A new unusual phytotoxic bis-amino acid N-glucoside, named ascaulitoxin, was isolated from the culture filtrate of Ascochyta caulina, the causal agent of leaf and stem necrosis of Chenopodium album, a promising mycoherbicide for the biological control of this common noxious weed. Ascaulitoxin, characterized by extensive use of NMR techniques and chemical methods as N-2-(2,4,7-triamino-5-hydroxy)-octanedioyl-beta-D-glucopyranoside, showed phytotoxic activity against host and non-host plants.

phytotoxins, ascaulitoxin, Ascochyta caulina, Chenopodium album, Chenopodiaceae, mycoherbicide, N-glucosides, nonproteigenic amino acids

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2	bDGlcp1N	91.2	72.8	80.0	72.5	79.5	63.7
	Subst


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2	bDGlcp1N	4.04	3.11	3.48	3.37	3.40	3.76-3.96
	Subst


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2	bDGlcp1N	91.2/4.04	72.8/3.11	80.0/3.48	72.5/3.37	79.5/3.40	63.7/3.76-3.96
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

N[C@@H](C[C@@H](O)[C@H](N)C[C@H](N[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O)C(=O)O

397.381 g/mol (C₁₄H₂₇N₃O₁₀)

A new unusual phytotoxic bis-amino acid N-glucoside, named ascaulitoxin, was isolated from the culture filtrate of Ascochyta caulina, the causal agent of leaf and stem necrosis of Chenopodium album, a promising mycoherbicide for the biological control of this common noxious weed. Ascaulitoxin, characterized by extensive use of NMR techniques and chemical methods as N-2-(2,4,7-triamino-5-hydroxy)-octanedioyl-beta-D-glucopyranoside, showed phytotoxic activity against host and non-host plants.

phytotoxins, ascaulitoxin, Ascochyta caulina, Chenopodium album, Chenopodiaceae, mycoherbicide, N-glucosides, nonproteigenic amino acids

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,1	Ac
2,2	Ac
2,3	Ac
2,4	Ac
2,6	Ac
2	bDGlcp1N	4.26	4.68	5.19	5.03	3.85	4.20-4.32
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)OC[C@H]1O[C@@H](N(C(C)=O)[C@@H](C[C@@H](N)[C@H](O)C[C@H](N)C(=O)O)C(=O)O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

607.566 g/mol (C₂₄H₃₇N₃O₁₅)

A new unusual phytotoxic bis-amino acid N-glucoside, named ascaulitoxin, was isolated from the culture filtrate of Ascochyta caulina, the causal agent of leaf and stem necrosis of Chenopodium album, a promising mycoherbicide for the biological control of this common noxious weed. Ascaulitoxin, characterized by extensive use of NMR techniques and chemical methods as N-2-(2,4,7-triamino-5-hydroxy)-octanedioyl-beta-D-glucopyranoside, showed phytotoxic activity against host and non-host plants.

phytotoxins, ascaulitoxin, Ascochyta caulina, Chenopodium album, Chenopodiaceae, mycoherbicide, N-glucosides, nonproteigenic amino acids

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,2	Ac
2,3	Ac
2,4	Ac
2,6	Ac
2	bDGlcp1N	4.17	4.87	5.21	5.09	3.87	4.19-4.33
7	Ac
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)N[C@@H](C[C@@H](O)[C@H](N)C[C@H](N[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)C(=O)O)C(=O)O

607.566 g/mol (C₂₄H₃₇N₃O₁₅)

A new unusual phytotoxic bis-amino acid N-glucoside, named ascaulitoxin, was isolated from the culture filtrate of Ascochyta caulina, the causal agent of leaf and stem necrosis of Chenopodium album, a promising mycoherbicide for the biological control of this common noxious weed. Ascaulitoxin, characterized by extensive use of NMR techniques and chemical methods as N-2-(2,4,7-triamino-5-hydroxy)-octanedioyl-beta-D-glucopyranoside, showed phytotoxic activity against host and non-host plants.

phytotoxins, ascaulitoxin, Ascochyta caulina, Chenopodium album, Chenopodiaceae, mycoherbicide, N-glucosides, nonproteigenic amino acids

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,1	Ac
2,2	Ac
2,3	Ac
2,4	Ac
2,6	Ac
2	bDGlcp1N	4.37	4.59	5.23	5.06	3.86	4.21-4.31
7	Ac
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)N[C@@H](C[C@@H](O)[C@H](N)C[C@@H](C(=O)O)N(C(C)=O)[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)C(=O)O

649.603 g/mol (C₂₆H₃₉N₃O₁₆)