . . . . . . . . . 687Rupali Gupta, Gautam Anand, and Rakesh Pandey

26 Peptaibols: Antimicrobial Peptides from Fungi . . . . . . . . . . . . . . . . 713V. N. Ramachander Turaga

Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 731

Contents ix

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About the Editors

Joginder Singh is presently working as a Professor at the Department of Microbi-ology, Lovely Professional University, Punjab, India. His training and researchexperience prepared him to work with microbial consortium formulation and studyits ecology. His particular areas of competence include planning and execution ofR&D facilities at scientist level. He is an active member of various scientificsocieties and organizations, including Indian Science Congress Association, theAssociation of Microbiologists of India, K. K. Nanda Foundation for Advancementof Plant Sciences, Indian Society of Salinity Research Scientists, Indian Society forRadiation Biology, Hong Kong Chemical, Biological & Environmental EngineeringSociety, and European Federation of Biotechnology. The Academy of PlantSciences, India (2016) conferred him certificate of excellence in the field of Micro-bial Technology. He serves as a reviewer for many prestigious journals and haspublished more than 60 research and review articles in peer-reviewed journals,edited 4 books, and authored/co-authored 25 book chapters.

Vineet Meshram is currently working as a Visiting Scientist at the Department ofPlant Pathology and Weed Research, the Volcani Centre, Agricultural ResearchOrganization, Israel. He previously served as an Assistant Professor at the Depart-ment of Biochemistry, DAV University, India (2016–2017). He has over 10 yearsof research experience in microbial secondary metabolites, microbial biochemistry,biological control, mycology, and drug discovery. His research work has resultedin over 15 referred journal articles, 21 abstracts and, 3 book chapters. He is also afounder member of the International Society for Fungal Conservation. In recogni-tion of his contributions, the Mycological Society of India (2012) and EuropeanMycological Society (2015) selected him for a Young Scientist Award. Recently,he has been awarded Karsons’s award (2019) by The Ministry of Agriculture,Agricultural Research Organization, Israel, for his studies on plant-microbeinteractions.

Mahiti Gupta is an Assistant Professor at the Department of Biotechnology,Lovely Professional University, India. Her research interests are in natural productsand drug discovery, enzyme inhibitors, protein purification, and characterization.

xi

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She is currently working on endophytes and Stevia. She has been honored with aUGC Meritorious Fellowship and a Young Scientist Award. She has publishedseven research articles in peer-reviewed international and national journals and hasauthored and co-authored several book chapters. She is a member of numerousscientific societies, including the Indian Science Congress.

xii About the Editors

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Part I

Plants Natural Products: Fountainheads forDrug Discovery and Development

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The Artemisia Genus: Panacea to SeveralMaladies 1Bhupendra Koul and Taslimahemad Khatri

AbstractThe genus Artemisia belongs to the family Asteraceae which has now become thesubject of great attraction because of its rich species diversity and phytochemicalcomposition. This genus has a very long history of use in the treatment of humandiseases in different parts of the world. This medicinally important genus haspromising therapeutic potential which includes antimalarial, anti-parasitic,hepato-protective, anti-nociceptive, anti-inflammatory, anti-ulcerogenic, antimi-crobial, antitumour, antioxidant, anticancer, anticonvulsant, anti-leishmanial,anti-diabetic, anti-promastigote, antidepressant and anticonvulsant. A total of839 chemical compounds (volatile and non-volatile) have been reported indifferent species of this genus. These chemical compounds can be categorisedinto major classes such as flavonoids, lignans, terpenes, fatty acids,phenylpropanoids, sterols, fatty esters, phenolics, hydrocarbons and miscella-neous compounds. Strategic conservation of Artemisia species shall continue toprovide molecules of pharmaceutical importance in future.

KeywordsSecondary metabolites · Herbal drugs · Antimalarial · Artemisinin · Mugwort

B. Koul (*)School of Bioengineering and Biosciences, Lovely Professional University, Phagwara, Punjab,Indiae-mail: [email protected]

T. KhatriDepartment of Chemistry, Government Science College, Chikhli, Gujarat, India

# Springer Nature Singapore Pte Ltd. 2020J. Singh et al. (eds.), Bioactive Natural Products in Drug Discovery,https://doi.org/10.1007/978-981-15-1394-7_1

3

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Abbreviations

2,4-D 2,4-Dichlorophenoxyacetic acidAA ascorbic acidAIDS acquired immune deficiency syndromeBAP 6-benzylaminopurineBC before the Christ’s birthcm centimetreDPPH 1,1-diphenyl-2-picrylhydrazyl radical scavenging activityFRAP ferric reducing antioxidant powerg grammeHCl hydrochloric acidHPLC high-performance liquid chromatographyHPTLC high-performance thin-layer chromatographyIAA indole 3-acetic acidKN kinetinmg milligramsml millilitreMS Murashige and SkoogMTCC Microbial Type Culture Collection and Gene BankNAA α-naphthalene acetic acidTCM traditional Chinese medicineμM micromolar

1.1 Introduction

Plants are being used from ancient times as a source of food, fuel and fodder and formedicinal purposes. Thus, they act as a supporting system for the existence of all theliving organisms on Earth. The plant kingdom is a reservoir of medicinally importantplants which are used to produce effective and non-toxic medicines for humanhealthcare (Liu et al. 2013). India contributes its maximum income for the produc-tion of herbal medicines and thus it is known as the ‘botanical garden of the world’.Andaman and Nicobar Islands, Eastern Himalayas and Western Ghats of India arethe major hotspots which constitute nearly 45,000 species of medicinally importantflora (Mohanty et al. 2018). The applications of herbs for various purposes have alsobeen mentioned in ancient Hindu scripts of India such as Sushruta Samhita(800–700 BC), Samhita (1000–800 BC), Rigveda (4500–1600 BC) and others (Paland Jain 1998; Chan et al. 2010; Leonti and Casu 2013; Kapur 2016).

During the ancient times, the knowledge regarding the medicinal properties ofplants was limited to local people, tribal communities, priests, etc. but in the presenttime the power of herbal remedies has become widespread (Koul et al. 2017). With

4 B. Koul and T. Khatri

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the advancements of medical and chemical sciences several synthetic drugs are nowavailable in the market for the treatment of various disorders. As a result, the demandof herbal medicines is continuously increasing day by day among the people becauseherbal medicines are safe, cost effective and eco-friendly. It has been reported thatmore than 60% of the commercially important drugs are obtained from plant sources(Cubukcu et al. 1990; WHO 2003).

Artemisia is a medicinally important genus belonging to Asteraceae family whichis also known as ‘Compositae family’, ‘thistle family’ or ‘daisy family’ and ‘sun-flower family’. This genus consists of 474 species which are generally known as‘mugwort’, ‘tarragon’, ‘worm wood’ or ‘sagebrush’ (Tajadod et al. 2012; Obistioiuet al. 2014). These species are either biannual, annual, perennial, herbs or shrubs.The word ‘Artemisia’ comes from the ancient Greek word ‘Artemis’¼ The Goddess(the Greek Queen Artemisia) and ‘absinthium’¼Unenjoyable or without sweetness.The plants possess peculiar bitter taste and pungent smell due to the presence ofsesquiterpene lactones and terpenoids (Abad et al. 2012). Some species of this genusare used for the preparations of herbal tea, alcoholic beverages, tonic and medicineswhile some are cultivated as crops.

As the Artemisia spp. are a rich source of volatile and non-volatile bioactivephytoconstituents, these species have been reported to possess numerous therapeuticpotential such as the following: antimalarial (Sarab et al. 2011; Mojarrab et al. 2016),antibacterial (Altunkaya et al. 2014; Saxena 2015; Kumar et al. 2017; Wani et al.2017), anti-diabetic (Ashok and Upadhyaya 2013; Nathar and Yatoo 2014), antican-cer (Taherkhani 2014; Martínez-Díaz et al. 2015), antifungal (Obistioiu et al. 2014;Saxena 2015), anti-helminthic (Rajeshkumar and Hosagoudar 2012), hepato-protective (Mohammadian et al. 2016), trichomonacidal (Nibret and Wink 2010),antiviral (Rajeshkumar and Hosagoudar 2012; Sharma et al. 2014), antispasmodic(Sarab et al. 2011; Joshi et al. 2016), anti-parasitic (Yildiz et al. 2011), anti-arthritis(Kim et al. 2015), anti-rheumatic (Saxena 2015), antihypertensive (Tigno et al. 2000;Sharopov et al. 2012), anti-inflammatory (Sarab et al. 2011; Nikhat et al. 2013),neuroprotective (Lachenmeier 2010), antitumour (Shafi et al. 2012; Mojarrab et al.2013), antipyretic (Hailu et al. 2013), antioxidant (Bora and Sharma 2011; Mojarrabet al. 2013; Msaada et al. 2015; Mohammadian et al. 2016), anti-fertility (Ashok andUpadhyaya 2013; Singh et al. 2019d), deobstruent (Nikhat et al. 2013), wormicidal(Bizhani 2015), trypanocidal, emmenagogue, diuretic, abortive (Kader and Delseny2011; Singh et al. 2016; Mishra et al. 2016; Kumar et al. 2016), analgesic (Saxena2015), acaricidal (Godara et al. 2014), vermifuge, febrifuge, antibiotic, urine stimu-lant (Saxena 2015), premenstrual syndrome, menopause, dysmenorrhoea andattention-deficit hyperactivity disorder (Adams et al. 2012), immunomodulatory(Zamanai et al. 2015), anti-ulcerogenic (Kim et al. 2017), anti-coccidal(Kostadinovic et al. 2012), diuretic, anti-cholesterolemic, cholagogue, febrifugeand vasodilator (Sajid et al. 2016), anti-plasmodial (Ramazani et al. 2010), bilestimulant (Saxena 2015), anti-hyperlipidaemic (Daradka et al. 2014; Khan 2015),anti-epileptic and anticonvulsant (de Almeida et al. 2013), disinfectant, choleretic,balsamic, depurative, digestive, emmenagogue, anti-leukaemia and anti-sclerosis(Ali and Abbasi 2014), abortifacient (Zadoks 2013), anti-nociceptive (Shoaib et al.2016), antifeedant (Barrero et al. 2013), insecticidal (Bouzenna and Krichen 2012),

1 The Artemisia Genus: Panacea to Several Maladies 5

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anti-leishmanial (Tariku et al. 2010; Jafroodi et al. 2015), antivenom (Nalbantsoyet al. 2013), anti-herpes virus (Gavanji et al. 2015; Kumar et al. 2015), antidote toinsect poison (Mckenna and Hughe 2014) and anti-migraine (Gohari et al. 2013;Kumar et al. 2014). In this chapter we have compiled the information regardingphytochemical constituents, pharmacological activities, commercialised productsand conservation of Artemisia species.

1.2 Phytochemistry

Artemisia genus is a source of numerous secondary metabolites which can becategorised into different classes such as oxygenated sesquiterpenes, oxygenatedmonoterpenes, phenylpropanoids, diterpene hydrocarbons, sesquiterpenehydrocarbons, monoterpene hydrocarbons, saturated fatty acids, azulenes, acyclicalkanes, norisoprenoids, saturated fatty aldehydes, oxygenated diterpenes, unsatu-rated ketone, unsaturated fatty alcohol, fatty esters, oxygenated hemiterpene, alkylketones, saturated fatty alcohol, unsaturated fatty aldehydes, lignan, phenolic acids,aromatic hydrocarbon, alkaloids, sterols, flavonoids, flavonoid glycosides, hydroxylcinnamic acids, phenolic glycosides, oxygenated triterpenes, butenolides,pyrethroids, benzenoids, alkyne, cyclic hydrocarbons, coumarins (expectedflavonoids), ester of caffeic acid and unsaturated fatty acids. Artemisinin is one ofthe important phytochemicals which has been isolated from two spp. of Artemisia:A. annua L. and A. vulgaris L. (Hussain et al. 2010). A total of 839 phytochemicalshave been isolated from 14 different species of Artemisia, viz. A. arborescens(Vaill.) L., A. abrotanum L., A. carvifolia Buch.-Ham. ex Roxb., A. dracunculusL., A. absinthium L., A. indica Willd., A. afra Jacq. ex Willd., A. capillaris Thunb.,A. cina Berg ex Poljakov, A. annua L., A. japonica Thunb., A. chamaemelifoliaVill.,A. vulgaris L. and A. herba-alba Asso (Brown 2010; Altunkaya et al. 2014;Martínez-Díaz et al. 2015) as shown in Table 1.1. These phytochemicals havebeen isolated using different techniques such as HPLC-MS, GC-MS, HPLC, X-raycrystallography and 1D and 2D NMR. Oxygenated terpenes and hydrocarbons arethe most abundant phytoconstituents found in this genera.

1.3 Conservation of Artemisia Species

All the medicinally important species of this genus have been reported to be in usesince ancient times for culinary preparations as well as therapeutic uses as mentionedin Table 1.2. Besides that, various commercialised products of these species in theform of tablets, syrups, oils, creams, etc. are also available in the market for humanhealthcare (Table 1.3). The species of Artemisia are also reported to accumulate heavymetals (Bhati et al. 2019; Kapoor et al. 2019). Thus they provide a solution toremediate the environment contaminants (Singh et al. 2019a, Kumar et al. 2019a;Singh et al. 2019b; Singh et al. 2019c). They work by the process of eitherphytoremediation or phytoaccumulation and transformed them into usefulby-products (Kumar et al. 2019b; Sidhu et al. 2019; Kumar et al. 2019c; Kumar and

6 B. Koul and T. Khatri

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Table

1.1

Phy

tochem

icalsandmedicinalprop

ertiesof

selected

Artem

isia

species

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

Artem

isia

abrotanu

mL.

(Sou

thernw

ood,

oldman,

boys

love,o

ldman’sworm

woo

d,lover’splant,

Europ

eansage,lem

onplant,

appleringie,garderob

e,maid’sruin,g

arden

sagebrush,

ourlord’swoo

d)

A.a

brotan

umisasm

allb

ush

andgainsaheightof

1.2m.It

grow

swild

oriscultivatedas

ornamentalplantin

gardens

intemperateregion

ofEurasiaandAfricaandsome

places

ofNorth

America

becauseitbearsflow

erswith

arom

a

Usedas

cond

iment;

tea/anthelmintic;

antiseptic;cholagog

ue;

deob

struent;

emmenagog

ue;

stom

achic;tonic/yello

wdy

eisob

tained

from

branches;hairtonic;

incense;po

t-po

urri;

insectrepellent

Who

leherb

Abadetal.(20

12),Ben-N

asr

etal.(20

13),Obistioiu

etal.

(201

4),O

zeketal.(20

14),Suresh

etal.(20

10),Sureshetal.(20

11)

Bioactiv

ecompo

unds

presentin

Artem

isia

abrotanu

mL.

Artedou

glasiaox

ideA(1)a�

Artedou

glasiaox

ideB(2)a�

Artedou

glasiaox

ideC(3)a�

Artedou

glasiaox

ideD(4)a�

Artem

isinin

(5)a�

cis-Arbusculone

(6)b�

cis-Davanon

e(7)a�

cis-β-Terpineol

(8)b�

Davanaether(9)a�

Estrago

le(10)

c�

Lavenderlacton

e(11)

b�

Nordavano

ne(12)

a�

o-Cym

ene(13)

f

Piperito

ne(14)

b�

Silp

hiperfol-5-en-3-ol

A(15)

a�

tran

s-Arbusculone

(16)

b�

tran

s-Piperito

l(17)

b�

α-Terpineol

(18)

b�

1,8-Cineole(19)

b

Artem

isia

absinthium

L.

(Absinthium,w

orm

woo

d,greenging

er,absintheworm

woo

d,common

worm

woo

dor

grandwormwoo

d,louisianaartemisia,cud

weed,

western

mug

wort,white

sage)

A.a

bsinthiumissilver

green,

perenn

ial,herbaceous

plant

grow

ingin

thetemperate

region

sof

Eurasia,N

orthern

AfricaandNorth

America.It

grow

sin

naturalhabitaton

uncultivated-grou

nd,rocky

slop

es,sides

offootpaths,

foot

ofhills

andfields.S

tem

iserect,4–12

in.tall

branched,fi

rm,leafy,

sometim

esalmosthard

Usedas

cond

iment/

anthelmintic;antiseptic;

antispasm

odic;appetizer;

carm

inative;cholagog

ue;

emmenagog

ue;

febrifug

e;ho

meopathy;

hypn

otic;stim

ulant;

stom

achic;tonic;

verm

ifug

e/repellent;

strewing

Who

leHerb

Abadetal.(20

12),Altu

nkaya

etal.(20

14)Ereletal.(20

12),

Lee

etal.(20

13),Obistioiu

etal.

(201

4),O

zeketal.(20

14),

Sharopo

vetal.(20

12),Wani

etal.(20

14)

(con

tinued)

1 The Artemisia Genus: Panacea to Several Maladies 7

Page 18: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Table

1.1

(con

tinued)

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

woo

dyatthebase.T

heleaves

oftheplantare

white

silver-green

incolour

having

bitter,strong

arom

adu

eto

presence

ofcompo

und

thujon

e.Asing

leplantcan

prod

uce50

,000

seeds.

Fibrous

rootsof

plantpossess

arom

atictaste.

Itisused

asherbal

medicationin

Ayu

rveda,

Unani,h

omeopathyand

Siddh

a.Ithaslong

been

used

asan

anti-helm

inthic

(wormwoo

d)andalso

asan

ingredient

intheliq

uor

Absinthe.Artem

isia

absinthium

iscommon

lycalledas

wormwoo

d.The

namewormwoo

dim

plies

thatitisapo

werfulw

orming

agent,becauseof

itsusage

forh

undredsof

yearstoexpel

tapeworms,threadwormsand

especially

roun

dwormsfrom

dogs,catsandhu

mans.

Absinth

wormwoo

disused

incompanion

plantin

gto

supp

ress

weeds,b

ecause

its

8 B. Koul and T. Khatri

Page 19: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

rootssecreteasubstance

calledabsinthin

(sesqu

iterpenelacton

e)that

inhibitsthegrow

thof

surrou

ndingplants.Itcan

repelinsectlarvae

when

plantedon

theedge

ofthe

cultivatedarea.Ithasalso

been

used

torepelfleasand

moths

indo

ors.Studies

ofits

effecton

thegerm

inationof

otherplantsareinconclusive

Bioactiv

ecompo

unds

presentin

Artem

isia

absinthium

L.

Artem

isiaketone

(20)

b�

Aromadendrene(21)

e�

Bicyclogerm

acrene

(22)

e�

Borneol

(23)

b�

Cam

phene(24)

f�

Carvacrol

(25)

b�

Carvo

ne(26)

b�

Caryo

phyllene

oxide(27)

a�

Chamazulene(28)

h�

Chrysanthenyl

acetate(29)

b�

cis-Chrysanthenol

(30)

b�

cis-Epo

xyocim

ene(31)

b�

cis-Piperito

neepox

ide(32)

b�

cis-Sabinol

(33)

b�

cis-Verbeno

l(34)

b�

Cub

enol

(35)

a�

Curcumene(36)

e�

Decanoicacid

(37)

g�

(E)-Nerolidol

(43)

a�

(E)-Nuciferolisob

utyrate

(44)

a�

(E)-Sabinyl

acetate(45)

b�

(E)-Sabinenehy

drate(46)

b�

(E)-3-Hexenyl

butyrate

(47)

b�

Farnesol(48

)a�

Germacrene

B(49)

e�

Germacrene

D(50)

e�

Geranial(51)

b�

Geraniol(52)

b�

Geranyl

acetate(53)

b�

Geranyl

butano

ate(54)

b�

Geranyl

isob

utanoate(55)

b�

Geranyl

isov

alerate(56)

b�

Geranyl

prop

ionate(57)

b�

Geranyl,2

-methy

lbutanoate

Linaloo

l(66)

b�

Myrtenal(67)

b�

Myrteno

l(68)

b�

n-Heneicosane

(69)

i�

n-Heptadecane

(70)

i�

n-Non

adecane(71)

i�

Nerol

(72)

b�

Neral(73)

b�

Neryl

acetate(74)

b�

Neryl

butano

ate(75)

b�

Neryl

isob

utanoate(76)

b�

Neryl

isov

alerate(77)

b�

Neryl

2-methy

lbutanoate

(78)

b�

Neryl-3-m

ethy

lbutanoate

(79)

b�

Neryl

prop

ionate(80)

b�

p-Cym

ene(81)

f

tran

s-Caryo

phyllene

(89)

e

tran

s-Epo

xyocim

ene

(90)

b�

tran

s-Pinocarveol

(91)

b�

tran

s-Sabinol

(92)

b�

tran

s-Verbeno

l(93)

b�

Terpinen-4-ol

(94)

b�

Terpino

lene

(95)

f

Terpiny

lpropion

ate

(96)

b�

Thy

mol

(97)

b�

Tricyclene(98)

f

tran

s-Muu

rolol(99)

a�

Valerenicacid

(100

)a�

Verbeno

ne(101

)b�

Viridiflorol

(102

)a�

(Z)-Anethole(103

)c�

α-Muu

rolene

(112

)e

α-Phelland

rene

(113

)f

α-Pinene(114

)f

α-Terpinene

(115

)f

α-Terpineol

(18)

b�

α-Terpiny

lacetate(116

)b�

α-Thu

jene

(117

)f

α-Thu

jone

(118

)b�

β-Bou

rbon

ene(119

)e

β-Citron

ellol(120

)b�

β-Elemene(121

)e�

β-Iono

ne(122

)j�

β-Pinene(123

)f�

β-Selinene(124

)e�

β-Thu

jone

(125

)b�

γ-Muu

rolene

(126

)e�

γ-Cadinene(127

)e�

γ-Dehyd

ro-A

r-himachalene

(con

tinued)

1 The Artemisia Genus: Panacea to Several Maladies 9

Page 20: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Table

1.1

(con

tinued)

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

Dihyd

ro-chamazulene(38)

h�

(E)-Anethole(39)

c�

(E)-Caryo

phyllene

(40)

(E)-Crysantenyl

acetate

(41)

b�

(E)-Linaloo

lox

ide(42)

b�

(58)

b�

Iso-3-thujanol

(59)

b�

Lavandu

lylacetate(60)

b�

Lavandu

lylisob

utanoate

(61)

b�

Lavandu

lyl2-methy

lbutyrate

(62)

b�

Ledol

(63)

a�

Lim

onene(64)

f

Linalyl

acetate(65)

b�

Perillaldehy

de(82)

b�

Piperiteno

neox

ide(83)

b�

Pog

ostol(84)

a�

Pulegon

e(85)

b�

Sabinene(86)

f�

Santolin

aalcoho

l(87

)b�

Spathylenol

(88)

a�

(Z)-Linaloo

lox

ide

(104

)b�

(Z)-Nuciferolisobutyrate

(105)a�

(Z)-Sabinylacetate

(106)b�

α-Copaene

(107)e

α-Bisabolol

(108)a�

α-Dehydro-ar-

himachalene

(109)e

α-Hum

ulene(110)e

α-Ionone

(111)j

(128

)e�

γ-Isog

eraniol(129

)b

γ-Terpinene

(130

)f

δ-Cadinene(131

)e�

1,8-Cineole(19)

b�

3,6-Dihyd

rocham

azulene(132

)h�

9-Geranyl-p-cym

ene(133

)d�

Artem

isia

afra

Jacq.ex

Willd(W

ildwormwoo

d,African

wormwoo

d,wild

e-als,um

hlon

yane,m

hlon

yane,

leng

ana,zeng

ana,ny

umba)

A.a

fraisacommon

species

which

iswidelygrow

nin

Africainclud

ingno

rthto

east

areasof

Africa,Ethiopiaand

Sou

thAfrica.A.a

fraisdark

greenin

colour

having

woo

dystem

reaching

from

0.5–2m

inheight,w

hile

leaves

aresimilarto

fern.

A.a

fraisawell-kn

own

medicinalplantinAfrica,

andisstill

used

bypeop

leof

manycultu

res.The

who

leplantp

artinclud

ingstem

,rootsandleaves

isused

inmothrepellent,lotions,

smok

ingandinsecticideor

as

Non

ekn

own.

The

roots,

stem

sandleaves

areused

asenem

as,p

oultices,

infusion

s,lotio

ns,

inhaled(e.g.smok

edor

snuffed),o

ras

anessentialoil/m

oth

repellent/organic

insecticidalspray

Roo

t,stem

andleaves

Abadetal.(20

12),Maggioetal.

(201

2),O

zek(201

4)

10 B. Koul and T. Khatri

Page 21: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

essentialoils.A

.afra

possessesstrong

,sticky

sweetfragrancethat

emanates

whencuto

rtouched.

The

othercommon

names

ofA.a

fraareAfrican

wormwoo

d,wild

wormwoo

d,wild

e-als

(Afrikaans),um

hlon

yane,

mhlon

yane,lengana,

zeng

anaandny

umba.T

heleaves

areused

totreat

fevers,chestinfections,

digestivedisturbances,

coug

hs,fl

u,em

physem

aand

asthma-lik

edisorders

Bioactiv

ecompo

unds

presentin

Artem

isia

afra

Jacq.exW

illd

Artem

isiaalcoho

l(13

4)b�

Artem

isiaketone

(20)

b�

Artedou

glasiaox

ideD(4)a

Allo

-aromadendrene(135

)e

Allo

-aromadendreneox

ide

(136

)a

Borneol

(23)

b�

Bicyclogerm

acrene

(22)

e

Borny

lacetate(137

)b�

Cam

phene(24)

f

Cam

phor

(138

)b�

Carvacrol

(25)

b�

Carvo

ne(26)

b�

Caryo

phyllene

oxide(27)

a�

cis-Carveol

(146

)b�

cis-Lanceol

(147

)a

cis-Muu

rola-4(14,5diene)

(148

)a

Decanal(149

)k

Dihyd

ronerolid

ol(150

)a

Davanon

eD(151

)a

Davanaether(9)a

(E)-β-Farnesene

(152

)e�

(E)-Nerolidol

(43)

a�

phytol

(153

)l

Guaiol(154

)a�

Geranial(51)

b�

Germacrene

B(49)

e�

Methy

leugeno

l(159

)c�

Myrtenal(67)

b

Myrteno

l(68)

b�

Myrteny

lacetate(160

)b�

Neolyratol(161

)b�

Nordavano

ne(12)

a�

Neral(73)

b�

Neryl

acetate(74)

b�

p-Cym

ene(81)

f

p-Cym

en-8-ol(162

)b�

Pinocarvo

ne(163

)b�

Piperito

ne(14)

b�

Spathulenol

(164

)a�

Santolin

aalcoho

l(87

)b�

tran

s-Chrysanthenyl

acetate(169

)b�

Terpinen-4-ol

(94)

b�

tran

s-Carveol

(170

)b�

Thy

mol

(97)

b�

tran

s-Cadinol

(171

)a�

tran

s-Muu

rolol(99)

a�

Viridiflorol

(102

)a�

(Z)-α-Bisabolene

epox

ide(172

)a�

α-Thu

jene

(117

)f

α-Pinene(114

)f

α-Cam

pholenal(173

)b�

α-Terpineol

(18)

b�

α-Cop

aene

(107

)e

β-Thu

jone

(125

)b�

β-Eud

esmene(β-Selinene)

(124

)e�

β-Guaiene

(181

)e�

β-Bisabolene(182

)e�

β-Pinene(123

)f

β-Bou

rbon

ene(119

)e�

β-Elemene(121

)e�

γ-Terpinene

(130

)f�

γ-Gurjunene

(183

)e�

γ-Muu

rolene

(126

)e�

γ-Cadinene(127

)e�

(2Z,6E)-Farnesylacetate(184

)a�

(con

tinued)

1 The Artemisia Genus: Panacea to Several Maladies 11

Page 22: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Table

1.1

(con

tinued)

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

Cabreuv

aox

ideB(139

)a

Chrysanthenon

e(140

)b�

cis-Sabinenehy

drate(46)

b�

cis-(Z)-α-Bisabolene(141

)e�

cis-Jasm

one(142

)b�

cis-Piperito

l(143

)b�

cis-Pinocam

phon

e(144

)b�

cis-Chrysanthenyl

acetate

(145

)b�

Germacrene

D(50)

e�

Hotrienol

(155

)b�

Isop

horone

(156

)m

Isospathulenol

(157

)a�

Ledol

(63)

a�

Linaloo

l(66)

b�

Lim

onene(64)

f

Linalylform

ate(158

)b

Santolin

atriene(165

)f

Sabinene(86)

f�

Safranal(166

)b�

tran

s-p-Menth-2-en-1-ol

(167

)b�

tran

s-Pinocarveol

(91)

b�

tran

s-Verbeno

l(93)

b�

tran

s-Chrysanthenol

(168

)b�

α-Bisabolol

(108

)a�

α-Bisabolol

oxideB

(174

)a�

α-Bisabolon

eox

ideA

(175

)a�

α-Eud

esmol

(176

)a�

α-Selinene(177

)e

α-Amorph

ene(178

)e

α-Hum

ulene(110

)e

α-Guaiene

(179

)e

α-Cub

ebene(180

)e

1-Octen-3-ol(185

)n

1-S-cis-Calam

enene(186

)e

1,3,8-p-Menthatriene(187

)f

1,8-Cineole(19)

b�

8-Cedren-13

-ol(188

)a�

(2Z,6E)-Farnesol(189

)b�

Artem

isia

annu

aL.

(QingHao,sweetworm

woo

d,sw

eetannie,sw

eet

sagewort,annu

almug

wort,

annu

alwormwoo

d)

A.a

nnua

isalso

know

nas

annu

almug

wort,sw

eet

sagewort,sw

eetannie,sw

eet

wormwoo

dor

annu

alwormwoo

d,belong

ingto

the

family

ofAsteraceae,which

isgrow

nnaturally

inAsia

(China,Ind

ia,P

akistan,

Japan,

Russia,Serbia,

Turkey),E

urop

e(A

lbania,

Bulgaria,Mon

tenegro,

Rom

ania,A

ustria,F

rance,

Germany,

Hun

gary,Italy,

Poland,

Slovakia,Spain,

Switzerland

),Sou

thAmerica

(Argentin

a)andNorth

America(U

SA).A.a

nnua

isan

annu

al,h

airless,sw

eetly

Usedas

cond

iment/

antib

acterial;anti-

period

ic;antiseptic;

carm

inative;digestive;

febrifug

e;essentialoil;

herbicide;flavou

ring

spirits

Leaves

Brown(201

0),T

zenk

ovaetal.

(201

0),A

badetal.(20

12),Ozek

etal.(20

14)

12 B. Koul and T. Khatri

Page 23: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

arom

aticplantg

rowth,fern-

likeleaves

andflow

ersare

bright

yello

wwith

strong

fragrancedu

eto

presence

ofbioactivecompo

und

camph

or.A

rtem

isinin

(antim

alarial)isabioactive

compo

undwhich

isextracted

from

A.a

nnua

,which

cures

infectionof

Plasm

odium

Bioactiv

ecompo

unds

presentin

Artem

isia

annu

aL.

Abscisicacid

(190

)a�

Abscisicacid

methy

lester

(191

)a�

Acetone

(192

)m�

Acetoph

enon

e,2-4-

dihy

drox

y-6-metho

xy(193

)af�

Aesculetin

(194

)y

allo-O

cimene(195

)f

Amorph

-4-en-7-ol

(196

)a�

Amyl

2-methy

lbutyrate

(197

)o�

Amyrenon

e,alph

a(198

)ac�

Amyrin,alpha

(α-A

myrin)

(199

)ac�

Amyrin,b

eta(β-A

myrin)

(200

)ac�

Amyrin,b

eta(β-A

myrin):

acetate(201

)ac�

Anethole(202

)c�

Cyclohexanecarbox

ylicacid,

3-[[3-(3,4-dihyd

roxy

phenyl)-

1-ox

o-2-prop

enyl]oxy

]-4,5-

dihy

drox

y-1-[[3-(4-hyd

roxy

-3-metho

xyph

enyl)-1-ox

o-2-

prop

enyl]oxy

](309

)c

Cyclooctane,1

,4-dipropy

l(310

)ah

Cyclopentanecarbo

xylic

acid,3

-methy

lene,1

,7,7-

trim

ethy

lbicyclo-[2.2.1]hept-

2-yl

ester(311

)b

Cycloprop

[7,8]azuleno

[3a,4-

b]ox

irene,decahy

dro-

1,4a,7,7-tetramethy

l-,

(1R,6aR

,7aR

,7bS

)(312

)a

Cycloprop

ane,(1-m

ethy

l-1,2-prop

adien-1-yl)(313

)ah

Cycloprop

ene,3-etheny

l-3-

methy

l(31

4)ah

Myrcene

alfa

hydrop

erox

ide(426

)b

Myrceno

l(427

)b

Myrtenal(67)

b�

Myrteno

l(68)

b�

Nerol

(72)

b

Nerolidol

(43)

a�

Neryl

acetate(74)

b

n-Hexanol

(428

)r

n-Hexyl

isov

alerate

(429

)o

n-Hexyl

tiglate(430

)o

n-Non

ylalcoho

l(431

)r

Non

acosan-1-ol(432

)r

Non

acosane,n(433

)i

Non

adecane(434

)i

Non

adecanoicacid

(435

)g

Norannu

icacid

(436

)a

Norannu

icacid

form

yl

Xanthox

ylin

(538

)af

Ylang

ene(539

)e

Yom

ogialcoho

l(54

0)b

Zeatin

(541

)w

Zeatin

,dihyd

ro:riboside

(542

)w

α-Aromadendrene

(135

)e

α-Bisabolol

(108

)a

α-Bou

rbon

ene(543

)e�

α-Cadinene(544

)e

α-Cadinol

(545

)a

α-Cedrene

(546

)e�

α-Cop

aene

(107

)e�

α-Elemene(547

)e�

α-Epo

xyartemisinicacid

(548

)a

α-Epo

xy-

dihy

droartem

isinic

(549

)a

2,6-Octadien-1-ol,2

,6-dim

ethy

l-8-[(tetrahyd

ro-2H-pyran-2-yl)

oxy]

(632

)b

2,7,10

-Bisabolatriene(633

)e

20,4

0 -Dim

ethy

lether(634

)af

20,4

0 ,60 -T

rihy

drox

yacetoph

enon

e20-m

ethy

lether(635

)af

20-M

ethy

lether4’-O

-β-D-

Glucopy

rano

sde(636

)af

20,4

0 ,60 -T

rihy

drox

yacetoph

enon

e40-m

ethy

lether2-O-β-D-

Glucopy

rano

side

(637

)af

2-Benzyloctanal(638

)s

2-Butenoicacid,3

-methy

l-(1S,2R,4S)-1,7,7-

trim

ethy

lbicyclo[2.2.1]hept-2-yl

ester(639

)b

2-Butyl-2-octenal(640

)s

2-Cyclohexen-1-on

e,2-Methy

l-5-(1-m

ethy

lcycloprop

yl)(641

)b

(con

tinued)

1 The Artemisia Genus: Panacea to Several Maladies 13

Page 24: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Table

1.1

(con

tinued)

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

Anisole(203

)af�

Ann

phenon

e(204

)af�

Ann

uadiepox

ide(205

)ag

Ann

uicacid,n

or(206

)a

Ann

ulide(207

)a

Ann

ulide,iso(208

)a

Apigenin(209

)y

Aromadendreneepox

ide

(210

)a

Arteann

uicacid

(211

)a

Arteann

uinA(212

)a

Arteann

uinB(213

)a

Arteann

uinB,d

eoxy

EPI

(214

)a

Arteann

uinB,d

ihyd

roEPI:

deox

y(215

)a

Arteann

uinB,dihyd

ro(216

)a

Arteann

uinC(217

)a

Arteann

uinD(218

)a

Arteann

uinE(219

)a

Arteann

uinF(220

)a

Arteann

uinG(221

)a

Arteann

uinH(222

)a

Arteann

uinI(223

)a

Arteann

uinJ(224

)a

Arteann

uinK(225

)a

Arteann

uinL(226

)a

Arteann

uinM

(227

)a

Arteann

uinN(228

)a

Cym

ol(p

-Cym

ene)

(81)

f

Cyn

aroside(315

)z

Cyn

eol(31

6)b�

Daucosterol

(317

)x

Decan-2-one

(318

)q

Decanoicacid

(37)

g

Deoxy

arteannu

inB(319

)a

Deoxy

artemisinin

(320

)a

Dihyd

roarteannu

inB(321

)a

Dihyd

roartemisinicacid

(322

)a

Dihyd

roartemisinicacid

hydrop

erox

ide(323

)a

Dihyd

roartemisinicalcoho

l(324

)a

Dihyd

roartemisinicaldehy

de(325

)a

Dihyd

ro-deoxy

arteannu

inB

(326

)a

Dihyd

ro-epi-

deox

yarteann

uinB(327

)a

Dihyd

ro-seco-cadinane

(328

)a

Dihyd

roxy

cadinano

lide

(329

)a

Docosan-2-one

(330

)q

Docosanoicacid

(331

)g

Dod

ecane(332

)i

Dod

ecanoicacid

(333

)g

ester(437

)a

Occidentalol(438

)a

Occidentalolacetate

(439

)a

Occidol

(440

)a

Octacosan-1-ol(441

)r

Octadecane(422

)i

Octadecanoicacid

(443

)g

Octadecanoicacid,

methy

lester(444

)o

Octan-1-ol(445

)r

Octanal(446

)k

Oleanolicacid

(447

)x

Oleicacid

(448

)ak

Pachy

podo

l(449

)y

p-Ally

lanisole(450

)c

Patuletin

(451

)y

Patuletin-3-O

-β-D-

glucoside(452

)z

p-Cym

en-8-ol(162

)b

Pendu

letin

(453

)y

Pentacosane,n

(454

)i

Pentadecano

icacid

(455

)g

Pentane

(456

)i

Pentano

icacid

(457

)g

Pentano

icacid,tert-bu

tyl

ester(458

)o

Perillaldehy

de(82)

b

α-Farnesene

(550

)e

α-Guaiene

(179

)e�

α-Gurjunene

(551

)e

α-Hum

ulene(110

)e�

α-Hyd

roxy

santon

in(552

)a

α-Linolenicacid

(553

)ak

α-Phelland

rene

(113

)f

α-Pinene(114

)f

α-Selinene(177

)e�

α-Terpinene

(115

)f

α-Terpineol

(18)

b�

α-Thu

jene

(117

)f

α-Thu

jone

(118

)b�

β-Bisabolene(182

)e�

β-Cadinene(554

)e

β-Caryo

phyllene

(555

)e

β-Cub

ebene(556

)e�

β-Elemene(121

)e

β-Eud

esmol

(557

)a

β-Farnesene

(152

)e

β-Guaiene

(181

)e

β-Phelland

rene

(558

)f

β-Pinene(123

)f

β-Pineneox

ide(559

)b

β-Sabinenehy

drate

(560

)b

β-Selinene(124

)e�

γ-Cadinene(127

)e

2-Decenal(642

)s

2-Ethylbu

tano

icacid,m

ethy

lester(643

)o

2-Ethylfuran(644

)al

2-Heptano

ne(645

)q

2-Heptenal(646

)s

2-Hexenal(647

)s

2-Hyd

roxy

benzoicacid,

3-methy

lbutyl

ester(648

)o

2-Metho

xy-3-(2-prop

enyl)

phenol

(649

)af

2-Methy

lbu

tano

icacid,ethyl

ester(650

)o

2-Methy

l-2-hexano

l(651

)r

2-Methy

l-2-pentanol

(652

)r

2-Methy

lbutanoicacid

(653

)g

2-Methy

lbutanoicacid

anhy

dride

(654

)al

2-Methy

l-bu

tano

icacid,

2-methy

lbutyl

ester(655

)o

2-Methy

lprop

ylprop

ionate

(656

)o

2-Naphthaleno

l,decahy

dro-1-

methy

l-6-methy

lene-4-

(1-m

ethy

lethenyl)(657

)a

2-Non

ynoicacid,m

ethy

lester

(658

)o

2-α-Hyd

roxy

-1,8-cineole(659

)b

3,3-Dim

ethy

l-1-bu

tene

(660

)i

14 B. Koul and T. Khatri

Page 25: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Arteann

uinO(229

)a

Arteanu

icacid,1

1(R)-

dihy

dro(230

)a

Artem

etin

(231

)y

Artem

isiaalcoho

l(13

4)b�

Artem

isia

dihy

drox

ycadinolide2-A

(232

)a

Artem

isiaketone

(20)

b�

Artem

isiasecocadinane

(233

)a

Artem

isiatriene

(234

)f

Artem

isin

(235

)a

Artem

isinicacid

(236

)a

Artem

isinicacid,m

ethy

lester(237

)a

Artem

isinicacid,6,7-dehyd

ro(238

)a

Artem

isinicacid

epox

y(239

)a

Artem

isinicaldehy

de(240

)a

Artem

isinin

(5)a

Artem

isinin

B(241

)a

Artem

isinin

deox

y(242

)a

Artem

isinin,d

ehyd

ro(243

)a

Artem

isinol

(244

)a

Artem

isitene

(245

)a

Artem

isyl

acetate(246

)b

Ascaridole(247

)b

Astragalin

(Kaempferol-3-O

-glucoside)

(248

)z

Aurantin

amideacetate

Dod

ecanoicacid,ethyl

ester

(334

)o

Eicosane(335

)i

Eicosanoicacid

(336

)g

Elemol

(337

)a

Elemyl

acetate(338

)a

Eleutheroside

B-1

(339

)ai

Elix

ene(340

)e�

endo

-Dehyd

rono

rborneol

(341

)b

epi-Cub

enol

(342

)a

epi-Deoxy

arteannu

inB

(343

)a

epi-Globu

lol(344

)a

Ethyl

form

ate(345

)k

Eud

esma-4(15)-11-diene,

5-alph

ahyd

roxy

(346

)a

Eug

enol

(347

)c�

Eug

enyl

isov

alerate(348

)c

Eup

alitin(349

)y

Eup

atin

(350

)y

Eup

atorin

(351

)y

Farnesal(352

)a

Farnesol(48

)a

Farnesylp

yrop

hosphate

(353

)a

Fenchol

(354

)b�

Fenchon

e(355

)b

Flavo

ne,2

0 -40 -5

-trihy

drox

y-50-6-7-trimetho

xy(356

)y

Flavo

ne,3

0 -5-7-8-

tetrahyd

roxy

-3-4

0 -dim

etho

xy

Perillene(459

)b

Phelland

ral(460

)b

Pheny

lacetic

acid

(461

)af

Pheny

lpropano

icacid

(462

)af

Phthalate,b

is-(hyd

roxy

-2-methy

lpropy

l)(463

)af

Phy

tene-1,2-diol(464

)l

Phy

tene-1-ol-2-

hydrop

erox

ide(465

)l

Phy

tol(153

)l

Phy

tone

(466

)m

Pinocam

phon

e(144

)b�

Pinocarveol,trans

(91)

b

Pinocarvo

ne(163

)b�

Pinocarvy

lacetate(467

)b

Piperito

ne(14)

b

p-Menth-1-en-5-ol(468

)b

p-Menth-2,8-dien-1-ol

(469

)b

p-Menth-3-ene

(470

)f

p-Mentha-1(7),5-dien-2-

ol(471

)b

p-Mentha-1(7),8-dien-2-

ol(472

)b

p-Mentha-1,4(8)-dien-3-

ol(473

)b

p-Mentha-2,4-diene

(474

)f

Pon

ticaepo

xide

(475

)ag

Pregeijerene

(476

)e

Propano

icacid,ethyl

γ-Cadinol

(561

)a

γ-Caryo

phyllene

(562

)e

γ-Elemene(563

)e

γ-Eud

esmol

(564

)a

γ-Gurjunene

(565

)e

γ-Muu

rolene

(126

)e

γ-Selinene(566

)e

γ-Terpinene

(130

)f

δ-Cadinene(131

)e

δ-Elemene(567

)e

δ-Muu

rolene

(568

)e

δ-Terpineol

(569

)b

(�)-Amorph

a-4,11

-diene(570

)e

(�)-Myrteny

lacetate

(160

)b

(�)-Spathulenol

(164

)a

(�)-tran

s-Pinocarveol

(91)

b

(�)-α-Thu

jone

(118

)b

(+)-Germacrene

A(571

)e

(1R,3Z,9S)-Bicyclo

[7.2.0]und

ec-3ene,

4,11

,11-trim

ethy

l-8-

methy

lene

(572

)e

(2E)-Hexadecene(573

)i

(2E,4E)-Non

adienal

(574

)s

(E)-3,7-Dim

ethy

l-1,3,6-

octatriene

(575

)f

(E)-2-Butenoicacid,

3,40,5,6,7-Pentahy

drox

yflavon

e3,40,6,7-Tetramethy

lether(661

)y

3,4-Diferuo

ylqu

inicacid

(662

)aj

3,4-Dihyd

roxy

benzoicacid

(663

)af

3,5-Cycloheptadieno

ne(664

)al

3,5-Diferuo

ylqu

inicacid

(665

)aj

3,7-Dim

ethy

l-1,5,7-octatrien-3-ol

(666

)b

3,7-Dim

ethy

l-2,6-octadienyl,

isob

utyricacid,ester

(667

)b

3,7-Octadien-2-ol,2

,6-dim

ethy

l(668

)b

3,7-Octadien-2-ol,2

-methy

l-6-

methy

lene

(669

)b

30,5,7,8-Tetrahy

drox

y-3,40-dim

etho

xyflavon

e(670

)y

3-Ally

l-6-metho

xyph

enol

(671

)c

3-Caffeoy

l-4-feruloylqu

inic

acid

(672

)aj

3-Cedren-12

-ol(673

)a

3-Cyclohexene-1-m

ethano

l2-hy

drox

y-α,α,4-trim

ethy

l-,

1-acetate(674

)b

3-Feruloy

l-5-caffeoylqu

inic

acid

(675

)aj

3-Hexenyl

butano

ate(676

)o

3-Hexenyl

hexano

ate(677

)o

3-Methy

l-1-bu

tano

l,acetate

(678

)o

3-Methy

lbutanal(679

)k

3-Methy

lbutanoicacid,3-m

ethy

l-

(con

tinued)

1 The Artemisia Genus: Panacea to Several Maladies 15

Page 26: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Table

1.1

(con

tinued)

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

(249

)w

Axillarin(250

)y

Baureno

l(251

)ac

Benzeneprop

anoicacid,3-

cyanop

heny

lester(252

)o

Benzoicacid

(253

)af

Benzyl2-methy

lbu

tyrate

(254

)o

Benzylcinn

amate(255

)o

Benzylisov

alerate(256

)o�

Benzylph

enylacetate(257

)o

Benzylvalerate(258

)o

Bicyclo[2.2.2]octa-2,5-

diene,1,2,3,6-tetram

ethy

l(259

)ah

Bicyclo[3.1.1.]hept-2ene,

3,7,7-trim

ethy

l(260

)ah

Bicyclo[3.1.1]heptan-3-on

e,2,6,6-trim

ethy

l-4-methy

lene

(261

)m

Bon

anzin(262

)y

Borneol

(23)

b�

Borneol

acetate(263

)b�

Borneol

isob

utyrate(264

)b

Borny

lvalerate(265

)b

But-2-en-1-al,3-m

ethy

l(266

)p

Butanal(267

)k

Cadin-4-en-11

-ol-3-iso-

(357

)y

Flavo

ne,3

-30 -5

-trihy

drox

y-40-6-7-trimetho

xy(358

)y

Flavo

ne,3

-5-dihyd

roxy

-30-4

0 -6-7-tetrametho

xy(359

)y

Flavo

ne,5

-hyd

roxy

-3-4

0 -6-

7-tetram

etho

xy(360

)y

Flavo

ne,5

-hyd

roxy

-3-4

0 -6-

7-tetram

enthox

y(361

)y

Flavo

ne,4-5-5

0 -trihy

drox

y-3-

5-6-7-tetram

etho

xy(362

)y

Fraxidin,

iso(363

)ai

Friedelan-3-β-ol(36

4)x

Friedelin

(365

)x

Geraniol(52)

b

Geranyl

acetate(53)

b

Germacrene

B(49)

e

Germacrene

D(50)

e�

Globu

lol(36

6)a

Glucoluteolin

(367

)z

Guaiazulene

(368

)e

Heneicosane

(69)

i

Hentriacontayl

triacontanoate(369

)o

Hepta-3-trans-5-diene-2-

one,6-methy

l(37

0)m

Heptadecane

(70)

i�

Heptadecano

icacid

(371

)g

ester(477

)o

Protocatechuicacid

4-glucoside(478

)af

Pseud

opinene(479

)f

Purine,7-8-dihy

dro:

6-(3

0 -methy

l-bu

tylamino)-2-hyd

roxy

(480

)w

Quercetagetin

3-methy

lether(481

)y

Quercetagetin-

3,40-dim

ethy

lether

(482

)y

Quercetagetin-3

0 -40 -6

-7-

tetram

ethy

lether(483

)y

Quercetagetin-4

0 -6-7-

trim

ethy

lether(484

)y

Quercetagetin-4

0 -methy

lether(485

)y

Quercetin

(486

)y

Quercetin

30-glucoside

(487

)z

Quercetin

3-rutin

oside

(488

)z

Quercetin-3’-O-beta-

D-

glucoside(489

)z

Quercetin-3-m

ethy

lether

(490

)y

Quercim

eritrin

(491

)z

2-methy

l-,

2,2-dimethy

l-1-

(2-m

ethy

l-1-prop

enyl)-

3-bu

teny

lester(576

)b

(E)-2-Hexenol

(577

)n

(E)-3-Hexen-1-ol(57

8)n

(E)-3-Hexen-1-ol,

acetate(579

)o

(E)-Nerolidyl

acetate

(580

)a

(Z)-1,3(15

),6,10

-Farnesatetraene

(581

)e

(Z)-2-Non

enal(582

)s

(Z)-3,7-Dim

ethy

l-1,3,6-

octatriene

(583

)f

(Z)-3-Hexen-1-ol(58

4)n

(Z)-3-Hexenyl

isov

alerate(585

)o

(Z)-3-Hexenyl

prop

anoate(586

)o

(Z)-3-Hexenyl

tiglate

(587

)o

1,10

-Oxy

-α-m

yrcene

hydrox

ide(588

)b

1,10

-Oxy

-β-m

yrcene

hydrox

ide(589

)b

1,10-Bicycloprop

yl,

2,20-dim

ethy

l(590

)ah

1,1-

3-bu

teny

lester(680

)o

3-Methy

lbutanoicacid,b

utyl

ester(681

)o

3-Methy

lbutanoicacid,ethyl

ester(682

)o

3-Methy

lfuran

(683

)al

3-Methy

lpentanal(684

)k

3-Non

en-2-one

(685

)q

3-Octen-5-yne,2

,7-dim

ethy

l-(686

)ag

3-Pinanol

(687

)b

3-Thu

jen-10

-al(688

)b

3-Thu

jen-2-ol

(689

)b

3-Und

ecen-1-yne

(690

)ag

3α,15-Dihyd

roxy

cedrane(691

)a

3α-H

ydroxy

-4α,5α

-epo

xy-7-oxo

-(8[7

!6]-abeo-am

orph

ane

(692

)a

4(15

),11

-Amorph

adien-9-on

e(693

)a

4(15

),5,11

-Cadinatriene(694

)e

4,5-Diferuo

ylqu

inicacid

(695

)aj

4,7(11

)-Amorph

adien-12

-al

(696

)a

4-Amorph

en,3,11-diol

(697

)a

4-Amorph

en,3,11-diol

3-(2-m

ethy

lpropano

yl)(698

)a

4-Amorph

ene-3,7-diol

(3α,7α

)(699

)a

16 B. Koul and T. Khatri

Page 27: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

butyryl(268

)a

Cadin-4-ene,3-alpha-7-

alhp

a-diyh

ydroxy

(269

)a

Cadina-4(15)-11-dien-9-one

(270

)a

Cadina-4(7)-11

-dien-12

-al

(271

)a

Cam

phene(24)

f

Cam

phenehy

drate(272

)b�

Cam

phor

(138

)b�

Capillene(273

)ag

Carvacrol

(25)

b

Carvo

ne(26)

b

Caryo

phylladienol

I(274

)a

Caryo

phylladienol

II(275

)a

Caryo

phyllene

oxide(27)

a�

Casticin

(276

)y

Cedra-8(15)-en-9α

-ol(277

)a

Cedra-8(15)-en-9α

-ol,acetate

(278

)a

Cedra-8-en-13

-ol,acetate

(279

)a

Cedrol(280

)a�

Cedrylacetate(281

)a

Chlorog

enicacid

(282

)aa

Chrom

ene,2-2-6-trihyd

roxy

(283

)ai

Chrom

ene,2-2-dihy

drox

y-6-

metho

xy(284

)ai

Chrysanthenon

e(140

)b�

Chrysoeriol

(285

)y

Chrysosplenetin

Hex-2-en-al(372

)s

Hexacosan-1-ol(373

)r

Hexacosane(374

)i

Hexadecane(375

)i

Hexadecanoicacid

(376

)g�

Hexadecanoicacid,ethyl

ester(377

)o

Hexadecanoicacid,m

ethy

lester(378

)o

Hexan-1-olacetate(379

)o�

Hexan-1-ol,2-ethy

l(38

0)r

Hexanal(381

)k

Hexane(382

)i

Hex-cis-3-en-1-ol

(383

)n

Hex-trans-2-en-1-ol

(384

)n

Hexylcycloh

exane(385

)ah

Hum

uleneepox

ideI(386

)a

Hum

uleneepox

ideII(387

)a

Ipsdieno

l(38

8)a

Isoann

ulide(389

)a

Isoaromadendrene(390

)a�

Isob

orny

lacetate(391

)b

Isochlorog

enicacid

A(392

)aj

Isochlorog

enicacid

B(393

)aj

Isochlorog

enicacid

C(394

)aj

Isocom

ene(395

)e

Isofraxidin(396

)ai

Iso-menthon

e(397

)b

Isop

hytol(398

)l

Isoq

uercitrin

(399

)z

Isorhamnetin

(400

)y

Isorhamnetin

3-glucoside

Quercitrin,iso

(492

)z

Resorcino

l,5-no

nadecyl:3

-O-m

ethy

lether

(493

)al

Retusin

(494

)y

Rhamnentin

(495

)y

Rhamno

citrin

(496

)y

Rutin

(497

)z

Sabinaketone

(498

)b

Sabinene(86)

f�

Sabinene,cishy

drate

(46)

b

Sabinol

(499

)b

Salicylicacid

(500

)af

Santolin

aalcoho

l(87

)b

Santolin

atriene(165

)f

Scoparone

(501

)ai

Scopo

letin

(502

)ai

Scopo

lin(503

)ai

seco-Cadinane(233

)a

Selina-4,11

-diene

(504

)e

Silp

hinene

(505

)e�

Sito

sterol,b

eta(506

)x

Spathulenol

(164

)a�

Stig

masterol(507

)x

Sylvestrene

(508

)f

Tam

arixetin

(509

)y

Taraxasterone

(510

)x

Taraxerol

acetate(511

)x

Terpinen-4-ol

(94)

b�

Terpino

lene

(95)

f

Tetracosane

(512

)i

Dicycloprop

ylethy

lene

(591

)ah

1,3-Pentadiene(592

)i

1,4-Cineol(593

)b

1,6-Octadien-4-on

e,7-methy

l-3-methy

lene-

(594

)b

1,7-Octadien-3-on

e,2-methy

l-6-methy

lene-

(595

)b

1,7-Octadiene

(596

)i

1,8-Cineol(19)

b�

10-D

odecyn

-1-ol

(597

)ag

10-Epi-γ-Eud

esmol

(598

)a

10-U

ndecenal(599

)s

11R-(�)

-Dihyd

roartemisinicacid

(600

)a

14-

Hyd

roxy

-α-hum

ulene

(601

)a

14-H

ydroxy

-δ-cadinene

(602

)a

15-N

or-10-Hyd

roxy

-op

lopan-4-oicacid

(603

)a

1-Caffeoy

l-5-

feruoy

lquinicacid

(604

)aj

1-Dod

ecyn

e(605

)ag

4-Amorph

ene-3,7-diol

(3α,7α

),acetate-

(700

)4-Caffeoy

l-5-feruloylqu

inic

acid

(701

)aj

4-Feruloy

l-5-caffeoylqu

inic

acid

(702

)aj

4H-1-Benzopy

ran-4-on

e5-hy

drox

y-2-(2-hyd

roxy

-3,4-di-

metho

xyph

enyl)-3,7-dimetho

xy(703

)y

4H-1-Benzopy

ran-4-on

e,2-(2,4-dihyd

roxy

phenyl)-5-

hydrox

y-6,7-dimetho

xy(704

)y

4H-1-Benzopy

ran-4-on

e,2-(3,5-dihyd

roxy

-4-

metho

xyph

enyl)-3-(β-D-

glucop

yranosylox

y)-5,7-

dihy

drox

y(705

)y

4H-1-Benzopy

ran-4-on

e,3-hy

drox

y-6,7-dimetho

xy-2-

(4-m

etho

xyph

enyl)(706

)y

4-Hyd

roxy

-2-isoprop

enyl-5-

methy

lene-hexan-1-ol(707

)b

4-Methy

l-2,3-dihy

drofuran

(708

)al

4-Methy

l-2-pentanon

e(709

)q

4-Muu

rolen-10

-ol(710

)a

4-Penten-1-ol,p

ropion

ate(711

)o

4-Pentenal(712

)s

4-Pentene-2-ol(713

)n

4-Terpiny

lacetate(714

)b

4α,5α-Epo

xy-6α-hy

drox

y

(con

tinued)

1 The Artemisia Genus: Panacea to Several Maladies 17

Page 28: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Table

1.1

(con

tinued)

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

(Chrysosplenol

B)(286

)y

Chrysosplenol

D(287

)y

Chrysosplenol

E(288

)y

Chrysosplenol,3

0 -metho

xy(289

)y

Cirsilin

eol(290

)y

Cirsilio

l(291

)y

Cirsimaritin(292

)y

cis-Arteann

uicalcoho

l(293

)a�

cis-Calam

enene(186

)e

cis-Carveol

(146

)b

cis-Carvy

lacetate(294

)b

cis-Caryo

phyllene

oxide

(295

)a

cis-Chrysanthenyl

acetate

(145

)b

cis-Epo

xyocim

ene(31)

b

cis-Lanceol

(147

)a�

cis-Pinocarveol

(296

)b

cis-p-Menth-2-en-1-ol

(297

)b

cis-Sabinene(298

)f

Citron

ellal(299

)b

Citron

ellol(300

)b

Corym

bolone

(301

)a�

Cou

maricacid

(302

)aa

Cou

marin

(303

)ai

Cub

enol

(35)

a

Cum

inal(724

)c�

(401

)z

Jasm

one(402

)b

Kaempferide,Iso(403

)y

Kaempferol

(404

)y

Kaempferol,6

-metho

xy:

3-O-beta-

D-glucoside

(405

)z

Kon

gol(40

6)a

Lavandu

lylacetate(60)

b

Ledeneox

ide(407

)a�

Ledol

(63)

a

Lim

onene(64)

f

Lim

onene-1,2-epox

ide

(408

)b

Linaloo

l(66)

b�

Linaloo

lacetate(67)

b�

Linoleicacid

(409

)ak

Lon

gipinene

(410

)e

Luteolin

(411

)y

Luteolin

-7-m

ethy

lether

(412

)y

Maaliene

(413

)r

Mearnsetin

(414

)y

Menthen-4-ol,para

(415

)b

Menthol

(416

)b�

Menthol,2

-hyd

roxy

(417

)b

Methy

l9-octadeceno

ate

(418

)o

Methy

lcinn

amate(419

)c

Methy

lcyclop

entane

(420

)ah

Tetracosano

icacid(513

)g

Tetradecane,

2,5-dimethy

l(514

)i

Tetradecano

icacid

(515

)g

Tetratriacontane(516

)i

Thu

jone,iso

(517

)b

Thy

mol

(97)

b

t-Muu

rolol(99)

a

Tom

entin

(518

)y

tran

s,tran

s-1,3,5-

Heptatriene

(519

)i

tran

s,tran

s-2,4-

Hexadiene

(520

)i

tran

s-1,5,9-Decatriene

(521

)i

tran

s-4-Methy

l-2-hexene

(522

)i

tran

s-5-Hyd

roxy

-2-

isop

ropeny

l-5-

methy

lhex-3-en-1-ol

(523

)n

tran

s-Arteann

uicalcoho

l(524

)a

tran

s-Carveol

(170

)b

tran

s-Carvy

lacetate

(525

)b

tran

s-Caryo

phyllene

(89)

e

1-Hepten-3-ol

(606

)n

1-Hepten-6-yn

e(607

)ag

1-Metho

xy-2-butyn

e(608

)ag

1-Octanol

(609

)g

1-Octen-3-ol(185

)n

1-Oxo

-2β-[3-butanon

e]-

3α-m

ethy

l-6β-[2-prop

anoicacid]-

cycloh

exane(610

)a

1-Oxo

-2β-[3-butanon

e]-

3α-m

ethy

l-6β-[2-prop

anol

form

ylester]-

cycloh

exane(611

)a

1-Pentano

l(612

)r

1α-A

ldehyd

e-2β-[3-bu

tano

ne]-

3α-m

ethy

l-6β-[2-prop

anoicacid]-

cycloh

exane(613

)a

1α-A

ldehyd

e-2β-[3-bu

tano

ne]-

3α-m

ethy

l-6β-[2-prop

enoicacid]-

cycloh

exane(614

)a

1β,6α-Dihyd

roxy

-4(15)-

eudesm

ane(615

)a

1β-H

ydroxy

-4(15),5

amorph

an-12-oicacid

(715

)a

5,30-D

ihyd

roxy

,3,6,7,50-tetrametho

xyflavon

e(716

)y

5-Hyd

roxy

-30 ,4

0 ,6,7-

tetram

etho

xyflavon

e(717

)y

5-Methy

l-1-hexano

l(718

)5-Methy

l-2-

furancarbo

xyaldehy

de(719

)al

5-Non

adecylresorcinol-3-O

-methy

lether(720

)al

5α-H

ydroperoxy

-eud

esma-4

(15),11-diene(721

)a

5α-H

ydroxy

-eud

esma-4(15

),11

-diene(722

)a

6,7-Dim

etho

xydihy

drocou

marin

(723

)ai

6-Methy

l-3,5-heptadien-2-on

e(724

)m

7-Oxabicyclo[4.1.0]

heptane,

4-(1,5-dim

ethy

l-4-hexen-1-

ylidene)-1-m

ethy

l-,(1R

,4Z,6S)-

(725

)a

8-Tricosano

ne,2

3-hy

drox

y-2-

methy

l-(726)r

9-Decen-1-ol(727

)r

9-Octadecenoicacid,

2,3-dihy

drox

ypropy

lester(728

)o

18 B. Koul and T. Khatri

Page 29: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Cum

inicalcoho

l(30

4)c

Cyclocoloreno

ne(305

)a

Cyclohexanecarbox

ylicacid,

1,3,4-trihyd

roxy

-5-

[[3-(4-hyd

roxy

-3-

metho

xyph

enyl)-1-ox

o-2-

prop

enyl]oxy

],(306

)c

Cyclohexanecarbox

ylicacid,

3,4,5-tris

[[3-(3,4-dihyd

roxy

phenyl)-1-

oxo-2-prop

enyl]oxy

]-1-

hydrox

y(307

)c

Cyclohexanecarbox

ylicacid,

3-[[3-(3,4-dihyd

roxy

phenyl)-

1-ox

o-2-prop

enyl]oxy

]-1,4,5-trihyd

roxy

(308

)c

Methy

leugeno

l(15

9)c

Methy

lhexadecano

ate

(421

)o�

Methy

lsalicylate(422

)af

Mikanin

(423

)y

MycereneBeta

Hyd

roperoxide

(424

)b

Myrcene

(425

)f

tran

s-Chrysanthenol

(168

)b

tran

s-Nerolidol

(43)

a

tran

s-Ocimene(526

)f

tran

s-Pinocarveol

(91)

b�

tran

s-p-Menth-2-en-1-ol

(167

)b

tran

s-Sabinyl

acetate

(45)

b

tran

s-α-Ocimene(527

)f

tran

s-β-Farnesene

(152

)e

Triacon

tane

(528

)i

Triacon

tane,-2-29

-dimethy

l(529

)i

Triacosan-8-on-23

-ol,2

-methy

l(530

)r

Tricosane

(531

)i

Tricyclene(98)

f

Tridecanal(532

)k

Tridecane

(533

)i�

Tridecane,5

-methy

l(534

)i

Tridecano

icacid

(535

)g

Verbeno

ne(101

)b

Verbeny

lacetate(536

)b

Verbo

ccidentene

(537

)e

(E),10

(14)-

germ

acratriene

(616

)a

1β-H

ydroxy

-4(15),5-

eudesm

adiene

(617

)a

1β-H

ydroxy

-4(15),7-

eudesm

adiene

(618

)a

2,2,3-Trimethy

lbutane

(619

)i

2,2,6-

Trihy

drox

ychrom

ene

(620

)ai

2,2-Dihyd

roxy

-6-

metho

xy-2H-1-

benzop

yran

(621

)ai

2,3-Dihyd

ro-1,8-cineole

(622

)b

2,3-Epo

xy-7,10-

bisabo

ladiene(623

)b

2,40,5

0 -Trihydroxy-

506,7-

trim

ethoxyflavone

(624)y

2,4-Decadienal(625)

s

2,4-Dim

ethyl-2-pentene

(626)i

2,5-Dihydro-3-

methylfuran

(627)al

2,6,10-Farnesatrien-1-ol

acetate(628)a

2,6-Dim

ethyl-1,3,5,7-

octatetraene

(629)f

2,6-Dim

ethyl-1,5,7-

octatrien-3-ol

(630)b

2,6-Dim

ethyl-3,5,7-

octatrien-2-ol

(631)b

(con

tinued)

1 The Artemisia Genus: Panacea to Several Maladies 19

Page 30: Bioactive Natural Products in Drug Discovery€¦ · Vineet Meshram Department of Plant Pathology and Weed Research Agricultural Research Organization, The Volcani Centre Rishon Lezion,

Table

1.1

(con

tinued)

Botanicalname/common

name

Botanicaldescription

Medicinalprop

erties/

otheruses

Partu

sed

References

Artem

isia

arbo

rescens

(Vaill.)L.(Treewormwoo

d)A.a

rborescens

(arborescens

means

’woo

dy’or

’tree-

like’),isalso

know

nas

tree

wormwoo

d,oldwom

anor

silvery.

Itiscommon

lygrow

nin

temperateregion

sof

Mediterraneanregion

.The

plantisperenn

ialor

annu

al,

silverygreen-leaved

bushy

shrubwith

yello

wdaisy-lik

eflow

erswhich

blossom

inlatesummer

Non

ekn

own.

Essential

oilismedicinal

Who

leplant

Abadetal.(20

12),Abd

errahim

etal.(20

10)Aranitietal.(20

13),

Dhibi

etal.(20

15),Ereletal.

(201

2),M

ilitello

etal.(20

11),

Ozeketal.(20

14),You

nesetal.

(201

2)

Bioactiv

ecompo

unds

presentin

Artem

isia

arbo

rescens(V

aill.)L

Allo

-aromadendrene(135

)e�

Arborescin(729

)a�

Alcoh

olperriliqu

e(730

)n

Aldehyd

eperriliqu

e(731

)s

Borneol

(23)

b�

Borny

lbutyrate(732

)b�

Bicyclogerm

acrene

(22)

e�

Bicyclo

[2.2.1]heptan-2-ol,

1,7,7-trim

ethy

l-acetate,

(1S-end

o){B

orny

lacetate}

(137

)b�

Cum

inaldehy

de(733

)c�

Catalpo

nol(734

)a�

Cam

phene(24)

f

Cam

phor

(138

)b�

Carvo

tanacetone

(735

)b�

(�)Canfene

(736

)f

Carvacrol

(25)

b�

Chamazulene(28)

h�

cis-Salvene

(738

)f

cis-Sabinenehy

drate(46)

b�

Dehyd

ro-sesqu

icineole

(739

)a�

Diethyl

phthalate(740

)o�

Borneol

(23)

b�

Elemol

(337

)a�

Eug

enol

(347

)c�

Fargesin(741

)t

Germacrene

D(50)

e�

Germacrene-D

-4-ol(742

)a�

Geranyl

isov

alerate(56)

b�

Hexadecanoicacid

(376

)g�

Him

achalol(743

)b�

Iso-3-thujanol

(59)

b�

Isochavicolisob

utyrate

(744

)c�

Isob

utyl

2-methy

lbutyrate

(745

)o�

Linaloo

l(66)

b�

Lim

onene(64)

f

Myrteno

l(68)

b�

Methy

lbenzoate(751

)af�

(7-Epi)-silphiperfol-5-

ene(752

)e�

Methyljasmonate(753)b�

Methylsalicylate(421)af�

Neryl

isovalerate(77)

b�

Neophytadiene

(754)d�

Norcalamenene(755)a

p-Cym

ene(81)

f

Perillaldehyde

(82)

b�

Phenylh

ydroquinone

(756)u

Pulegone(85)

b�

Terpinolene

(95)

f

Terpinen-4-ol

(94)

b�

Thymol

(97)

b�

tran

s-Sabinol

(92)

b�

Toluene

(758

)af�

Und

ecan-2-one

(759

)q

α-Bisabolol

(108

)a�

α-Cop

aene

(107

)e

α-Thu

jene

(117

)f

α-Pinene(114

)f

α-Phelland

rene

(113

)f

α-Terpinene

(115

)f

α-Thu

jone

(118

)b�

α-Terpineol

(18)

b

α-Hum

ulene(110

)e

β-Eud

esmol

(557

)a�

β-Selinene(124

)e

β-Pinene(123)f

β-Phelland

rene

(558

)f

β-Thu

jone

(125

)b�

β-Bou

rbon

ene(119

)e

β-Cop

aene

(760

)e

γ-Terpinene

(130

)f

1,8-Cineole(19)

b�

1,4-Dihyd

ro-p-m

enth-2-ene

(762

)b�

2-Methy

lbutyl-2-m

ethy

lbutyrate

(763

)o�

2,3-Dim

etho

xytoluene(764

)af�

6-Methy

l-5-hepten-2-one

(765

)m

3,4-Dim

ethy

lcinn

oline(766

)w�

2,2,3-Trimethy

lnaphtalen-1(2H)-

one(767

)m

2.alph

a./2.beta-Hyd

roxy

cholest-

4-en-3-one

(768

)x

3,30-D

imethy

ldipheny

l(769

)v�

(3Z)-Hexenyl

2-methy

lbutanoate

(770

)o�

9,12

-Octadecadieno

icacid,

methy

lester(771

)o�

(E,E)-9,12

,15-octadecatrieno

ic

20 B. Koul and T. Khatri