In our screening for antitubercular agents, five naphtho-γ-pyrones including two new naphtho-γ-pyrones glycosides, indigotides G and H (1 and 2), and two diphenyl ethers were isolated from the extract of a sponge-derived fungus Metarhizium anisopliae mxh-99. Their structures were established on the basis of chemical and spectroscopic evidence. The antitubercular activities of all the compounds were evaluated against Mycobacterium phlei. The known isochaetochromin B2 (6) and ustilaginoidin D (7) exhibited the highest activity with MICs 50.0 μg/mL.

secondary metabolites, sponge-derived fungus, naphtho-γ-pyrones, diphenyl ethers, antitubercular activity

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15
6,4	Me	60.2
6	bDGlcp	101.3	74.2	76.3	79.4	76.7	60.7
	Subst	75.3	44.5	202.4	102.6	165.6	106.1	159.6	100.8	161.3	103.3	143.1	100.5	155.4	16.6	10.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15
6,4	Me	3.47
6	bDGlcp	4.94	3.40	3.43	3.10	3.44	3.54-3.67
	Subst	4.63	2.77	-	-	-	-	-	6.52	-	6.52	-	6.45	-	1.28	1.09


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
6,4	Me	60.2/3.47
6	bDGlcp	101.3/4.94	74.2/3.40	76.3/3.43	79.4/3.10	76.7/3.44	60.7/3.54-3.67
	Subst	75.3/4.63	44.5/2.77						100.8/6.52		103.3/6.52		100.5/6.45		16.6/1.28	10.1/1.09

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](Oc2cc(O)cc3cc4c(c(O)c23)C(=O)[C@H](C)[C@@H](C)O4)[C@H](O)[C@H]1O

450.44 g/mol (C₂₂H₂₆O₁₀)

In our screening for antitubercular agents, five naphtho-γ-pyrones including two new naphtho-γ-pyrones glycosides, indigotides G and H (1 and 2), and two diphenyl ethers were isolated from the extract of a sponge-derived fungus Metarhizium anisopliae mxh-99. Their structures were established on the basis of chemical and spectroscopic evidence. The antitubercular activities of all the compounds were evaluated against Mycobacterium phlei. The known isochaetochromin B2 (6) and ustilaginoidin D (7) exhibited the highest activity with MICs 50.0 μg/mL.

secondary metabolites, sponge-derived fungus, naphtho-γ-pyrones, diphenyl ethers, antitubercular activity

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15
8,4	Me	59.7
8	bDGlcp	99.5	73.4	76.3	78.9	75.7	60.1
	Subst	78.9	45.6	200.7	102.1	164.0	105.5	159.0	99.9	160.5	101.6	141.8	100.9	155.0	19.4	9.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15
8,4	Me	3.46
8	bDGlcp	4.99	3.25	3.41	3.07	3.43	3.53-3.64
	Subst	4.31	2.84	-	-	-	-	-	6.37	-	6.70	-	6.54	-	1.43	1.15


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
8,4	Me	59.7/3.46
8	bDGlcp	99.5/4.99	73.4/3.25	76.3/3.41	78.9/3.07	75.7/3.43	60.1/3.53-3.64
	Subst	78.9/4.31	45.6/2.84						99.9/6.37		101.6/6.70		100.9/6.54		19.4/1.43	9.8/1.15

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](Oc2cc(O)c3c(O)c4c(cc3c2)O[C@H](C)[C@@H](C)C4=O)[C@H](O)[C@H]1O

450.44 g/mol (C₂₂H₂₆O₁₀)

In our screening for antitubercular agents, five naphtho-γ-pyrones including two new naphtho-γ-pyrones glycosides, indigotides G and H (1 and 2), and two diphenyl ethers were isolated from the extract of a sponge-derived fungus Metarhizium anisopliae mxh-99. Their structures were established on the basis of chemical and spectroscopic evidence. The antitubercular activities of all the compounds were evaluated against Mycobacterium phlei. The known isochaetochromin B2 (6) and ustilaginoidin D (7) exhibited the highest activity with MICs 50.0 μg/mL.

secondary metabolites, sponge-derived fungus, naphtho-γ-pyrones, diphenyl ethers, antitubercular activity

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15
6,4	Me	60.3
6	bDGlcp	101.4	74.1	76.7	79.4	76.3	60.7
	Subst	77.9	46.5	200.8	102.7	165.2	106.1	159.6	100.9	161.2	103.3	143.0	100.4	155.7	20.0	10.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15
6,4	Me	3.48
6	bDGlcp	4.96	3.45	3.41	3.11	3.44	3.55-3.67
	Subst	4.28	2.80	-	-	-	-	-	6.53	-	6.53	-	6.46	-	1.42	1.15


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
6,4	Me	60.3/3.48
6	bDGlcp	101.4/4.96	74.1/3.45	76.7/3.41	79.4/3.11	76.3/3.44	60.7/3.55-3.67
	Subst	77.9/4.28	46.5/2.80						100.9/6.53		103.3/6.53		100.4/6.46		20.0/1.42	10.7/1.15

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](Oc2cc(O)cc3cc4c(c(O)c23)C(=O)[C@@H](C)[C@H](C)O4)[C@H](O)[C@H]1O

450.44 g/mol (C₂₂H₂₆O₁₀)

In our screening for antitubercular agents, five naphtho-γ-pyrones including two new naphtho-γ-pyrones glycosides, indigotides G and H (1 and 2), and two diphenyl ethers were isolated from the extract of a sponge-derived fungus Metarhizium anisopliae mxh-99. Their structures were established on the basis of chemical and spectroscopic evidence. The antitubercular activities of all the compounds were evaluated against Mycobacterium phlei. The known isochaetochromin B2 (6) and ustilaginoidin D (7) exhibited the highest activity with MICs 50.0 μg/mL.

secondary metabolites, sponge-derived fungus, naphtho-γ-pyrones, diphenyl ethers, antitubercular activity

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@H]1[C@@H](CO)O[C@@H](Oc2cc(C)cc(Oc3cc(C)cc(O)c3)c2)[C@H](O)[C@H]1O

406.431 g/mol (C₂₁H₂₆O₈)