Three new aromatic polyketides (±)-puniceusone A (1), (±)-2,3-dihydroxypropyl 6-ethyl-2,4-dihydroxy-3-methylbenzoate (2), (5-ethyl-3-hydroxy-2-methyl) phenyl-β-D-glucoside (3), and two new isoquinoline alkaloids puniceusine O (4) and (±)-puniceusine P (5), were isolated from the deep-sea-derived fungus Aspergillus puniceus SCSIO z021. Their structures were determined by spectroscopic analyses. Compound 1 contains an uncommon hydrogenated benzochromene scaffold, 3 and 4 are glycosides, and 5 is unexpectedly composed of a polysubstituted benzyl and an isoquinoline nucleus.

Structures, Aspergillus, polyketides, marine-derived fungi, isoquinoline alkaloids

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13
8	bDGlcp	105.7	74.1	77.1	69.7	76.4	60.9
	Subst	143.4	-	134.5	141.8	138.3	101.6	163.9	125.1	152.6	119.0	-	56.8	10.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13
8	bDGlcp	4.76	3.48	3.05	3.20	3.27	3.40-3.57
	Subst	9.72	-	8.49	8.12	-	7.50	-	-	-	-	-	4.05	2.39


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	bDGlcp	105.7/4.76	74.1/3.48	77.1/3.05	69.7/3.20	76.4/3.27	60.9/3.40-3.57
	Subst	143.4/9.72		134.5/8.49	141.8/8.12		101.6/7.50						56.8/4.05	10.4/2.39

The spectrum also has 2 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COc1cc2ccncc2c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1C

351.355 g/mol (C₁₇H₂₁NO₇)