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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Host organism: (Rhodophyta)
Associated disease: infection due to Aspergillus [ICD11: XN0WC

]

The structure was elucidated in this paper
NCBI PubMed ID: 26651366
Publication DOI: 10.1021/acs.jnatprod.5b00614
Journal NLM ID: 7906882
Publisher: American Society of Pharmacognosy
Correspondence: Kim YC <yckim

wku.ac.kr>; Oh H <hoh

wonkwang.ac.kr>
Institutions: Institute of Pharmaceutical Research and Development, College of Pharmacy, Wonkwang University, Iksan, Korea, Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam, College of Medical and Life Sciences, Silla University, Busan, Korea, Korea Polar Research Institute, KORDI, Yeonsu-gu, Korea, Beijing Ditan Hospital, Capital Medical University, Beijing, China, Beijing Institute of Pharmacology & Toxicology, Beijing, China

Chemical investigation of the EtOAc extracts of marine-derived fungal isolates Aspergillus sp. SF-5974 and Aspergillus sp. SF-5976 yielded a new dihydroisocoumarin derivative (1) and 12 known metabolites. The structures of the isolated metabolites were established by extensive spectroscopic analyses, including 1D and 2D NMR spectra and MS data. Among the metabolites, the absolute configuration of 5′-hydroxyasperentin (6) was determined by single-crystal X-ray diffraction analysis. The in vitro antineuroinflammatory effects of the metabolites were also evaluated in lipopolysaccharide (LPS)- stimulated microglial cells. Among the isolated metabolites, dihydroisocoumarin derivatives 1−6 (10−80 μM) were shown to inhibit LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production by suppressing the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2), respectively, in LPS-stimulated BV2 microglia. Further, 1 (20−80 μM) was found to suppress the phosphorylation of the inhibitor of nuclear factor kappa B-α (IκB-α), interrupt the nuclear translocation of nuclear factor kappa B (NF-κB), and decrease the activation of p38 mitogen-activated protein kinase (MAPK)

Aspergillus, antiinflammatory activity, dihydroisocoumarin glycosides

Structure type: monomer ; 425.1812 [M+H]+
C₂₁H₂₈O₉
Location inside paper: p. 2949, structure 1, Fig. 2, Table 1
Compound class: glycoside
Contained glycoepitopes: IEDB_149136

Methods: 13C NMR, 1H NMR, NMR-2D, X-ray, DNA techniques, ELISA, Western blotting, biological assays, HPLC, extraction, optical rotation measurement, CC, cell growth, RNA sequencing, HR-ESI-MS, determination of NO production, cell viability assay
Biological activity: compound was shown to inhibits the production of pro-inflammatory mediators in LPS-stimulated BV2 microglia and inhibits the activation of NF-κB and p38 signaling pathways in a dose-dependent manner
Comments, role: atom enumeration is according to the structure 1, p. 2949 in the paper

NCBI Taxonomy refs (TaxIDs): 1483725, 1729139
Show glycosyltransferases

NMR conditions: in CD3OD [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
8	aDRibf	101.5	73.4	71.0	88.1	63.1
	Subst	171.1	77.9	34.3	143.1	108.7	164.9	103.6	165.1	103.5	39.1	68.2	31.4	19.2	32.7	68.3	19.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19
8	aDRibf	5.71	4.20	4.10	4.10	3.64-3.70
	Subst	-	4.69	2.96	-	6.56	-	6.58	-	-	2.13	1.77	4.13	1.72	1.39	1.69	1.67	1.30	3.91	1.18


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	C16/H16	C17/H17	C18/H18	C19/H19
8	aDRibf	101.5/5.71	73.4/4.20	71.0/4.10	88.1/4.10	63.1/3.64-3.70
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19
8	aDRibf	5.71	4.20	4.10	4.10	3.64 3.70
	Subst		4.69	2.96		6.56		6.58			2.13	1.77	4.13	1.72	1.39	1.69	1.67	1.30	3.91	1.18

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
8	aDRibf	101.5	73.4	71.0	88.1	63.1
	Subst	171.1	77.9	34.3	143.1	108.7	164.9	103.6	165.1	103.5	39.1	68.2	31.4	19.2	32.7	68.3	19.9

There is only one chemically distinct structure:

C[C@H]1CCC[C@H](C[C@H]2Cc3cc(O)cc(O[C@H]4O[C@H](CO)[C@@H](O)[C@H]4O)c3C(=O)O2)O1

SVG MW SMILES 3D mol Ionize