
Jan SchlauerUniversity of Tübingen | EKU Tübingen · Pflanzenbiochemie
Jan Schlauer
PD. Dr.
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96
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Introduction
Jan does research in Systematics (Taxonomy), Evolutionary Biology and Botany. His current project is 'Chemotaxonomy of Carnivorous Plants'.
Additional affiliations
October 1995 - August 2000
September 1991 - July 1995
Publications
Publications (96)
Continuing our search for bioactive compounds in species from the Juncaceae family, Juncus articulatus was investigated. Ten previously undescribed phenanthrenes—articulins A–J (1–10)—and ten known compounds—juncuenin B, dehydrojuncuenin B, juncatrin B, ensifolins E, F, H, I, K, juncuenin D, and luzulin A (11–20)—along with other compounds, have be...
Chemotaxonomy is the link between the state of the art in analytical chemistry and the systematic classification and phylogenetic analysis of biota. Although the characteristic secondary metabolites from diverse biotic sources have been used in pharmacology and biological systematics since the dawn of mankind, only comparatively recently establishe...
Abstract: The distribution of the naphthoquinones ramentaceone and plumbagin was studied among 50 taxa of the genus Nepenthes. Naphthoquinone patterns support classifications based on homology of plastid and/or nuclear genes to some extent, with plumbagin predominant in sections Nepenthes, Urceolatae, Tentaculatae, and Regiae, ramentaceone predomin...
In a screening of 43 accessions of predominantly Australian sundew species (Drosera), naphthoquinones were detected convincingly for the first time in D. section Lasiocephala (D. petiolaris group, or ‘wooly sundews’), where these metabolites remain restricted to a minority of four closely related species. Great chemical similarity across the large...
Obituary on German botanist S. Jost Casper (1929-2021), well-known expert and monographer of the genus Pinguicula.
A detailed study of 44 accessions representing 38 taxa (76% of the diversity known at present) of pygmy sundews (Drosera sect. Bryastrum) reveals the first naphthoquinone patterns in this lineage, in which previous studies have not yielded reliable evidence for naphthoquinones. While most samples do not display detectable amounts of naphthoquinones...
For consistency with a classification using infraspecific ranks, the geographically overlapping and closely related taxa D. parvula (syn. D. minutiflora sensu auct. non Planch.: Lowrie, A. and D. pedicellaris are combined as varieties under the older species name. A new combination is thus proposed here.
Culitivars registerd in 2020: Heliamphora 'Cyclops', 'Scylla'; Sarracenia 'Arthur Wheeler', 'Christophe Maerten', 'Glynis Wheeler', 'Sarramphor', 'Super-duper', 'Wizzleberry Toad', 'Yvaine Little'; Cephalotus 'OG Black'; Dionaea 'Axe', 'CCCP Tasmanian Devil', 'FFT Stegosaurus', 'Genepine', 'Morano', 'Stove Fire'; Pinguicula 'Eye Spy', 'Razzberry Bl...
Dihydronaphthoquinones are described as constituents of sundews (Drosera), Venus flytraps (Dionaea), and dewy pines (Drosophyllum) for the first time. As in the corresponding naphthoquinones, these reduced derivatives may occur in two regio-isomeric series distinguished by the relative position of a methyl group (at position 2 or 7 in the naphthale...
W.R. Witanowski isolated and characterized the naphthoquinone ramentaceone from Drosera rotundifolia in 1934 and named the compound droserone. This constitutes the first publication that described the correct detailed structure of the main naphthoquinone in a sundew species, the first publication that identified ramentaceone as a natural product, a...
The Japanese sundews that have previously been collectively called D. indica L. (especially after the influential Flora of Japan, Ohwi 1965:492) are being split up. Various authors (e.g., Watanabe 2013) are trying to re-establish or create one or two additional species assumed endemic to Japan, following the contemporary trend to recognize a number...
The northern, tropical part of Australia is inhabited by numerous sundew species, of which most are endemic (Brewer & Schlauer 2018). In northernmost Western Australia and the Northern Territory these species predominantly belong to Drosera sections Lasiocephala Planch. (D. banksii, D. subtilis, and the “D. petiolaris group” or “woolly sundews”) an...
In his recently published monograph on the genus Pinguicula in the Greater Antilles, Casper (2019: 100) writes with respect to the "dubious taxon" P. benedicta Barnhart: "Holotype: Cuba, Oriente, trail [from] Camp La Barga to Camp San Benito 43, 23 [" 22-26 "] Feb 1910, Shafer 4025 (NY, destroyed in 1943 while on loan to B)". There is apparently no...
The acetogenic naphthoquinones, plumbagin (P in this paper) and ramentaceone (7-methyljuglone, M in this paper) are important chemotaxonomic markers in sundews (Drosera L., Culham & Gornall 1994, Schlauer et al. 2017, 2018). Further accessions have been investigated, and the results are presented and discussed here
The acetogenic naphthoquinones, plumbagin (P in this paper) and ramentaceone (= 7-methyl- juglone, M in this paper), are important chemotaxonomic markers in sundews (Drosera L.) (Du- rand & Zenk 1974; Culham & Gornall 1994; Schlauer & Fleischmann 2016; Schlauer et al. 2017; 2018). Most of the previous phytochemical data relate to the chemotaxonomy...
Plumbagin and 7-methyljuglone are characteristic acetogenic (= derived from acetic acid) naphthoquinones
(see Scheme 1) that allow a chemotaxonomic delimitation and the distinction between sundew (Drosera L.) species or species groups (Zenk et al. 1969; Durand & Zenk 1974; Culham & Gornall 1994; Schlauer et al. 2005). This has recently (Schlauer et...
Understanding the processes involved in generating distribution patterns of carnivorous plants requires investigation at multiple scales. Carnivorous plants typically occur in warm or hot and humid or wet climates in subtropical to tropical regions of all continents. Carnivorous plants tend to grow in wet, open, and nutrient-poor habitats. Most car...
Nepenthes is a genus of 130-160 species, almost half of which were described after 2001. The recent, rapid increase in species descriptions has been driven by application of a less rigorous species concept by botanists, taxonomic inflation, and discoveries of new taxa during explorations of remote parts of Southeast Asia. Many recently published sp...
Naphthoquinones are characteristic constituents that have been detected in numerous plant families. There are at least four fundamentally different biosynthetic routes that lead to the naphthoquinone skeleton. Some naphthoquinones are formed via the acetatepolymalonate (= polyketide) pathway, and plant families notoriously known for containing such...
Naphthoquinone patterns found in Drosera hybrids between quinone-heterogenous parent species are reported here for the first time. Quinone patterns are constant in and characteristic for all taxa investigated. Each investigated parent species contains only one quinone isomer (either plumbagin or 7-methyljuglone), whereas all investigated hybrids be...
In late April 2013 Jürg Steiger, Heiko Rischer, and I performed a field trip to Andalusia (Andalucía), southern Spain in order to see and study some carnivorous plant species in situ. The following text is a report of our findings and conclusions.
There are approximately 700 identified species of carnivorous plants placed in 15 genera of nine families of dicotyledonous plants.
The distribution of the seven species of Utricularia (Lentibulariaceae) native to Bavaria is explained in detail and displayed in distribution maps. All species are illustrated by short diagnoses and photographs, and diagnostic morphological characters for identification of these taxa often difficult in delimitation are provided. Utricularia austra...
Aymeric Roccia (2013) described a new hybrid butterwort from the Alps of Isère, SE France. Unfortunately, the present author did not have a chance to review the manuscript before the article went to print, so a nomenclatural problem was overlooked.
(Review of Rivadavia & al. 2012. Is Drosera meristocaulis a pygmy sundew? Annals of Botany 110(1): 11-21)
The impressive list of similarities mentioned in the paper above can be augmented by a personal observation by the reviewer (JS), as an investigation of dried material of D. meristocaulis (kindly provided by Fernando Rivadavia) for naphthoquino...
Names published by Peter Geoffrey Taylor and plants named in honour of Peter Geoffrey Taylor.
As noted before (Carniv. Pl. Newslett. 37:118-119, 2008), there can be only one legitimate name for all hybrids (including hybridogenic stabilized segregates) between two taxa at the rank that distinguishes the two parent taxa. In the case of Drosera linearis and D. rotundifolia as the parents (which are distinguished at species rank), this name is...
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
As can be expected in an ecologically defined group of organisms, carnivorous plants (unlike orchids or cacti) do not constitute one single natural taxonomic unit marked by common descent and close interrelationship. On the contrary, several lines (derived from four different orders of flowering plants) have given rise to carnivorous families or ge...
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
The naming of plants for scientific purposes is governed by a set of rules that have been coined in order to reduce ambiguity and confusion. This set of rules is called the International Code for Botanical Nomenclature (ICBN), and the text is published online (http://ibot.sav.sk/icbn/main.htm).
The twining parasitic plant Cuscuta reflexa is able to attack the tropical liana Ancistrocladus heyneanus by invading the stem tissues and forming haustoria that penetrate the vascular bundles of the host. Subsequent reactions by the host, including phytoalexin production and hypersensitive reactions, lead to a degeneration of the parasite's hausto...
Phytochemical data are contrasted with phylogenetic
relationships of carnivorous plants. Naphthoquinone profiles of
a representative set of Nepenthes species are evaluated in
comparison with previously published chemical data for
Nepenthales (containing four distinct carnivorous plant
families). The iridoids sarracenin and aucubin are ide...
From plantlets of Byblis liniflora Salisb. (Byblidaceae), propagated by in vitro culture, four phenylethanoid glycosides - acteoside, isoacteoside, desrhamnosylacteoside and desrhamnosylisoacteoside were isolated. The presence of acteoside substantially supports a placement of the family Byblidaceae in order Scrophulariales and subclass Asteridae....
Three new monomeric naphthylisoquinoline alkaloids, ancistrogriffines A, B, and C, and the first dimer of a 7,8'-coupled naphthylisoquinoline, ancistrogriffithine A, have been detected by phytochemical online screening of plant extracts of Ancistrocladus griffithii, using the analytical 'triad' HPLC-MS/MS, HPLC-NMR, and HPLC-CD. Ancistrogriffithine...
The complete life cycle of Triphyophyllum peltatum (Dioncophyllaceae) has been observed under greenhouse conditions. Without passing through the carnivorous stage, the plant reached maturity and, after flowering abundantly, developed the unusual seeds. This cultivation success permitted valuable observations on floral and fruit biology of T. peltat...
A new species of Drosera (sect. Arachnopus) from Kununurra, northern Western Australia is described.
An efficient evaluation procedure for the chemical screening and on-line structural elucidation of dimeric naphthylisoquinoline alkaloids has been developed. The method is based on the lead tetraacetate oxidation of the central binaphthalene core of the alkaloids. UV spectra of the extracts after addition of the oxidant show, in the presence of nap...
The uptake of organic matter by the insect-trapping glandular leaves of the Western tropical African liana Triphyophyllum peltatum (Dioncophyllaceae) is demonstrated for the first time. After feeding carbon-13 labelled L-alanine to the trapping leaves, the label is detected in apical shoot parts and normal (non-trapping) leaves within 2d of applica...
Antidesmone, a novel acetogenic quinolone alkaloid from the African shrub Antidesma membranaceum, has been found to exhibit potent antitrypanosomal activity against Trypanasoma cruzi, the pathogenic agent of Chagas disease. The activity seems to be highly selective, being much larger than that towards other protozoan parasites causing tropical dise...
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Antidesmone (3), known from several species of Antidesma and Hyeronima (Euphorbiaceae), is a quinoline alkaloid with an unusual substitution pattern. It carries a linear aliphatic side chain that indicates an at least partially acetogenic origin of the carbon skeleton. Feeding experiments with 13C and 15N labeled precursors administered to cell cul...
The structure of antidesmone, an alkaloid from Antidesma membranaceum Müll. Arg. and A. venosum E. Mey. (Euphorbiaceae), was revised to be (S)-4,8-dioxo-3-methoxy-2-methyl-5-n-octyl-1,4,5,6,7,8-hexahydroquinoline [(S)-2], not the isoquinoline derivative 1, as assumed previously. The revision was initiated by biosynthetic feeding experiments of one...
The isolation of 6-hydroxyluteolin-7-O-(1"-alpha-rhamnoside) from the Central American epiphyte Vriesea sanguinolenta Cogn. and Marchal (Bromeliaceae) is described here. Its stereostructure was established by spectroscopic methods and an X-ray structure analysis of its hepta-O-acetyl derivative. This flavonoid glycoside had previously been reported...
Built up from acetate, dioncophylline A is the only acetogenic tetrahydroisoquinoline alkaloid as yet known (see scheme). This new biosynthetic pathway was proved by feeding experiments with [13C2]acetate.
Aus Acetat aufgebaut wird Dioncophyllin A als das bisher einzige acetogenine Tetrahydroisochinolin-Alkaloid (siehe Schema). Dieser neuartige Biosyntheseweg wurde durch Verfütterungsexperimente mit [¹³C2]Acetat bewiesen.
The growth and droserone content of callus cultures of Triphyophyllum peltatum grown in liquid 1/5 Linsmaier and Skoog medium was studied. During a lag phase in growth, droserone concentrations in the medium reached a value of 2.1 mg g-1 fr. wt. After this maximum value the concentration decreased slightly to 1.8 mg g-1 fr. wt., while the growth of...
: Despite intensive morphological, chemical and cladistic studies on Caryophyllidae, the circumscription of this subclass and the interfamilial relationships are still under discussion. Using comparative sequencing of the chloroplast matK gene, hypotheses of relationships between the carnivorous Droseraceae, Nepenthaceae and Dioncophyllaceae and te...
The structure of antidesmone, an alkaloid from
Antidesma membranaceum Mull. Arg. and A. venosum E. Mey.
(Euphorbiaceae), was revised to be
(S)-4,8-dioxo-3-methoxy-2-methyl-5-n-octyl-1,4,5,6,7,8-hexahydro
quinolin e [(S)-2], not the isoquinoline derivative 1, as assumed
previously. The revision was initiated by biosynthetic feeding
experi...
Antidesmone (3), known from several species of
Antidesma and Hyeronima (Euphorbiaceae), is a quinoline
alkaloid with an unusual substitution pattern. It carries a linear
aliphatic side chain that indicates an at least partially acetogenic
origin of the carbon skeleton. Feeding experiments with C-13 and
N-15 labeled precursors administered...
The Florentine collections of O. Beccari contain a number of specimens that have been neglected in most recent taxonomic treatments on the genus Nepenthes although they constitute original material. Lectotypification of the names of several taxa described by O. Beccari, J. M. Macfarlane, and J. D. Hooker based on material in the Herbarium Beccarian...
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and...
: The twining parasitic plant Cuscuta reflexa is able to attack the tropical liana Ancistrocladus heyneanus by invading the stem tissues and forming haustoria that penetrate the vascular bundles of the host. Subsequent reactions by the host, including phytoalexin production and hypersensitive reactions, lead to a degeneration of the parasite's haus...
Ancistrocladus abbreviatus Airy Shaw (Ancistrocladaceae), a West African liana producing naphthylisoquinoline alkaloids, was
successfully raised from seeds in vitro. Clonal propagation was best achieved growing nodal stem segments on 1/5 Linsmaier
and Skoog medium with full strength organics and supplemented with 0.02 μM thidiazuron, 4.44 μM 6-benz...
Cultivation of Triphyophyllum peltatum, a rarely grown part-time carnivorous plant, is presented.
The biosynthetic origins of the tetralone
isoshinanolone and the related naphthoquinone plumbagin were
investigated by feeding [C-13(2)]-acetate to suspended callus
cultures of Ancistrocladus heyneanus. The orientation of the
acetate subunits was elucidated by a similar experiment using
[2-C-13]-acetate. The polyketide folding mode found...
The atropodiastereomeric dimeric naphthylisoquinoline alkaloids, michellamines A (1a), B (1b) and C (1c), together with their monomers, korupensamines A (2a) and B (2b), were investigated using electrospray ionization tandem mass spectrometry coupled to liquid chromatography (LC-ESI-MS-MS). From the spectra obtained, characteristic product ions wer...
The atropodiastereomeric dimeric naphthylisoquinoline alkaloids, michellamines A (1a), B (1b) and C (1c), together with their monomers, korupensamines A (2a) and B (2b), were investigated using electrospray ionization tandem mass spectrometry coupled to liquid chromatography (LC–ESI-MS–MS). From the spectra obtained, characteristic product ions wer...
Directly coupled 600-MHz HPLC−1H NMR was used for the first time to investigate the potential of this technique in the screening of tropical plants for naphthylisoquinoline alkaloids. A leaf extract of Ancistrocladus guineënsis was analyzed both in the on-flow mode and in the stop-flow mode using reversed-phase isocratic and gradient compositions o...
Peroxidase active preparations from three Ancistrocladus species and from Triphyophyllum peltatum have been partially purified. They catalyze the oxidative dimerization of korupensamines A and B to michellamines A and C, respectively, as well as the mixed coupling to michellamines A, B, and C. All of these enzymes consist of single polypeptides of...
A great diversity of naphthylisoquinolines, presumably acetogenic biaryl alkaloids, has been obtained from the West-African liana Triphyophyllum peltatum. By the example of dioncophylline A, the main alkaloid from T. peltatum, we illustrate the various methods of structural
elucidation established in our laboratory. The structural peculiarities of...
Cdc48p from Saccharomyces cerevisiae and its highly conserved mammalian homologue VCP (valosin-containing protein) are ATPases with essential functions in cell division and homotypic fusion of endoplasmic reticulum vesicles. Both are mainly attached to the endoplasmic reticulum, but relocalize in a cell cycle-dependent manner: Cdc48p enters the nuc...
Cdc48p is essential for homotypic endoplasmic reticular fusion in Saccharomyces cerevisiae. It is localized at the endoplasmic reticulum during most of the cell division cycle but concentrates in the nucleus at the G1/S-transition. Its mammalian homologue VCP alternates between the endoplasmic reticulum and the centrosome in dependence of the cell...
Recent research on the biological activities and the biosynthesis of naphthylisoquinoline alkaloids is presented. The various pharmacological properties of these unusual bi- and quateraryls make them interesting new lead structures for antiviral and antimalarial drug research. Feeding experiments and biochemical investigations on the biosynthetic r...
The preparation of the naturally occurring anti-HIV michellamines was achieved by synthetic methods and by enzymic dimerization of their natural monomers, the korupensamines. Starting from naturally occurring monomers (e.g. dioncophylline A, dioncophylline C, ancistrocladine), but also from novel non-natural analogs, new dimeric naphthylisoquinolin...
The hexameric ATPase VCP, or p97 (97 kD/protein monomer) from pig shows a phase-dependent intracellular distribution pattern in mitosis in cultivated WISH cells (Schlauer & al. 1993).
In situ hybridization experiments using a DNA fragment coding for the N- terminus of VCP as a probe have shown that the protein is expressed throughout the whole cell...
VCP, a 97 kD protein from pig (Koller & Brownstein,1987), which has been shown to be represented by orthologues in various vertebrates as well as in other Eucaryotes, Eubacteria, and Archae- bacteria, is a Mg2+-dependent ATPase, forming ring-like hexameres (Peters & al., 1990 and 1992). The protein from rat, mouse, and human cells was shown to be b...
A revised, uniform, and unequivocal nomenclature for the various derivatives of the sesquiterpene antibiotic pentalenolactone is proposed, some strains of Streptomyces hitherto described to produce these antibiotics are listed, and a hypothetical biosynthetic pathway based on recently published results is presented.