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EbookBell Team
4.4
82 reviewsISBN 13: 9783642068102
Author: Guido Cimino, Margherita Gavagnin
Marine molluscs are very promising candidates for a wide range of biotechnological applications. For example, they possess analgesic drugs more potent than morphine and very effective anticancer agents. The present book gives an up-to-date overview of the main classes of bioactive compounds from molluscs, moving from ecological observations, to chemical characterization, to biosynthesis, to large-scale synthesis, and to pharmacological applications. A truly outstanding international panel of experts from all continents provides complete coverage of the most stimulating topics related to molluscs. This knowledge of their history and current studies provides an open door to the future.
Molluscan Natural Products as Biological Models: Chemical Ecology, Histology, and Laboratory Culture
1.1 Introduction
1.2 Chemical Ecology of Molluscs
1.3 Histology: from Tissues to Cell Location
1.4 Laboratory Culture: Producing Bioactive Compounds
1.5 Conclusions
References
Shellfish Poisons
2.1 Introduction
2.2 Pinnatoxins, Ca2+ Channel-Activating Polyether Toxins from the Okinawan Bivalve Pinna muricata
2.2.1 Isolation and Structure of Pinnatoxin A
2.2.2 Structure of Pinnatoxins B and C
2.2.3 Biological Activity of Pinnatoxins
2.2.4 Biogenesis and Synthesis of Pinnatoxins
2.2.5 Symbioimine, a Potential Antiresorptive Drug
2.3 Pteriatoxins, Pinnatoxin Analogs from the Okinawan Bivalve Pteria penguin – Nanomole- Order St
2.3.1 Isolation of Pteriatoxins
2.3.2 Structure of Pteriatoxins
2.3.3 Other Macrocyclic Iminium Toxins Related to Pinnatoxins
2.4 Turbotoxins, Diiodotyramine Derivatives from the Japanese Gastropod Turbo marmorata
2.4.1 Isolation and Structure of Turbotoxins
2.4.2 Structure–Activity Relationship
2.5 Pinnamine and Pinnaic Acids, Alkaloidal Marine Toxins from Pinna muricata
2.5.1 Pinnamine
2.5.2 Pinnaic Acids: cPLA Inhibitors
2.5.3 Halichlorine: an Inhibitor of VCAM-1 Induction
2.5.4 Biogenesis of Pinnaic Acid
2.6 Conclusions
Acknowledgments
References
Bivalve Molluscs as Vectors of MarineBiotoxins Involved in Seafood Poisoning
3.1 Introduction
3.2 Marine Biotoxins
3.2.1 Paralytic Shellfish Poisoning
Paralytic Shellfish Toxins
Clinical Symptoms of PSP
3.2.2 Diarrhetic Shellfish Poisoning
Diarrhetic Shellfish Toxins
Clinical Symptoms of DSP
3.2.3 Toxins Found in Association with DSP Toxins
Pectenotoxins
Yessotoxins
Azaspiracids
3.2.4 Neurotoxic Shellfish Poisoning
Neurotoxic Shellfish Toxins
Clinical Symptoms of NSP
3.2.5 Amnesic Shellfish Poisoning
Amnesic Shellfish Toxins
Clinical Symptoms of ASP
3.2.6 Spirolides and Shellfish Syndrome Related to Dinoflagellates
3.3 DSP Toxins in Phytoplankton and Mussels from the Northwestern Adriatic Sea
3.3.1 New YTX Analogs Isolated from Adriatic Mussels
3.3.2 LC–MS Method for Analysis of YTXs
3.3.3 LC–MS Analysis of an Adriatic Strain of P. reticulatum
3.4 Detection of Domoic Acid in Adriatic Shellfish by Hydrophilic Interaction Liquid Chromatography
3.5 Cytotoxins from Contaminated Adriatic Blue Mussels
3.5.1 Oxazinins
3.5.2 Chlorosulfolipids
3.6 Conclusions
References
Hyperhydroxylation: A New Strategy for Neuronal Targeting by Venomous Marine Molluscs
4.1 Introduction
4.2 Hydroxylation of α-Conotoxins
4.3 Hydroxylation of Mini-M Conotoxins
4.4 Hyperhydroxylation of Conophans: D-γ- Hydroxyvaline and γ-Hydroxyconophans
4.5 Conclusions
Acknowledgments
References
The Chemistry of Marine Pulmonate Gastropods
5.1 Introduction
5.2 Secondary Metabolites from Siphonaria
5.2.1 Class I Siphonariid Polypropionates
5.2.2 Structural Analogy Between Class I and Cephalaspidean Polypropionates
5.2.3 Class II Siphonariid Polypropionates
5.2.4 Class II Polypropionates with a Noncontiguous Propionate Skeleton
5.2.5 Structural Analogy Between Class II and Bacterial Metabolites
5.2.6 Siphonariid Nonpropionate-Derived Metabolites
5.3 Secondary Metabolites from Onchidium
5.3.1 Structural Analogy Between Onchidiid and Class II Siphonariid Polypropionates
5.4 Secondary Metabolites from Trimusculus
5.5 Conclusions
References
Secondary Metabolites from the Marine Gastropod Molluscs of Antarctica, Southern Africa and South Am
6.1 Introduction
6.2 Prosobranch Secondary Metabolites
6.2.1 Antarctic Marine Prosobranchs
6.3 Opisthobranch Secondary Metabolites
6.3.1 Antarctic Marine Opisthobranchs
Pteropods (Order Gymnosomata)
Nudibranchs (Order Nudibranchia)
6.3.2 Southern African Marine Opisthobranchs
Nudibranchs (Order Nudibranchia)
Sea Hares (Order Anaspidea)
6.3.3 South American Marine Opisthobranchs
Nudibranchs (Order Nudibranchia)
Sea Hares (Order Anaspidea)
6.4 Pulmonate Secondary Metabolites
6.4.1 Southern African Marine Pulmonates
Siphonarids (Order Basommatophora)
Trimusculids (Order Eupulmonata)
6.4.2 South American Marine Pulmonates
Trimusculids (Order Eupulmonata)
6.5 Conclusions
References
Marine Mollusks from Australia and New Zealand: Chemical and Ecological Studies
7.1 Introduction
7.2 Polyketide and Polypropionate Metabolites
7.2.1 Polypropionate Metabolites in Australian and New Zealand Mollusks
7.2.2 Polyketides
7.2.3 Biosynthetic Studies
7.3 Terpenes
7.3.1 Terpene Metabolites from Australian and New Zealand Mollusks
7.3.2 Chemical and Biosynthetic Studies on Phyllidid Nudibranchs
7.4 Miscellaneous Metabolites
7.5 Conclusions
Acknowledgments
References
Chemical Diversity in Opisthobranch Molluscs from Scarcely Investigated Indo-Pacific Areas
8.1 Introduction
8.2 Studies on Nudibranchs
8.3 Studies on Sacoglossans
8.4 Studies on Cephalaspideans
8.5 Studies on Anaspideans
8.6 Comparative Discussion
8.6.1 Nudibranchs
8.6.2 Sacoglossans
8.6.3 Cephalaspideans
8.6.4 Anaspideans
8.7 Conclusions
References
Selected Bioactive Compounds from Japanese Anaspideans and Nudibranchs
9.1 Introduction
9.2 Metabolites of Anaspideans
9.2.1 Halogenated Compounds
Acetogenins
Cyclic Monoterpenoids
Pyrano-Monoterpenoids
Sesquiterpenoids
9.2.2 Degraded Sterols
9.3 Metabolites of Nudibranchs
9.3.1 Sesquiterpenes
9.3.2 Diterpenes
9.3.3 Sesterterpenes
9.4 Conclusions
References
Bioactive Molecules from Sea Hares
10.1 Introduction
10.2 Bioactive Small Molecules from Aplysiidae
10.2.1 Cytotoxic Metabolites form Dolabella auricularia
10.2.2 Cytotoxic Metabolites from Aplysia sp.
10.3 Bioactive Proteins: Aplysianin A Family
10.3.1 Isolation and Amino Acid Sequence of Aplysianin A
10.3.2 Related Sea Hare-Derived Proteins of Aplysianin A
10.3.3 Aplysianin A as LAAO
10.3.4 Biological Activities of the ApA Family Proteins
Antimicrobial Activity
Cytotoxicity
10.4 Conclusions
References
Trisoxazole Macrolides from Hexabranchus Nudibranchs and Other Marine Invertebrates
11.1 Introduction
11.2 Isolation and Structure Elucidation of Trisoxazole Macrolides from Marine Invertebrates
11.2.1 Ulapualides
11.2.2 Kabiramides
11.2.3 Halichondramide and Congeners
11.2.4 Mycalolides
11.2.5 Stereochemistry of Mycalolides
11.3 Cellular Target of Trisoxazole Macrolides
11.4 Modes of Binding of Trisoxazole Macrolides to Actin
11.5 Structure–Activity Relationships of Trisoxazole Macrolides
11.6 Biological Significance of Trisoxazole Macrolides in the Nudibranch H. sanguineus
11.7 Conclusions
References
Sequestration and Possible Role of Dietary Alkaloids in the Sponge-Feeding Mollusk Tylodinaperversa
12.1 Introduction
12.2 Sequestration of Alkaloids from the Prey Sponge by Tylodina perversa
12.3 Choice Feeding Experiments with Tylodina perversa
12.4 Impact of Different Aplysina Sponges on the Alkaloid Patterns in Tylodina perversa
12.5 Conclusions
Acknowledgments
References
Skin Chemistry of Nudibranchs from the West Coast of North America
13.1 Introduction
13.2 Secondary Metabolites Reported from Northeastern Pacific Nudibranchs
13.3 De Novo Biosynthesis by Northeastern Pacific Nudibranchs
13.4 Conclusions
References
Biogenetic Proposals and Biosynthetic Studies on Secondary Metabolites of Opisthobranch Molluscs
14.1 Introduction
14.2 Polyketides
14.3 Terpenes
14.4 Conclusions
Acknowledgements
References
Total Synthesis of Bioactive Peptides and Depsipeptides from Marine Opisthobranch Molluscs
15.1 Introduction
15.2 Linear Peptides
15.2.1 Janolusimide
15.2.2 Dolastatin 10
15.2.3 Dolastatin 18
15.2.4 Dolastatin H and Isodolastatin H
15.3 Cyclic Peptides
15.3.1 Dolastatin 3
15.3.2 Dolastatin E
15.3.3 Dolastatin I
15.4 Linear Depsipeptides
15.4.1 Dolastatin 15
15.4.2 Dolastatin C
15.5 Cyclic Depsipeptides
15.5.1 Dolastatin 11
15.5.2 Dolastatin D
15.5.3 Dolastatin G and Nordolastatin G
15.5.4 Doliculide
15.5.5 Aurilide
15.5.6 Kahalalide B
15.5.7 Kahalalide F
Appendix 15.1
References
Kahalalide F and ES285: Potent Anticancer Agents from Marine Molluscs
16.1 Introduction
16.2 Kahalalide F
16.2.1 Mechanism of Action
16.2.2 Preclinical Pharmacology
16.2.3 Preclinical Toxicology
16.2.4 Synthesis of Kahalalide F
16.2.5 Clinical Trials
16.3 ES285
16.3.1 Mechanism of Action
16.3.2 Non-Clinical Studies
16.3.3 Synthesis of ES285
16.3.4 Clinical Trials
16.4 Conclusions
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Tags: Guido Cimino, Margherita Gavagnin, Molluscs, Chemo