Found 43 structures.
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1. Compound ID: 282
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b-D-Glcp-(1-2)-+ R-Lac-(2-4)-+ R-Lac-(2-6)-+
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-4)-b-L-Altp-(1-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_153543,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 75
Ferreira F, Kenne L, Cotta MA, Stack RJ "Structural studies of the extracellular polysaccharide from Butyrivibrio fibrisolvens strain CF3" -
Carbohydrate Research 301(3-4) (1997) 193-203
The structure of the Butyrivibrio fibrisolvens strain CF3 capsular polysaccharide has been investigated mainly by sugar and methylation analyses, Smith degradation, NMR spectroscopy, and mass spectrometry. The results indicate that the polysaccharide is composed of pentasaccharide repeating units having the following structure: →4)-[β-D-Glcp-(1→2)-]-β-L-Altp-(1→4)-β-D-Glcp-(1→3)-4-O-[(R)-1-carboxyethyl]-β- D-Glcp-(1→4)-6-O-[(R)-1-carboxyethyl]-α-D-Galp-(1→
Bacterial polysaccharide, Butyrivibrio fibrisolvens, (1-carboxyethyl)-galactose, (1-carboxyethyl)-glucose, L-altrose
NCBI PubMed ID: 9232840Publication DOI: 10.1016/s0008-6215(97)00097-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Catedra de Farmacognosia y Productos Naturales, Facultad de Quimica, Montevideo, Uruguay, Departement of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, National Center for Argicultural Utilization Research, Agricultural Research Service, US Departement of Agriculture, Peoria, IL, USA, Glycomed Incorporated, Alameda, USA
Methods: methylation, NMR-2D, NMR, sugar analysis, carboxyl reduction, Smith degradation
- 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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2. Compound ID: 283
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b-D-Glcp-(1-2)-+ Subst-(2-4)-+ Subst-(2-6)-+
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-4)-b-L-Altp-(1-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-4)-a-D-Galp-(1-
Subst = R-2-dihydroxypropanol (reduced R-lactic acid) = SMILES OC{2}[C@H](O)C |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_153543,IEDB_190606,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 75
Ferreira F, Kenne L, Cotta MA, Stack RJ "Structural studies of the extracellular polysaccharide from Butyrivibrio fibrisolvens strain CF3" -
Carbohydrate Research 301(3-4) (1997) 193-203
The structure of the Butyrivibrio fibrisolvens strain CF3 capsular polysaccharide has been investigated mainly by sugar and methylation analyses, Smith degradation, NMR spectroscopy, and mass spectrometry. The results indicate that the polysaccharide is composed of pentasaccharide repeating units having the following structure: →4)-[β-D-Glcp-(1→2)-]-β-L-Altp-(1→4)-β-D-Glcp-(1→3)-4-O-[(R)-1-carboxyethyl]-β- D-Glcp-(1→4)-6-O-[(R)-1-carboxyethyl]-α-D-Galp-(1→
Bacterial polysaccharide, Butyrivibrio fibrisolvens, (1-carboxyethyl)-galactose, (1-carboxyethyl)-glucose, L-altrose
NCBI PubMed ID: 9232840Publication DOI: 10.1016/s0008-6215(97)00097-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Catedra de Farmacognosia y Productos Naturales, Facultad de Quimica, Montevideo, Uruguay, Departement of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, National Center for Argicultural Utilization Research, Agricultural Research Service, US Departement of Agriculture, Peoria, IL, USA, Glycomed Incorporated, Alameda, USA
Methods: methylation, NMR-2D, NMR, sugar analysis, carboxyl reduction, Smith degradation
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3. Compound ID: 8495
Structure type: oligomer
Trivial name: inhibitor of bacterial growth
The structure is contained in the following publication(s):
- Article ID: 3705
Kang YS, Lee Y, Cho SK, Lee KH, Kim BJ, Kim M, Lim Y, Cho M "Antibacterial activity of a disaccharide isolated from Streptomyces sp. strain JJ45 against Xanthomonas sp" -
FEMS Microbiology Letters 294(1) (2009) 119-125
Of the 316 actinomycetes strains isolated from various habitats, Streptomyces sp. strain JJ45 showed the strongest antibiotic activity against the plant pathogenic bacteria Xanthomonas campestris pv. campestris and was thus chosen for further study. The 16S rRNA gene sequence (1500 bp) and rpoB gene partial sequence (306 bp) of Streptomyces strains JJ45A and JJ45B were determined. The respective strain JJ45B sequences exhibited 96.8% identity with the Streptococcus gelaticus 16S rRNA gene sequence and 98.4% identity with the Streptococcus vinaceus ATCC 27478 rpoB partial sequence. The fermentation broth of the JJ45B strain was extracted to find an inhibitor of bacterial growth. The distilled water extract showed the highest activity against pathogenic bacteria. The active molecule was isolated by column chromatography on polyacrylamide or silica gel, thin-layer chromatography, and HPLC. It showed growth inhibition activity only toward phytopathogenic Xanthomonas sp. The structure of the compound was identified as α-L-sorbofuranose (3→2)-β-D-altrofuranose based on the interpretation of the nuclear magnetic resonance spectra.
Xanthomonas, Xanthomonas campestris, antibacterial activity, α-L-sorbofuranose (3→2)-β-D-altrofuranose
NCBI PubMed ID: 19493015Publication DOI: 10.1111/j.1574-6968.2009.01561.xJournal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: moonjcho@cheju.ac.kr
Institutions: Department of Biochemistry, Cheju National University, Jeju, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, serological methods, genetic methods, HPLC
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4. Compound ID: 10016
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_142488,IEDB_146664,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
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5. Compound ID: 12589
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a-L-Altf-(1-3)-+
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-2)-a-L-Fucp-(1-3)-a-D-Manp-(1-4)-a-L-Fucp-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_136045,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_152206,IEDB_152214,IEDB_174333,IEDB_885822,IEDB_983930,SB_44,SB_67,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 5010
Kenyon JJ, Cunneen MM, Reeves PR "Genetics and evolution of Yersinia pseudotuberculosis O-specific polysaccharides: a novel pattern of O-antigen diversity" -
FEMS Microbiology Reviews 41(2) (2017) 200-217
O-antigen polysaccharide is a major immunogenic feature of the lipopolysaccharide of Gram-negative bacteria, and most species produce a large variety of forms that differ substantially from one another. There are 18 known O-antigen forms in the Yersinia pseudotuberculosis complex, which are typical in being composed of multiple copies of a short oligosaccharide called an O unit. The O-antigen gene clusters are located between the hemH and gsk genes, and are atypical as 15 of them are closely related, each having one of five downstream gene modules for alternative main-chain synthesis, and one of seven upstream modules for alternative side-branch sugar synthesis. As a result, many of the genes are in more than one gene cluster. The gene order in each module is such that, in general, the earlier a gene product functions in O-unit synthesis, the closer the gene is to the 5 end for side-branch modules or the 3 end for main-chain modules. We propose a model whereby natural selection could generate the observed pattern in gene order, a pattern that has also been observed in other species.
Lipopolysaccharide, serotype, O antigen, gene cluster, O-specific polysaccharide, Yersinia pseudotuberculosis, O-antigen polysaccharide
NCBI PubMed ID: 28364730Publication DOI: 10.1093/femsre/fux002Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience, The University of Sydney, Sydney, NSW 2006, Australia, Institute of Health and Biomedical Innovation, Queensland University of Technology. Brisbane, QLD 4001, Australia
Methods: function analysis of gene clusters
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6. Compound ID: 17638
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b-D-Altp-(1-19)-Subst
Subst = sandaracopimara-8(14),15-diene-3β,7α,19-triol = SMILES C[C@@]1(CCC(C2=C1)[C@@](C)(CCC([C@@]3({19}CO)C)O)C3C[C@H]2O)C=C |
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Structure type: monomer
; 505.2790
Trivial name: virescenoside O
The structure is contained in the following publication(s):
- Article ID: 6931
Afiyatullov SS, Kalinovsky AI, Kuznetsova TA, Isakov VV, Pivkin MV, Dmitrenok PS, Elyakov GB "New diterpene glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 65 (2002) 641-644
Three new diterpene glycosides, virescenosides O (1), P (2), and Q (3), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of HRMALDIMS and NMR data as β-D-altropyranosido-19-isopimara-8(14),15-diene-7α,3β-diol (1), β-D-altropyranosido-19-7-oxoisopimara-8(9),15-diene-3β-ol (2), and β-D-mannopyranosido-19-isopimara-7,15-diene-3β-ol (3). The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np010503yJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: piboc@stl.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, UV, HR-MALDI-MS
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7. Compound ID: 17639
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b-D-Altp-(1-19)-Subst
Subst = 7-oxoisopimara-8(9),15-diene-3β,19β-diol = SMILES C[C@](C1)(C=C)CCC([C@@](C2C3)(C)CC{3}C(O)[C@]2(C){19}CO)=C1C3=O |
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Structure type: monomer
; 503.2630
Trivial name: virescenoside P
The structure is contained in the following publication(s):
- Article ID: 6931
Afiyatullov SS, Kalinovsky AI, Kuznetsova TA, Isakov VV, Pivkin MV, Dmitrenok PS, Elyakov GB "New diterpene glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 65 (2002) 641-644
Three new diterpene glycosides, virescenosides O (1), P (2), and Q (3), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of HRMALDIMS and NMR data as β-D-altropyranosido-19-isopimara-8(14),15-diene-7α,3β-diol (1), β-D-altropyranosido-19-7-oxoisopimara-8(9),15-diene-3β-ol (2), and β-D-mannopyranosido-19-isopimara-7,15-diene-3β-ol (3). The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np010503yJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: piboc@stl.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, UV, HR-MALDI-MS
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8. Compound ID: 17641
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b-D-Altp-(1-19)-Subst
Subst = virescenoside M aglycon = SMILES C[C@]1(C=C)CCC([C@@](C{3}[C@H]({2}[C@H](O)[C@]2(C){19}CO)O)(C2CC3=O)C)=C3C1 |
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Structure type: monomer
; 519.2589
Trivial name: virescenoside M
The structure is contained in the following publication(s):
- Article ID: 6932
Afiyatullov SS, Kuznetsova TA, Isakov VV, Pivkin MV, Prokof'eva NG, Elyakov GB "New diterpenic altrosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 63 (2000) 848-850
Two new diterpenic glycosides, virescenosides M (1) and N (2), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of MS and NMR data as β-D-altropyranosido-19-7-oxo-isopimara-8,15-diene-2α,3β-diol (1) and β-D-altropyranosido-19-isopimara-7,15-diene-2α,3β,6β-triol (2). Three other altrosides (3−5), identified as virescenosides A, B, and C from the terrestrial strain Acremonium luzulae, were also isolated. The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np9904004Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: piboc@stl.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, EI-MS, acid hydrolysis, biological assays, HPLC, UV, CD, HR-MALDI-MS
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9. Compound ID: 17642
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b-D-Altp-(1-19)-Subst
Subst = virescenoside N aglycon = SMILES C[C@]1(C=C)CCC2[C@@](C{3}[C@H]({2}[C@H](O)[C@]3(C){19}CO)O)(C3{6}[C@@H](C=C2C1)O)C |
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Structure type: monomer
; 521.2726
Trivial name: virescenoside N
The structure is contained in the following publication(s):
- Article ID: 6932
Afiyatullov SS, Kuznetsova TA, Isakov VV, Pivkin MV, Prokof'eva NG, Elyakov GB "New diterpenic altrosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 63 (2000) 848-850
Two new diterpenic glycosides, virescenosides M (1) and N (2), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of MS and NMR data as β-D-altropyranosido-19-7-oxo-isopimara-8,15-diene-2α,3β-diol (1) and β-D-altropyranosido-19-isopimara-7,15-diene-2α,3β,6β-triol (2). Three other altrosides (3−5), identified as virescenosides A, B, and C from the terrestrial strain Acremonium luzulae, were also isolated. The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np9904004Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: piboc@stl.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, EI-MS, acid hydrolysis, biological assays, HPLC, UV, CD, HR-MALDI-MS
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10. Compound ID: 17643
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b-D-Altp-(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 |
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Structure type: monomer
Trivial name: virescenoside A
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5654
Gomes NGM, Buttachon S, Kijjoa A "Meroterpenoids from marine microorganisms: potential scaffolds for new chemotherapy leads" -
Book: Handbook of Anticancer Drugs from Marine Origin (2015) Chapter 16, 323-366
Meroterpenoids, including several biologically active metabolites from marine microorganisms mainly fungi and actinomycete bacteria, represent promising structural scaffolds with not only diverse biological activities such as antimicrotubule, cytotoxic and antiproliferative but also different mechanisms of action. In this chapter, an overview on structural diversity and anticancer activity of mixed biogenesis terpenoid derivatives (meroterpenoids) from marine microorganisms is presented with highlight on individual examples of the most promising candidates in cancer chemotherapy and prevention
cytotoxicity, Marine bacteria, marine microorganisms, anticancer activities, marine-derived fungi, marine-derived actinomycetes, meroterpenoids, terpenyl alkaloids, terpenyl glycosides, terpenyl polyketides
Publication DOI: 10.1007/978-3-319-07145-9_16Publisher: Cham: Springer
Correspondence: ankijjoa@icbas.up.pt
Editors: Kim S-K
Institutions: ICBAS—Instituto de Ciências Biomédicas Abel Salazar and Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Porto, Portugal
- 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: 6932
Afiyatullov SS, Kuznetsova TA, Isakov VV, Pivkin MV, Prokof'eva NG, Elyakov GB "New diterpenic altrosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 63 (2000) 848-850
Two new diterpenic glycosides, virescenosides M (1) and N (2), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of MS and NMR data as β-D-altropyranosido-19-7-oxo-isopimara-8,15-diene-2α,3β-diol (1) and β-D-altropyranosido-19-isopimara-7,15-diene-2α,3β,6β-triol (2). Three other altrosides (3−5), identified as virescenosides A, B, and C from the terrestrial strain Acremonium luzulae, were also isolated. The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np9904004Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: piboc@stl.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, EI-MS, acid hydrolysis, biological assays, HPLC, UV, CD, HR-MALDI-MS
- Article ID: 8342
Ebel R "Terpenes from marine-derived fungi" -
Marine Drugs 8(8) (2010) 2340-2368
Terpenes from marine-derived fungi show a pronounced degree of structural diversity, and due to their interesting biological and pharmacological properties many of them have aroused interest from synthetic chemists and the pharmaceutical industry alike. The aim of this paper is to give an overview of the structural diversity of terpenes from marine-derived fungi, highlighting individual examples of chemical structures and placing them in a context of other terpenes of fungal origin. Wherever possible, information regarding the biological activity is presented
biological activity, marine-derived fungi, natural products chemistry, terpenes
NCBI PubMed ID: 20948911Publication DOI: 10.3390/md8082340Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: r.ebel@abdn.ac.uk
Institutions: Marine Biodiscovery Centre, University of Aberdeen, Aberdeen, UK
- Article ID: 8346
Cagnoli-Bellavita N, Ceccherelli P, Mariani R, Polonsky J, Baskevitch Z "Structure du virescenoside C, nouveau métabolite de Oospora virescens (Link) Wallr." -
European Journal of Biochemistry 15(2) (1970) 356-359
Chemical investigation of the glycosidic constituents of Oospora virescens (Link) Wallr. resulted in the isolation of several glycosides. We have shown recently [l] that two of them, named virescenoside A (I) and B (II) are β-D-altropyranosides of virescenol A and B; these diterpenic aglycones have been found to have the structure of isopimaradien-2α,3β-l9-triol (IV) and isopimaradien-3β,19-diol (V), respectively [2]. In this paper we describe the isolation and structure of virescenoside C, a new metabolite of Oospora virescens. The results obtained show that virescenoside C (IIIa), C26H40O7, m. p. 160-162°, [α]D - 71,4°, is a β-D-altropyranoside of virescenol C, which is found to have the structure of 3-keto-19-hydroxy-isopimaradiene (VIa). These results are based on physical evidence (infra-red, nuclear magnetic resonance and mass spectra) and particularly on the chemical correlation with virescenol B and virescenoside B. Virescenoside C seems to be the third example of an altroside found in nature.
glycosides, virescenoside C, Oospora virescens
NCBI PubMed ID: 5533846Publication DOI: 10.1111/j.1432-1033.1970.tb01015.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Istituto di Chimica Organica, Facolta di Farmacia dell’Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France
Methods: 13C NMR, IR, MS, UV, extraction, optical rotation measurement, acetylation, elemental analysis, reduction, CC, cell growth, evaporation
- 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: 17644
|
b-D-Altp-(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
Trivial name: virescenoside B
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5654
Gomes NGM, Buttachon S, Kijjoa A "Meroterpenoids from marine microorganisms: potential scaffolds for new chemotherapy leads" -
Book: Handbook of Anticancer Drugs from Marine Origin (2015) Chapter 16, 323-366
Meroterpenoids, including several biologically active metabolites from marine microorganisms mainly fungi and actinomycete bacteria, represent promising structural scaffolds with not only diverse biological activities such as antimicrotubule, cytotoxic and antiproliferative but also different mechanisms of action. In this chapter, an overview on structural diversity and anticancer activity of mixed biogenesis terpenoid derivatives (meroterpenoids) from marine microorganisms is presented with highlight on individual examples of the most promising candidates in cancer chemotherapy and prevention
cytotoxicity, Marine bacteria, marine microorganisms, anticancer activities, marine-derived fungi, marine-derived actinomycetes, meroterpenoids, terpenyl alkaloids, terpenyl glycosides, terpenyl polyketides
Publication DOI: 10.1007/978-3-319-07145-9_16Publisher: Cham: Springer
Correspondence: ankijjoa@icbas.up.pt
Editors: Kim S-K
Institutions: ICBAS—Instituto de Ciências Biomédicas Abel Salazar and Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Porto, Portugal
- 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: 6932
Afiyatullov SS, Kuznetsova TA, Isakov VV, Pivkin MV, Prokof'eva NG, Elyakov GB "New diterpenic altrosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 63 (2000) 848-850
Two new diterpenic glycosides, virescenosides M (1) and N (2), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of MS and NMR data as β-D-altropyranosido-19-7-oxo-isopimara-8,15-diene-2α,3β-diol (1) and β-D-altropyranosido-19-isopimara-7,15-diene-2α,3β,6β-triol (2). Three other altrosides (3−5), identified as virescenosides A, B, and C from the terrestrial strain Acremonium luzulae, were also isolated. The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np9904004Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: piboc@stl.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, EI-MS, acid hydrolysis, biological assays, HPLC, UV, CD, HR-MALDI-MS
- Article ID: 8342
Ebel R "Terpenes from marine-derived fungi" -
Marine Drugs 8(8) (2010) 2340-2368
Terpenes from marine-derived fungi show a pronounced degree of structural diversity, and due to their interesting biological and pharmacological properties many of them have aroused interest from synthetic chemists and the pharmaceutical industry alike. The aim of this paper is to give an overview of the structural diversity of terpenes from marine-derived fungi, highlighting individual examples of chemical structures and placing them in a context of other terpenes of fungal origin. Wherever possible, information regarding the biological activity is presented
biological activity, marine-derived fungi, natural products chemistry, terpenes
NCBI PubMed ID: 20948911Publication DOI: 10.3390/md8082340Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: r.ebel@abdn.ac.uk
Institutions: Marine Biodiscovery Centre, University of Aberdeen, Aberdeen, UK
- Article ID: 8346
Cagnoli-Bellavita N, Ceccherelli P, Mariani R, Polonsky J, Baskevitch Z "Structure du virescenoside C, nouveau métabolite de Oospora virescens (Link) Wallr." -
European Journal of Biochemistry 15(2) (1970) 356-359
Chemical investigation of the glycosidic constituents of Oospora virescens (Link) Wallr. resulted in the isolation of several glycosides. We have shown recently [l] that two of them, named virescenoside A (I) and B (II) are β-D-altropyranosides of virescenol A and B; these diterpenic aglycones have been found to have the structure of isopimaradien-2α,3β-l9-triol (IV) and isopimaradien-3β,19-diol (V), respectively [2]. In this paper we describe the isolation and structure of virescenoside C, a new metabolite of Oospora virescens. The results obtained show that virescenoside C (IIIa), C26H40O7, m. p. 160-162°, [α]D - 71,4°, is a β-D-altropyranoside of virescenol C, which is found to have the structure of 3-keto-19-hydroxy-isopimaradiene (VIa). These results are based on physical evidence (infra-red, nuclear magnetic resonance and mass spectra) and particularly on the chemical correlation with virescenol B and virescenoside B. Virescenoside C seems to be the third example of an altroside found in nature.
glycosides, virescenoside C, Oospora virescens
NCBI PubMed ID: 5533846Publication DOI: 10.1111/j.1432-1033.1970.tb01015.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Istituto di Chimica Organica, Facolta di Farmacia dell’Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France
Methods: 13C NMR, IR, MS, UV, extraction, optical rotation measurement, acetylation, elemental analysis, reduction, CC, cell growth, evaporation
- 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
Expand this compound
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12. Compound ID: 17645
|
b-D-Altp-(1-19)-Subst
Subst = 3-oxo-isopimara-7(8),15-diene-19-ol = SMILES C[C@@]1(CCC2[C@@](C)(CCC([C@@]3({19}CO)C)=O)C3CC=C2C1)C=C |
Show graphically |
Structure type: monomer
C26H40O7
Trivial name: virescenoside C
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5654
Gomes NGM, Buttachon S, Kijjoa A "Meroterpenoids from marine microorganisms: potential scaffolds for new chemotherapy leads" -
Book: Handbook of Anticancer Drugs from Marine Origin (2015) Chapter 16, 323-366
Meroterpenoids, including several biologically active metabolites from marine microorganisms mainly fungi and actinomycete bacteria, represent promising structural scaffolds with not only diverse biological activities such as antimicrotubule, cytotoxic and antiproliferative but also different mechanisms of action. In this chapter, an overview on structural diversity and anticancer activity of mixed biogenesis terpenoid derivatives (meroterpenoids) from marine microorganisms is presented with highlight on individual examples of the most promising candidates in cancer chemotherapy and prevention
cytotoxicity, Marine bacteria, marine microorganisms, anticancer activities, marine-derived fungi, marine-derived actinomycetes, meroterpenoids, terpenyl alkaloids, terpenyl glycosides, terpenyl polyketides
Publication DOI: 10.1007/978-3-319-07145-9_16Publisher: Cham: Springer
Correspondence: ankijjoa@icbas.up.pt
Editors: Kim S-K
Institutions: ICBAS—Instituto de Ciências Biomédicas Abel Salazar and Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Porto, Portugal
- 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: 6932
Afiyatullov SS, Kuznetsova TA, Isakov VV, Pivkin MV, Prokof'eva NG, Elyakov GB "New diterpenic altrosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 63 (2000) 848-850
Two new diterpenic glycosides, virescenosides M (1) and N (2), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined on the basis of MS and NMR data as β-D-altropyranosido-19-7-oxo-isopimara-8,15-diene-2α,3β-diol (1) and β-D-altropyranosido-19-isopimara-7,15-diene-2α,3β,6β-triol (2). Three other altrosides (3−5), identified as virescenosides A, B, and C from the terrestrial strain Acremonium luzulae, were also isolated. The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np9904004Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: piboc@stl.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, EI-MS, acid hydrolysis, biological assays, HPLC, UV, CD, HR-MALDI-MS
- Article ID: 8342
Ebel R "Terpenes from marine-derived fungi" -
Marine Drugs 8(8) (2010) 2340-2368
Terpenes from marine-derived fungi show a pronounced degree of structural diversity, and due to their interesting biological and pharmacological properties many of them have aroused interest from synthetic chemists and the pharmaceutical industry alike. The aim of this paper is to give an overview of the structural diversity of terpenes from marine-derived fungi, highlighting individual examples of chemical structures and placing them in a context of other terpenes of fungal origin. Wherever possible, information regarding the biological activity is presented
biological activity, marine-derived fungi, natural products chemistry, terpenes
NCBI PubMed ID: 20948911Publication DOI: 10.3390/md8082340Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: r.ebel@abdn.ac.uk
Institutions: Marine Biodiscovery Centre, University of Aberdeen, Aberdeen, UK
- Article ID: 8346
Cagnoli-Bellavita N, Ceccherelli P, Mariani R, Polonsky J, Baskevitch Z "Structure du virescenoside C, nouveau métabolite de Oospora virescens (Link) Wallr." -
European Journal of Biochemistry 15(2) (1970) 356-359
Chemical investigation of the glycosidic constituents of Oospora virescens (Link) Wallr. resulted in the isolation of several glycosides. We have shown recently [l] that two of them, named virescenoside A (I) and B (II) are β-D-altropyranosides of virescenol A and B; these diterpenic aglycones have been found to have the structure of isopimaradien-2α,3β-l9-triol (IV) and isopimaradien-3β,19-diol (V), respectively [2]. In this paper we describe the isolation and structure of virescenoside C, a new metabolite of Oospora virescens. The results obtained show that virescenoside C (IIIa), C26H40O7, m. p. 160-162°, [α]D - 71,4°, is a β-D-altropyranoside of virescenol C, which is found to have the structure of 3-keto-19-hydroxy-isopimaradiene (VIa). These results are based on physical evidence (infra-red, nuclear magnetic resonance and mass spectra) and particularly on the chemical correlation with virescenol B and virescenoside B. Virescenoside C seems to be the third example of an altroside found in nature.
glycosides, virescenoside C, Oospora virescens
NCBI PubMed ID: 5533846Publication DOI: 10.1111/j.1432-1033.1970.tb01015.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Istituto di Chimica Organica, Facolta di Farmacia dell’Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France
Methods: 13C NMR, IR, MS, UV, extraction, optical rotation measurement, acetylation, elemental analysis, reduction, CC, cell growth, evaporation
- 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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13. Compound ID: 17849
|
a-D-Glcp-(1-6)-b-D-Altp-(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: oligomer
; 645 [M+H]+
C32H52O13
Trivial name: virescenoside R
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7018
Afiyatullov SS, Kalinovsky AI, Kuznetsova TA, Pivkin MV, Prokof'eva NG, Dmitrenok PS, Elyakov GB "New glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 67(6) (2004) 1047-1051
Four new diterpene glycosides, virescenosides R (1), S (2), T (3), and U (4), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of HRFABMS, 1D and 2D NMR (H-1, C-13, DEPT, COSY-45, COSY-RCT, HSQC, HMBC, and NOESY spectra), and the results of acidic hydrolysis as 19-O-{β-D-glucopyranosyl(1→6)-β-D-altropyranosyl}-isopimara-7,15-diene-2α,3β-diol (1), 19-O-β-D-altropyranosyl-3-oxo-isopimara-8(14),15-diene-7α-ol (2), 19-O-β-D-altropyranosyl-3,7-dioxo-isopimara-8,15-diene (3), and 19-O-β-D-altropyranosyl-3,7-dioxo-isopimara-8(14),15-diene (4). The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np0305324Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: kuzta@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, GC-MS, sugar analysis, acid hydrolysis, GLC, GC, HPLC, UV, extraction, CD
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14. Compound ID: 17850
|
b-D-Altp-(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: oligomer
Trivial name: virescenoside A
The structure is contained in the following publication(s):
- Article ID: 7018
Afiyatullov SS, Kalinovsky AI, Kuznetsova TA, Pivkin MV, Prokof'eva NG, Dmitrenok PS, Elyakov GB "New glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 67(6) (2004) 1047-1051
Four new diterpene glycosides, virescenosides R (1), S (2), T (3), and U (4), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of HRFABMS, 1D and 2D NMR (H-1, C-13, DEPT, COSY-45, COSY-RCT, HSQC, HMBC, and NOESY spectra), and the results of acidic hydrolysis as 19-O-{β-D-glucopyranosyl(1→6)-β-D-altropyranosyl}-isopimara-7,15-diene-2α,3β-diol (1), 19-O-β-D-altropyranosyl-3-oxo-isopimara-8(14),15-diene-7α-ol (2), 19-O-β-D-altropyranosyl-3,7-dioxo-isopimara-8,15-diene (3), and 19-O-β-D-altropyranosyl-3,7-dioxo-isopimara-8(14),15-diene (4). The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np0305324Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: kuzta@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, GC-MS, sugar analysis, acid hydrolysis, GLC, GC, HPLC, UV, extraction, CD
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15. Compound ID: 17851
|
b-D-Altp-(1-19)-Subst
Subst = 3-oxo-isopimara-8(14),15-diene-7α,19-diol = SMILES C[C@]1(C=C)CCC2[C@@](CCC([C@]3(C){19}CO)=O)(C3C[C@@H](O)C2=C1)C |
Show graphically |
Structure type: monomer
; 503.2707 [M+Na]+
C26H40O8
Trivial name: virescenoside S
The structure is contained in the following publication(s):
- Article ID: 7018
Afiyatullov SS, Kalinovsky AI, Kuznetsova TA, Pivkin MV, Prokof'eva NG, Dmitrenok PS, Elyakov GB "New glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber" -
Journal of Natural Products 67(6) (2004) 1047-1051
Four new diterpene glycosides, virescenosides R (1), S (2), T (3), and U (4), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of HRFABMS, 1D and 2D NMR (H-1, C-13, DEPT, COSY-45, COSY-RCT, HSQC, HMBC, and NOESY spectra), and the results of acidic hydrolysis as 19-O-{β-D-glucopyranosyl(1→6)-β-D-altropyranosyl}-isopimara-7,15-diene-2α,3β-diol (1), 19-O-β-D-altropyranosyl-3-oxo-isopimara-8(14),15-diene-7α-ol (2), 19-O-β-D-altropyranosyl-3,7-dioxo-isopimara-8,15-diene (3), and 19-O-β-D-altropyranosyl-3,7-dioxo-isopimara-8(14),15-diene (4). The cytotoxic activity of the virescenosides was examined.
Publication DOI: 10.1021/np0305324Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: kuzta@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 22, Russian Federation
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, GC-MS, sugar analysis, acid hydrolysis, GLC, GC, HPLC, UV, extraction, CD
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Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
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