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

]

The structure was elucidated in this paper
NCBI PubMed ID: 16176910
Publication DOI: 10.1080/1028602042000324853
Journal NLM ID: 100888334
Publisher: Harwood Academic Publishers; London: Informa Healthcare
Correspondence: maouyang

hqu.edu.cn
Institutions: Department of Bio-engineering & Technology, Huaqiao University, Quanzhou, China, Department of Chemistry, Taiwan University, Taipei, Taiwan

A new cerebroside, asperiamide A, and adenosine were produced from a marine fungus, identified as Asperillus sp., collected in the Mei Zhou Gulf, China. Two-dimensional NMR methods, FAB-MS, were used to established the structure of the new compound.

cerebroside, Marine fungus, Asperillus

Structure type: monomer ; 906.7403 [M-H]-
C₅₄H₁₀₁NO₉
Location inside paper: Fig.1, Table 1
Trivial name: asperiamide A
Compound class: cerebroside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, extraction, optical rotation measurement, HPTLC, CC, cell growth
Comments, role: NMR temperature was not specified

Related record ID(s): 45690
NCBI Taxonomy refs (TaxIDs): 5052
Reference(s) to other database(s): GTC:G02177KX
Show glycosyltransferases

NMR conditions: in DMSO-d6 [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	C29	C30	C31
1,1	bDGlcp	103.5	73.4	76.9	70.1	76.6	61.1
1	Subst	68.8	52.9	70.6	130.9	131.1	32.2	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	39.0	134.7	15.7	123.6	31.8	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	31.3	22.4	13.8
	Subst1	172.1	72.0	129.0	130.6	31.8	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	28.9-29.3	31.3	22.4	13.8


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	H29	H30	H31
1,1	bDGlcp	4.66	3.42	3.50	3.54	3.59	3.89-4.06
1	Subst	3.95-4.35	4.19	4.32	5.67	5.92	1.95	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.88	-	1.52	5.34	1.93	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.25	1.25	0.84
	Subst1	-	4.79	5.74	6.05	1.94	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.20-1.46	1.25	1.25	0.84


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	C29/H29	C30/H30	C31/H31
1,1	bDGlcp	103.5/4.66	73.4/3.42	76.9/3.50	70.1/3.54	76.6/3.59	61.1/3.89-4.06
1	Subst	68.8/3.95-4.35	52.9/4.19	70.6/4.32	130.9/5.67	131.1/5.92	32.2/1.95	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	39.0/1.88		15.7/1.52	123.6/5.34	31.8/1.93	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	31.3/1.25	22.4/1.25	13.8/0.84
	Subst1		72.0/4.79	129.0/5.74	130.6/6.05	31.8/1.94	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	28.9-29.3/1.20-1.46	31.3/1.25	22.4/1.25	13.8/0.84

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	H29	H30	H31
1,1	bDGlcp	4.66	3.42	3.50	3.54	3.59	3.89 4.06
1	Subst	3.95 4.35	4.19	4.32	5.67	5.92	1.95	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.88		1.52	5.34	1.93	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.25	1.25	0.84
	Subst1		4.79	5.74	6.05	1.94	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.20 1.46	1.25	1.25	0.84

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	C29	C30	C31
1,1	bDGlcp	103.5	73.4	76.9	70.1	76.6	61.1
1	Subst	68.8	52.9	70.6	130.9	131.1	32.2	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	39.0	134.7	15.7	123.6	31.8	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	31.3	22.4	13.8
	Subst1	172.1	72.0	129.0	130.6	31.8	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	28.9 29.3	31.3	22.4	13.8

There is only one chemically distinct structure:

$CCCCCCCCCCCC/C=C(\C)CCCCCCCCCCC/C=C/C(O)C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)NC(=O)C(O)/C=C/CCCCCCCCCCCCC$

SVG MW SMILES 3D mol Ionize