Six new compounds [ascherlactones A (1) and B (2), ascherchromanone A (3), phenethyl 4'-O-methylglucoside (8), 4'-O-methylpleoside (10), and 4'-O-methyltorachrysone 8-O-glucoside (11)] and one naturally new compound [4'-O-methyl-β-D-benzylglucoside (9)] together with fourteen known compounds, including paecilodepsipeptides A (5), B (7), and D (4), conoideocrellide A (6), eugenin (12), 5-hydroxy-2,3-dimethyl-7-methoxychromone (13), (S)-1-phenyl-1,2-ethanediol (14), (2S)-l-3-phenyllactic acid (15), papuline [or (2S)-l-3-phenyllactic acid methyl ester, 16], 2'-epi terpendole A (17), terpendoles C (18) and D (19), cholic acid, and zeorin were isolated from the entomopathogenic fungus Aschersonia confluens BCC53152. Their chemical structures were elucidated on the basis of NMR spectroscopic and mass spectrometric analyses. The absolute configurations were determined by using the evidence from NOESY correlations, chemical means, optical rotation values together with comparison of ECD spectroscopic data with the calculated ECD spectra. The plausible biosynthetic pathway of compounds 1-3 was also proposed. Moreover, antimicrobial activity such as antimalarial, antitubercular, antifungal, and antibacterial activities and cytotoxicity against cancerous (MCF-7, KB, and NCI-H187) and non-cancerous (Vero) cells of the isolated compounds were evaluated.

ascherchromanone, ascherlactone, Aschersonia, Aschersonia confluens, chromanone

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
1,4	Me	60.4
1	bDGlcp	104.2	75.4	78.3	80.9	77.1	62.8
	Subst	71.0	37.2	140.3	129.9	129.2	127.0	129.2	129.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
1,4	Me	3.52
1	bDGlcp	4.29	3.17	3.48	3.08	3.23	3.63-3.77
	Subst	3.70-4.02	2.89	-	7.25-7.30	7.25-7.30	7.16-7.22	7.25-7.30	7.25-7.30


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
1,4	Me	60.4/3.52
1	bDGlcp	104.2/4.29	75.4/3.17	78.3/3.48	80.9/3.08	77.1/3.23	62.8/3.63-3.77
	Subst	71.0/3.70-4.02	37.2/2.89		129.9/7.25-7.30	129.2/7.25-7.30	127.0/7.16-7.22	129.2/7.25-7.30	129.9/7.25-7.30

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](OCCc2ccccc2)[C@H](O)[C@H]1O

298.335 g/mol (C₁₅H₂₂O₆)

Six new compounds [ascherlactones A (1) and B (2), ascherchromanone A (3), phenethyl 4'-O-methylglucoside (8), 4'-O-methylpleoside (10), and 4'-O-methyltorachrysone 8-O-glucoside (11)] and one naturally new compound [4'-O-methyl-β-D-benzylglucoside (9)] together with fourteen known compounds, including paecilodepsipeptides A (5), B (7), and D (4), conoideocrellide A (6), eugenin (12), 5-hydroxy-2,3-dimethyl-7-methoxychromone (13), (S)-1-phenyl-1,2-ethanediol (14), (2S)-l-3-phenyllactic acid (15), papuline [or (2S)-l-3-phenyllactic acid methyl ester, 16], 2'-epi terpendole A (17), terpendoles C (18) and D (19), cholic acid, and zeorin were isolated from the entomopathogenic fungus Aschersonia confluens BCC53152. Their chemical structures were elucidated on the basis of NMR spectroscopic and mass spectrometric analyses. The absolute configurations were determined by using the evidence from NOESY correlations, chemical means, optical rotation values together with comparison of ECD spectroscopic data with the calculated ECD spectra. The plausible biosynthetic pathway of compounds 1-3 was also proposed. Moreover, antimicrobial activity such as antimalarial, antitubercular, antifungal, and antibacterial activities and cytotoxicity against cancerous (MCF-7, KB, and NCI-H187) and non-cancerous (Vero) cells of the isolated compounds were evaluated.

ascherchromanone, ascherlactone, Aschersonia, Aschersonia confluens, chromanone

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
7,4	Me	60.4
7	bDGlcp	103.0	74.9	77.7	80.5	76.7	62.2
	Bn	139.0	128.6	128.9	128.2	128.9	128.6	71.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
7,4	Me	3.50
7	bDGlcp	4.35	3.25	3.47	3.09	3.21-3.29	3.64-3.79
	Bn	-	7.39	7.31	7.25	7.31	7.39	4.61-4.87


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7
7,4	Me	60.4/3.50
7	bDGlcp	103.0/4.35	74.9/3.25	77.7/3.47	80.5/3.09	76.7/3.21-3.29	62.2/3.64-3.79
	Bn		128.6/7.39	128.9/7.31	128.2/7.25	128.9/7.31	128.6/7.39	71.1/4.61-4.87

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](OCc2ccccc2)[C@H](O)[C@H]1O

284.308 g/mol (C₁₄H₂₀O₆)

Six new compounds [ascherlactones A (1) and B (2), ascherchromanone A (3), phenethyl 4'-O-methylglucoside (8), 4'-O-methylpleoside (10), and 4'-O-methyltorachrysone 8-O-glucoside (11)] and one naturally new compound [4'-O-methyl-β-D-benzylglucoside (9)] together with fourteen known compounds, including paecilodepsipeptides A (5), B (7), and D (4), conoideocrellide A (6), eugenin (12), 5-hydroxy-2,3-dimethyl-7-methoxychromone (13), (S)-1-phenyl-1,2-ethanediol (14), (2S)-l-3-phenyllactic acid (15), papuline [or (2S)-l-3-phenyllactic acid methyl ester, 16], 2'-epi terpendole A (17), terpendoles C (18) and D (19), cholic acid, and zeorin were isolated from the entomopathogenic fungus Aschersonia confluens BCC53152. Their chemical structures were elucidated on the basis of NMR spectroscopic and mass spectrometric analyses. The absolute configurations were determined by using the evidence from NOESY correlations, chemical means, optical rotation values together with comparison of ECD spectroscopic data with the calculated ECD spectra. The plausible biosynthetic pathway of compounds 1-3 was also proposed. Moreover, antimicrobial activity such as antimalarial, antitubercular, antifungal, and antibacterial activities and cytotoxicity against cancerous (MCF-7, KB, and NCI-H187) and non-cancerous (Vero) cells of the isolated compounds were evaluated.

ascherchromanone, ascherlactone, Aschersonia, Aschersonia confluens, chromanone

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
1,4	Me	60.6
1	bDGlcp	101.8	74.8	78.3	80.2	77.3	62.1
5	Me	56.0
	Subst	161.9	107.1	167.7	96.0	167.0	94.4	204.5	33.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
1,4	Me	3.56
1	bDGlcp	5.12	3.56-3.63	3.65	3.21	3.53-3.59	3.70-3.88
5	Me	3.84
	Subst	-	-	-	6.09	-	6.30	-	2.71


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
1,4	Me	60.6/3.56
1	bDGlcp	101.8/5.12	74.8/3.56-3.63	78.3/3.65	80.2/3.21	77.3/3.53-3.59	62.1/3.70-3.88
5	Me	56.0/3.84
	Subst				96.0/6.09		94.4/6.30		33.4/2.71

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COc1cc(O)c(C(C)=O)c(O[C@@H]2O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]2O)c1

358.343 g/mol (C₁₆H₂₂O₉)

Six new compounds [ascherlactones A (1) and B (2), ascherchromanone A (3), phenethyl 4'-O-methylglucoside (8), 4'-O-methylpleoside (10), and 4'-O-methyltorachrysone 8-O-glucoside (11)] and one naturally new compound [4'-O-methyl-β-D-benzylglucoside (9)] together with fourteen known compounds, including paecilodepsipeptides A (5), B (7), and D (4), conoideocrellide A (6), eugenin (12), 5-hydroxy-2,3-dimethyl-7-methoxychromone (13), (S)-1-phenyl-1,2-ethanediol (14), (2S)-l-3-phenyllactic acid (15), papuline [or (2S)-l-3-phenyllactic acid methyl ester, 16], 2'-epi terpendole A (17), terpendoles C (18) and D (19), cholic acid, and zeorin were isolated from the entomopathogenic fungus Aschersonia confluens BCC53152. Their chemical structures were elucidated on the basis of NMR spectroscopic and mass spectrometric analyses. The absolute configurations were determined by using the evidence from NOESY correlations, chemical means, optical rotation values together with comparison of ECD spectroscopic data with the calculated ECD spectra. The plausible biosynthetic pathway of compounds 1-3 was also proposed. Moreover, antimicrobial activity such as antimalarial, antitubercular, antifungal, and antibacterial activities and cytotoxicity against cancerous (MCF-7, KB, and NCI-H187) and non-cancerous (Vero) cells of the isolated compounds were evaluated.

ascherchromanone, ascherlactone, Aschersonia, Aschersonia confluens, chromanone

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13
8,4	Me	60.6
8	bDGlcp	103.7	75.0	77.9	80.2	77.7	62.0
6	Me
	Subst	153.1	124.2	135.3	119.8	138.5	102.1	159.8	104.0	156.8	110.1	204.4	32.4	20.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13
8,4	Me	3.58
8	bDGlcp	5.20	3.61-3.64	3.71	3.28	3.64-3.68	3.74-3.96
6	Me
	Subst	-	-	-	7.06	-	6.89	-	6.99	-	-	-	2.52	2.27


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
8,4	Me	60.6/3.58
8	bDGlcp	103.7/5.20	75.0/3.61-3.64	77.9/3.71	80.2/3.28	77.7/3.64-3.68	62.0/3.74-3.96
6	Me
	Subst				119.8/7.06		102.1/6.89		104.0/6.99				32.4/2.52	20.1/2.27

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COc1cc(O[C@@H]2O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]2O)c2c(O)c(C(C)=O)c(C)cc2c1

422.43 g/mol (C₂₁H₂₆O₉)