Four new amide derivatives, designated as cordycepiamides A-D (1-4), together with 14 known compounds (5-18), were isolated from the EtOAc-soluble fraction of the 95% EtOH extract of long-grain rice fermented with the endophytic fungus C. ninchukispora BCRC 31900, derived from the seeds of medicinal plant Beilschmiedia erythrophloia Hayata. Their structures were elucidated by means of spectroscopic and mass-spectrometric analyses, particularly 1D and 2D NMR spectroscopy as well as HRESIMS. All known isolates except 11, were isolated for the first time from this species. The antiinflammatory activities of selected isolated 10 compounds (1, 2, 4-6, 9-12, and 14) were evaluated as inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Compound 3→4 was shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated RAW264.7 cells.

Amides, secondary metabolites, anti-inflammatory activity, Cordyceps ninchukispora, Clavicipitaceae

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
4,4	Me	60.9
4	bDGlcp	106.2	75.2	78.0	80.6	77.4	62.1
	Subst	132.1	111.4	155.2	141.5	122.0	109.2	171.5	24.2


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
4,4	Me	3.55
4	bDGlcp	4.48	3.46	3.52	3.20	3.29	3.72-3.84
	Subst	-	7.71	-	-	7.10	6.44	-	2.15


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
4,4	Me	60.9/3.55
4	bDGlcp	106.2/4.48	75.2/3.46	78.0/3.52	80.6/3.20	77.4/3.29	62.1/3.72-3.84
	Subst		111.4/7.71			122.0/7.10	109.2/6.44		24.2/2.15

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](Oc2ccc(NC(C)=O)cc2O)[C@H](O)[C@H]1O

343.332 g/mol (C₁₅H₂₁NO₈)

Four new amide derivatives, designated as cordycepiamides A-D (1-4), together with 14 known compounds (5-18), were isolated from the EtOAc-soluble fraction of the 95% EtOH extract of long-grain rice fermented with the endophytic fungus C. ninchukispora BCRC 31900, derived from the seeds of medicinal plant Beilschmiedia erythrophloia Hayata. Their structures were elucidated by means of spectroscopic and mass-spectrometric analyses, particularly 1D and 2D NMR spectroscopy as well as HRESIMS. All known isolates except 11, were isolated for the first time from this species. The antiinflammatory activities of selected isolated 10 compounds (1, 2, 4-6, 9-12, and 14) were evaluated as inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Compound 3→4 was shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated RAW264.7 cells.

Amides, secondary metabolites, anti-inflammatory activity, Cordyceps ninchukispora, Clavicipitaceae

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
2,4	Me	60.9
2	bDGlcp	104.4	75.0	77.9	80.5	77.4	61.9
	Subst	130.5	148.7	119.3	125.7	124.6	122.9	171.7	24.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
2,4	Me	3.59
2	bDGlcp	4.71	3.52	3.57	3.22	3.37	3.72-3.85
	Subst	-	-	7.25	7.06	7.04	8.07	-	2.17


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
2,4	Me	60.9/3.59
2	bDGlcp	104.4/4.71	75.0/3.52	77.9/3.57	80.5/3.22	77.4/3.37	61.9/3.72-3.85
	Subst			119.3/7.25	125.7/7.06	124.6/7.04	122.9/8.07		24.0/2.17

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](Oc2ccccc2NC(C)=O)[C@H](O)[C@H]1O

327.333 g/mol (C₁₅H₂₁NO₇)

Four new amide derivatives, designated as cordycepiamides A-D (1-4), together with 14 known compounds (5-18), were isolated from the EtOAc-soluble fraction of the 95% EtOH extract of long-grain rice fermented with the endophytic fungus C. ninchukispora BCRC 31900, derived from the seeds of medicinal plant Beilschmiedia erythrophloia Hayata. Their structures were elucidated by means of spectroscopic and mass-spectrometric analyses, particularly 1D and 2D NMR spectroscopy as well as HRESIMS. All known isolates except 11, were isolated for the first time from this species. The antiinflammatory activities of selected isolated 10 compounds (1, 2, 4-6, 9-12, and 14) were evaluated as inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Compound 3→4 was shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated RAW264.7 cells.

Amides, secondary metabolites, anti-inflammatory activity, Cordyceps ninchukispora, Clavicipitaceae

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
2,4	Me	60.9
2	bDGlcp	103.5	75.2	78.1	80.7	77.4	62.1
	Subst	129.4	157.5	117.3	130.0	123.8	130.5	39.8	173.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
2,4	Me	3.57
2	bDGlcp	4.83	3.52	3.58	3.20	3.43	3.72-3.87
	Subst	-	-	7.24	7.23	7.00	7.25	4.53	4.31	-


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
2,4	Me	60.9/3.57
2	bDGlcp	103.5/4.83	75.2/3.52	78.1/3.58	80.7/3.20	77.4/3.43	62.1/3.72-3.87
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](Oc2ccccc2CNC(C)=O)[C@H](O)[C@H]1O

341.36 g/mol (C₁₆H₂₃NO₇)

Four new amide derivatives, designated as cordycepiamides A-D (1-4), together with 14 known compounds (5-18), were isolated from the EtOAc-soluble fraction of the 95% EtOH extract of long-grain rice fermented with the endophytic fungus C. ninchukispora BCRC 31900, derived from the seeds of medicinal plant Beilschmiedia erythrophloia Hayata. Their structures were elucidated by means of spectroscopic and mass-spectrometric analyses, particularly 1D and 2D NMR spectroscopy as well as HRESIMS. All known isolates except 11, were isolated for the first time from this species. The antiinflammatory activities of selected isolated 10 compounds (1, 2, 4-6, 9-12, and 14) were evaluated as inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Compound 3→4 was shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated RAW264.7 cells.

Amides, secondary metabolites, anti-inflammatory activity, Cordyceps ninchukispora, Clavicipitaceae

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
8,4	Me	60.8
8	bDGlcp	105.0	75.1	77.8	80.7	77.3	62.2
	Subst	128.4	155.8	118.6	126.3	116.0	121.3	169.6	70.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
8,4	Me	3.57
8	bDGlcp	4.38	3.36	3.50	3.16	3.29	3.68-3.81
	Subst	-	-	6.74	6.85	6.51	7.92	-	4.26-4.44


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
8,4	Me	60.8/3.57
8	bDGlcp	105.0/4.38	75.1/3.36	77.8/3.50	80.7/3.16	77.3/3.29	62.2/3.68-3.81
	Subst			118.6/6.74	126.3/6.85	116.0/6.51	121.3/7.92		70.4/4.26-4.44

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](OCC(=O)Nc2ccccc2O)[C@H](O)[C@H]1O

343.332 g/mol (C₁₅H₂₁NO₈)