Two new N-glucosylated indole alkaloids were isolated from fruiting bodies of the basidiomycete Cortinarius brunneus (Pers.) Fr. The structures were elucidated by means of the spectroscopic data. Additionally, the very recently reported compounds N-1-β-glucopyranosyl-3-(carboxymethyl)-1H-indole (3) and N-1-β-glucopyranosyl-3-(2-methoxy-2-oxoethyl)-1H-indole (4) could be detected. Compound 3 is the N-glucoside of the plant-growth regulator 1H-indole-3-acetic acid (IAA), but, in contrast, it does not exhibit auxin-like activity in an Arabidopsis thaliana tap root elongation assay.

bioactive secondary metabolite

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
1	bDGlcp1N	86.7	73.7	79.0	71.5	80.6	62.7
8	Me	57.6
	Subst	126.6	113.9	129.7	120.0	121.1	123.1	111.7	138.7	67.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
1	bDGlcp1N	5.44	3.91	3.59	3.50	3.57	3.70-3.87
8	Me	3.36
	Subst	7.43	-	-	7.61	7.09	7.18	7.53	-	4.65


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
1	bDGlcp1N	86.7/5.44	73.7/3.91	79.0/3.59	71.5/3.50	80.6/3.57	62.7/3.70-3.87
8	Me	57.6/3.36
	Subst	126.6/7.43			120.0/7.61	121.1/7.09	123.1/7.18	111.7/7.53		67.9/4.65

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COCc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2ccccc12

323.345 g/mol (C₁₆H₂₁NO₆)

Two new N-glucosylated indole alkaloids were isolated from fruiting bodies of the basidiomycete Cortinarius brunneus (Pers.) Fr. The structures were elucidated by means of the spectroscopic data. Additionally, the very recently reported compounds N-1-β-glucopyranosyl-3-(carboxymethyl)-1H-indole (3) and N-1-β-glucopyranosyl-3-(2-methoxy-2-oxoethyl)-1H-indole (4) could be detected. Compound 3 is the N-glucoside of the plant-growth regulator 1H-indole-3-acetic acid (IAA), but, in contrast, it does not exhibit auxin-like activity in an Arabidopsis thaliana tap root elongation assay.

bioactive secondary metabolite

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
1	bDGlcp1N	87.7	73.9	78.9	71.7	80.8	62.9
	Subst	140.6	120.2	126.8	122.7	124.3	125.5	113.0	139.1	187.6


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
1	bDGlcp1N	5.55	3.91	3.6	3.51	3.57	3.73-3.87
	Subst	8.30	-	-	8.17	7.28	7.33	7.68	-	9.90


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
1	bDGlcp1N	87.7/5.55	73.9/3.91	78.9/3.6	71.7/3.51	80.8/3.57	62.9/3.73-3.87
	Subst	140.6/8.30			122.7/8.17	124.3/7.28	125.5/7.33	113.0/7.68		187.6/9.90

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2ccccc12

307.302 g/mol (C₁₅H₁₇NO₆)

Two new N-glucosylated indole alkaloids were isolated from fruiting bodies of the basidiomycete Cortinarius brunneus (Pers.) Fr. The structures were elucidated by means of the spectroscopic data. Additionally, the very recently reported compounds N-1-β-glucopyranosyl-3-(carboxymethyl)-1H-indole (3) and N-1-β-glucopyranosyl-3-(2-methoxy-2-oxoethyl)-1H-indole (4) could be detected. Compound 3 is the N-glucoside of the plant-growth regulator 1H-indole-3-acetic acid (IAA), but, in contrast, it does not exhibit auxin-like activity in an Arabidopsis thaliana tap root elongation assay.

bioactive secondary metabolite

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=C(O)Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2ccccc12

337.328 g/mol (C₁₆H₁₉NO₇)

Two new N-glucosylated indole alkaloids were isolated from fruiting bodies of the basidiomycete Cortinarius brunneus (Pers.) Fr. The structures were elucidated by means of the spectroscopic data. Additionally, the very recently reported compounds N-1-β-glucopyranosyl-3-(carboxymethyl)-1H-indole (3) and N-1-β-glucopyranosyl-3-(2-methoxy-2-oxoethyl)-1H-indole (4) could be detected. Compound 3 is the N-glucoside of the plant-growth regulator 1H-indole-3-acetic acid (IAA), but, in contrast, it does not exhibit auxin-like activity in an Arabidopsis thaliana tap root elongation assay.

bioactive secondary metabolite

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COC(=O)Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2ccccc12

351.355 g/mol (C₁₇H₂₁NO₇)