Novel Plant Natural Product Skeletons : Discoveries From 1999-2021

This book provides an overview of the new plant natural product skeletons discovered from 1999 to 2021. It categorizes these natural products by providing their names, source distributions, structural types, structure characteristics, and bioactivities. A total of 1373 plant products in 99 families are presented, which cover 36 different structure types within the Hypericaceae family of which the majority are alkaloid structures. In addition, it presents the biological profiling in the last 23 years by summarizing the biological activities and potential disadvantages. The new natural products skeleton presented are unprecedented structural scaffolds and could bring new opportunities for biological/pharmaceutical areas and provide new structure templates for synthetic chemists. This book helps readers gain in-depth insight into the past and recent trends of natural products; it also assists those interested in assessing the potential biological function of the natural products. Preface Contents 1 Introduction References 2 Classification of Diverse Novel Sesquiterpenoids 2.1 Solo-Sesquiterpenoids 2.1.1 Asteraceae/Compositae 2.1.2 Magnoliaceae 2.1.3 Annonaceae 2.1.4 Valerianaceae 2.1.5 Apocynaceae 2.1.6 Anacardiaceae 2.1.7 Coriariaceae 2.1.8 Plagiochilaceae 2.1.9 Lepidolaenaceae 2.1.10 Zingiberaceae 2.1.11 Myrtaceae 2.1.12 Oleaceae 2.1.13 Illiciaceae 2.1.14 Thymelaeaceae 2.2 Sesquitepenoid Oligomers 2.2.1 Chloranthaceae 2.2.2 Lauraceae 2.2.3 Asteraceae/Compositae 2.2.4 Burseraceae 2.2.5 Valerianaceae 2.2.6 Zingiberaceae 2.2.7 Annonaceae 2.2.8 Myrtaceae References 3 Classification of Diverse Novel Diterpenoids 3.1 Euphorbiaceae 3.1.1 Euphorbia 3.1.2 Croton 3.1.3 Trigonostemon 3.1.4 Jatropha 3.2 Lamiaceae 3.2.1 Isodon 3.2.2 Salvia 3.2.3 Leonurus 3.2.4 Hyptis 3.3 Ericaceae 3.3.1 Rhododendron 3.3.2 Pieris 3.4 Zingiberaceae 3.4.1 Amomum 3.4.2 Hedychium 3.5 Taxaceae 3.5.1 Cephalotaxus 3.5.2 Amentotaxus 3.5.3 Torreya 3.5.4 Taxus 3.6 Viburnum (Caprifoliaceae) 3.7 Ranunculaceae 3.7.1 Paeonia 3.7.2 Nigella 3.8 Meliaceae 3.8.1 Aphanamixis 3.8.2 Dysoxylum 3.9 Taxodiaceae 3.9.1 Cunninghamia 3.9.2 Taxodium 3.10 Cinnamomum (Lauraceae) 3.11 Annonaceae 3.11.1 Mitrephora 3.11.2 Annona 3.12 Others References 4 Diverse Novel Sesterterpenoids References 5 Classification of Diverse Triterpenoids 5.1 Schisandraceae 5.1.1 Schisandra 5.1.2 Kadsura 5.2 Indaceae 5.2.1 Iris 5.2.2 Belamcanda 5.3 Euphorbiaceae 5.3.1 Phyllanthus 5.3.2 Euphorbia 5.4 Meliaceae 5.4.1 Dysoxylum 5.4.2 Aglaia 5.4.3 Walsura 5.4.4 Turraea 5.5 Pinaceae 5.5.1 Abies 5.5.2 Pseudolarix 5.6 Ranunculacea 5.6.1 Actaea 5.6.2 Cimicifuga 5.7 Lygodium (Lygodiaceae) 5.8 Malpighia (Malpighiaceae) 5.9 Sinocalamus (Poaceae) 5.10 Alstonia (Apocynaceae) 5.11 Panax (Araliaceae) 5.12 Others References 6 Classification of Diverse Novel Limonoids 6.1 Demolition of a Single Ring 6.1.1 Ring A-Seco Group 6.1.2 Ring B-Seco Group 6.1.3 Ring D-Seco Group 6.2 Demolition of Two Rings 6.2.1 Rings A,B-Seco Group 6.2.2 Rings B,D-Seco Group 6.2.3 Ring C,D-Seco Group 6.3 Demolition of Three Rings 6.3.1 Ring A,B,D-Seco Group 6.3.2 Ring B,C,D-Seco Group References 7 Classification of Diverse Novel Phloroglucinols 7.1 Bicyclic Polyprenylated Acylphloroglucinols (BPAPs) 7.1.1 Type A BPAPs 7.1.2 Type B BPAPs 7.1.3 Seco-BPAPs 7.2 Caged PPAPs with Adamantane and Homoadamantane Skeletons 7.2.1 Adamantane-Type PPAPs 7.2.2 Homoadamantane-Type PPAPs 7.2.3 Other Caged PPAPs 7.3 Other PPAPs 7.3.1 Spirocyclic PPAPs with Octahydrospiro[Cyclohexan-1,5′-Indene] Core 7.3.2 Complex PPAPs via Intramolecular [4+2] Cycloadditions from MPAPs 7.4 Phloroglucinol‒Monoterpenoid Meroterpenoids (PMMs) 7.4.1 PMMs Containing Sabinene Moiety 7.4.2 PMMs Containing Pinene Moiety 7.4.3 Other PMMs 7.5 Phloroglucinol‒Sesquiterpenoid Meroterpenoids (PSMs) 7.5.1 PSMs Containing Caryophyllene Moiety 7.5.2 PSMs Containing Germacrene Moiety 7.5.3 PSMs Containing Humulene Moiety 7.5.4 PSMs Containing Daucene Moiety 7.5.5 PSMs Containing Cadinane Moiety 7.5.6 PSMs Containing Eudesmene Moiety 7.5.7 PSMs Containing Maaliene Moiety 7.5.8 PSMs Containing Cubebene Moiety 7.5.9 Other PSMs 7.6 Phloroglucinol‒Diterpenoid Meroterpenoids (PDMs) 7.7 Prenylated Phloroglucinols (PPs) 7.8 Phloroglucinol‒Phenylpropanoids References 8 Classification of Diverse Novel Meroterpenoids 8.1 Monoterpenoid Meroterpenoids 8.1.1 Verbenaceae 8.1.2 Ericaceae 8.1.3 Magnoliaceae 8.2 Sesquiterpenoid Meroterpenoids 8.2.1 Annonaceae 8.2.2 Hypericaceae 8.2.3 Valerianaceae 8.2.4 Piperaceae 8.2.5 Zingiberaceae 8.2.6 Compositae/Asteraceae 8.2.7 Chloranthaceae 8.2.8 Solanaceae 8.3 Diterpenoid Meroterpenoids 8.3.1 Lamiaceae 8.3.2 Thymelaeaceae 8.3.3 Meliaceae 8.3.4 Euphorbiaceae 8.3.5 Myristicaceae 8.4 Triterpenoid Meroterpenoids 8.4.1 Celastraceae 8.5 Others References 9 Classification of Diverse Novel Flavonoid Hybrids 9.1 Leguminosae 9.1.1 Millettia 9.1.2 Caesalpinia 9.1.3 Cajanus 9.2 Carthamus (Compositae/Asteraceae) 9.3 Moraceae 9.3.1 Morus 9.3.2 Brosimum 9.4 Tephrosia (Papilionaceae) 9.5 Houttuynia (Saururaceae) 9.6 Horsfieldia (Myristicaceae) 9.7 Forsythia (Oleaceae) 9.8 Aronia (Rosaceae) 9.9 Polygonum (Polygonaceae) 9.10 Pinaceae 9.10.1 Abies 9.10.2 Pinus 9.11 Daemonorops (Palmaceae) 9.12 Alchornea (Euphorbiaceae) References 10 Diverse Novel Lignins References 11 Classification of Diverse Novel Alkaloids 11.1 Euphorbiaceae 11.1.1 Flueggea 11.1.2 Trigonostemon 11.1.3 Croton 11.2 Lycopodiaceae 11.2.1 Lycopodium 11.2.2 Palhinhaea 11.3 Apocynaceae 11.3.1 Tabernaemontana 11.3.2 Alstonia 11.3.3 Aspidosperma 11.3.4 Melodinus 11.3.5 Kopsia 11.3.6 Rauvolfia 11.3.7 Bousigonia 11.3.8 Hunteria 11.3.9 Gonioma 11.3.10 Pleiocarpa 11.3.11 Winchia 11.3.12 Leuconotis 11.4 Leguminosae 11.4.1 Sophora 11.4.2 Erythrina 11.5 Daphniphyllum (Daphniphyllaceae) 11.6 Rubiaceae 11.6.1 Myrioneuron 11.6.2 Uncaria 11.6.3 Psychotria 11.6.4 Ophiorrhiza 11.6.5 Coffea 11.7 Rutaceae 11.7.1 Flindersia 11.7.2 Raputia 11.7.3 Zanthoxylum 11.7.4 Geijera 11.8 Ancistrocladus (Ancistrocladaceae) 11.9 Loganiaceae 11.9.1 Gelsemium 11.9.2 Strychnos 11.10 Cruciferae 11.10.1 Isatis 11.10.2 Orychophragmus 11.11 Macleaya (Papaveraceae) 11.12 Cassia (Caesalpiniaceae) 11.13 Ranunculaceae 11.13.1 Aconitum 11.13.2 Ranunculus 11.14 Huperziaceae 11.14.1 Huperzia 11.14.2 Phlegmariurus 11.15 Piper (Piperaceae) 11.16 Dysoxylum (Meliaceae) 11.17 Others References 12 Diverse Novel Steroids References 13 Other Novel Skeletal Plant Natural Products 13.1 Natural Pentacyclic Compound 13.2 Thapsigargin 13.3 Dimeric Cyclohexylethanoid Derivative 13.4 Benzothiophene 13.5 Phthalide Polymer 13.6 Macrolactams 13.7 Macrolide 13.8 Toluylene 13.9 Diarylheptanoid 13.9.1 Phenol 13.9.2 Iridoid 13.10 Amantane 13.11 Xanthone 13.12 Quinone 13.13 Spiro Compound 13.14 Naphthalene 13.15 Lactone 13.16 Tannin 13.17 Thiophene 13.18 Tetraterpene 13.19 Peptide 13.20 Cyclopentadienedione 13.21 Coumarin 13.22 Isopentylphenylpropanol 13.23 Isopentenyl Acetyl Benzene References 14 Biological Activities 14.1 Cytotoxic Activity 14.2 Anti-inflammatory Activity 14.3 Antiviral Activity 14.4 Immunomodulatory Activity 14.5 Antioxidant Activity 14.6 Neuroprotective Activity 14.7 Antibacterial Activity 14.8 Anti-malarial Activity References 15 Conclusions and Outlook Appendix