Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 10423860Publication DOI: 10.1016/s0031-9422(99)00128-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Botany, University of British Columbia, Vancouver, Canada, North American Reishi, Gibsons, British Columbia, Canada, Department of Medicine, Terry Fox Laboratory, University of British Columbia, Vancouver, Canada, North American Reishi, Gibsons, Canada
Activity guided fractionations led to the isolation of two antitumor compounds 5a,8a-epidioxy-24(R)-methylcholesta-6,22-dien-3β-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3β-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-β-D-glucopyranoside and 22-dihydroergosteryl-3-O-β-D-glucopyranoside were also isolated. The structures of hitherto unknown sterols were established by 1D and 2D NMR spectroscopic techniques with the former synthesized in order to confirm the identity of the sugar moiety by chemical correlation. The glycosylated form of ergosterol peroxide was found to be a greater inhibitor to the proliferation of K562, Jurkat, WM-1341, HL-60 and RPMI-8226 tumor cell lines by 10 to 40% at 10 mg/ml than its previously identified aglycone, 5a,8a-epidioxy-24(R)-methylcholesta-6,22-dien-3β-ol
antitumor activity, Cordyceps sinensis, steroidal glycosides, Cordyceps sinenis
Structure type: monomer
C
34H
56O
10Location inside paper: p.892, structure 3, Table 1, 3, Table 2, 3
Trivial name: ergosterol-β-D-glucopyranoside, ergosterol β-D-glucopyranoside
Compound class: saponin glycoside, glycoside, steroid glycoside, sterylglycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ESI-MS, FTIR, extraction, optical rotation measurement, CC, HMBC, antitumor activity assay, HMQC, APT, HRMS
Biological activity: Compound shows no inhibitorial activity of the malignant cell lines
Synthetic data: chemical
Comments, role: NMR temperature was not specified
Related record ID(s): 46035, 46037, 49634
NCBI Taxonomy refs (TaxIDs): 72228Reference(s) to other database(s): GenDB:KT240140
Show glycosyltransferases
NMR conditions: in (C)
[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 bDGlcp 100.9 73.3 76.2 69.8 77.4 61.5
Subst 36.9 29.5 73.3 37.9 139.0 119.6 115.9 141.1 45.9 29.3 20.7 38.7 42.5 54.2 22.6 27.6 55.4 11.6 15.7 40.1 20.6 135.3 131.6 42.5 32.7 22.6 19.4 17.1
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 bDGlcp 4.24 2.98 3.13 3.14 3.45 3.46-3.61
Subst ? ? ? ? - 5.52 5.34 - ? - ? ? - ? ? ? ? 0.58 0.86 ? 1.00 5.2 5.2 - ? 0.80 0.79 0.88
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 bDGlcp 100.9/4.24 73.3/2.98 76.2/3.13 69.8/3.14 77.4/3.45 61.5/3.46-3.61
Subst 36.9/? 29.5/? 73.3/? 37.9/? 119.6/5.52 115.9/5.34 45.9/? 20.7/? 38.7/? 54.2/? 22.6/? 27.6/? 55.4/? 11.6/0.58 15.7/0.86 40.1/? 20.6/1.00 135.3/5.2 131.6/5.2 32.7/? 22.6/0.80 19.4/0.79 17.1/0.88
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 | bDGlcp | 4.24 | 2.98 | 3.13 | 3.14 | 3.45 | 3.46
3.61 | |
| | Subst | ? | ? | ? | ? |
| 5.52 | 5.34 |
| ? |
| ? | ? |
| ? | ? | ? | ? | 0.58 | 0.86 | ? | 1.00 | 5.2 | 5.2 |
| ? | 0.80 | 0.79 | 0.88 |
|
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 | bDGlcp | 100.9 | 73.3 | 76.2 | 69.8 | 77.4 | 61.5 | |
| | Subst | 36.9 | 29.5 | 73.3 | 37.9 | 139.0 | 119.6 | 115.9 | 141.1 | 45.9 | 29.3 | 20.7 | 38.7 | 42.5 | 54.2 | 22.6 | 27.6 | 55.4 | 11.6 | 15.7 | 40.1 | 20.6 | 135.3 | 131.6 | 42.5 | 32.7 | 22.6 | 19.4 | 17.1 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
(later renamed to: Ophiocordyceps sinensis)