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Kulakovskaya T, Shashkov A, Kulakovskaya E, Golubev W, Zinin A, Tsvetkov Y, Grachev A, Nifantiev N
Extracellular Cellobiose Lipid from Yeast and Their Analogues: Structures and Fungicidal Activities
Journal of Oleo Science 58(3) (2009)
133-140
Cryptococcus humicola 9-6
(later renamed to: Vanrija humicola 9-6)
(Ancestor NCBI TaxID 5417,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 19202311Publication DOI: 10.5650/jos.58.133Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: alla
ibpm.pushchino.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142290, Pushchino, pr. Nauki, 5, Moscow Region, Russia
Basidiomycetous yeasts Cryptococcus humicola and Pseudozyma fusiformata secrete cellobiose lipids into the culture broth. In the case of Cr. humicola, 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2-hydroxyhexadecanoic acid was defined as major product and 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2,15-dihydrohexadecanoic acid was defined as minor product, while Ps. fusiformata secreted mainly 16-[6-O-acetyl-2'-O-(3-hydroxyhexanoyl)-beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid. These compounds exhibit similar fungicidal activities against different yeasts including pathogenic Cryptococcus and Candida species. The cells of Filobasidiella neoformans causing systemic cryptococcosis completely died after 30-min incubation with 0.02 mg mL(-1) of cellobiose lipids. The same effect on ascomycetous yeast, including pathogenic Candida species, is achieved at 0.1-0.3 mg mL(-1) of cellobiose lipids depending on the test culture used. Cellobiose lipid of Ps. fusiformata inhibits the growth of phytopathogenic fungi Sclerotinia sclerotiorum and Phomopsis helianthi more efficiently than cellobiose lipids from Cr. humicola. Fully O-deacylated analogue, namely 16-(beta-cellobiosyloxy)-2-hydroxyhexadecanoic acid, and totally synthetic compound, 16-(beta-cellobiosyloxy)-hexadecanoic acid, do not inhibit the growth of F. neoformans and Saccharomyces cerevisiae, while 16-(beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid inhibits the growth of both test cultures but at higher concentrations than cellobiose lipids of Cr. humicola and Ps. fusiformata. The amide of 16-(beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid possessed no fungicide activity. Thus, the structures of both the carbohydrate part and fatty acid aglycon moiety are important for the fungicidal activity of cellobiose lipids.
Candida albicans, biosurfactant, cellobiose lipid, fungicide, O-deacylated analogue, Cryptococcus humicola, Pseudozyma fusiformata, Filobasidiella neoformans
Structure type: oligomer
Location inside paper: p.134, fig.1, compound 1
Trivial name: 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical methods, fungicidal activity assay
Biological activity: fungicidal activity
Comments, role: minor product
Related record ID(s): 41964, 42161
NCBI Taxonomy refs (TaxIDs): 5417
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There is only one chemically distinct structure:
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Kulakovskaya T, Shashkov A, Kulakovskaya E, Golubev W, Zinin A, Tsvetkov Y, Grachev A, Nifantiev N
Extracellular Cellobiose Lipid from Yeast and Their Analogues: Structures and Fungicidal Activities
Journal of Oleo Science 58(3) (2009)
133-140
Pseudozyma fusiformata VKM Y-2821
(later renamed to: Kalmanozyma fusiformata VKM Y-2821)
(Ancestor NCBI TaxID 84755,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 19202311Publication DOI: 10.5650/jos.58.133Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: alla
ibpm.pushchino.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142290, Pushchino, pr. Nauki, 5, Moscow Region, Russia
Basidiomycetous yeasts Cryptococcus humicola and Pseudozyma fusiformata secrete cellobiose lipids into the culture broth. In the case of Cr. humicola, 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2-hydroxyhexadecanoic acid was defined as major product and 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2,15-dihydrohexadecanoic acid was defined as minor product, while Ps. fusiformata secreted mainly 16-[6-O-acetyl-2'-O-(3-hydroxyhexanoyl)-beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid. These compounds exhibit similar fungicidal activities against different yeasts including pathogenic Cryptococcus and Candida species. The cells of Filobasidiella neoformans causing systemic cryptococcosis completely died after 30-min incubation with 0.02 mg mL(-1) of cellobiose lipids. The same effect on ascomycetous yeast, including pathogenic Candida species, is achieved at 0.1-0.3 mg mL(-1) of cellobiose lipids depending on the test culture used. Cellobiose lipid of Ps. fusiformata inhibits the growth of phytopathogenic fungi Sclerotinia sclerotiorum and Phomopsis helianthi more efficiently than cellobiose lipids from Cr. humicola. Fully O-deacylated analogue, namely 16-(beta-cellobiosyloxy)-2-hydroxyhexadecanoic acid, and totally synthetic compound, 16-(beta-cellobiosyloxy)-hexadecanoic acid, do not inhibit the growth of F. neoformans and Saccharomyces cerevisiae, while 16-(beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid inhibits the growth of both test cultures but at higher concentrations than cellobiose lipids of Cr. humicola and Ps. fusiformata. The amide of 16-(beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid possessed no fungicide activity. Thus, the structures of both the carbohydrate part and fatty acid aglycon moiety are important for the fungicidal activity of cellobiose lipids.
Candida albicans, biosurfactant, cellobiose lipid, fungicide, O-deacylated analogue, Cryptococcus humicola, Pseudozyma fusiformata, Filobasidiella neoformans
Structure type: oligomer
Location inside paper: p.134, fig.1, compound 3
Trivial name: 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical methods, fungicidal activity assay
Biological activity: fungicidal activity
Comments, role: major product compound (3)
Related record ID(s): 41748, 42161
NCBI Taxonomy refs (TaxIDs): 84755
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There is only one chemically distinct structure:
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Kulakovskaya T, Shashkov A, Kulakovskaya E, Golubev W, Zinin A, Tsvetkov Y, Grachev A, Nifantiev N
Extracellular Cellobiose Lipid from Yeast and Their Analogues: Structures and Fungicidal Activities
Journal of Oleo Science 58(3) (2009)
133-140
|
b-D-Glcp2Ac3Ac4Ac-(1-4)-b-D-Glcp6Ac-(1-16)-Subst
Subst = 2,16-dihydroxyhexadecanoic acid = SMILES O{16}CCCCCCCCCCCCCC{2}C(O){1}C(O)=O |
Show graphically |
Cryptococcus humicola 9-6
(later renamed to: Vanrija humicola 9-6)
(Ancestor NCBI TaxID 5417,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 19202311Publication DOI: 10.5650/jos.58.133Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: alla
ibpm.pushchino.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142290, Pushchino, pr. Nauki, 5, Moscow Region, Russia
Basidiomycetous yeasts Cryptococcus humicola and Pseudozyma fusiformata secrete cellobiose lipids into the culture broth. In the case of Cr. humicola, 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2-hydroxyhexadecanoic acid was defined as major product and 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2,15-dihydrohexadecanoic acid was defined as minor product, while Ps. fusiformata secreted mainly 16-[6-O-acetyl-2'-O-(3-hydroxyhexanoyl)-beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid. These compounds exhibit similar fungicidal activities against different yeasts including pathogenic Cryptococcus and Candida species. The cells of Filobasidiella neoformans causing systemic cryptococcosis completely died after 30-min incubation with 0.02 mg mL(-1) of cellobiose lipids. The same effect on ascomycetous yeast, including pathogenic Candida species, is achieved at 0.1-0.3 mg mL(-1) of cellobiose lipids depending on the test culture used. Cellobiose lipid of Ps. fusiformata inhibits the growth of phytopathogenic fungi Sclerotinia sclerotiorum and Phomopsis helianthi more efficiently than cellobiose lipids from Cr. humicola. Fully O-deacylated analogue, namely 16-(beta-cellobiosyloxy)-2-hydroxyhexadecanoic acid, and totally synthetic compound, 16-(beta-cellobiosyloxy)-hexadecanoic acid, do not inhibit the growth of F. neoformans and Saccharomyces cerevisiae, while 16-(beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid inhibits the growth of both test cultures but at higher concentrations than cellobiose lipids of Cr. humicola and Ps. fusiformata. The amide of 16-(beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid possessed no fungicide activity. Thus, the structures of both the carbohydrate part and fatty acid aglycon moiety are important for the fungicidal activity of cellobiose lipids.
Candida albicans, biosurfactant, cellobiose lipid, fungicide, O-deacylated analogue, Cryptococcus humicola, Pseudozyma fusiformata, Filobasidiella neoformans
Structure type: oligomer
Location inside paper: p.134, fig.1, compound 2
Trivial name: 16-(tetra-O-acetyl-beta-cellobiosyloxy)-2,15-dihydroxyhexadecanoic acid
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical methods, fungicidal activity assay
Biological activity: fungicidal activity
Comments, role: major product compound (2) with aglycon = 2,16-dihydroxy-hexadecanoic acid
Related record ID(s): 41748, 41964
NCBI Taxonomy refs (TaxIDs): 5417
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There is only one chemically distinct structure:
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