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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 12732526
Publication DOI: 10.1128/aem.69.5.2595-2602.2003
Journal NLM ID: 7605801
Publisher: American Society for Microbiology
Correspondence: richard.belanger

plg.ulaval.ca
Institutions: Centre de Recherche en Horticulture, Université Laval, Québec, Canada, Pavillon Marchand, Université Laval, Québec, Canada, Département de Phytologie, Centre de Recherche sur la Function, la Structure et l’Ingénierie des Protéines, Université Laval, Québec, Canada, Département de Chimie, Université Laval, Québec, Canada, Département de Phytologie, Université Laval, Québec, Canada, Centre de Recherche sur la Function, la Structure et l’Ingénierie des Protéines, Département de Chimie, Université Laval, Québec, Canada

Insertional mutagenesis was applied for the first time to a fungal biocontrol agent, Pseudozyma flocculosa, in an attempt to obtain mutants with altered antagonistic properties. Transformants were obtained via DNA-mediated transformation. Molecular analyses of the transformants revealed that multiple copies of the plasmid were integrated in tandem at one to many chromosomal loci. The transformants were screened for their biocontrol properties using standard bioassays, and the 160 tested transformants were classified into four groups: group I mutants (22 transformants) showed a stronger antagonistic effect than the wild type (WT) while those of group II (107 transformants) had a comparable antagonistic effect; group III mutants (17 transformants) had a decreased antagonistic effect relative to WT and group IV mutants (14 transformants) had lost their biocontrol properties. Culture extracts of the mutants (group IV) and WT were analyzed and compared for the presence of active metabolites which were then separated by solid-phase extraction and purified using conventional methods. Nuclear magnetic resonance experiments and analytical studies on a metabolite specifically produced by the WT revealed the presence of 2-(2',4'-diacetoxy-5'-carboxy-pentanoyl) octadecyl cellobioside (flocculosin), a novel glycolipid with strong antifungal properties; the production of this compound would account for the biocontrol activity of P. flocculosa

NMR, structure, antifungal activity, cellobiose lipid, Pseudozyma flocculosa, insertional mutagenesis, DNA-mediated transformation, flocculosin, antifungal actiivity

Structure type: oligomer ; 877.5 [M+Na]+
C₄₀H₇₀O₁₉
Location inside paper: Fig. 4, Table 3, Table 4
Trivial name: flocculosin
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, DNA techniques, 31P NMR, electrophoresis, HPLC, TOCSY, LC-ESI-MS, cell growth, mutagenesis, HMQC, COSY, antifungal activity assay, antifungal activity test, FABMS, LCMS-ESI
Biological activity: flocculosin is most effective against P. aphanidermatum, showing potent fungitoxicity at 20 μg (in 100 μl of MeOH). It is equally effective in inhibiting the growth of B. cinerea and P. infestans at 100 μg as well as that of C. albicans. No activity is detected against F. oxysporum and I. bolleyi
Comments, role: atom enumeration is according to the Fig. 4 in the paper

NCBI Taxonomy refs (TaxIDs): 1277687
Show glycosyltransferases

NMR conditions: in CD3OD [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18
1,4	bDGlcp	101	76	74	70	75	62
1	aDGlcp	104	73	77	80	73	61
2,2	Ac	171	20-21
2,4	Ac	171	20-21
2	Subst1	171	68	42	69	43	176
	Subst	75	67	36	34	26	29	29	29	29	29	29	29	29	29	29	32	22	14


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1,4	bDGlcp	4.6	3.6	3.4	3.4	3.5	4.0-4.3
1	aDGlcp	4.3	3.5	3.6	3.5	3.6	3.6-3.9
2,2	Ac	-	2.1-2.2
2,4	Ac	-	2.1-2.2
2	Subst1	-	3.9	2.3	4.0	2.6	-
	Subst	3.8	3.9	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.0


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18
1,4	bDGlcp	101/4.6	76/3.6	74/3.4	70/3.4	75/3.5	62/4.0-4.3
1	aDGlcp	104/4.3	73/3.5	77/3.6	80/3.5	73/3.6	61/3.6-3.9
2,2	Ac		20-21/2.1-2.2
2,4	Ac		20-21/2.1-2.2
2	Subst1		68/3.9	42/2.3	69/4.0	43/2.6	
	Subst	75/3.8	67/3.9	36/1.3-1.5	34/1.3-1.5	26/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	29/1.3-1.5	32/1.3-1.5	22/1.3-1.5	14/1.0

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1,4	bDGlcp	4.6	3.6	3.4	3.4	3.5	4.0 4.3
1	aDGlcp	4.3	3.5	3.6	3.5	3.6	3.6 3.9
2,2	Ac		2.1 2.2
2,4	Ac		2.1 2.2
2	Subst1		3.9	2.3	4.0	2.6
	Subst	3.8	3.9	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.0

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18
1,4	bDGlcp	101	76	74	70	75	62
1	aDGlcp	104	73	77	80	73	61
2,2	Ac	171	20 21
2,4	Ac	171	20 21
2	Subst1	171	68	42	69	43	176
	Subst	75	67	36	34	26	29	29	29	29	29	29	29	29	29	29	32	22	14

There is only one chemically distinct structure:

CCCCCCCCCCCCCCCCC(CO[C@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)OC(=O)C(CC(CC(=O)O)OC(C)=O)OC(C)=O

SVG MW SMILES 3D mol Ionize

Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Organ / tissue: cell wall

The structure was elucidated in this paper
NCBI PubMed ID: 12732526
Publication DOI: 10.1128/aem.69.5.2595-2602.2003
Journal NLM ID: 7605801
Publisher: American Society for Microbiology
Correspondence: richard.belanger

NMR, structure, antifungal activity, cellobiose lipid, Pseudozyma flocculosa, insertional mutagenesis, DNA-mediated transformation, flocculosin, antifungal actiivity

Structure type: oligomer ; 854.6
C₄₀H₇₀O₁₉
Location inside paper: Fig. 4, table 3, table 4
Trivial name: flocculosin
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, DNA techniques, 31P NMR, electrophoresis, HPLC, TOCSY, LC-ESI-MS, cell growth, mutagenesis, HMQC, COSY, antifungal activity assay, antifungal activity test, FABMS, LCMS-ESI
Biological activity: potent antifungal activity against Phomopsis sp. at 0.2 g/ml
Comments, role: assignment of the name ''flocculosin'' to structure is under question

Related record ID(s): 48564
NCBI Taxonomy refs (TaxIDs): 84751
Reference(s) to other database(s): GTC:G49108TO
Show glycosyltransferases

NMR conditions: in CD3OH [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19
1,1,4	bDGlcp	101	76	74	70	75	62
1,1	bDGlcp	104	73	7	80	73	61
1	Subst	75	67	36	34	26	29	29	29	29	29	29	29	29	29	29	29	32	22	14
2	Ac	171	20-21
4	Ac	171	20-21
	Subst1	171	68	42	69	43	176


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1,1,4	bDGlcp	4.6	3.6	3.4	3.4	3.5	4.0
1,1	bDGlcp	4.3	3.5	3.6	3.5	3.6	3.6-3.9
1	Subst	3.8	3.9	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.3-1.5	1.0
2	Ac	-	2.1-2.2
4	Ac	-	2.1-2.2
	Subst1	-	3.9	2.3	4.0	2.6	-


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18
1,1,4	bDGlcp	101/4.6	76/3.6	74/3.4	70/3.4	75/3.5	62/4.0
1,1	bDGlcp	104/4.3	73/3.5	7/3.6	80/3.5	73/3.6	61/3.6-3.9
1	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets
2	Ac		20-21/2.1-2.2
4	Ac		20-21/2.1-2.2
	Subst1		68/3.9	42/2.3	69/4.0	43/2.6

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18
1,1,4	bDGlcp	4.6	3.6	3.4	3.4	3.5	4.0
1,1	bDGlcp	4.3	3.5	3.6	3.5	3.6	3.6 3.9
1	Subst	3.8	3.9	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.3 1.5	1.0
2	Ac		2.1 2.2
4	Ac		2.1 2.2
	Subst1		3.9	2.3	4.0	2.6

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19
1,1,4	bDGlcp	101	76	74	70	75	62
1,1	bDGlcp	104	73	7	80	73	61
1	Subst	75	67	36	34	26	29	29	29	29	29	29	29	29	29	29	29	32	22	14
2	Ac	171	20 21
4	Ac	171	20 21
	Subst1	171	68	42	69	43	176

There is only one chemically distinct structure:

SVG MW SMILES 3D mol Ionize