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Aimanianda V, Clavaud C, Simenel C, Fontaine T, Delepierre M, Latge JP
Cell wall β-(1,6)-glucan of Saccharomyces cerevisiae: Structural characterization and in situ synthesis
Journal of Biological Chemistry 284(20) (2009)
13401-13412
Saccharomyces cerevisiae BY4741
(NCBI TaxID 1247190,
species name lookup)
Saccharomyces cerevisiae Δkre9/YJL174W
(Ancestor NCBI TaxID 4932,
species name lookup)
Saccharomyces cerevisiae kre5-ts2
(Ancestor NCBI TaxID 4932,
species name lookup)
Saccharomyces cerevisiae YG0091
(Ancestor NCBI TaxID 4932,
species name lookup)
Saccharomyces cerevisiae Δkre9 (haploid mutant)
(Ancestor NCBI TaxID 4932,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: cell wall
The structure was elucidated in this paperNCBI PubMed ID: 19279004Publication DOI: 10.1074/jbc.M807667200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: jplatge
pasteur.fr
Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France, Unité de Résonance Magnétique Nucléaire des Biomolécules, CNRS URA 2185, Institut Pasteur, Paris, France, Unité de Résonance Magnétique Nucléaire des Biomolécules, Institut Pasteur, Paris, France, Unité des Aspergillus, CNRS URA 2185, Institut Pasteur, Paris, France
Despite its essential role in the yeast cell wall, the exact composition of the β-(1,6)-glucan component is not well characterized. While solubilizing the cell wall alkali-insoluble fraction from a wild type strain of Saccharomyces cerevisiae using a recombinant β-(1,3)-glucanase followed by chromatographic characterization of the digest on an anion exchange column, we observed a soluble polymer that eluted at the end of the solvent gradient run. Further characterization indicated this soluble polymer to have a molecular mass of ~38 kDa and could be hydrolyzed only by β-(1,6)-glucanase. Gas chromatography, mass spectrometry and NMR(1H and 13C) analyses confirmed it to be a β-(1,6)-glucan polymer with, on average, branching at every fifth residue with one or two β-(1,3)-linked glucose units in the side chain. This polymer peak was significantly reduced in the corresponding digests from mutants of the kre genes (kre9 and kre5) that are known to play a crucial role in the β-(1,6)-glucan biosynthesis. In the current study, we have developed a biochemical assay wherein incubation of UDP-[14C]glucose with permeabilized S. cerevisiae yeasts resulted in the synthesis of a polymer chemically identical to the branched β-(1,6)-glucan isolated from the cell wall. Using this assay, parameters essential for β-(1,6)-glucan synthetic activity were defined.
mutants, cell wall, β-glucan, Saccharomyces cerevisiae, biochemical assay, carbon isotope
Structure type: oligomer
Location inside paper: Fig.3
Trivial name: gentiobiose, bruceacanthinoside
Compound class: glycoside, Apotirucallane triterpe glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GLC-MS, gel filtration, TLC, GC, Smith degradation, MALDI-TOF MS, radiolabeling, HPLC, enzymatic digestion, extraction, 15N NMR, reduction, CC, cell growth, enzymatic assay, Bradford method, LPLC
Enzymes that release or process the structure: endo-β-(1,6)-glucanase
Related record ID(s): 44171, 44172, 44173, 44174, 44175, 44176, 44177, 44178
NCBI Taxonomy refs (TaxIDs): 1247190,
4932Reference(s) to other database(s): GTC:G09183JD, CCSD:
37198, CBank-STR:4177
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Oguro Y, Nakamura A, Kurahashi A
Effect of temperature on saccharification and oligosaccharide production efficiency in koji amazake
Journal of Bioscience and Bioengineering 127(5) (2019)
570-574
Aspergillus oryzae
(NCBI TaxID 5062,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 30414826Publication DOI: 10.1016/j.jbiosc.2018.10.007Journal NLM ID: 100888800Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
Correspondence: Oguro Y <y.oguro
hakkaisan.jp>; Nakamura A <a.nakamura
hakkaisan.jp>; Kurahashi A <a.kurahashi
hakkaisan.jp>
Institutions: Hakkaisan Brewery Co., Ltd., Minamiuonuma, Japan
Koji amazake, prepared from rice koji, is a traditional Japanese sweet beverage. The main source of sweetness is glucose derived from rice starch following digestion by enzymes of Aspergillus oryzae during saccharification. The temperature of this process was empirically determined as 45°C–60°C, but no studies have systematically investigated the effect of temperature on saccharification efficiency. We addressed this in the present study by evaluating saccharification efficiency at various temperatures. We found that glucose content was the highest at 50°C (100%) and was reduced at temperatures of 40°C (66.4%), 60°C (91.9%), and 70°C (76.6%). We previously reported that 12 types of oligosaccharides are present in koji amazake; the levels of eight of these, namely nigerose, kojibiose, trehalose, isomaltose, gentiobiose, raffinose, panose, and isomaltotriose, were the highest at 50°C–60°C, whereas sophorose production was maximal at 70°C. Based on these findings, we initially performed saccharification at 50°C and then switched the temperature to 70°C. The maximum amount of each saccharide including sophorose that was produced was close to the values obtained at these two temperatures. Thus, oligosaccharide composition of koji amazake is dependent on saccharification temperature. These findings provide useful information for improving the consumer appeal of koji amazake by enhancing oligosaccharide content.
oligosaccharide, sophorose, koji, amazake, saccharification
Structure type: oligomer
Location inside paper: Fig. 3, E
Trivial name: gentiobiose, bruceacanthinoside
Compound class: glycoside, Apotirucallane triterpe glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Methods: HPLC, cell growth, enzymatic assay, spectrophotometry, centrifugation
Enzymes that release or process the structure: β-glucosidase
Synthetic data: enzymatic in vivo
Related record ID(s): 49548, 49549, 49550, 49551, 49553, 49554, 49555, 49556
NCBI Taxonomy refs (TaxIDs): 5062Reference(s) to other database(s): GTC:G09183JD, CCSD:
37198, CBank-STR:4177
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Rüdiger H, Siebert H-C, Solis D, Jiménez-Barbero J, Romero A, von der Lieth C-W, Diaz-Mariño T, Gabius H-J
Medicinal chemistry based on the sugar code: fundamentals of lectinology and experimental strategies with lectins as targets
Current Medicinal Chemistry 7(4) (2000)
389-416
(plant)
(NCBI TaxID 33090,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
NCBI PubMed ID: 10702616Publication DOI: 10.2174/0929867003375164Journal NLM ID: 9440157Publisher: Saif Zone, Sharjah, U.A.E.: Bentham Science Publishers
Institutions: Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität, Würzburg, Germany, Institut für Physiologische Chemie, Ludwig-Maximilians-Universität, Tierärztliche Fakultät, München, Germany, Instituto de Química Física ‘Rocasolano’, Consejo Superior de Investigaciones Científicas, Madrid, Spain, Instituto de Química Orgánica, Consejo Superior de Investigaciones Científicas, Madrid, Spain, Centro de Investigaciones Biológicas, Consejo Superior de Investigaciones Científicas, Madrid, Spain, Zentrale Spektroskopie, Deutsches Krebsforschungszentrum, Heidelberg, Germany
Theoretical calculations reveal that oligosaccharides are second to no other class of biochemical oligomery in terms of coding capacity. As integral part of cellular glycoconjugates they can serve as recognitive units for receptors (lectins). Having first been detected in plants, lectins are present ubiquitously. Remarkably for this field, they serve as bacterial and viral adhesins. Following a description of these branches of lectinology to illustrate history, current status and potential for medicinal chemistry, we document that lectins are involved in a wide variety of biochemical processes including intra- and intercellular glycoconjugate trafficking, initiation of signal transduction affecting e. g. growth regulation and cell adhesion in animals. It is thus justified to compare crucial carbohydrate epitopes with the postal code ensuring correct mail routing and delivery. In view of the functional relevance of lectins the design of high-affinity reagents to occupy their carbohydrate recognition domains offers the perspective for an attractive source of new drugs. Their applications can be supposed to encompass the use as cell-type-selective determinant for targeted drug delivery and as blocking devices in anti-adhesion therapy during infections and inflammatory disease. To master the task of devising custom-made glycans/glycomimetics for this purpose, the individual enthalpic and entropic contributions in the molecular rendezvous between the sugar receptor under scrutiny and its ligand in the presence of solvent molecules undergoing positional rearrangements need to be understood and rationally exploited. As remunerative means to this end, cleverly orchestrated deployment of a panel of methods is essential. Concerning the carbohydrate ligand, its topological parameters and flexibility are assessed by the combination of computer-assisted molecular-mechanics and molecular-dynamics calculations and NMR-spectroscopic measurements. In the presence of the receptor, the latter technique will provide insights into conformational aspects of the bound ligand and into spatial vicinity of the ligand to distinct side chains of amino acids establishing the binding site in solution. Also in solution, the hydrogen-bonding pattern in the complex can be mapped with monodeoxy and monofluoro derivatives of the oligosaccharide. Together with X-ray crystallographic and microcalorimetric studies the limits of a feasible affinity enhancement can be systematically probed. With galactoside-binding lectins as instructive mo del, recent progress in this area of drug design will be documented, emphasizing the general applicability of the outlined interdisciplinary approach.
Molecular mechanics, Rhizobium meliloti, lectinology, lectins as targets, computer assisted, NMR spectoscopic, crystallographic elucidation, sugar code, chemioal tailoring, phosphodiester backbone, microheterogeneity of glycan, monomer variability, N acetylneuramicinic, transgenic pollen, nitrogen enriched nutrients, non agglutinating ricin, hydrophobic molecules, phytopathogenic fungus, phosphomannose mutase, B bearing individuals, anti adhesion therapy, NMR spectrum, parenchymal host cells
Structure type: oligomer
Location inside paper: p. 392, Table 1
Trivial name: gentiobiose, bruceacanthinoside
Compound class: glycoside, Apotirucallane triterpe glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
Related record ID(s): 67517, 67518, 67519, 67520, 67521, 67522, 67523, 67525
NCBI Taxonomy refs (TaxIDs): 33090Reference(s) to other database(s): GTC:G09183JD, CCSD:
37198, CBank-STR:4177
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Kitagawa I, Mahmud T, Simanjuntak P, Hori K, Uji T, Shibuya H
Indonesian medicinal plants. VIII. Chemical structures of three new triterpenoids, bruceajavanin A, Dihydrobruceajavanin A, and bruceajavanin B, and a new alkaloidal glycoside, bruceacanthinoside, from the stems of Brucea javanica (Simaroubaceae)
Chemical and Pharmaceutical Bulletin 42 (1994)
1416-1421
Brucea javanica
(NCBI TaxID 210348,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: stem
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003631157Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan, Herbarium Bogoriense, Research and Development Centre for Biology-LIPI, Indonesia, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Japan
Three new apotirucallane-type triterpenoids named bruceajavanin A (1) dihydrobruceajavanin A (2), and bruceajavanin B (3), and a novel β-carboline alkaloidal glycoside named bruceacanthinoside (4) were isolated from the stems of Brucea javanica (Simaroubaceae), a traditional medicine used to treat malaria in the Bengkulu area, Sumatra, Indonesia. Their chemical structures have been elucidated on the bases of their chemical and physicochemical properties. Bruceajavanin A (1), dihydrobruceajavanin A (2) and bruceacanthinoside (4) were shown to inhibit growth of the cultured malarial parasite Plasmodium falciparum K1 of a chloroquine-resistant strain.
Structure type: oligomer
Location inside paper: 4
Trivial name: gentiobiose, bruceacanthinoside
Compound class: glycoside, Apotirucallane triterpe glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
NCBI Taxonomy refs (TaxIDs): 210348Reference(s) to other database(s): GTC:G09183JD, CCSD:
37198, CBank-STR:4177
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