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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Host organism: Helianthus annuus
Associated disease: Verticillium wilt

The structure was elucidated in this paper
NCBI PubMed ID: 19962895
Publication DOI: 10.1016/j.bmcl.2009.11.063
Journal NLM ID: 9107377
Publisher: Elsevier
Correspondence: Hashimoto M <hmasaru

cc.hirosaki-u.ac.jp>
Institutions: Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan, Graduate School of Health Sciences, Hirosaki University, Hirosaki, Japan

Novel fusapyrone analogs, deoxyneofusapyrone and 7-desmethyldeoxyneofusapyrone were isolated from a pathogenic fungus, Verticillium dahliae, which causes Verticillium wilt disease in Helianthus annuus. Spectral analyses revealed that these are 2-pyrone type analogs of deoxyfusapyrone and its 7-desmethyl derivative, respectively. Biological assay disclosed that 10microg of deoxyneofusapyrone inhibited the growth of MRSA clinical isolate 87-7927.

isolation and structure determination, NMR spectral analysis, 4-hydroxy-2-pyrone, IR spectra, theoretical 13C NMR chemical shift, inhibition of MRSA clinical isolate 87-7927

Structure type: monomer ; 591.3925 [M+H]+
C₃₄H₅₄O₈
Location inside paper: Fig.1, structure 1, Table 1, 1
Trivial name: deoxyneofusapyrone
Compound class: glycoside

Methods: 13C NMR, 1H NMR, IR, biological assays, HPLC, UV, optical rotation measurement, CC, cell growth, HR-ESI-MS, HMBC, evaporation, NOESY
Biological activity: Deoxyneofusapyrone inhibited the growth of Cochliobolus miyabeanus in 100 μg/mL concentration and showed no cytotoxicity against HeLa (human cervix carcinoma) and HepG2 (human hepatocellular carcinoma).
Comments, role: NMR temperature was not specified

Related record ID(s): 46015, 46016, 46017
NCBI Taxonomy refs (TaxIDs): 27337
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	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28
3	bD1,4dxylHexp	75.67	73.52	74.07	36.58	78.46	65.70
	Subst	167.06	100.30	170.59	100.86	172.15	45.52	78.16	125.97	139.20	131.46	139.56	32.99	131.93	134.01	40.99	32.27	38.31	28.40	30.71	33.07	23.72	14.47	20.39	23.00	13.03	22.17	23.91	20.05


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27	H28
3	bD1,4dxylHexp	4.48	3.99	3.63	1.57-1.95	3.60	3.56
	Subst	-	-	-	6.08	-	-	4.32	5.55	6.23	-	5.31	3.42	5.06	-	1.95	1.59	1.10-1.31	1.30	1.28	1.28	1.28	0.89	1.21	1.15	1.75	0.97	1.63	0.85


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	C20/H20	C21/H21	C22/H22	C23/H23	C24/H24	C25/H25	C26/H26	C27/H27	C28/H28
3	bD1,4dxylHexp	75.67/4.48	73.52/3.99	74.07/3.63	36.58/1.57-1.95	78.46/3.60	65.70/3.56
	Subst				100.86/6.08			78.16/4.32	125.97/5.55	139.20/6.23		139.56/5.31	32.99/3.42	131.93/5.06		40.99/1.95	32.27/1.59	38.31/1.10-1.31	28.40/1.30	30.71/1.28	33.07/1.28	23.72/1.28	14.47/0.89	20.39/1.21	23.00/1.15	13.03/1.75	22.17/0.97	23.91/1.63	20.05/0.85

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27	H28
3	bD1,4dxylHexp	4.48	3.99	3.63	1.57 1.95	3.60	3.56
	Subst				6.08			4.32	5.55	6.23		5.31	3.42	5.06		1.95	1.59	1.10 1.31	1.30	1.28	1.28	1.28	0.89	1.21	1.15	1.75	0.97	1.63	0.85

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28
3	bD1,4dxylHexp	75.67	73.52	74.07	36.58	78.46	65.70
	Subst	167.06	100.30	170.59	100.86	172.15	45.52	78.16	125.97	139.20	131.46	139.56	32.99	131.93	134.01	40.99	32.27	38.31	28.40	30.71	33.07	23.72	14.47	20.39	23.00	13.03	22.17	23.91	20.05

There is only one chemically distinct structure:

$CCCCCCC(C)C/C(C)=C\C(C)/C=C(C)/C=C/C(O)C(C)(C)c1cc(O)c([C@@H]2O[C@H](CO)C[C@H](O)[C@H]2O)c(=O)o1$

SVG MW SMILES 3D mol Ionize