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Ancistrocladus Naphthylisoquinoline Alkaloids

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Dettagli

Genere:Libro
Lingua: Inglese
Editore:

Springer

Pubblicazione: 01/2023
Edizione: 1st ed. 2023





Trama

This book describes a unique class of secondary metabolites, the mono- and dimeric-naphthylisoquinoline alkaloids. They exclusively occur in lianas of the palaeotropical Ancistrocladaceae and Dioncophyllaceae plant families. Their unprecedented structures include stereogenic centers and rotationally hindered, and therefore stereogenic, axes. Extended recent investigations on six Ancistrocladus species from Asia, as reported in this contribution, shed light on their fascinating phytochemical productivity, with over 100 intriguing natural products. This high chemodiversity arises from a similarly unique biosynthesis from acetate-malonate units, following a novel polyketidic pathway to plant-derived isoquinoline alkaloids. Some of the compounds show most promising anti-parasitic activities. Additionally, strategies for the regio- and stereoselective total synthesis of the alkaloids, including the directed construction of the chiral axis, are also presented.





Sommario

Contents

  1. Introduction   …………………………………………………………………..

  2. Naphthylisoquinoline Alkaloids, a Fascinating Class of Axially  

Chiral Biaryl Natural Products   ……………………………………………….

2.1 Structural Diversity and Classification of Naphthylisoquinoline  

Alkaloids – A Short Overview   ……………………………………..…………

2.2 Mono- and Dimeric Dioncophyllaceae-Type Naphthylisoquinolines  

and Related Compounds   …………………….………………………..………

2.2.1 Occurrence of Dioncophyllaceous Alkaloids in Nature   …..….………………

2.2.2 Artificial Dimers of Dioncophyllaceae-Type Monomers as Promising  

Antiplasmodial Agents: Design and Total Synthesis   …………………….…..

2.3 A Novel Biosynthesis Pathway in Plants: Acetogenic  

Naphthylisoquinoline Alkaloids   ………………………………………………

2.4 The Tool Box Used for the Isolation, Structural Elucidation, and  

Stereochemical Assignment of Naphthylisoquinoline Alkaloids –   

A Short Overview   ……………………………………………………………..

  1. Ancistrocladus, a Genus of Woody Lianas of the Monotypic Plant  

Family Ancistrocladaceae Widely Occurring in India, Sri Lanka, and   

Southeast Asia   …………………………………………………………………

3.1 Ancistrocladus heyneanus, a Large Climbing Shrub from the Indian  

Subcontinent   …………………………………………………………………...

3.2 Ancistrocladus hamatus, Endemic to the Lowland Evergreen Forests  

of Sri Lanka   ……………………………………………………………………

3.3 Ancistrocladus griffithii from Submontane Forests in the  

West and South of Southeast Asia   …………………………………………….

3.4 Ancistrocladus attenuatus from Lowland Evergreen Forests of  

Myanmar and the Indian Andaman Islands   …………………………………

3.5 Ancistrocladus benomensis, a New Submontane Liana from  

Peninsular Malaysia   ………………………………………………………….

3.6 Ancistrocladus tectorius, Widely Distributed in the Rain Forests  

All Over Southeast Asia   ……………………………………………………..

    The Indian Liana Ancistrocladus heyneanus and Ancistrocladus hamatus  

from Sri Lanka: Early Studies and More Recent Discoveries   ……..………..

4.1. Ancistrocladine and Further 5,1'-Coupled Naphthylisoquinoline  

Alkaloids from the Roots and Leaves of Ancistrocladus heyneanus   ………..

4.2 Directed Total Synthesis of Ancistrocladine and Its Atropo-Diastereomer 

Hamatine by the Lactone Methodology   ………………………………..…....

4.3 Directed Synthesis of Ancistrocladisine via Configurationally  

Unstable Lactone-Bridged Biaryl Lactones   …………………………….…..

4.4 Total Synthesis of Ancistrocladidine by ortho-Arylation of a Naphthol  

with an Aryllead Triacetate   …………………………………………………

4.5 Atroposelective Total Synthesis of Enantiomerically Pure  

Ancistrocladidine and Ancistrotectorine Using the Lactone Method   ……

4.6 Produced in Aging Shoots and in Cell Cultures of Ancistrocladus  

heyneanus: The 7,8'-Coupled Naphthylisoquinoline Alkaloid   

Ancistroheynine A and Further Stress Metabolites   …………………………

4.7 A Series of 7,3'-Coupled Naphthylisoquinoline Alkaloids Isolated  

from Fresh Leaves of Ancistrocladus heyneanus   ……………………...……

4.8 Ancisheynine A, a Novel-Type N,C-Coupled Naphthylisoquinolinium  

Alkaloid: Total Synthesis and Stereoanalysis   …………………..……………

4.9 Simplified N,C-Coupled Arylisoquinolinium Salts as Promising   Candidates for the Development of Antiparasitic Agents   ………….….………

4.9.1 Inhibitory Activities of Synthetic Arylisoquinolinium Salts against  

Leishmania major   …………………………………………………..………….

4.9.2 Inhibitory Activities of Synthetic Arylisoquinolinium Salts against  

Trypanosoma brucei brucei   ……………………………………………..……..

4.9.3 Antiplasmodial Activities of Synthetic Arylisoquinolinium Salts and  

the Formation of Complexes with Hemin   ………………….………………….

4.9.4 Antibiotic Effects of Dimeric Isoquinolinium Salts on Staphylococcus  

aureus, Staphylococcus epidermidis and Candida albicans   ……………….…

  1. Full Absolute Stereostructures of Naphthylisoquinoline Alkaloids  

Directly from Crude Extracts: Characterization of New Metabolites   

from Ancistrocladus griffithii by the HPLC-MS/MS-NMR-ECD Triad   ……...

5.1 Hyphenation of HPLC with UV, MS, NMR, and ECD   ……………….………

5.1.1 Characterization of Mono- and Dimeric Naphthylisoquinoline  

Alkaloids by HPLC-ESI-MS/MS   ………………………………..…………….

5.1.2 Constitution and Relative Configuration of Naphthylisoquinoline  

Alkaloids by HPLC-NMR   …………………………………………..…………

5.1.3 Online Assignment of Absolute Configurations of  

Naphthylisoquinoline Alkaloids by HPLC-ECD   …………………..………….

5.2 A Photometric Chemical Screening Method to Trace Up  

Michellamine-Type Naphthylisoquinoline Dimers   ……………………..……..

5.3 Online-Discovery of the First Ancistrocladaceae-Type Dimer  

Ancistrogriffithine A, in Crude Leaf Extracts of Ancistrocladus griffithii,   

by the LC-MS/MS/LC-NMR/LC-ECD Triad   …………………………....…....

5.4 Complete Structural Elucidation of Ancistrogriffines A–C, Three New  

Monomeric Naphthylisoquinoline Alkaloids Online, Directly from   

Ancistrocladus griffithii   ……………………………………..…………………

6 Ancistrocladus benomensis, a New Species from Malaysia, with an  

Unprecedented Series of Non-Hydrogenated Ancistrocladaceae- and   

Dioncophyllaceae-Type Naphthylisoquinoline Alkaloids   ………..……….......

6.1 Ancistrobenomine A, the First Naphthylisoquinoline Alkaloid with a  

Hydroxymethylene Function at C-3, and Related 5,1'-Coupled   

Compounds   …………………………………………………………………….

6.2 Discovery of the First Dioncophyllaceae-Type Naphthylisoquinoline  

Alkaloids in the Leaves of an Asian Ancistrocladus Species, A. benomensis   ...

6.3 Online Structural Assignment and Observation of the  

Atropisomerization of the N,6'-Coupled Alkaloid Ancistrocladinium B   ..……

6.4 The New Species Ancistrocladus benomensis and its Extraordinary  

Chemotaxonomic Position within the Ancistrocladaceae Family   …..…….…..

  • Ancistrocladus cochinchinensis from Central Vietnam, a Distinct  

  • Ancistrocladus Taxon? — Metabolite Pattern und Phylogenetic   

    Relationship to Ancistrocladus aff. tectorius from China   …………....……….

    7.1 In the Leaves of Ancistrocladus cochinchinensis: Predominant  

    Occurrence of Naphthylisoquinoline Alkaloids with a 5,1'-Coupling Site   ..….

    7.2 7-epi-Ancistrobrevine D and Related 7,1'-Coupled  

    Naphthyltetrahydroisoquinoline Alkaloids   ………………….………………..

    7.3 N,8'-Coupled Naphthylisoquinoline Alkaloids Directly Analyzed  

    Online, by LC-MS/MS-NMR-ECD: Ancistrocladinium A and Two   

    New Phenolic Analogues   ……………………………………………….…..…

    7.4 Biosynthetically Related, Mostly Non-Coupled Naphthoquinones,  

    Tetralones, and Free Isoquinolines from Ancistrocladus cochinchinensis   ……

    7.5 Phytochemical Relationship of Ancistrocladus cochinchinensis and  

    Ancistrocladus aff. tectorius from the Chinese Island of Hainan   ……….…….

      Wid











    Altre Informazioni

    ISBN:

    9783031104565

    Condizione: Nuovo
    Collana: Progress in the Chemistry of Organic Natural Products
    Dimensioni: 235 x 155 mm Ø 751 gr
    Formato: Copertina rigida
    Illustration Notes:XI, 335 p. 246 illus., 106 illus. in color.
    Pagine Arabe: 335
    Pagine Romane: xi


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