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1. Compound ID: 3294
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a-L-AltpA-(1-3)-+
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-4)-a-D-GalpNAc-(1-3)-a-D-GalpA-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 1212
Shashkov AS, Senchenkova SN, Toukach FV, Ziolkowski A, Paramonov NA, Kaca W, Knirel YA, Kochetkov NK "Structure of the O-specific polysaccharide of the bacterium Proteus mirabilis O10 containing L-altruronic acid, a new component of O-antigens" -
Biochemistry (Moscow) 61(9) (1996) 1100-1105
Lipopolysaccharide, NMR, LPS, structure, polysaccharide, O-antigen, O antigen, acidic, acid, O antigens, O-antigens, bacteria, O-specific, O-specific polysaccharide, Proteus, Proteus mirabilis, serogroup, component, D-galacturonic acid, L-altruronic acid
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Moscow,Russia
Methods: NMR
- Article ID: 1278
Swierzko A, Shashkov AS, Senchenkova SN, Toukach FV, Ziolkowski A, Cedzynski M, Paramonov NA, Kaca W, Knirel YA "Structural and serological studies of the O-specific polysaccharide of the bacterium Proteus mirabilis O10 containing L-altruronic acid, a new component of O-antigens" -
FEBS Letters 398 (1996) 297-302
An acidic O-specific polysaccharide from the lipopolysaccharide of Proteus mirabilis O10 contains 2-acetamido-2-deoxy-D-glucose, 2-acetamido-2-deoxy-D-galactose, D-galacturonic acid, and L-altruronic acid, the last-named sugar having not been found hitherto in O-antigens. Structure of a branched tetrasaccharide repeating unit of the polysaccharide was established by 1H and 13C NMR spectroscopy, including two-dimensional COSY and rotating-frame NOE spectroscopy. The lateral L-altruronic acid residue plays the immunodominant role in manifestation of the O10 specificity of Proteus, whereas a disaccharide fragment of the main chain in common with the O-specific polysaccharide of P. mirabilis O43 provides the one-way serological cross-reactivity between anti-O10 serum and O43-antigen.
Lipopolysaccharide, NMR, LPS, structure, structural, polysaccharide, O-antigen, O antigen, acidic, acid, O antigens, O-antigens, bacteria, O-specific, O-specific polysaccharide, Proteus, Proteus mirabilis, serological, serogroup, bacterial polysaccharide structure, component, D-galacturonic acid, L-altruronic acid, lipopolysaccharide serological specificity
NCBI PubMed ID: 8977126Publication DOI: 10.1016/S0014-5793(96)01061-7Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: Centre of Microbiology and Virology, Polish Academy of Sciences, 93-232 Lodz, Poland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: periodate oxidation, NMR-2D, NMR, carboxyl reduction, serological methods
- Article ID: 1467
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry 73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
structure, O-antigen, Proteus, Bacterial polysaccharide, epitope specificity
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895Publisher: Państwowe Wydawnictwo Naukowe
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
- Article ID: 4043
Kaca W, Glenska J, Lechowicz L, Grabowski S, Brauner A, Kwinkowski M "Serotyping of Proteus mirabilis clinical strains based on lipopolysaccharide O-polysaccharide and core oligosaccharide structures" -
Biochemistry (Moscow) 76(7) (2011) 851-861
The aim of this work was to serotype Proteus mirabilis urinary tract infection (UTI) strains based on chemically defined O-antigens with the use of two clinical collections from Sweden and Poland consisting of 99 and 24 UTI strains, respectively. A simple two-step serotyping scheme was proposed using enzyme immunoassay with heat-stable surface antigens of Proteus cells and immunoblotting with isolated lipopolysaccharides (LPSs). Using polyclonal anti-P. mirabilis rabbit antisera, 50 Swedish and 8 Polish strains were classified into serogroups O10, O38, O36, O30, O17, O23, O9, O40, O49, O27, O5, O13, O24, O14, and O33. From the Swedish strains, 10 belonged to serogroup O10 and five to each of serogroups O38, O36, and O9. Therefore, none of the O-serogroups was predominant. The majority of the serotyped clinical strains possess acidic O-antigens containing uronic acids and various acidic non-carbohydrate substituents. In immunoblotting, antisera cross-reacted with both O-antigen and core of LPSs. The core region of 19 LPSs bound a single serum, and that of 12 LPSs bound more than two sera. Following bioinformatic analysis of the available sequences, a molecular approach to the prediction of Proteus core oligosaccharide structures was proposed. The identification of the core type of P. mirabilis R110, derived from a serogroup O3 wild strain, using restriction fragments length polymorphism analysis of galacturonic acid transferase is shown as an example. In summary, the most frequent O-serogroups among P. mirabilis UTI stains were identified. The diversity of serological reactions of LPSs is useful for serotyping of P. mirabilis clinical isolates. A possible role of the acidic components of O-antigens in UTI is discussed.
Lipopolysaccharide, O-antigen, Proteus mirabilis, serology, serotyping, glycosyl transferas
NCBI PubMed ID: 21999547Publication DOI: 10.1134/S0006297911070169Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: wieslaw.kaca@ujk.edu.pl
Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland
Methods: PCR, SDS-PAGE, EIA, serological methods, immunoblotting, bioinformatic analysis
- Article ID: 4662
Wang Q, Torzewska A, Ruan X, Wang X, Rozalski A, Shao Z, Guo X, Zhou H, Feng L, Wang L "Molecular and genetic analyses of the putative Proteus O antigen gene locus" -
Applied and Environmental Microbiology 76(16) (2010) 5471-5478
Proteus species are well-characterized opportunistic pathogens primarily associated with urinary tract infections (UTI) of humans. The Proteus O antigen is one of the most variable constituents of the cell surface, and O antigen heterogeneity is used for serological classification of Proteus isolates. Even though most Proteus O antigen structures have been identified, the O antigen locus has not been well characterized. In this study, we identified the putative Proteus O antigen locus and demonstrated this region's high degree of heterogeneity by comparing sequences of 40 Proteus isolates using PCR-restriction fragment length polymorphism (RFLP). This analysis identified five putative Proteus O antigen gene clusters, and the probable functions of these O antigen-related genes were proposed, based on their similarity to genes in the available databases. Finally, Proteus-specific genes from these five serogroups were identified by screening 79 strains belonging to the 68 Proteus O antigen serogroups. To our knowledge, this is the first molecular characterization of the putative Proteus O antigen locus, and we describe a novel molecular classification method for the identification of different Proteus serogroups.
structure, O-antigen, gene cluster, Proteus, serological classification, Cluster Analysis, database
Publication DOI: 10.1128/AEM.02946-09Journal NLM ID: 7605801Publisher: American Society for Microbiology
Correspondence: wanglei@nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China
Methods: PCR, serological methods, genetic methods
- Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology 120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen
NCBI PubMed ID: 32087569Publication DOI: 10.1016/j.molimm.2020.02.005Journal NLM ID: 7905289Publisher: Elsevier
Correspondence: professorbovin@yandex.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
- Article ID: 6050
Drzewiecka D, Palusiak A, Siwinska M, Zablotni A "The prevailing O serogroups among the serologically differentiated clinical Proteus spp. strains in central Poland" -
Scientific Reports 11(1) (2021) 18982
In the years 2006-2011, 617 Proteus spp. strains isolated mostly from urine and wounds or other clinical sources were collected in Lodz, Poland, to determine the offensive O serotypes frequently occurring among patients. P. mirabilis exhibited the most intensive swarming growth and was dominating species (86.9%), followed by P. genomospecies, P. vulgaris, and P. penneri. Ninety four per cent strains were recognized as S (smooth) forms. Serological studies (involving ELISA-enzyme-linked immunosorbent assay and Western blotting using native and adsorbed rabbit antisera) enabled classification of 80% S isolates into respective Proteus O serogroups among the 83 ones, described so far. The remaining strains seemed to be serologically unique. Despite the observed big serological variety of Proteus spp. isolates, we found the O78 serogroup recently described in Poland as dominating and identified other widespread serotypes: O3, O6, O10, O11, O27, O28, and O30 reported earlier as predominating also in other countries; O77 and O79 detected lately in Poland; O16, O18, O20, and O50. No unique structural feature of the prevalent O serotypes has been indicated. However, the prevalence of some O serogroups indicates that particular serotypes may be in some ways beneficial to the strains producing these kinds of O antigen.
clinical, strain, O antigen, Proteus, serogroup, Serotypes, ELISA, O serotype
NCBI PubMed ID: 34556711Publication DOI: 10.1038/s41598-021-98228-wJournal NLM ID: 101563288Publisher: London: Nature Publishing Group
Correspondence: dominika.drzewiecka@biol.uni.lodz.pl
Institutions: Department of Biology of Bacteria, Faculty of Biology and Environmental Protection, University of Łódź, Banacha 12/16, 90-237, Łódź, Poland
Methods: ELISA, Western blotting, serological methods, serotyping analysis
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2. Compound ID: 6851
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S-Lac-(2-4)-b-D-Glcp-(1-4)-+
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-3)-b-D-QuipNAc-(1-3)-b-D-GlcpA-(1-3)-a-L-AltpA-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 3136
Hermansson K, Kenne L, Lindberg B, Arie B, Brown RG, Stewart JE "Structural studies of the capsular polysaccharide from Aerococcus viridans var. homari" -
Carbohydrate Research 208 (1990) 145-152
The capsular polysaccharide from Aerococcus viridans var. homari has been investigated, using n.m.r. spectroscopy, methylation analysis, and specific degradations as the main methods. The polysaccharide is composed of tetrasaccharide repeating-units having the following structure. (Formula; see text) In this structure, D-QuiN stands for 2-amino-2,6-dideoxy-D-glucose (quinovosamine). Two of the three acidic sugars found, namely, L-altruronic acid and 4-O-[(S)-1-carboxyethyl]-D-glucose, have not been found in any other natural source. As evident from the n.m.r. spectra, the L-altruronic acid is not present in the 1C4 conformation, but flips to a conformation close to this on carboxyl reduction.
NCBI PubMed ID: 2085808Publication DOI: 10.1016/0008-6215(90)80094-jJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
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3. Compound ID: 9557
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a-L-AltpA-(1-3)-+
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-4)-a-D-GalpNAc-(1-3)-a-D-GalpA-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 4049
Knirel YA, Perepelov AV, Kondakova AN, Senchenkova SN, Sidorczyk Z, Rozalski A, Kaca W "Structure and serology of O-antigens as the basis for classification of Proteus strains" -
Innate Immunity 17(1) (2011) 70-96
This review is devoted to structural and serological characteristics of the O-antigens (O-polysaccharides) of the lipopolysaccharides of various Proteus species, which provide the basis for classifying Proteus strains to O-serogroups. The antigenic relationships of Proteus strains within and beyond the genus as well as their O-antigen-related bioactivities are also discussed.
Lipopolysaccharide, O-antigen, Proteus, polysaccharide structure, classification, Serological cross-reactivity, immunospecificity
NCBI PubMed ID: 20305038Publication DOI: 10.1177/1753425909360668Journal NLM ID: 101469670Publisher: Sage Publications
Correspondence: yknirel@gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, Lodz, Poland, Department of Microbiology, Jan Kochanowski University, Kielce, Poland
- Article ID: 5057
Yu X, Torzewska A, Zhang X, Yin Z, Drzewiecka D, Cao H, Liu B, Knirel YA, Rozalski A, Wang L "Genetic diversity of the O antigens of Proteus species and the development of a suspension array for molecular serotyping" -
PLoS One 12(8) (2017) e0183267
Proteus species are well-known opportunistic pathogens frequently associated with skin wound and urinary tract infections in humans and animals. O antigen diversity is important for bacteria to adapt to different hosts and environments, and has been used to identify serotypes of Proteus isolates. At present, 80 Proteus O-serotypes have been reported. Although the O antigen structures of most Proteus serotypes have been identified, the genetic features of these O antigens have not been well characterized. The O antigen gene clusters of Proteus species are located between the cpxA and secB genes. In this study, we identified 55 O antigen gene clusters of different Proteus serotypes. All clusters contain both the wzx and wzy genes and exhibit a high degree of heterogeneity. Potential functions of O antigen-related genes were proposed based on their similarity to genes in available databases. The O antigen gene clusters and structures were compared, and a number of glycosyltransferases were assigned to glycosidic linkages. In addition, an O serotype-specific suspension array was developed for detecting 31 Proteus serotypes frequently isolated from clinical specimens. To our knowledge, this is the first comprehensive report to describe the genetic features of Proteus O antigens and to develop a molecular technique to identify different Proteus serotypes.
O-antigen, gene cluster, Proteus, glycosyltransferases, serotyping, genomics, genetic diversity, serotype-specific
NCBI PubMed ID: 28817637Publication DOI: 10.1371/journal.pone.0183267Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Lei Wang
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, P. R. China, Tianjin Research Center for Functional Genomics and Biochips, TEDA College, Nankai University, Tianjin, P. R. China, Tianjin Key Laboratory of Microbial Functional Genomics, TEDA College, Nankai University, Tianjin, P. R. China, Key Laboratory of Molecular Microbiology and Technology of the Ministry of Education, TEDA College, Nankai University, Tianjin, P. R. China, Department of Immunobiology of Bacteria, Department of General Microbiology Institute of Microbiology, Biotechnology and Immunology, Faculty of Biology and Environmental Protection, University of Lodz, Lodz, Poland
Methods: PCR, DNA sequencing, genetic methods, function analysis of gene clusters, serotyping
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4. Compound ID: 12081
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a-D-Glcp-(1-2)-+
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-4)-a-L-Fucp-(1-4)-b-D-Glcp-(1-3)-a-L-Fucp-(1-3)-a-L-Fucp-(1-3)-a-L-AltpA-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_136045,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 4820
Kodali S, Vinogradov E, Lin F, Khoury N, Hao L, Pavliak V, Jones CH, Laverde D, Huebner J, Jansen KU, Anderson AS, Donald RG "A Vaccine Approach for the Prevention of Infections by Multidrug-resistant Enterococcus faecium" -
Journal of Biological Chemistry 290(32) (2015) 19512-19526
The incidence of multidrug-resistant Enterococcus faecium hospital infections has been steadily increasing. With the goal of discovering new vaccine antigens, we systematically fractionated and purified four distinct surface carbohydrates from E. faecium endocarditis isolate Tx16, shown previously to be resistant to phagocytosis in the presence of human serum. The two most abundant polysaccharides consist of novel branched heteroglycan repeating units that include signature sugars altruronic acid and legionaminic acid, respectively. A minor high molecular weight polysaccharide component was recognized as the fructose homopolymer levan, and a glucosylated lipoteichoic acid (LTA) was identified in a micellar fraction. The polysaccharides were conjugated to the CRM197 carrier protein, and the resulting glycoconjugates were used to immunize rabbits. Rabbit immune sera were evaluated for their ability to kill Tx16 in opsonophagocytic assays and in a mouse passive protection infection model. Although antibodies raised against levan failed to mediate opsonophagocytic killing, the other glycoconjugates induced effective opsonic antibodies, with the altruronic acid-containing polysaccharide antisera showing the greatest opsonophagocytic assay activity. Antibodies directed against either novel heteroglycan or the LTA reduced bacterial load in mouse liver or kidney tissue. To assess antigen prevalence, we screened a diverse collection of blood isolates (n = 101) with antibodies to the polysaccharides. LTA was detected on the surface of 80% of the strains, and antigens recognized by antibodies to the two major heteroglycans were co-expressed on 63% of these clinical isolates. Collectively, these results represent the first steps toward identifying components of a glycoconjugate vaccine to prevent E. faecium infection.
antigen, teichoic acid, vaccine, uronic acids, carbohydrate structure, glycoconjugate vaccine, Enterococcus faecium, sialic acids
NCBI PubMed ID: 26109072Publication DOI: 10.1074/jbc.M115.655852Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: robert.donald@pfizer.com
Institutions: the National Research Council, Ottawa, Ontario K1A 0R6, Canada, the Division of Infectious Diseases, Department of Medicine, University Hospital, Hugstetter Strasse 55, 79106 Freiburg, Germany, and the Department of Pediatrics, Dr. von Hauner Children's Hospital, Ludwig-Maximilians-University, Lindwurmstrasse 4, 80338 Munich, Germany, From Pfizer Vaccine Research and Early Development, Pearl River, New York 10654
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, SDS-PAGE, sugar analysis, ELISA, ESI-MS, GC, biological assays, serological methods, UV, HPAEC-PAD, bioinformatic analysis, SEC, conjugatation, SEC-MALLS
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5. Compound ID: 12082
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86
The structure is contained in the following publication(s):
- Article ID: 4820
Kodali S, Vinogradov E, Lin F, Khoury N, Hao L, Pavliak V, Jones CH, Laverde D, Huebner J, Jansen KU, Anderson AS, Donald RG "A Vaccine Approach for the Prevention of Infections by Multidrug-resistant Enterococcus faecium" -
Journal of Biological Chemistry 290(32) (2015) 19512-19526
The incidence of multidrug-resistant Enterococcus faecium hospital infections has been steadily increasing. With the goal of discovering new vaccine antigens, we systematically fractionated and purified four distinct surface carbohydrates from E. faecium endocarditis isolate Tx16, shown previously to be resistant to phagocytosis in the presence of human serum. The two most abundant polysaccharides consist of novel branched heteroglycan repeating units that include signature sugars altruronic acid and legionaminic acid, respectively. A minor high molecular weight polysaccharide component was recognized as the fructose homopolymer levan, and a glucosylated lipoteichoic acid (LTA) was identified in a micellar fraction. The polysaccharides were conjugated to the CRM197 carrier protein, and the resulting glycoconjugates were used to immunize rabbits. Rabbit immune sera were evaluated for their ability to kill Tx16 in opsonophagocytic assays and in a mouse passive protection infection model. Although antibodies raised against levan failed to mediate opsonophagocytic killing, the other glycoconjugates induced effective opsonic antibodies, with the altruronic acid-containing polysaccharide antisera showing the greatest opsonophagocytic assay activity. Antibodies directed against either novel heteroglycan or the LTA reduced bacterial load in mouse liver or kidney tissue. To assess antigen prevalence, we screened a diverse collection of blood isolates (n = 101) with antibodies to the polysaccharides. LTA was detected on the surface of 80% of the strains, and antigens recognized by antibodies to the two major heteroglycans were co-expressed on 63% of these clinical isolates. Collectively, these results represent the first steps toward identifying components of a glycoconjugate vaccine to prevent E. faecium infection.
antigen, teichoic acid, vaccine, uronic acids, carbohydrate structure, glycoconjugate vaccine, Enterococcus faecium, sialic acids
NCBI PubMed ID: 26109072Publication DOI: 10.1074/jbc.M115.655852Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: robert.donald@pfizer.com
Institutions: the National Research Council, Ottawa, Ontario K1A 0R6, Canada, the Division of Infectious Diseases, Department of Medicine, University Hospital, Hugstetter Strasse 55, 79106 Freiburg, Germany, and the Department of Pediatrics, Dr. von Hauner Children's Hospital, Ludwig-Maximilians-University, Lindwurmstrasse 4, 80338 Munich, Germany, From Pfizer Vaccine Research and Early Development, Pearl River, New York 10654
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, SDS-PAGE, sugar analysis, ELISA, ESI-MS, GC, biological assays, serological methods, UV, HPAEC-PAD, bioinformatic analysis, SEC, conjugatation, SEC-MALLS
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6. Compound ID: 12083
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_142489,IEDB_144562,IEDB_152214,SB_86
The structure is contained in the following publication(s):
- Article ID: 4820
Kodali S, Vinogradov E, Lin F, Khoury N, Hao L, Pavliak V, Jones CH, Laverde D, Huebner J, Jansen KU, Anderson AS, Donald RG "A Vaccine Approach for the Prevention of Infections by Multidrug-resistant Enterococcus faecium" -
Journal of Biological Chemistry 290(32) (2015) 19512-19526
The incidence of multidrug-resistant Enterococcus faecium hospital infections has been steadily increasing. With the goal of discovering new vaccine antigens, we systematically fractionated and purified four distinct surface carbohydrates from E. faecium endocarditis isolate Tx16, shown previously to be resistant to phagocytosis in the presence of human serum. The two most abundant polysaccharides consist of novel branched heteroglycan repeating units that include signature sugars altruronic acid and legionaminic acid, respectively. A minor high molecular weight polysaccharide component was recognized as the fructose homopolymer levan, and a glucosylated lipoteichoic acid (LTA) was identified in a micellar fraction. The polysaccharides were conjugated to the CRM197 carrier protein, and the resulting glycoconjugates were used to immunize rabbits. Rabbit immune sera were evaluated for their ability to kill Tx16 in opsonophagocytic assays and in a mouse passive protection infection model. Although antibodies raised against levan failed to mediate opsonophagocytic killing, the other glycoconjugates induced effective opsonic antibodies, with the altruronic acid-containing polysaccharide antisera showing the greatest opsonophagocytic assay activity. Antibodies directed against either novel heteroglycan or the LTA reduced bacterial load in mouse liver or kidney tissue. To assess antigen prevalence, we screened a diverse collection of blood isolates (n = 101) with antibodies to the polysaccharides. LTA was detected on the surface of 80% of the strains, and antigens recognized by antibodies to the two major heteroglycans were co-expressed on 63% of these clinical isolates. Collectively, these results represent the first steps toward identifying components of a glycoconjugate vaccine to prevent E. faecium infection.
antigen, teichoic acid, vaccine, uronic acids, carbohydrate structure, glycoconjugate vaccine, Enterococcus faecium, sialic acids
NCBI PubMed ID: 26109072Publication DOI: 10.1074/jbc.M115.655852Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: robert.donald@pfizer.com
Institutions: the National Research Council, Ottawa, Ontario K1A 0R6, Canada, the Division of Infectious Diseases, Department of Medicine, University Hospital, Hugstetter Strasse 55, 79106 Freiburg, Germany, and the Department of Pediatrics, Dr. von Hauner Children's Hospital, Ludwig-Maximilians-University, Lindwurmstrasse 4, 80338 Munich, Germany, From Pfizer Vaccine Research and Early Development, Pearl River, New York 10654
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, partial acid hydrolysis, GC-MS, SDS-PAGE, sugar analysis, ELISA, ESI-MS, GC, biological assays, serological methods, UV, HPAEC-PAD, bioinformatic analysis, SEC, conjugatation, SEC-MALLS
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7. Compound ID: 20889
|
b-D-AltpA-(1-19)-Subst
Subst = isopimara-7,15-diene-2α,3β,19-triol = SMILES C[C@@]1(CCC2[C@@](C)(C[C@@H](O)[C@@H]([C@@]3({19}CO)C)O)C3CC=C2C1)C=C |
Show graphically |
Structure type: monomer
C26H40O9
Trivial name: virescenoside F
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 6181
Hussain H, Mamadalieva NZ, Ali I, Elizbit, Green IR, Wang D, Zou L, Simal-Gandara J, Cao H, Xiao J "Fungal glycosides: Structure and biological function" -
Trends in Food Science and Technology 110 (2021) 611-651
Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.
glycoside, antimicrobial, fungi, food preservative, secondary metabolites
Publication DOI: 10.1016/j.tifs.2021.02.029Journal NLM ID: 9426004Publisher: Cambridge, UK: Elsevier Trends Journals
Correspondence: Hussain H
; Hussain H ; Xiao J ; Xiao J
Institutions: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany, Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent, Uzbekistan, School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China, Department Materials Engineering, National University of Sciences and Technology (NUST) H12, Islamabad, Pakistan, Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa, Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Chengdu University, Chengdu, China, Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo - Ourense Campus, Ourense, Spain
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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8. Compound ID: 20890
|
b-D-AltpA-(1-19)-Subst
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
C26H40O8
Trivial name: virescenoside G
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 6181
Hussain H, Mamadalieva NZ, Ali I, Elizbit, Green IR, Wang D, Zou L, Simal-Gandara J, Cao H, Xiao J "Fungal glycosides: Structure and biological function" -
Trends in Food Science and Technology 110 (2021) 611-651
Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.
glycoside, antimicrobial, fungi, food preservative, secondary metabolites
Publication DOI: 10.1016/j.tifs.2021.02.029Journal NLM ID: 9426004Publisher: Cambridge, UK: Elsevier Trends Journals
Correspondence: Hussain H
; Hussain H ; Xiao J ; Xiao J
Institutions: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany, Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent, Uzbekistan, School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China, Department Materials Engineering, National University of Sciences and Technology (NUST) H12, Islamabad, Pakistan, Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa, Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Chengdu University, Chengdu, China, Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo - Ourense Campus, Ourense, Spain
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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9. Compound ID: 20891
|
b-D-AltpA6Me-(1-19)-Subst
Subst = isopimara-7,15-diene-2α,3β,19-triol = SMILES C[C@@]1(CCC2[C@@](C)(C[C@@H](O)[C@@H]([C@@]3({19}CO)C)O)C3CC=C2C1)C=C |
Show graphically |
Structure type: monomer
C26H40O9
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
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10. Compound ID: 20892
|
b-D-AltpA6Me-(1-19)-Subst
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
C26H40O8
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
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11. Compound ID: 20893
|
b-D-AltpA2Ac3Ac4Ac6Me-(1-19)-Subst3Ac
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
C26H40O8
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
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12. Compound ID: 22021
|
b-D-AltpA-(1-19)-Subst
Subst = virescenoside Z10 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)CC{3}[C@H](O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z10
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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13. Compound ID: 22022
|
b-D-AltpA-(1-19)-Subst
Subst = virescenoside Z11, Z15 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)C{2}[C@@H](O){3}[C@H](O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z11
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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14. Compound ID: 22023
|
b-D-AltpA6Me-(1-19)-Subst
Subst = virescenoside Z12, Z18 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O)CC[C@]12C)C3 |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z12
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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15. Compound ID: 22024
|
b-D-AltpA6Me-(1-19)-Subst
Subst = virescenoside Z13, Z17 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O){2}[C@H](O)C[C@]12C)C3 |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z13
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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