Progress in the Chemistry of Organic Natural Products 113

1. Auflage 2020
ISBN: 978-3-030-53027-3
Verlag: Springer-Verlag GmbH

Buch, Englisch, Band 113, 247 Seiten, Book, Format (B × H): 160 mm x 241 mm, Gewicht: 599 g

Reihe: Progress in the Chemistry of Organic Natural Products

In this book, chemical studies are described mainly from literature reports appearing since 2000, inclusive of investigations performed by the present authors, on the diversity in secondary metabolites of Ligularia growing in the Hengduan Mountains area of China, focusing on eremophilane sesquiterpenoids and other metabolites. More than 100 Ligularia species and their related genera in the plant family Senecioneae plants (Cremanthodium, Cacalia, Senecio, and others) grow in East Asia. For many years, researchers have studied the chemical constituents of these plants, and terpenoids, flavonoids, steroids, alkaloids, and aromatic compounds have been isolated. Among these, in particular, numerous sesquiterpenoids were reported. Within this book terpenoids and aromatic compounds (total 1049), both previously unknown and known, are presented. Finally, genetic studies and synthesis investigations are briefly reviewed.

Zielgruppe

Research

Autoren/Hrsg.

Kinghorn, A Douglas

Falk, Heinz

Gibbons, Simon

Kobayashi, Jun'Ichi

Asakawa, Yoshinori

Liu, Ji-Kai

Fachgebiete

• Naturwissenschaften Chemie Analytische Chemie
• Naturwissenschaften Biowissenschaften Botanik
• Naturwissenschaften Biowissenschaften Biochemie (nichtmedizinisch)
• Naturwissenschaften Chemie Organische Chemie

Inhaltsverzeichnis

1                 Introduction

2                 Compounds

3                 Ligularia Species

3.1           Ligularia virgaurea (Maximowicz) Mattfeld ex Rehder & Kobuski

3.2           Ligularia dentata (A. Gray) H. Hara

3.3           Ligularia japonica (Thunberg) Lessing

3.4           Ligularia hookeri (C. B. Clarke) Handel-Mazzetti

3.5           Ligularia atroviolacea (Franchet) Handel-Mazetti

3.6           Ligularia kanaitzensis (Franchet) Handel-Mazzetti

3.7           Ligularia intermedia Nakai

3.8           Ligularia vellerea (Franchet) Handel-Mazzetti

3.9           Ligularia wilsoniana (Hemsley) Greenman

3.10       Ligularia melanothyrsa Handel-Mazzetti

3.11       Ligularia lapathifolia (Franchet) Handel-Mazzetti

3.12       Ligularia macrophylla (Ledebour) Candolle

3.13       Ligulariaknorringiana Pojarkova (= L. thyrsoidea) and Ligularianarynensis (C. Winkler) O. Fedtschenko & B. Fedtschenko

3.14       Ligularia rumicifolia S. W. Liu

3.15       Ligulariasongarica (Fischer) Y. Ling

3.16       Ligularia stenocephala (Maximowicz) Matsumura & Koidzumi

3.17       Ligularia alticola Voroschilov

3.18       Ligularia brassicoides Handel-Mazzetti

3.19       Ligulariacaloxantha (Diels) Handel-Mazzetti

3.20       Ligularia przewalskii (Maximowicz) Diels

3.21       Ligularia sagitta (Maximowicz) Mattfield ex Rehder & Kobuski

3.22       Ligularia pleurocaulis (Franchet) Handel-Mazzetti

3.23       Ligulariafischeri (Ledebour) Turczaninow, Ligulariaanoleuca Handel-Mazzetti, and Ligulariaveitchiana (Hemsley) Greenman

3.24       Ligulariacyathiceps Handel-Mazzetti

3.25       Ligulariacymbulifera (W. W. Smith) Handel-Mazzetti

3.26       Ligulariadictyoneura (Franchet) Handel-Mazzetti

3.27       Ligulariaduciformis (C. Winkler) Handel-Mazzetti, Ligulariakonkalingensis Handel-Mazzetti, Ligularianelumbifolia (Bureau & Franchet) Handel-Mazzetti, and Ligularialimprichtii (Diels) Handel-Mazzetti

3.28       Ligulariahodgsonii J. D. Hooker

3.29       Ligularialamarum (Diels) C. C. Chang and Ligulariasubspicata (Bureau & Franchet) Handel-Mazzetti

3.30       Ligularialankongensis (Franchet) Handel-Mazzetti

3.31       Ligularialatihastata (W. W. Smith) Handel-Mazzetti and Ligulariavillosa (Handel-Mazzetti) S. W. Liu

3.32       Ligularialongihastata Handel-Mazzetti

3.33       Ligulariaoligonema Handel-Mazzetti

3.34       Ligulariatongolensis (Franchet) Handel-Mazzetti

3.35       Ligulariatsangchanensis (Franchet) Handel-Mazzetti

3.36       Ligulariayunnanensis (Franchet) C. C. Chang

3.37       Hybrid

3.38       Further Ligularia I: L. altaica Candolle, L. dolichobotrys Diels, L. dolichobotrys Diels, L. franchetiana (H. Léveillé) Handel-Mazzetti, L. persica Boissier, L. speciosa Fischer et Meyer, L. thyrsoidea (Ledebour) Candolle

3.39            Further Ligularia II: L. achyrotricha (Diels) Y. Ling, L. nanchuanica S. W. Liu, L. purdomii (Turrill) Chittenden, L. odontomanes Handel-Mazzetti, L. sibirica (Linnaeus) Cassini, L. thomsonii (C. B. Clarke) Pojarkova

3.40            Further Ligularia III: L. angusta (Nakai) Kitamura, L. calthifolia Maximowicz, L. fauriei (Franchet) Koidzumi, L. hiberniflorum (Makino) Kitamura, L. kangtingensis S. W. Liu, L. lingiana S. W. Liu, L. myriocephala Y. Ling ex S. W. Liu, L. platyglossa (Franchet) Handel-Mazzetti, L. schmidtii (Maximowicz) Makino

3.41            Further Ligularia IV: L. brachyphylla Handel- Mazzetti (= L. lathihastata), L. caltaefolia (Maximowicz) Diels, L. clivorum Maximowicz (= L. dentata), L. sachalinensis Nakai, L. tangutica (Maximowicz) Bergmans, L. trichocephala (Maximowicz) Matsumura et Koidzumi, L. vorobierii Worosh

4       Genetic Analyses

5        Synthesis Aspects

5.1         Synthesis of Ligularol = Petasalbin, Ligularone, and Related Compounds

5.2         Synthesis of Tetrahydroligularenolide Using Biogenetic Type Rearrangement

5.3         Synthesis of Furanoeremophilan-15,6-olide

5.4         Synthesis of Isopetasol

5.5         Synthesis of Eremophila-9,11-dien-8-one, Dehydrofukinone, and Furanoeremophilanes 5.6         Synthesis of Eremoligenol and Eremophilone 5.7         Synthesis of Eremophiladienes 5.8         Synthesis of Fukinone and Related Compounds 5.9         Synthesis of Eremohiladiene 5.10     Synthesis of 6-Hydroxyeuryopsin

5.11     Synthesis of 3b-Angeloyloxyfuranoeremophilane

5.12     Synthesis of Ligularone and Isoligularone

5.13     Synthesis of (–)-(R)-Ligularenolide and (–)-(R)-PF1092C

5.14     Synthesis of Nootkatone

5.15     Synthesis of Cacalol

5.16     Synthesis of Noreremophilanes

5.17     Synthesis of Bakkane Type Sesquiterpenoids

5.18     Synthesis of Bisabolane Type Sesquiterpenoids

5.19     Synthesis of Nelumol A

6           Biological Activities Acknowledgement

Acknowledgements

References