Rahman Studies in Natural Products Chemistry

1. Auflage 2015
ISBN: 978-0-08-100051-9
Verlag: Elsevier Science & Techn.
Format: EPUB
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, Band Volume 45, 554 Seiten

Reihe: Studies in Natural Products Chemistry

Natural products in the plant and animal kingdom offer a huge diversity of chemical structures that are the result of biosynthetic processes that have been modulated over the millennia through genetic effects. With the rapid developments in spectroscopic techniques and accompanying advances in high-throughput screening techniques, it has become possible to isolate and then determine the structures and biological activity of natural products rapidly, thus opening up exciting opportunities in the field of new drug development to the pharmaceutical industry. The series also covers the synthesis or testing and recording of the medicinal properties of natural products, providing cutting edge accounts of the fascinating developments in the isolation, structure elucidation, synthesis, biosynthesis and pharmacology of a diverse array of bioactive natural products. - Focuses on the chemistry of bioactive natural products - Contains contributions by leading authorities in the field - Presents sources of new pharmacophores

Autoren/Hrsg.

Rahman, Atta-ur

Inhaltsverzeichnis

1;Front Cover;1
2;Studies in Natural Products Chemistry;4
3;Copyright;5
4;Contents;6
5;Contributors;12
6;Preface;16
7;Chapter 1 - Fabrication of Cellulose Hydrogels and Characterization of Their Biocompatible Films;18
7.1;INTRODUCTION;18
7.2;FABRICATION OF CELLULOSE FILMS AND THEIR PROPERTIES;20
7.3;CELLULOSE HYDROGEL BIOACTIVITY;25
7.4;CONCLUDING REMARKS;29
7.5;LIST OF ABBREVIATIONS;30
7.6;ACKNOWLEDGMENTS;30
7.7;REFERENCES;30
8;Chapter 2 - Cannabis and Bioactive Cannabinoids;34
8.1;CANNABIS;35
8.2;THE ENDOCANNABINOID SYSTEM;39
8.3;CANNABINOIDS;43
8.4;THE THERAPEUTIC POTENTIAL.OF CANNABINOIDS;66
8.5;CONCLUDING REMARKS;67
8.6;LIST OF ABBREVIATIONS;68
8.7;REFERENCES;69
9;Chapter 3 - Electrochemical Monitoring of the Pharmacological Activity of Natural Products;76
9.1;INTRODUCTION;76
9.2;GENERAL ASPECTS;77
9.3;MATERIALS AND TECHNIQUES;79
9.4;CORRELATION BETWEEN.ELECTROCHEMICAL DATA.AND ACTIVITY;81
9.5;FINAL CONSIDERATIONS;96
9.6;LIST OF ABBREVIATIONS;97
9.7;ACKNOWLEDGMENTS;97
9.8;REFERENCES;98
10;Chapter 4 - Structural Elucidation of Saponins: A Combined Approach Based on High-Resolution Spectroscopic Techniques;102
10.1;INTRODUCTION;102
10.2;SAPONIN CLASSIFICATION;103
10.3;SAPONIN STRUCTURAL ELUCIDATION;105
10.4;NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;106
10.5;STRUCTURAL ELUCIDATION OF THE.AGLYCONE PORTION;110
10.6;STRUCTURAL ELUCIDATION OF THE.SUGAR PORTION;111
10.7;GLYCOSYLATION SITE AND SUGAR.CHAIN BRANCHING;112
10.8;FURTHER STRUCTURAL FEATURES;113
10.9;ADVANCES IN STRUCTURAL ELUCIDATION.OF SAPONINS USING MS;113
10.10;TANDEM MS;120
10.11;NMR AND MS AT WORK IN SAPONIN STRUCTURAL ELUCIDATION;121
10.12;LIST OF ABBREVIATIONS;133
10.13;REFERENCES;133
11;Chapter 5 - Ecdysteroids in Plants and their Pharmacological Effects in Vertebrates and Humans;138
11.1;INTRODUCTION;138
11.2;CHEMICAL STRUCTURE OF PHYTOECDYSTEROIDS;139
11.3;OCCURRENCE OF ECDYSTEROIDS.IN PLANTS;145
11.4;BIOSYNTHESIS AND METABOLISM OF PHYTOECDYSTEROIDS;147
11.5;FUNCTION OF ECDYSTEROIDS.IN PLANTS;149
11.6;PHARMACOLOGICAL EFFECTS OF PHYTOECDYSTEROIDS;151
11.7;CONCLUDING REMARKS;159
11.8;LIST OF ABBREVIATIONS;159
11.9;ACKNOWLEDGMENTS;160
11.10;REFERENCES;160
12;Chapter 6 - Drimane-Related Merosesquiterpenoids, a Promising Library of Metabolites for Drug Development;164
12.1;INTRODUCTION;165
12.2;OCCURRENCE, CLASSIFICATION,.AND BIOSYNTHESIS OF.POLYKETIDE-MSRDS;167
12.3;OCCURRENCE, CLASSIFICATION,.AND BIOSYNTHESIS OF.SHIKIMATE-MSRDS;184
12.4;OCCURRENCE, CLASSIFICATION, AND BIOSYNTHESIS OF AMINO.ACID-MSRDS;202
12.5;BIOLOGICAL ACTIVITIES;205
12.6;CONCLUSIONS;216
12.7;STRUCTURAL ABBREVIATIONS USED.IN THE CHAPTER;217
12.8;REFERENCES;217
13;Chapter 7 - The Structure–Activity Relationships of Plant Secondary Metabolites with Antimicrobial, Free Radical Scavenging and Inhibitory Activity toward Selected Enzymes;234
13.1;INTRODUCTION;235
13.2;SARS FOR COMPOUNDS WITH.INHIBITORY ACTIVITY AGAINST.SELECTED ENZYMES;236
13.3;INHIBITORS OF MMPS;249
13.4;ANTIBACTERIAL AND ANTIFUNGAL MECHANISM OF ACTION OF SELECTED SECONDARY PLANT METABOLITES;252
13.5;STRUCTURE–FREE RADICAL.SCAVENGING ACTIVITY RELATIONSHIPS.FOR SELECTED SECONDARY PLANT METABOLITES;256
13.6;ANTIOXIDANT–ACTIVITY.RELATIONSHIP FOR POLYPHENOLS;257
13.7;ANTIOXIDANT–ACTIVITY RELATIONSHIP.FOR NON-PHENOLICS;259
13.8;MONO- DI- AND SESQUITERPENES;259
13.9;CAROTENOIDS;262
13.10;CONCLUDING REMARKS;263
13.11;LIST OF ABBREVIATIONS;264
13.12;REFERENCES;264
14;Chapter 8 - Marine Polyacetylenes: Distribution, Biological Properties, and Synthesis;268
14.1;INTRODUCTION;268
14.2;MARINE ORGANISMS AS SOURCE OF POLYACETYLENES;269
14.3;SYNTHESIS OF POLYACETYLENES;301
14.4;CONCLUSION;308
14.5;LIST OF ABBREVIATIONS;309
14.6;REFERENCES;309
15;Chapter 9 - Bioactive Natural Products from Marine-Derived Fungi: An Update;314
15.1;ALKALOIDS ISOLATED FROM.MARINE-DERIVED FUNGI;315
15.2;POLYPEPTIDES ISOLATED FROM.MARINE-DERIVED FUNGI;326
15.3;POLYKETIDES AND POLYKETIDE.DERIVATIVE COMPOUNDS ISOLATED.FROM MARINE-DERIVED FUNGI;334
15.4;LACTONES AND MACROLIDES-BASED POLYKETIDES ISOLATED FROM.MARINE-DERIVED FUNGI;349
15.5;STEROIDS ISOLATED FROM.MARINE-DERIVED FUNGI;357
15.6;TERPENOIDS ISOLATED FROM.MARINE-DERIVED FUNGI;360
15.7;MISCELLANEOUS METABOLITES.ISOLATED FROM.MARINE-DERIVED FUNGI;367
15.8;REFERENCES;372
16;Chapter 10 - Mushrooms: A Source of Exciting Bioactive Compounds;380
16.1;INTRODUCTION;380
16.2;ISOLATED BIOACTIVE.COMPOUNDS;382
16.3;CONCLUSION;438
16.4;LIST OF ABBREVIATIONS;467
16.5;ACKNOWLEDGMENTS;468
16.6;REFERENCES;468
17;Chapter 11 - Natural Bioactive Molecules: Mechanism of Actions and Perspectives in Organ Pathophysiology;474
17.1;INTRODUCTION;475
17.2;ROLE OF SMALL BIOACTIVE MOLECULES.IN ORGAN PATHOPHYSIOLOGY;476
17.3;BENEFICIAL ROLE OF MACROMOLECULES.IN ORGAN PATHOPHYSIOLOGY;490
17.4;CONCLUSION;494
17.5;LIST OF ABBREVIATIONS;495
17.6;REFERENCES;496
18;Chapter 12 - Oxindole Alkaloids of Uncaria (Rubiaceae, Subfamily Cinchonoideae): A Review on Its Structure, Properties, and Bioactivities;502
18.1;BACKGROUND;503
18.2;PHYTOCHEMISTRY OF UNCARIA:.OXINDOLE ALKALOIDS;504
18.3;BIOGENESIS OF OXINDOLE ALKALOIDS.IN UNCARIA;514
18.4;BIOLOGICAL AND PHARMACOLOGICAL STUDIES ON OXINDOLES.OF UNCARIA;515
18.5;CONCLUSION;539
18.6;REFERENCES;539
19;Index;544

Leseproben

Chapter 2

Cannabis and Bioactive Cannabinoids

Federica Messina, Ornelio Rosati, Massimo Curini and M. Carla Marcotullio1     Department of Pharmaceutical Science, University of Perugia, Perugia, Italy
1 Corresponding author: E-mail: [e-mail]

Abstract

The therapeutic use of Cannabis dates back to ancient times and this plant has been used for centuries as remedy for a large number of diseases. Today it is well known that biological activity of Cannabis is related to the endocannabinoid system (ECS), a complex signaling network that comprises classical cannabinoid receptors (CB1 and CB2), arachidonic acid-derived ligands, and enzymes degrading the endocannabinoids anandamide and 2-arachidonoyl glycerol, namely fatty acid amide hydrolase and monoacylglycerol lipase. The modulation of the ECS activity turned out to be a therapeutic promise in a wide range of diseases. A problem to the development of Cannabis and cannabinoid medications is the psychoactive property of natural or synthetic agonists, mediated by CB1 receptor. This review deals with the literature analysis of the important biological activities of Cannabis and the efforts aimed to the discovery of natural and nonnatural selective cannabinoids.

Keywords

Cannabinoid receptors; Cannabis; Endocannabinoid system; Phytocannabinoids; Synthetic cannabinoids

Cannabis

Cannabis is a genus of flowering plants of the Moraceae family [1]. It includes three putative varieties: Cannabis indica, Cannabis sativa, and Cannabis ruderalis, showing some morphological difference from each other, e.g., height of the mature plant, quantity of branches, bushy growth, and quantity of bore flowers. Some of these characteristics are shown in Fig. 1.

Cannabis is dioecious, flowering herb. C. indica is annual while C. sativa is biannual. The leaf shape is digitate, palmately compound, with serrate leaflets. The first pair of leaves usually have a single leaflet, the number gradually increasing up to usually seven or nine leaflets per leaf, depending on variety and growing conditions. At the top of a flowering plant, this number diminishes to a single leaflet per leaf. The lower leaf pairs usually occur in an opposite leaf arrangement and the upper leaf pairs in an alternate arrangement on the main stem of a mature plant. The leaves have a peculiar and diagnostic venation pattern [2]. Cannabis normally has imperfect flowers, with staminate “male” and pistillate “female” flowers occurring on separate plants [3]. It is not unusual for individual plants to bear both male and female flowers [4]. Male flowers are usually borne on loose panicles while female flowers are borne on racemes. All known strains of Cannabis are wind-pollinated.

The fruit is an achene. Most strains of Cannabis are short-day plants, with the possible exception of C. ruderalis which is commonly described as “auto-flowering” and may be day-neutral [5]. Cannabinoids, terpenoids, and other compounds are secreted by glandular trichomes that occur most abundantly on the floral calyxes and bracts of female plants. As a drug it usually comes in the form of dried flower buds (marijuana), resin (hashish), or various extracts collectively known as hashish oil.

Figure 1 Morphologic differences between Cannabis subspecies.

Cannabis in History

The therapeutic use C. sativa, commonly known as hemp, is known since ancient times. It was certainly cultivated in China in 4000 BC, and is included in the oldest known pharmacopoeia, the Pen Ts’ao Ching, traditionally attributed to the legendary emperor Shen Nung (III millennium BC), where it is recommended against “female’s disorders, gout, rheumatism, malaria, constipation, and muscular weakness” [6]. Around AD 220 the great Chinese surgeon Hua T’o describes the use of Cannabis as analgesic and anesthetic. Later, the therapeutic indications were further extended to wounds healing, against emaciation, in the removal of pus, in rheumatism treatment, and to reduce fever and anxiety [7–9].

In India, Cannabis is cited in Atharvaveda (II millennium BC) as “plant that releases anxiety,” while in the oldest medical textbook of Ayurvedic tradition, based on the doctrine of Sushruta (II millennium BC), it is mentioned as “remedy.” Actually, in Indian culture Cannabis plays a peculiar role: as a plant sacred to Shiva, it is used in religious rituals; as intoxicating is widely used in popular culture; and finally, as drug is used in various traditional medicines (i.e., Ayurveda, Unani, Tibbi).

According to the note written by J. M. Campbell included in Appendix III of the famous Indian Hemp Drugs Commission Report (1893–1894), Cannabis is used in the treatment of fever, described as “being active not directly or physically as an ordinary drug, but indirectly or spiritually, calming the angry spirits that the fever is due to,” also is described to have many other medicinal virtues [10]. With regard to the Middle East and the Mediterranean area, where the Cannabis has a role as intoxicating and “social drug,” there are only few ancient citations of medical interest. Among the others, the Assyrian medical tablets from the library of Ashurbanipal (seventh century BC) report hemp as an antidepressant. The most important handbook referring to Cannabis dates back to AD 70: in Materia Medica, Dioscorides shows the oldest known depiction of the plant and recommends its use in earache, to reduce edema, and against yellow jaundice. A century later according to Galen (second century AD), the most famous physician of the Roma Empire, hemp preparations are useful against flatulence and a panacea in the treatment of all kinds of pain, admonishing “if you overdo the dose it affects the head, getting into it hot vapors and intoxicants.” Throughout the Middle Age and the Renaissance, the most important use of Cannabis is to obtain fibers for rope, textiles, and paper [11]. The ropes, rigging, and sails of the ships were usually obtained from hemp and this is the main reason why the plant, already widely cultivated in Europe, was imported to America, to the south by Spanish and Portuguese vessels, and to the north by British and French. In this period there are also interesting medical notations from Garcia de Orta, a physician at the service of the Portuguese viceroy in Goa, India. In his “Colloquies on the Simples and Drugs of India” (1563) he mentions the use of Cannabis as an appetite stimulant, as well as a “sleeping adjuvant,” hypnotic, aphrodisiac, and euphoric [12]. Unfortunately almost all the copies were burned under the Inquisition. A similar contribution was given shortly after by Cristobal Acosta in the opera Treatise of the drugs and medicines of the East Indies (1578) [13]. Later, Englebert Kampfer, medical-botanical-historical German diplomat, ambassador of the King of Sweden in Persia, and later chief physician of the fleet of the Dutch East India Company (VOC), describes in his Amoenitates exoticarum (1712) the use of many medicinal plants, including Cannabis [14].

With regards of Europe, Robert Burton in his classic The anatomy of melancholy (1621) [15] suggests the possible utility of Cannabis to treat depression. In the famous The Complete Herbal by Nicolas Culpeper (1653) are listed in detail all the at-the-time known medical applications of Cannabis [16]. In 1682, the New London Dispensatory states that Cannabis “cures cough and jaundice but fills the head of steam of dizziness.” The New English Dispensatory (1764) recommends to boil the hemp’s roots and apply the decoction on the skin to reduce inflammation, as well as to “dry out cancer” and to dissolve the “deposits in the joints” [17].

In 1753 Linnaeus named hemp as C. sativa, considering the existence of a single species [18], while in 1785 Lamarck, on the basis of significant morphological differences, distinguished the genus Cannabis into two distinct species: C. sativa, native to Europe, and C. indica, native to Asia [19]. The Dictionnaire des Sciences Médicales (1812) reports that the part of the plant used for medical purposes in Europe is the seeds [20]. The importance of Cannabis, been always marginal in Western medicine, was definitely increased in result of Napoleon’s Egyptian campaign (1798), after which the hashish, essentially an intoxicant and euphoric, became well-known in France, especially among intellectual circles such as the famous Club des Hashishins, attended by figures such as the psychiatrist J.J. Moreau de Tours [21] and artists such as Gautier, Dumas, Nerval, Hugo, Baudelaire, and Delacroix. The books having the most influence in the West were On the preparations of the Indian Hemp, or Gunjah by William B. O’Shaughnessy [22], a British physician serving in India and De typhus fever ou...