Show legend Show as text

Structure type: cyclic polymer repeating unit ; n=1, 1199.5584 [M]+
C₅₄N₁₂O₁₉H₇₉
Trivial name: occidiofungin A
Compound class: glycopeptide
Contained glycoepitopes: IEDB_114701,IEDB_136017,IEDB_150900,IEDB_167188,IEDB_174332

• Article ID: 5360
  Lu SE, Novak J, Austin FW, Gu G, Ellis D, Kirk M, Wilson-Stanford S, Tonelli M, Smith L "Occidiofungin, a unique antifungal glycopeptide produced by a strain of Burkholderia contaminans" - Biochemistry 48(35) (2009) 8312-8321
  

  Bacterial strain Burkholderia contaminans MS14 was isolated from soil that suppressed brown patch disease of lawn grass. An antifungal compound was purified from the liquid culture of this bacterium. In this study, complete covalent structures of two purified closely related antifungal compounds were determined by the experiments of TOCSY, NOESY, ROESY, 13C HSQC 2D NMR, and ESI-MS and GC. The analysis of monoisotopic masses of the purified preparation indicated the presence of two related compounds with masses determined to be 1199.543 and 1215.518 Da; the difference corresponds to the mass of an oxygen atom. GC analysis identified a xylose sugar attached to the antifungal compound. NMR experiments revealed that the compound is cyclic and composed of eight amino acids, two of which are beta-hydroxy derivatives of Tyr and Asn, and one being a novel amino acid. The novel amino acid serves as the scaffold for the attachment of the xylose and a short acyl chain. The spectrum and concentration of antifungal activity were determined using a microtiter plate assay. The antifungal compound demonstrated potent antifungal activities against a broad panel of fungal plant and animal pathogens, as well as two Pythium spp. Microscopic observations showed that the antifungal compound disrupts normal membrane morphology. The cells fill with large inclusion bodies and the membrane becomes irregularly shaped and swollen following the exposure to subinhibitory concentrations of the antifungal compound. Our data support the identification of a novel fungicide and the compound has been named occidiofungin, meaning fungal killer.

  NCBI PubMed ID: 19673482
  Publication DOI: 10.1021/bi900814c
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Correspondence: Smith L
  Institutions: Mississippi State University, Department of Entomology and Department of Plant Pathology, Mississippi, USA, University of Alabama at Birmingham, Department of Microbiology, Birmingham, USA, Mississippi State University, College of Veterinary Medicine, Department of Pathobiology and Population Medicine, Mississippi, USA, Mississippi State University, Department of Biological Sciences, Mississippi, USA, University of Alabama at Birmingham, Comprehensive Cancer Center Mass Spectrometry Shared Facility, Birmingham, USA, University of Wisconsin-Madison, National Magnetic Resonance Facility at Madison (NMRFAM), Madison, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, ESI-MS, acid hydrolysis, GLC, MS/MS, biological assays, cell growth, antifungal activity assay
  
   
  
  Burkholderia contaminans MS14
  CSDB ID 45906 (all data & tools)

Show legend Show as text

Structure type: cyclic polymer repeating unit ; n=1, 1215.55331 [M]+
C₅₄N₁₂O₂₀H₇₉
Trivial name: occidiofungin B
Compound class: glycopeptide
Contained glycoepitopes: IEDB_114701,IEDB_136017,IEDB_150900,IEDB_167188,IEDB_174332

• Article ID: 5360
  Lu SE, Novak J, Austin FW, Gu G, Ellis D, Kirk M, Wilson-Stanford S, Tonelli M, Smith L "Occidiofungin, a unique antifungal glycopeptide produced by a strain of Burkholderia contaminans" - Biochemistry 48(35) (2009) 8312-8321
  

  Bacterial strain Burkholderia contaminans MS14 was isolated from soil that suppressed brown patch disease of lawn grass. An antifungal compound was purified from the liquid culture of this bacterium. In this study, complete covalent structures of two purified closely related antifungal compounds were determined by the experiments of TOCSY, NOESY, ROESY, 13C HSQC 2D NMR, and ESI-MS and GC. The analysis of monoisotopic masses of the purified preparation indicated the presence of two related compounds with masses determined to be 1199.543 and 1215.518 Da; the difference corresponds to the mass of an oxygen atom. GC analysis identified a xylose sugar attached to the antifungal compound. NMR experiments revealed that the compound is cyclic and composed of eight amino acids, two of which are beta-hydroxy derivatives of Tyr and Asn, and one being a novel amino acid. The novel amino acid serves as the scaffold for the attachment of the xylose and a short acyl chain. The spectrum and concentration of antifungal activity were determined using a microtiter plate assay. The antifungal compound demonstrated potent antifungal activities against a broad panel of fungal plant and animal pathogens, as well as two Pythium spp. Microscopic observations showed that the antifungal compound disrupts normal membrane morphology. The cells fill with large inclusion bodies and the membrane becomes irregularly shaped and swollen following the exposure to subinhibitory concentrations of the antifungal compound. Our data support the identification of a novel fungicide and the compound has been named occidiofungin, meaning fungal killer.

  NCBI PubMed ID: 19673482
  Publication DOI: 10.1021/bi900814c
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Correspondence: Smith L
  Institutions: Mississippi State University, Department of Entomology and Department of Plant Pathology, Mississippi, USA, University of Alabama at Birmingham, Department of Microbiology, Birmingham, USA, Mississippi State University, College of Veterinary Medicine, Department of Pathobiology and Population Medicine, Mississippi, USA, Mississippi State University, Department of Biological Sciences, Mississippi, USA, University of Alabama at Birmingham, Comprehensive Cancer Center Mass Spectrometry Shared Facility, Birmingham, USA, University of Wisconsin-Madison, National Magnetic Resonance Facility at Madison (NMRFAM), Madison, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, ESI-MS, acid hydrolysis, GLC, MS/MS, biological assays, cell growth, antifungal activity assay
  
   
  
  Burkholderia contaminans MS14
  CSDB ID 45907 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside

• Article ID: 7408
  Cheng MJ, Wu MD, Su YS, Yuan GF, Chen YL, Chen IS "Secondary metabolites from the fungus Monascus kaoliang and inhibition of nitric oxide production in lipopolysaccharide-activated macrophages" - Phytochemistry Letters 5(2) (2012) 262-266
  

  Phytochemical analysis of the n-BuOH-soluble fraction of the 95% EtOH extract of the red yeast rice fermented with the yellow mutant of the fungus Monascus kaoliang BCRC 31506 led to the isolation of one new azaphilone metabolite, designated as monascuskaolin (1), along with 9 known compounds (2-10). Monascuskaolin (1) contains an isochroman-6-one azaphilone skeleton connected with one γ-lactone ring, one propan-2-yl acetate moiety, and one decanoyl side chain. Their structures were elucidated by detailed spectroscopic analyses, including HRESIMS and 1D and NMR-2D data (COSY, HSQC, HMBC, and NOESY). The relative configuration of 1 was confirmed by NOESY experiment. Other known compounds were identified by comparison of their spectral data with the literature data of authentic samples. Inhibitory effects of some isolates on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages were evaluated. Compounds 1-4 showed inhibition on NO production in LPS-stimulated RAW 264.7 macrophages in vitro, showing MIC values of 7.62, 18.78, 26.72, and 32.80 μg/mL, respectively.

  metabolites, red yeast rice, azaphilone derivatives, Monascus kaoliang, NO production

  Publication DOI: 10.1016/j.phytol.2012.01.008
  Journal NLM ID: 101513432
  Publisher: Amsterdam: Elsevier
  Correspondence: Cheng MJ
  Institutions: Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, Taiwan, Graduate Institute of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung, Taiwan, School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ESI-MS, UV, extraction, CC, determination of NO production, cell viability assay, DEPT
  
   
  
  Monascus kaoliang BCRC 31506
  CSDB ID 43878 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7656
  Koh A, Todd K, Sherbourne E, Gross RA "Fundamental characterization of the micellar self-assembly of sophorolipid esters" - Langmuir: the ACS Journal of Surfaces and Colloids 33(23) (2017) 5760-5768
  

  Surfactants are ubiquitous constituents of commercial and biological systems that function based on complex structure-dependent interactions. Sophorolipid (SL) n-alkyl esters (SL-esters) comprise a group of modified naturally derived glycolipids from Candida bombicola. Herein, micellar self-assembly behavior as a function of SL-ester chain length was studied. Surface tensions as low as 31.2 mN/m and critical micelle concentrations (CMCs) as low as 1.1 μM were attained for diacetylated SL-decyl ester (dASL-DE) and SL-octyl ester, respectively. For deacetylated SL-esters, CMC values reach a lower limit at SL-ester chains above n-butyl (SL-BE, 1-3 μM). This behavior of SL-esters with increasing hydrophobic tail length is unlike other known surfactants. Diffusion-ordered spectroscopy (DOSY) and T1 relaxation NMR experiments indicate this behavior is due to a change in intramolecular interactions, which impedes the self-assembly of SL-esters with chain lengths above SL-BE. This hypothesis is supported by micellar thermodynamics where a disruption in trends occurs at n-alkyl ester chain lengths above those of SL-BE and SL-hexyl ester (SL-HE). Diacetylated (dA) SL-esters exhibit an even more unusual trend in that CMC increases from 1.75 to 815 μM for SL-ester chain lengths of dASL-BE and dASL-DE, respectively. Foaming studies, performed to reveal the macroscopic implications of SL-ester micellar behavior, show that the observed instability in foams formed using SL-esters are due to coalescence, which highlights the importance of understanding intermicellar interactions. This work reveals that SL-esters are an important new family of green high-performing surfactants with unique structure-property relationships that can be tuned to optimize micellar characteristics.

  NCBI PubMed ID: 28510440
  Publication DOI: 10.1021/acs.langmuir.7b00480
  Journal NLM ID: 9882736
  Publisher: Washington, DC: American Chemical Society
  Correspondence: grossr@rpi.edu
  Institutions: Center for Biotechnology and Interdisciplinary Studies, Department of Chemical & Biological Engineering, Rensselaer Polytechnic Institute (RPI), Biotechnology Building, Troy, USA, Center for Biotechnology and Interdisciplinary Studies, Department of Biology, Rensselaer Polytechnic Institute (RPI), Biotechnology Building, Troy, USA, Center for Biotechnology and Interdisciplinary Studies, Department of Chemistry, Rensselaer Polytechnic Institute (RPI), Biotechnology Building, Troy, USA
  Methods: 13C NMR, 1H NMR, LS-MS
  
   
  
  Candida bombicola
  CSDB ID 43039 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 475.64 [M+Na]+
C₁₈H₃₂N₂O₁₁
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531

• Article ID: 8213
  Gyore J, Parameswar AR, Hebbard CF, Oh Y, Bi E, Demchenko AV, Price NP, Orlean P "2-Acylamido analogues of N-acetylglucosamine prime formation of chitin oligosaccharides by yeast chitin synthase 2" - Journal of Biological Chemistry 289(18) (2014) 12835-12841
  

  Chitin, a homopolymer of β1,4-linked N-acetylglucosamine (GlcNAc) residues, is a key component of the cell walls of fungi and the exoskeletons of arthropods. Chitin synthases transfer GlcNAc from UDP-GlcNAc to preexisting chitin chains in reactions that are typically stimulated by free GlcNAc. The effect of GlcNAc was probed by using a yeast strain expressing a single chitin synthase, Chs2, by examining formation of chitin oligosaccharides (COs) and insoluble chitin, and by replacing GlcNAc with 2-acylamido analogues of GlcNAc. Synthesis of COs was strongly dependent on inclusion of GlcNAc in chitin synthase incubations, and N,N'-diacetylchitobiose (GlcNAc2) was the major reaction product. Formation of both COs and insoluble chitin was also stimulated by GlcNAc2 and by N-propanoyl-, N-butanoyl-, and N-glycolylglucosamine. MALDI analyses of the COs made in the presence of 2-acylamido analogues of GlcNAc showed they that contained a single GlcNAc analogue and one or more additional GlcNAc residues. These results indicate that Chs2 can use certain 2-acylamido analogues of GlcNAc, and likely free GlcNAc and GlcNAc2 as well, as GlcNAc acceptors in a UDP-GlcNAc-dependent glycosyltransfer reaction. Further, formation of modified disaccharides indicates that CSs can transfer single GlcNAc residues.

  polysaccharide, glycosyltransferases, carbohydrate biosynthesis, chitin, yeast physiology

  NCBI PubMed ID: 24619411
  Publication DOI: 10.1074/jbc.M114.550749
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: Orlean P
  Institutions: Department of Microbiology, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA, Departments of Chemistry and Biochemistry, University of Missouri, St. Louis, Missouri, USA, Department of Cell and Developmental Biology, University of Pennsylvania Perelman School of Medicine, Philadelphia, Pennsylvania, USA, Renewable Product Technology, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, Peoria, Illinois, USA
  Methods: TLC, MALDI-TOF
  
   
  
  Saccharomyces cerevisiae YO1535 cts1Δ
  CSDB ID 47542 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 678.76 [M+Na]+
C₂₆H₄₅N₃O₁₆
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_153212,SB_74,SB_85

• Article ID: 8213
  Gyore J, Parameswar AR, Hebbard CF, Oh Y, Bi E, Demchenko AV, Price NP, Orlean P "2-Acylamido analogues of N-acetylglucosamine prime formation of chitin oligosaccharides by yeast chitin synthase 2" - Journal of Biological Chemistry 289(18) (2014) 12835-12841
  

  Chitin, a homopolymer of β1,4-linked N-acetylglucosamine (GlcNAc) residues, is a key component of the cell walls of fungi and the exoskeletons of arthropods. Chitin synthases transfer GlcNAc from UDP-GlcNAc to preexisting chitin chains in reactions that are typically stimulated by free GlcNAc. The effect of GlcNAc was probed by using a yeast strain expressing a single chitin synthase, Chs2, by examining formation of chitin oligosaccharides (COs) and insoluble chitin, and by replacing GlcNAc with 2-acylamido analogues of GlcNAc. Synthesis of COs was strongly dependent on inclusion of GlcNAc in chitin synthase incubations, and N,N'-diacetylchitobiose (GlcNAc2) was the major reaction product. Formation of both COs and insoluble chitin was also stimulated by GlcNAc2 and by N-propanoyl-, N-butanoyl-, and N-glycolylglucosamine. MALDI analyses of the COs made in the presence of 2-acylamido analogues of GlcNAc showed they that contained a single GlcNAc analogue and one or more additional GlcNAc residues. These results indicate that Chs2 can use certain 2-acylamido analogues of GlcNAc, and likely free GlcNAc and GlcNAc2 as well, as GlcNAc acceptors in a UDP-GlcNAc-dependent glycosyltransfer reaction. Further, formation of modified disaccharides indicates that CSs can transfer single GlcNAc residues.

  polysaccharide, glycosyltransferases, carbohydrate biosynthesis, chitin, yeast physiology

  NCBI PubMed ID: 24619411
  Publication DOI: 10.1074/jbc.M114.550749
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: Orlean P
  Institutions: Department of Microbiology, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA, Departments of Chemistry and Biochemistry, University of Missouri, St. Louis, Missouri, USA, Department of Cell and Developmental Biology, University of Pennsylvania Perelman School of Medicine, Philadelphia, Pennsylvania, USA, Renewable Product Technology, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, Peoria, Illinois, USA
  Methods: TLC, MALDI-TOF
  
   
  
  Saccharomyces cerevisiae YO1535 cts1Δ
  CSDB ID 47543 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 592, 676
Trivial name: mannosylerythritol
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

• Article ID: 8526
  Alimadadi N, Soudi MR, Talebpour Z "Efficient production of tri-acetylated mono-acylated mannosylerythritol lipids by Sporisorium sp. aff. sorghi SAM20" - Journal of Applied Microbiology 124(2) (2018) 457-468
  

  AIMS: The aim of this study was to isolate a novel yeast strain, evaluate biosurfactant production by the strain and characterize the major product. METHODS AND RESULTS: The strain SAM20, isolated from grass, identified as Sporisorium sp. aff. sorghi based on phylogenetic analyses. The strain produced approximately 32 g l-1 glycolipid biosurfactants from 40 g l-1 soybean oil after 7 days at 28°C. The glycolipids showed a unique pattern of mannosylerythritol lipids (MELs) on thin layer chromatography plate compared to those hitherto reported. Structural characterization of the major product, called GL-A, revealed that it was mainly tri-acetylated mono-acylated MELs (MEL-A2) with C14:0, C16:0, C12:0 or C14:1 as the hydrophobic chain. The critical micelle concentration (CMC), the surface tension at CMC and hydrophilic-lipophilic balance value for GL-A were estimated to be 20 mg l-1 , 30·0 mN m-1 and 8·7, respectively. CONCLUSIONS: A MEL-A2 with novel composition and surface activities was efficiently produced from a novel MEL producer. This is the first report on production of MEL-A2 as the major product and from soybean oil. The biosurfactant has potential application as a wetting agent and oil-in-water emulsifier. SIGNIFICANCE AND IMPACT OF THE STUDY: Discovery of novel structures and novel strains is valuable for further commercial development and application of MELs. Sporisorium sp. aff. sorghi SAM20 can be considered as a potential candidate for commercial production of biosurfactants.

  glycolipid, biosurfactant, mannosylerythritol lipid, surface activity, Sporisorium sp. aff. sorghi, hydrophilic-lipophilic balance

  NCBI PubMed ID: 29154479
  Publication DOI: 10.1111/jam.13642
  Journal NLM ID: 9706280
  Publisher: Oxford: Blackwell Publishing for the Society for Applied Bacteriology
  Correspondence: Soudi MR
  Institutions: Department of Microbiology, Faculty of Biological Sciences, Alzahra University, Tehran, Iran, Department of Chemistry, Faculty of Physics & Chemistry, Alzahra University, Tehran, Iran
  Methods: 13C NMR, 1H NMR, PCR, GC-MS, TLC, ESI-MS, extraction, LC-MS, CC, HMBC, DEPT, COSY, determination of surface tension, HSQC
  
   
  
  Sporisorium sorghi SAM20, Dirkmeia churashimaensis OK96
  CSDB ID 48597 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8603
  Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" - Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
  

  Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.

  enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering

  Publication DOI: 10.1016/B978-0-12-813167-1.00014-1
  Publisher: N.J.: Academic Press and AOCS Press
  Editors: Bornscheuer UT
  Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
  
   
  
  Starmerella bombicola
  CSDB ID 48834 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61

• Article ID: 8603
  Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" - Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
  

  Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.

  enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering

  Publication DOI: 10.1016/B978-0-12-813167-1.00014-1
  Publisher: N.J.: Academic Press and AOCS Press
  Editors: Bornscheuer UT
  Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
  
   
  
  Starmerella bombicola
  CSDB ID 48846 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8603
  Delbeke EIP, Van Geem KM, Stevens CV, Van Bogaert INA "Sophorolipid modification: the power of yeasts and enzymes" - Book: Lipid modification by enzymes and engineered microbes (2018) Vol. 1, Chapter 14, 315-341
  

  Sophorolipids are biosurfactants or biological detergents composed of a hydroxylated fatty acid and the glucose disaccharide sophorose. These commercially relevant molecules are produced by the yeast Starmerella bombicola and offer a green and renewable alternative for traditional surfactants.To further broaden up the application potential of sophorolipids, introduction of structural variation is essential as this influences their physicochemical and biological properties. However, creating molecular variants is not as straightforward as for petrochemically derived surfactants. This is, on the one hand, a consequence of the biological origin and restricting biochemistry behind it, and is, on the other hand, caused by the complexity of chemical processes regarding the necessity of protection and deprotection of the glucose units.In this chapter, several strategies to overcome these limitations will be discussed, such as the use of special substrates during yeast cultivation, design of engineered strains, and enzymatic modification.

  enzymatic modification, yeast, sophorolipid, Starmerella bombicola, lipase, Novozym 435, strain engineering

  Publication DOI: 10.1016/B978-0-12-813167-1.00014-1
  Publisher: N.J.: Academic Press and AOCS Press
  Editors: Bornscheuer UT
  Institutions: SynBioC, Ghent University, Ghent, Belgium, LCT, Ghent University, Ghent, Belgium, Centre for Synthetic Biology, Ghent University, Ghent, Belgium
  
   
  
  Starmerella bombicola
  CSDB ID 48847 (all data & tools)

Show legend Show as text

Structure type: monomer ; 259.1 [M+Na]+
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8734
  Guo J, Ran H, Zeng J, Liu D, Xin Z "Tafuketide, a phylogeny-guided discovery of a new polyketide from Talaromyces funiculosus Salicorn 58" - Applied Microbiology and Biotechnology 100(12) (2016) 5323-5338
  

  A phylogeny-guided approach was applied to screen endophytic fungi containing type I polyketide synthase (PKS I) biosynthetic gene sequences and aimed to correlate genotype to chemotype for the discovery of novel bioactive polyketides. Salicorn 58, which was identified as Talaromyces funiculosus based on its internal transcribed spacer (ITS) and ribosomal large-subunit (LSU) DNA sequences, showed significant target bands. A chemical investigation of the culture of Salicorn 58 was allowed for the isolation of a new polyketide, Talafun (1), and a new natural product, N-(2'-hydroxy-3'-octadecenoyl)-9-methyl-4,8-sphingadienin (2), together with six known compounds, including chrodrimanin A (3), chrodrimanin B (4), N-(4-hydroxy-2-methoxyphenyl) acetamide (5), butyl β-glucose (6), 3β,15β-dihydroxyl-(22E, 24R)-ergosta-5,8(14),22-trien-7-dione (7), and (3β,5a,8a,22E)-5,8-epidioxyergosta-6,22-dien-3-ol (8). Their chemical structures were elucidated by extensive spectroscopic analysis and electro circular dichroism (ECD) spectrum calculations. Antioxidant experiments revealed that compound 5 showed strong ABTS(+) radical scavenging activity with an IC50 value of 11.43±1.61 μM and potent ferric reducing activity (FRAP assay) with FRAP value of 187.52±2.97. Antimicrobial assays revealed that compounds 1 and 4 showed high levels of selectivity toward Escherichia coli with MIC values of 18±0.40 and 43±0.52 μM, respectively. Compounds 2 and 3 exhibited broad-spectrum antimicrobial activity against Staphylococcus aureus, Mycobacterium smegmatis, Micrococcus tetragenus, Mycobacterium phlei, and E. coli, respectively. The results from the current research highlight the advantage of phylogeny-guided pipeline for the screening of new polyketides from endophytic fungi containing PKS I genes.

  antimicrobial activity, Antioxidant activity, PKS I gene. a phylogeny-guided approach

  NCBI PubMed ID: 26810200
  Publication DOI: 10.1007/s00253-016-7311-4
  Journal NLM ID: 8406612
  Publisher: Springer
  Correspondence: Xin Z
  Institutions: School of Food Science, Henan Institute of Science and Technology, Xinxiang, China, Key laboratory of Food Processing and Quality Control, College of Food Science and Technology, nanjing agricultural University, Nanjing, China, Shenzhen Key Laboratory of Fermentation, Purification and Analysis, Shenzhen Polytechnic, Shenzhen, China
  Methods: 13C NMR, 1H NMR, IR, ESI-MS, UV, CD
  
   
  
  Talaromyces funiculosus
  CSDB ID 42842 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8741
  Hsiao Y, Cheng MJ, Changa HS, Wu MD, Hsieh SY, Liu TW, Lina CH, Yuan GF, Chen IS "Six new metabolites produced by Colletotrichum aotearoa 09F0161, an endophytic fungus isolated from Bredia oldhamii" - Natural Product Research 30(3) (2016) 251-258
  

  Six new compounds, colletobredins A-D (1-4) and colletomelleins A and B (5 and 6), along with 12 previously identified compounds, were isolated from the culture broth of Colletotrichum aotearoa BCRC 09F0161, a fungal endophyte residing in the leaves of an endemic Formosan plant Bredia oldhamii Hook. f. (Melastomataceae). The structures of the new compounds were established by spectroscopic methods, including UV, IR, HR-ESIMS and extensive 1D and 2D NMR techniques. The effects of some isolates on the inhibition of nitric oxide (NO) production in lipopolysaccharide-activated murine macrophage RAW264.7 cells were evaluated. All these compounds inhibited NO production in activated macrophages without any cytotoxicity at a concentration of 100 μM. Of these isolates, 1 showed weak NO inhibitory activity with IC50 value of 182.2 μM. To the best of our knowledge, this is the first report on isochroman glycoside metabolites (1-4) from the genus Colletotrichum.

  Colletotrichum aotearoa, leaves, isochroman

  Publication DOI: 10.1080/14286419.2015.1054285
  Journal NLM ID: 101167924
  Publisher: Milton Park, UK : Taylor & Francis Health Sciences
  Correspondence: Chen IS
  Institutions: Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, Taiwan, School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, College of Pharmacy, Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
  Methods: 13C NMR, 1H NMR, FTIR, UV, optical rotation measurement, HR-ESI-MS, HMBC, DEPT, COSY, NOESY, HSQC, TLCESI-MS
  
   
  
  Colletotrichum aotearoa 09F0161
  CSDB ID 42854 (all data & tools)

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Structure type: monomer
Trivial name: virescenoside Z17
Compound class: glycoside, diterpene glycoside

• 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: 31671910
  Publication DOI: 10.3390/md17110616
  Journal NLM ID: 101213729
  Publisher: 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
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49738 (all data & tools)

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Structure type: oligomer ; 1195 [M+Na]+
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192

• Article ID: 11189
  Fan GJ, He ZS, Wu HM, Xu JF "27-Ald-triterpenoid saponins from Adina rubella" - Chinese Journal of Chemistry = Zhongguo Hua Xue 15(5) (1997) 431-437
  

  Four new triterpenoid saponins were isolated from the roots of Adina rubella Hance. They were characterized as adinaic acid 3 β-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucurono-pyranoside-6-O-methyl ester]-28-O-β-D-glucopyranoside, adinaic acid 3 β-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyranoside-6-O-butyl ester]-28-O-β-D-glucopyranoside, adinaic acid 3 β-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyrnaosyl]-(28→1)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester, 27-hydroxyursolic acid 3 β-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyranoside-6-O-methyl ester]-28-O-β-D-glycopyranoside. Their structures were elucidated by spectral methods, especially with the aid of 2D NMR techniques. Their complete assignments of the H-1 and C-13 NMR signals were carried out.

  Rubiaceae, Adina rubella Hance, adinaic acid glycosides, 27-ald-terpenoids

  Publication DOI: 10.1002/cjoc.19970150508
  Journal NLM ID: 101312673
  Publisher: Beijing, China: Science Press
  Institutions: Shanghai Institute of Materia Mcdica, Chineae Academy of Scienas, Shanghai 200031, China
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, sugar analysis, chemical methods, extraction
  
   
  
  Adina rubella
  CSDB ID 60655 (all data & tools)

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Structure type: oligomer ; 719 [M+Na]+
C₃₃H₄₄₀₁₆
Trivial name: suspensaside B
Compound class: phenylethanoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 11691
  Ming DS, Yu DQ, Yu SS "Two new caffeyol glycosides from Forsythia suspensa" - Journal of Asian Natural Products Research 1(4) (1999) 327-335
  

  Two new caffeoyl glycosides of phenethyl alcohol, suspensaside A (1) and suspensaside B (2), were isolated from the fruits of Forsythia suspensa. Also obtained in this investigation were two known compounds forsythiaside (3) and suspensaside (4). The structures of compounds 1 and 2 were established by 1D and 2D NMR techniques and chemical methods.

  Forsythia suspensa, suspensaside A, suspensaside B, suspensaside, forsythiaside

  NCBI PubMed ID: 11523554
  Publication DOI: 10.1080/10286029908039882
  Journal NLM ID: 100888334
  Publisher: Harwood Academic Publishers; London: Informa Healthcare
  Correspondence: Yu DQ
  Institutions: Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, optical rotation measurement, HMBC, DEPT, COSY, sulfuric acid hydrolysis, HR-SI-MS
  
   
  
  Forsythia suspensa
  CSDB ID 62524 (all data & tools)