{"product_id":"ancistrocladus-naphthylisoquinoline-alkaloids-9783031104565","title":"Ancistrocladus Naphthylisoquinoline Alkaloids","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003e\u003cp\u003eThis 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.\u003cb\u003e\u003c\/b\u003e\u003c\/p\u003e\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cp\u003eContents\u003c\/p\u003e\u003col\u003e\n\u003cli\u003eIntroduction   …………………………………………………………………..\t\u003cp\u003e\u003c\/p\u003e\n\u003c\/li\u003e\n\u003cli\u003eNaphthylisoquinoline Alkaloids, a Fascinating Class of Axially   \t\u003cp\u003e\u003c\/p\u003e\n\u003c\/li\u003e\n\u003c\/ol\u003e\u003cp\u003e\tChiral Biaryl Natural Products   ……………………………………………….\u003c\/p\u003e\u003cp\u003e2.1\tStructural Diversity and Classification of Naphthylisoquinoline   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloids – A Short Overview   ……………………………………..…………\u003c\/p\u003e\u003cp\u003e2.2\tMono- and Dimeric Dioncophyllaceae-Type Naphthylisoquinolines   \t\u003c\/p\u003e\u003cp\u003e\tand Related Compounds   …………………….………………………..………\u003c\/p\u003e\u003cp\u003e2.2.1\tOccurrence of Dioncophyllaceous Alkaloids in Nature   …..….………………\t\u003c\/p\u003e\u003cp\u003e2.2.2\tArtificial Dimers of Dioncophyllaceae-Type Monomers as Promising   \t\u003c\/p\u003e\tAntiplasmodial Agents: Design and Total Synthesis   …………………….…..\u003cp\u003e\u003c\/p\u003e\u003cp\u003e2.3\tA Novel Biosynthesis Pathway in Plants: Acetogenic   \t\u003c\/p\u003e\tNaphthylisoquinoline Alkaloids   ………………………………………………\u003cp\u003e\u003c\/p\u003e\u003cp\u003e2.4\tThe Tool Box Used for the Isolation, Structural Elucidation, and   \t\u003c\/p\u003e\tStereochemical Assignment of Naphthylisoquinoline Alkaloids –   \u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tA Short Overview   ……………………………………………………………..\u003c\/p\u003e\u003col\u003e\u003cli\u003e\u003cp\u003eAncistrocladus, a Genus of Woody Lianas of the Monotypic Plant   \t\u003c\/p\u003e\u003c\/li\u003e\u003c\/ol\u003e\u003cp\u003e\tFamily Ancistrocladaceae Widely Occurring in India, Sri Lanka, and   \u003c\/p\u003e\u003cp\u003e\tSoutheast Asia   …………………………………………………………………\u003c\/p\u003e\u003cp\u003e3.1\tAncistrocladus heyneanus, a Large Climbing Shrub from the Indian   \t\u003c\/p\u003e\u003cp\u003e\tSubcontinent   …………………………………………………………………...\u003c\/p\u003e\u003cp\u003e3.2\tAncistrocladus hamatus, Endemic to the Lowland Evergreen Forests   \t\u003c\/p\u003e\tof Sri Lanka   ……………………………………………………………………\u003cp\u003e\u003c\/p\u003e\u003cp\u003e3.3\tAncistrocladus griffithii from Submontane Forests in the   \t\u003c\/p\u003e\u003cp\u003e\tWest and South of Southeast Asia   …………………………………………….\u003c\/p\u003e3.4\tAncistrocladus attenuatus from Lowland Evergreen Forests of   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tMyanmar and the Indian Andaman Islands   …………………………………\u003c\/p\u003e\u003cp\u003e3.5\tAncistrocladus benomensis, a New Submontane Liana from   \t\u003c\/p\u003e\u003cp\u003e\tPeninsular Malaysia   ………………………………………………………….\u003c\/p\u003e\u003cp\u003e3.6\tAncistrocladus tectorius, Widely Distributed in the Rain Forests   \t\u003c\/p\u003e\tAll Over Southeast Asia   ……………………………………………………..\u003cp\u003e\u003c\/p\u003e\u003col\u003e\u003cli\u003e\u003cp\u003eThe Indian Liana Ancistrocladus heyneanus and Ancistrocladus hamatus   \t\u003c\/p\u003e\u003c\/li\u003e\u003c\/ol\u003e\u003cp\u003e\tfrom Sri Lanka: Early Studies and More Recent Discoveries   ……..………..\u003c\/p\u003e\u003cp\u003e4.1.\tAncistrocladine and Further 5,1'-Coupled Naphthylisoquinoline   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloids from the Roots and Leaves of Ancistrocladus heyneanus   ………..\u003c\/p\u003e\u003cp\u003e4.2\tDirected Total Synthesis of Ancistrocladine and Its Atropo-Diastereomer  \t\u003c\/p\u003e\tHamatine by the Lactone Methodology   ………………………………..…....\u003cp\u003e\u003c\/p\u003e\u003cp\u003e4.3\tDirected Synthesis of Ancistrocladisine via Configurationally   \t\u003c\/p\u003e\tUnstable Lactone-Bridged Biaryl Lactones   …………………………….…..\u003cp\u003e\u003c\/p\u003e\u003cp\u003e4.4\tTotal Synthesis of Ancistrocladidine by ortho-Arylation of a Naphthol   \t\u003c\/p\u003e\u003cp\u003e\twith an Aryllead Triacetate   …………………………………………………\u003c\/p\u003e\u003cp\u003e4.5\tAtroposelective Total Synthesis of Enantiomerically Pure   \t\u003c\/p\u003e\u003cp\u003e\tAncistrocladidine and Ancistrotectorine Using the Lactone Method   ……\u003c\/p\u003e\u003cp\u003e4.6\tProduced in Aging Shoots and in Cell Cultures of Ancistrocladus   \t\u003c\/p\u003e\theyneanus: The 7,8'-Coupled Naphthylisoquinoline Alkaloid   \u003cp\u003e\u003c\/p\u003e\tAncistroheynine A and Further Stress Metabolites   …………………………\u003cp\u003e\u003c\/p\u003e\u003cp\u003e4.7\tA Series of 7,3'-Coupled Naphthylisoquinoline Alkaloids Isolated   \t\u003c\/p\u003e\tfrom Fresh Leaves of Ancistrocladus heyneanus   ……………………...……\u003cp\u003e\u003c\/p\u003e\u003cp\u003e4.8\tAncisheynine A, a Novel-Type N,C-Coupled Naphthylisoquinolinium   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloid: Total Synthesis and Stereoanalysis   …………………..……………\u003c\/p\u003e4.9\tSimplified N,C-Coupled Arylisoquinolinium Salts as Promising   \t\tCandidates for the Development of Antiparasitic Agents   ………….….………\u003cp\u003e\u003c\/p\u003e\u003cp\u003e4.9.1\tInhibitory Activities of Synthetic Arylisoquinolinium Salts against   \t\u003c\/p\u003e\tLeishmania major   …………………………………………………..………….\u003cp\u003e\u003c\/p\u003e4.9.2\tInhibitory Activities of Synthetic Arylisoquinolinium Salts against   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tTrypanosoma brucei brucei   ……………………………………………..……..\u003c\/p\u003e\u003cp\u003e4.9.3\tAntiplasmodial Activities of Synthetic Arylisoquinolinium Salts and   \t\u003c\/p\u003e\u003cp\u003e\tthe Formation of Complexes with Hemin   ………………….………………….\u003c\/p\u003e\u003cp\u003e4.9.4\tAntibiotic Effects of Dimeric Isoquinolinium Salts on Staphylococcus   \t\u003c\/p\u003e\u003cp\u003e\taureus, Staphylococcus epidermidis and Candida albicans   ……………….…\u003c\/p\u003e\u003col\u003e\u003cli\u003e\u003cp\u003eFull Absolute Stereostructures of Naphthylisoquinoline Alkaloids   \t\u003c\/p\u003e\u003c\/li\u003e\u003c\/ol\u003e\u003cp\u003e\tDirectly from Crude Extracts: Characterization of New Metabolites   \u003c\/p\u003e\u003cp\u003e\tfrom Ancistrocladus griffithii by the HPLC-MS\/MS-NMR-ECD Triad   ……...\u003c\/p\u003e5.1\tHyphenation of HPLC with UV, MS, NMR, and ECD   ……………….………\t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e5.1.1\tCharacterization of Mono- and Dimeric Naphthylisoquinoline   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloids by HPLC-ESI-MS\/MS   ………………………………..…………….\u003c\/p\u003e5.1.2\tConstitution and Relative Configuration of Naphthylisoquinoline   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tAlkaloids by HPLC-NMR   …………………………………………..…………\u003c\/p\u003e\u003cp\u003e5.1.3\tOnline Assignment of Absolute Configurations of   \t\u003c\/p\u003e\tNaphthylisoquinoline Alkaloids by HPLC-ECD   …………………..………….\u003cp\u003e\u003c\/p\u003e\u003cp\u003e5.2\tA Photometric Chemical Screening Method to Trace Up   \t\u003c\/p\u003e\tMichellamine-Type Naphthylisoquinoline Dimers   ……………………..……..\u003cp\u003e\u003c\/p\u003e\u003cp\u003e5.3\tOnline-Discovery of the First Ancistrocladaceae-Type Dimer   \t\u003c\/p\u003e\tAncistrogriffithine A, in Crude Leaf Extracts of Ancistrocladus griffithii,   \u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tby the LC-MS\/MS\/LC-NMR\/LC-ECD Triad   …………………………....…....\u003c\/p\u003e5.4\tComplete Structural Elucidation of Ancistrogriffines A–C, Three New   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tMonomeric Naphthylisoquinoline Alkaloids Online, Directly from   \u003c\/p\u003e\u003cp\u003e\tAncistrocladus griffithii   ……………………………………..…………………\u003c\/p\u003e6\tAncistrocladus benomensis, a New Species from Malaysia, with an   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tUnprecedented Series of Non-Hydrogenated Ancistrocladaceae- and   \u003c\/p\u003e\u003cp\u003e\tDioncophyllaceae-Type Naphthylisoquinoline Alkaloids   ………..……….......\u003c\/p\u003e\u003cp\u003e6.1\tAncistrobenomine A, the First Naphthylisoquinoline Alkaloid with a   \t\u003c\/p\u003e\tHydroxymethylene Function at C-3, and Related 5,1'-Coupled   \u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tCompounds   …………………………………………………………………….\u003c\/p\u003e\u003cp\u003e6.2\tDiscovery of the First Dioncophyllaceae-Type Naphthylisoquinoline   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloids in the Leaves of an Asian Ancistrocladus Species, A. benomensis   ...\u003c\/p\u003e\u003cp\u003e6.3\tOnline Structural Assignment and Observation of the   \t\u003c\/p\u003e\u003cp\u003e\tAtropisomerization of the N,6'-Coupled Alkaloid Ancistrocladinium B   ..……\u003c\/p\u003e\u003cp\u003e6.4\tThe New Species Ancistrocladus benomensis and its Extraordinary   \t\u003c\/p\u003e\u003cp\u003e\tChemotaxonomic Position within the Ancistrocladaceae Family   …..…….…..\u003c\/p\u003e\u003cli\u003e\u003cp\u003eAncistrocladus cochinchinensis from Central Vietnam, a Distinct   \t\u003c\/p\u003e\u003c\/li\u003e\u003cp\u003e\tAncistrocladus Taxon? — Metabolite Pattern und Phylogenetic   \u003c\/p\u003e\u003cp\u003e\tRelationship to Ancistrocladus aff. tectorius from China   …………....……….\u003c\/p\u003e\u003cp\u003e7.1\tIn the Leaves of Ancistrocladus cochinchinensis: Predominant   \t\u003c\/p\u003e\tOccurrence of Naphthylisoquinoline Alkaloids with a 5,1'-Coupling Site   ..….\u003cp\u003e\u003c\/p\u003e\u003cp\u003e7.2\t7-epi-Ancistrobrevine D and Related 7,1'-Coupled   \t\u003c\/p\u003e\u003cp\u003e\tNaphthyltetrahydroisoquinoline Alkaloids   ………………….………………..\u003c\/p\u003e7.3\tN,8'-Coupled Naphthylisoquinoline Alkaloids Directly Analyzed   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tOnline, by LC-MS\/MS-NMR-ECD: Ancistrocladinium A and Two   \u003c\/p\u003e\u003cp\u003e\tNew Phenolic Analogues   ……………………………………………….…..…\u003c\/p\u003e\u003cp\u003e7.4\tBiosynthetically Related, Mostly Non-Coupled Naphthoquinones,   \t\u003c\/p\u003e\tTetralones, and Free Isoquinolines from Ancistrocladus cochinchinensis   ……\u003cp\u003e\u003c\/p\u003e\u003cp\u003e7.5\tPhytochemical Relationship of Ancistrocladus cochinchinensis and   \t\u003c\/p\u003e\u003cp\u003e\tAncistrocladus aff. tectorius from the Chinese Island of Hainan   ……….…….\u003c\/p\u003e\u003col\u003e\u003cli\u003e\u003cp\u003eWidespread Throughout Southeast Asia: Ancistrocladus tectorius, a  \t\u003c\/p\u003e\u003c\/li\u003e\u003c\/ol\u003e\u003cp\u003e\tRich Source of Unique, Structurally Most Diverse Mono- and Dimeric   \u003c\/p\u003e\u003cp\u003e\tNaphthylisoquinoline Alkaloids   ……………………………………...………..\u003c\/p\u003e\u003cp\u003e8.1\tEvidence for Species Differentiation within the Ancistrocladus   \t\u003c\/p\u003e\u003cp\u003e\ttectorius complex in Southeast Asia   ………………………………..…………\u003c\/p\u003e\u003cp\u003e8.2\tAncistrocladus aff. tectorius from Laos   ……………………………………….\t\u003c\/p\u003e\u003cp\u003e8.3\tAncistrocladus aff. tectorius from Thailand   …………………………………..\t\u003c\/p\u003e\u003cp\u003e8.4\tAncistrocladus aff. tectorius from Malaysia   ………………………………….\t\u003c\/p\u003e\u003cp\u003e8.5\tAncistrocladus aff. tectorius from the Chinese Island of Hainan   …………….\t\u003c\/p\u003e\u003cp\u003e8.5.1\tAncistrocline from Early Isolation Work and its Total Synthesis   ……………\t\u003c\/p\u003e\u003cp\u003e8.5.2\tFurther Naphthylisoquinoline Alkaloids with a 5,1'-Coupling Site   \t\u003c\/p\u003e\u003cp\u003e\tand Their Broad Structural Diversity   …………………………..………..……\u003c\/p\u003e\u003cp\u003e8.5.3\tAncistrotanzanine A and Two Further New Examples of the Rare   \t\u003c\/p\u003e\u003cp\u003e\tSubclass of 5,3'-Coupled Naphthylisoquinoline Alkaloids   …………….……..\u003c\/p\u003e\u003cp\u003e8.5.4\tAncistrotectoriline A and Related 5,8'-Coupled Naphthylisoquinoline   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloids, the Only Five Representatives of this Coupling Type   \u003c\/p\u003e\u003cp\u003e\tIsolated from an Asian Ancistrocladus Liana   …………………………….…...\u003c\/p\u003e\u003cp\u003e8.5.5\tAncistrotectoriline B, Ancistrotectorines B1 and B2, and Related   \t\u003c\/p\u003e\u003cp\u003e\t7,1'-Coupled Naphthyltetrahydroisoquinoline Alkaloids   …………………..…\u003c\/p\u003e\u003cp\u003e8.5.6\tAncistrotectoquinones A and B, Novel-Type Quinoid Natural   \t\u003c\/p\u003e\tProducts and Related 7,3'-Coupled Naphthylisoquinoline Alkaloids   …….…..\u003cp\u003e\u003c\/p\u003e\u003cp\u003e8.5.7\tAncistrotectoriline C and Ancistrotectorines A and B, the First   \t\u003c\/p\u003e\t7,6'-Coupled Ancistrocladaceae-Type Naphthylisoquinoline Alkaloids   ……...\u003cp\u003e\u003c\/p\u003e\u003cp\u003e8.5.8\tAncistectorine C1, the Only Known Example of a 7,8'-Coupled   \t\u003c\/p\u003e\u003cp\u003e\tNaphthylisoquinoline Alkaloid Isolated from A. aff. tectorius   ………………..\u003c\/p\u003e\u003cp\u003e8.5.9\tN,C-Coupled Naphthyldihydroisoquinolinium Alkaloids:   \t\u003c\/p\u003e\u003cp\u003e\tAncistrocladinium A and B and Related Compounds   …………….…………..\u003c\/p\u003e\u003cp\u003e8.5.10\tAncistrocyclinones A and B, Unprecedented Pentacyclic N,C-Coupled   \t\u003c\/p\u003e\u003cp\u003e\tNaphthylisoquinoline Alkaloids   ……………………………………………….\u003c\/p\u003e\u003cp\u003e8.5.11\tShuangancistrotectorines A–E, Dimeric Naphthylisoquinoline Alkaloids   \t\u003c\/p\u003e\tWith Three Consecutive Chiral Biaryl Axes   ………………………………….\u003cp\u003e\u003c\/p\u003e\u003cp\u003e9\tTables of the Naphthylisoquinoline Alkaloids and Related Compounds   \t\u003c\/p\u003e\tIsolated from Asian Ancistrocladus Species   ………………………….……….\u003cp\u003e\u003c\/p\u003e\u003cp\u003e9.1\t5,1'-Coupled Naphthylisoquinoline Alkaloids (Table)   ………………………..\t\u003c\/p\u003e\u003cp\u003e9.2\t5,3'-Coupled Naphthylisoquinoline Alkaloids (Table)   ………………………..\t\u003c\/p\u003e\u003cp\u003e9.3\t5,8'-Coupled Naphthylisoquinoline Alkaloids (Table)   ……………………….\t\u003c\/p\u003e9.4\t7,1'-Coupled Ancistrocladaceae-Type Naphthylisoquinoline   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tAlkaloids (Table)   ………………………………………………………………\u003c\/p\u003e\u003cp\u003e9.5\t7,1'-Coupled Dioncophyllaceae-Type Naphthylisoquinoline   \t\u003c\/p\u003e\tAlkaloids (Table)   ………………………………………………...…………….\u003cp\u003e\u003c\/p\u003e\u003cp\u003e9.6\t7,3'-Coupled Naphthylisoquinoline Alkaloids (Table)   ………………………..\t\u003c\/p\u003e9.7\t7,6'-Coupled Naphthylisoquinoline Alkaloids (Table)   ………………………..\t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e9.8\t7,8'-Coupled Ancistrocladaceae-Type Naphthylisoquinoline   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloids (Table)   ………………………………………………………………\u003c\/p\u003e9.9\t7,8'-Coupled Dioncophyllaceae-Type Naphthylisoquinoline   \t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e\tAlkaloids (Table)   ………………………………………………………………\u003c\/p\u003e\u003cp\u003e9.10\tNaphthylisoquinoline Alkaloids with a 1,4-Naphthoquinone   \t\u003c\/p\u003e\tPortion (Table)   ………………………………………………………………...\u003cp\u003e\u003c\/p\u003e\u003cp\u003e9.11\tNaphthylisoquinoline Alkaloids with a Stereogenic N-Iminium   \t\u003c\/p\u003e\u003cp\u003e\tAryl Axis (Table)   …………………………………………………..………….\u003c\/p\u003e9.12\tPentacyclic N,C-Coupled Naphthylisoquinoline Alkaloids (Table)   …………..\t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e9.13\tConstitutionally Symmetric Ancistrocladaceae-Type   \t\u003c\/p\u003e\u003cp\u003e\tNaphthylisoquinoline Dimers (Table)   …………………………………………\u003c\/p\u003e\u003cp\u003e9.13.1\t6',6''-Dimerized Naphthylisoquinoline Alkaloids (Table)   …………………….\t\u003c\/p\u003e\u003cp\u003e9.13.2\t3',3''-Dimerized Naphthylisoquinoline Alkaloids (Table)   …………………….\t\u003c\/p\u003e9.13.3\t1',1''-Dimerized Naphthylisoquinoline Alkaloids (Table)   …………………….\t\u003cp\u003e\u003c\/p\u003e\u003cp\u003e9.14\tNaphthoquinones and Tetralones Related to Naphthylisoquinoline   \t\u003c\/p\u003e\u003cp\u003e\tAlkaloids (Table)   ……………………………………………………………..\u003c\/p\u003e\u003cp\u003e9.15\tNaphthalene-Devoid Isoquinolines from Asian Ancistrocladus   \t\u003c\/p\u003e\u003cp\u003e\tSpecies (Table)   ……………………………………………………………….\u003c\/p\u003e\u003cp\u003eAcknowledgments   ……………………………………………………………………..\t\u003c\/p\u003e\u003cp\u003eReferences   ……………………………………………………………………………..\t\u003c\/p\u003e\u003cp\u003e\u003c\/p\u003e","brand":"Springer International Publishing AG","offers":[{"title":"Default Title","offer_id":53516335055191,"sku":"9783031104565","price":999.99,"currency_code":"GBP","in_stock":false}],"url":"https:\/\/bookcurl.com\/products\/ancistrocladus-naphthylisoquinoline-alkaloids-9783031104565","provider":"Book Curl","version":"1.0","type":"link"}