Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: whole plant
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(99)00056-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: College of Pharmacy, Seoul National University, Seoul 151-742, South Korea, College of Pharmacy, Ewha Womans University, Seoul 120-750, South Korea
A new steroidal glycoside, 2α,3β-(22R)-trihydroxycholestan-6-one-22-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside, was isolated from the whole plants of Lepisorus ussuriensis, together with α-ecdysone and ecdysterone. Their structures were determined by means of spectroscopic and chemical methods.
ecdysterone, Lepisorus ussuriensis, Polypodiaceae, steroid glycoside, 2α, 3β-(22R)-trihydroxycholestane-6-one-22-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside, α-ecdysone
Structure type: oligomer ; 729 [M+Na]+
C
38H
64O
13Location inside paper: compound 1, p. 453, table 1
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 1H NMR, IR, FAB-MS, TLC, HPLC, optical rotation measurement, HMBC, HCl hydrolysis, 13C NMR COSY
Comments, role: NMR temperature was not specified
NCBI Taxonomy refs (TaxIDs): 699700
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 C20 C21 C22 C23 C24 C25 C26 C27
22,2 bDGlcp 105.5 75.5 78.1 71.8 78.1 62.9
22 aLArap 103.4 80.1 72.5 67.4 63.9
Subst 38.1 67.4 68.7 33.2 54.6 214.3 43.4 41.0 37.1 40.6 21.6 39.8 43.1 56.3 24.2 27.7 53.5 12.0 23.9 40.7 13.6 83.8 27.1 36.2 28.6 23.1 22.8
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
22,2 bDGlcp 5.15 4.1-4.4 4.1-4.4 4.1-4.4 3.81-4.4 4.1-4.4
22 aLArap 5.13 4.1-4.4 4.1-4.4 4.1-4.4 3.81-4.4
Subst ? ? ? ? 2.99 - ? ? ? - ? ? - ? ? ? ? 0.57 0.86 ? 1.12 3.81 ? ? ? 0.95 0.95
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
22,2 bDGlcp 105.5/5.15 75.5/4.1-4.4 78.1/4.1-4.4 71.8/4.1-4.4 78.1/3.81-4.4 62.9/4.1-4.4
22 aLArap 103.4/5.13 80.1/4.1-4.4 72.5/4.1-4.4 67.4/4.1-4.4 63.9/3.81-4.4
Subst 38.1/? 67.4/? 68.7/? 33.2/? 54.6/2.99 43.4/? 41.0/? 37.1/? 21.6/? 39.8/? 56.3/? 24.2/? 27.7/? 53.5/? 12.0/0.57 23.9/0.86 40.7/? 13.6/1.12 83.8/3.81 27.1/? 36.2/? 28.6/? 23.1/0.95 22.8/0.95
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 |
|---|
| 22,2 | bDGlcp | 5.15 | 4.1
4.4 | 4.1
4.4 | 4.1
4.4 | 3.81
4.4 | 4.1
4.4 | |
| 22 | aLArap | 5.13 | 4.1
4.4 | 4.1
4.4 | 4.1
4.4 | 3.81
4.4 | |
| | Subst | ? | ? | ? | ? | 2.99 |
| ? | ? | ? |
| ? | ? |
| ? | ? | ? | ? | 0.57 | 0.86 | ? | 1.12 | 3.81 | ? | ? | ? | 0.95 | 0.95 |
|
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 |
|---|
| 22,2 | bDGlcp | 105.5 | 75.5 | 78.1 | 71.8 | 78.1 | 62.9 | |
| 22 | aLArap | 103.4 | 80.1 | 72.5 | 67.4 | 63.9 | |
| | Subst | 38.1 | 67.4 | 68.7 | 33.2 | 54.6 | 214.3 | 43.4 | 41.0 | 37.1 | 40.6 | 21.6 | 39.8 | 43.1 | 56.3 | 24.2 | 27.7 | 53.5 | 12.0 | 23.9 | 40.7 | 13.6 | 83.8 | 27.1 | 36.2 | 28.6 | 23.1 | 22.8 |
|
There is only one chemically distinct structure:
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