Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 11432466Publication DOI: 10.1007/s11745-001-0752-2Journal NLM ID: 0060450Publisher: American Oil Chemists' Society
Correspondence: jkliu
mail.kib.ac.cn
Institutions: Department of Phytochemisty, Kunming Institute of Botany, Kunming, China, College of Life Sciences, Northwest Science and Technology University of Agriculture and Forestry, Shaanxi, China, Department of Phytochemisty, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China, College of Life Sciences, Northwest Science and Technology, University of Agriculture and Forestry, Yangling, China
A new 9-methyl-sphinga-4,8-dienine-containing glucocerebroside (1), together with two additional known analogs, cerebrosides B and D, was isolated from the chloroform-soluble lipid fraction of the ethanol and chloroform/methanol extract of the fruiting bodies of the basidiomycete Polyporus ellisii Berk. and characterized. The structure and relative stereochemistry of the new compound were identified as (25,3R,4E,8E)-I -(β-D-glucopyranosyl)-3-hydroxy-2-[(R)-2′hydroxyheptadecanoyl] amino-9-methyl-4,8-octadecadiene by means of spectroscopic (1H, 13C, and two-dimensional nuclear magnetic resonance; mass spectrometry) and chemical methods.
glycosphingolipid, cerebroside, Polyporus ellisii
Structure type: monomer ; 754 [M−H]−
C
43H
80NO
9Location inside paper: p.526, scheme 2(3), table 2
Trivial name: cerebroside D
Compound class: glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, GC-MS, TLC, MS, NMR-1D, methanolysis, extraction, optical rotation measurement, acetylation, CC, reversed-phase chromatography, melting point determination, LC
Biological activity: antifungal activity
Related record ID(s): 40549, 40812, 40813, 40814, 42250, 42251, 42252, 42253, 42254, 42255, 42256, 42257, 42258, 42259, 42260, 42261, 42262, 42263, 42264, 42265, 42266, 42267, 42268, 42269, 42270, 42271, 42272, 42273, 42274, 42275, 42276, 42279, 42280, 42281, 42282, 42287, 42288, 43402, 43403, 43418, 43419, 43672, 43673, 43674, 43679, 43680, 43704, 50150
NCBI Taxonomy refs (TaxIDs): 80570
Show glycosyltransferases
NMR conditions: in C5D5N
[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
1 bDGlcp 105.30 74.87 78.23 71.45 78.23 62.55
2 lR2HOSte 175.52 72.21 35.46 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 28.04 22.73 14.05
xXSR9b1SphdC19 69.83 54.47 72.37 131.64 132.22 32.86 31.93 123.99 135.64 39.80 28.17 29.41-29.80 29.41-29.80 29.41-29.80 29.41-29.80 31.93 22.73 14.05 15.93
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19
1 bDGlcp 4.87 4.00 4.20 4.18 3.87 4.32-4.47
2 lR2HOSte - 4.52 1.75-2.15 1.25 1.25 1.25 1.25 1.25 1.25 1.25 1.25 1.25 1.25 1.25 1.25 1.25 1.25 0.84
xXSR9b1SphdC19 4.20-4.69 4.73 4.68 5.93 5.97 2.15 2.15 5.23 - 1.98 1.35 1.25 1.25 1.25 1.25 1.25 1.25 0.84 1.59
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
1 bDGlcp 105.30/4.87 74.87/4.00 78.23/4.20 71.45/4.18 78.23/3.87 62.55/4.32-4.47
2 lR2HOSte 72.21/4.52 35.46/1.75-2.15 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 28.04/1.25 22.73/1.25 14.05/0.84
xXSR9b1SphdC19 69.83/4.20-4.69 54.47/4.73 72.37/4.68 131.64/5.93 132.22/5.97 32.86/2.15 31.93/2.15 123.99/5.23 39.80/1.98 28.17/1.35 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 29.41-29.80/1.25 31.93/1.25 22.73/1.25 14.05/0.84 15.93/1.59
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 |
|---|
| 1 | bDGlcp | 4.87 | 4.00 | 4.20 | 4.18 | 3.87 | 4.32
4.47 | |
| 2 | lR2HOSte |
| 4.52 | 1.75
2.15 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 0.84 | |
| | xXSR9b1SphdC19 | 4.20
4.69 | 4.73 | 4.68 | 5.93 | 5.97 | 2.15 | 2.15 | 5.23 |
| 1.98 | 1.35 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 1.25 | 0.84 | 1.59 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 |
|---|
| 1 | bDGlcp | 105.30 | 74.87 | 78.23 | 71.45 | 78.23 | 62.55 | |
| 2 | lR2HOSte | 175.52 | 72.21 | 35.46 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 28.04 | 22.73 | 14.05 | |
| | xXSR9b1SphdC19 | 69.83 | 54.47 | 72.37 | 131.64 | 132.22 | 32.86 | 31.93 | 123.99 | 135.64 | 39.80 | 28.17 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 29.41
29.80 | 31.93 | 22.73 | 14.05 | 15.93 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
(later renamed to: Albatrellus ellisii)