Alkaloid diversification in the genus Palicourea (Rubiaceae: Palicoureeae) viewed from a (retro-)biogenetic perspective

The species-rich genus Palicourea (Rubiaceae: Palicoureeae) is source of an intriguing diversity of alkaloids derived from tryptamine and its precursor tryptophan. So far simple tryptamine analogues, polypyrroloindoline, β-carboline, and, most importantly, monoterpene-indole, i.e., tryptamine-iridoid alkaloids of various structural types including javaniside, alstrostine and strictosidine derivatives have been identified. Here the diverse alkaloids that numerous studies have found in the genus are examined and organized according to their structures and biosynthetic groups. Using a parsimony-based approach that follows the concept of retro-biogenesis usually applied in synthetic chemistry, possible biosynthetic pathways are proposed and important steps and relationships between these alkaloids are highlighted. Understanding alkaloid diversification is of importance in studying the ecological significance and evolution of biosynthetic capabilities of the genus Palicourea , and should stimulate future investigations on the biochemical and genetic background.

• Publication year

  2021

• Venue

  Phytochemistry Reviews

• Publication date

  2021-08-28

• Fields of study

  Biology, Chemistry

• Identifiers
  DOI 10.1007/s11101-021-09768-y
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• A novel tryptophan-derived alkaloid and other constituents from Guettarda speciosa (Rubiaceae: Cinchonoideae–Guettardeae)

  2021cited by this paper
• A revised classification of the sister tribes Palicoureeae and Psychotrieae (Rubiaceae) indicates genus-specific alkaloid accumulation

  2021cited by this paper
• Alkaloid and iridoid glucosides from Palicourea luxurians (Rubiaceae: Palicoureeae) indicate tryptamine- and tryptophan-iridoid alkaloid formation apart the strictosidine pathway.

  2020cited by this paper
• Neotropical Rubiaceae: Synthesis of Chromosome Data from Costa Rican Taxa, with Insights on the Systematics of the Family1

  2020cited by this paper
• Rubiacearum Americanarum Magna Hama Pars XLV: More New Species and Taxonomic Changes in Palicourea (Rubiaceae, Palicoureeae) and Psychotria subg. Heteropsychotria

  2019cited by this paper
• Rubiacearum Americanarum Magna Hama Pars XLIV: Review of the Palicourea Pilosa Group, with Some New Species and a New Subspecies (Palicoureeae)

  2019cited by this paper
• Chromosomal dynamics in space and time: evolutionary history of Mycetophylax ants across past climatic changes in the Brazilian Atlantic coast

  2019cited by this paper
• Unnatural spirocyclic oxindole alkaloids biosynthesis in Uncaria guianensis

  2019cited by this paper
• Rubiacearum Americanarum Magna Hama Pars XXXVIII: A New Circumscription of Palicourea sect. Bracteiflorae, an Andean Radiation with Several New Species (Palicoureeae)

  2018cited by this paper
• Conspectus of Palicourea section Potaroenses (Rubiaceae), with a new species from French Guiana and a new combination

  2018cited by this paper
• Asymmetric Synthesis of (R)‐1‐Alkyl‐Substituted Tetrahydro‐ß‐carbolines Catalyzed by Strictosidine Synthases

  2018cited by this paper
• Two new combinations, lectotypifications and a new name for Costa Rican Palicourea s.l.

  2017cited by this paper
• Catalyst-controlled oligomerization for the collective synthesis of polypyrroloindoline natural products

  2017cited by this paper
• Rubiacearum Americanarum Magna Hama Pars XXXVII: The New Group Palicourea sect. Chocoanae of the Chocó Biogeographic Region, with Two New Species (Palicoureeae)

  2017cited by this paper
• A Retrosynthesis Approach for Biocatalysis in Organic Synthesis.

  2017cited by this paper
• Chemodiversity of tryptamine-derived alkaloids in six Costa Rican Palicourea species (Rubiaceae-Palicoureeae).

  2017cited by this paper
• New reports on flavonoids, benzoic- and chlorogenic acids as rare features in the Psychotria alliance (Rubiaceae)

  2016cited by this paper
• An NPF Transporter Exports a Central Monoterpene Indole Alkaloid Intermediate from the Vacuole

  2016cited by this paper
• Structural Characterization of Dimeric Indole Alkaloids from Psychotria brachybotrya by NMR Spectroscopy and Theoretical Calculations.

  2016cited by this paper
• Structural investigation of heteroyohimbine alkaloid synthesis reveals active site elements that control stereoselectivity

  2016cited by this paper
• Biocatalytic retrosynthesis: Redesigning synthetic routes to high-value chemicals

  2016cited by this paper
• A biosynthesis-inspired approach to over twenty diverse natural product-like scaffolds.

  2016cited by this paper
• Rubiacearum Americanarum Magna Hama Pars XXXV: The New Group Palicourea sect. Nonatelia, with Five New Species (Palicoureeae)

  2016cited by this paper
• Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives.

  2016cited by this paper
• Rubiacearum Americanarum Magna Hama Pars XXXIV: The New Group Palicourea sect. Tricephalium with Eight New Species and a New Subspecies (Palicoureeae)

  2015cited by this paper
• Design of computational retrobiosynthesis tools for the design of de novo synthetic pathways.

  2015cited by this paper
• Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae).

  2015cited by this paper
• Rubiacearum Americanarum Magna Hama XXXIII: The New Group Palicourea sect. Didymocarpae with Four New Species and Two New Subspecies (Palicoureeae)

  2015cited by this paper
• Alkaloids: Chemistry, Biology, Ecology, and Applications

  2015cited by this paper
• Chemotaxonomy of the Ericales

  2015cited by this paper
• A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol

  2015cited by this paper
• [A new taxonomic system of the genus Murraya (Rutaceae) based on integration of morphology-based taxonomy and chemotaxonomy; and a philological survey on M. exotica in view of the relationship between Okinawa and China].

  2014cited by this paper
• Phylogeny and generic limits in the sister tribes Psychotrieae and Palicoureeae (Rubiaceae): Evolution of schizocarps in Psychotria and origins of bacterial leaf nodules of the Malagasy species.

  2014cited by this paper
• Bioretrosynthetic construction of a didanosine biosynthetic pathway

  2014cited by this paper
• Making iridoids/secoiridoids and monoterpenoid indole alkaloids: progress on pathway elucidation.

  2014cited by this paper
• Phytochemical and biological studies of Stachys species in relation to chemotaxonomy: a review.

  2014cited by this paper
• Noncompetitive Inhibition of Indolethylamine-N-methyltransferase by N,N-Dimethyltryptamine and N,N-Dimethylaminopropyltryptamine

  2014cited by this paper
• Highly efficient and stereocontrolled oxidative coupling of tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and (+)-WIN 64745

  2014cited by this paper
• Cyclotide discovery in Gentianales revisited--identification and characterization of cyclic cystine-knot peptides and their phylogenetic distribution in Rubiaceae plants.

  2013cited by this paper
• Evolution of secondary metabolites in legumes (Fabaceae)

  2013cited by this paper
• The impact of structural biology on alkaloid biosynthesis research.

  2012cited by this paper
• Antiprotozoal alkaloids from Psychotria prunifolia (Kunth) Steyerm

  2012cited by this paper
• Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae

  2012cited by this paper
• β-Carbolines: Occurrence, Biosynthesis, and Biodegradation

  2012cited by this paper
• Alstrostines in Rubiaceae: Alstrostine A from Chassalia curviflora var. ophioxyloides and a novel derivative, rudgeifoline from Rudgea cornifolia

  2012cited by this paper
• Various types of tryptamine-iridoid alkaloids from Palicourea acuminata (=Psychotria acuminata, Rubiaceae)

  2012cited by this paper
• Distribution and systematic significance of selected secondary metabolites within Psychotrieae/Palicoureeae (Rubiaceae)

  2012cited by this paper
• The Rise of Chemodiversity in Plants

  2012cited by this paper
• Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole.

  2011cited by this paper
• Macrophyllionium and macrophyllines A and B, oxindole alkaloids from Uncaria macrophylla.

  2011cited by this paper
• Taxonomy and Chemotaxonomy of the Genus Hypericum.

  2011cited by this paper
• A new type of monoterpenoid indole alkaloid precursor from Alstonia rostrata.

  2011cited by this paper
• Alkaloid and other chemical constituents from Psychotria stachyoides Benth.

  2011cited by this paper
• Biosynthesis: is it time to go retro?

  2010cited by this paper
• Structure elucidation and NMR assignments of two unusual monoterpene indole alkaloids from Psychotria stachyoides

  2010cited by this paper
• Composition, standardization and chemical profiling of Banisteriopsis caapi, a plant for the treatment of neurodegenerative disorders relevant to Parkinson's disease.

  2010cited by this paper
• Quaternary β-carboline alkaloids from Psychotria prunifolia (Kunth) Steyerm.

  2010cited by this paper
• Biocatalytic asymmetric formation of tetrahydro-β-carbolines.

  2010cited by this paper
• Rubiacearum Americanarum Magna Hama Pars XXV: The Nocturnally Flowering Psychotria domingensis–Coussarea hondensis Group Plus Three Other Mesoamerican Psychotria Species Transfer to Palicourea

  2010cited by this paper
• Unusual monoterpene indole alkaloids from Psychotria stachyoides Benth.

  2010cited by this paper
• Strictosidine activation in Apocynaceae: towards a "nuclear time bomb"?

  2010cited by this paper
• Phytochemical diversity: The sounds of silent metabolism

  2009cited by this paper
• A Parsimony Approach to Biological Pathway Reconstruction/Inference for Genomes and Metagenomes

  2009cited by this paper
• [Studies on the chemical constituents in herb of Hedyotis diffusa].

  2008cited by this paper
• Enzymatic features of serotonin biosynthetic enzymes and serotonin biosynthesis in plants

  2008cited by this paper
• New Strategies for the Synthesis of Hexahydropyrroloindole Alkaloids Inspired by Biosynthetic Hypotheses

  2008cited by this paper
• A new FeII quaterpyridyl M4L6 tetrahedron exhibiting selective anion binding.

  2008cited by this paper
• Catharanthus terpenoid indole alkaloids: biosynthesis and regulation

  2007cited by this paper
• Molecular Architecture of Strictosidine Glucosidase: The Gateway to the Biosynthesis of the Monoterpenoid Indole Alkaloid Family[W]

  2007cited by this paper
• The iridoid pathway in Catharanthus roseus alkaloid biosynthesis

  2007cited by this paper
• Totalsynthese komplexer Cyclotryptaminalkaloide: stereokontrollierter Aufbau quartärer Kohlenstoffstereozentren

  2007cited by this paper
• The Structure of Rauvolfia serpentina Strictosidine Synthase Is a Novel Six-Bladed β-Propeller Fold in Plant Proteins[W]

  2006cited by this paper
• Chemistry and biology of monoterpene indole alkaloid biosynthesis.

  2006cited by this paper
• Substrate specificity of strictosidine synthase.

  2006cited by this paper
• Metabolon formation and metabolic channeling in the biosynthesis of plant natural products.

  2005cited by this paper
• Aglaia (Meliaceae): an evaluation of taxonomic concepts based on DNA data and secondary metabolites.

  2005cited by this paper
• Environmental and Ontogenetic Control of Accumulation of Brachycerine, a Bioactive Indole Alkaloid from Psychotria brachyceras

  2004cited by this paper
• Javaniside, a novel DNA cleavage agent from Alangium javanicum having an unusual oxindole skeleton.

  2004cited by this paper
• Taxonomic significance of alkaloids and iridoid glucosides in the tribe Psychotrieae (Rubiaceae)

  2004cited by this paper
• Novel bis(monoterpenoid) indole alkaloids from Psychotria bahiensis.

  2003cited by this paper
• Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids.

  2002cited by this paper
• Iridoid Patterns In Galium L. And Some Phylogenetic Considerations

  2002cited by this paper
• Indole monoterpene alkaloids from leaves of Psychotria suterella Müll. Arg. (Rubiaceae)

  2001cited by this paper
• The potential of alkaloids in drug discovery

  2001cited by this paper
• Two stereoisomeric pentacyclic oxin­dole alkaloids from Uncaria tomentosa: uncarine C and uncarine E

  2001cited by this paper
• Main glucosidase conversion products of the gluco-alkaloids dolichantoside and palicoside.

  2001cited by this paper
• Secologanin synthase which catalyzes the oxidative cleavage of loganin into secologanin is a cytochrome P450.

  2001cited by this paper
• Molecular Cloning and Analysis of Strictosidine β-d-Glucosidase, an Enzyme in Terpenoid Indole Alkaloid Biosynthesis in Catharanthus roseus *

  2000cited by this paper
• Reorganization of the genus Psychotria and tribe Psychotrieae (Rubiaceae) inferred from ITS and rbcL sequence data

  1999cited by this paper
• Bacterial biotransformation of 3α(S)-Strictosidine to the monoterpenoid indole alkaloid vallesiachotamine

  1998cited by this paper
• Deppeaninol, A New -Carboline Alkaloid from Deppea blumenaviensis (Rubiaceae)

  1995cited by this paper
• Alkaloids and other compounds from Psychotria correae

  1995cited by this paper
• Unified Strategy for Synthesis of Indole and 2-Oxindole Alkaloids

  1991cited by this paper
• 10-O-benzoyltheveside and 10-dehydrogeniposide from the leaves of Cerbera manghas

  1990cited by this paper
• Alkaloids of Strychnos johnsonii

  1987cited by this paper
• Direct proof of the involvement of a spiro intermediate in the Pictet-Spengler reaction

  1987cited by this paper
• Intracellular compartmentation of two enzymes of berberine biosynthesis in plant cell cultures

  1986cited by this paper
• Structure of ophiorines A and B; novel type gluco indole alkaloids isolated from ophiorrhiza spp.

  1985cited by this paper
• N-methyltransferase activities in phalaris aquatica

  1983cited by this paper
• The biosynthesis of the β-carboline alkaloids, harman and eleagnine

  1982cited by this paper

• Establishment of Psychotria viridis Ruiz & Pav. callus cultures, plantlet regeneration and in vitro production of the hallucinogenic indole alkaloid N,N-dimethyltryptamine

  2025cites this paper
• Poisoning in Ruminants by Palicourea Aubl. Species (Rubiaceae) in Brazil: A Review

  2025cites this paper
• Unveiling the Anatomical and Functional Attributes of Stipular Colleters in Palicourea tetraphylla Cham. & Schltdl. and Palicourea rudgeoides (Müll. Arg.) Standl. (Rubiaceae)

  2024cites this paper
• Structural diversity and chemical logic underlying the assembly of monoterpene indole alkaloids oligomers.

  2024cites this paper
• Novel spirooxindole-triazole derivatives: unveiling [3+2] cycloaddition reactivity through molecular electron density theory and investigating their potential cytotoxicity against HepG2 and MDA-MB-231 cell lines

  2024cites this paper
• Ethnopharmacology, phytochemistry and a new chemotaxonomic marker in Oldenlandia affinis (Roem. & Schult.) DC. Rubiaceae

  2022cites this paper
• Ursane-type triterpenoids, steroids and phenolics from the stem bark and leaves of Nauclea orientalis (L.) L. (Rubiaceae)

  2022cites this paper
• Yellow Twig (Nauclea orientalis) from Thailand: Strictosamide as the Key Alkaloid of This Plant Species

  2022cites this paper
• A revised classification of the sister tribes Palicoureeae and Psychotrieae (Rubiaceae) indicates genus-specific alkaloid accumulation

  2021cites this paper
• A revised classification of the sister tribes Palicoureeae and Psychotrieae (Rubiaceae) indicates genus-specific alkaloid accumulation

  2021influential citation