Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1248/cpb.46.355Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Phytochemistry Department of Shenyang Pharmaceutical University, Shenyang, China, Kyoritsu College of Pharmacy, Minato-ku, Tokyo, Japan
A new flavonol glycoside, epimedin L (1), a new chromone, 5,7-dihydroxy- 2-(p-hydroxy-phenoxy)-6-prenylchromone (2), and icariside A7 (3) were isolated from the aerial parts of Epimedium koreanum NAKAI (Berberidaceae) together with six known compounds, chaohuoside A (epimedin L) (4), 8- prenylkaempferol (5), anhydroicaritin (6), ginkgetin (7), isoginkgetin (8) and bilobetin (9). Their structures were established by spectroscopic methods and chemical evidence.
Epimedium koreanum, Berberidaceae, epimedin I, chromone derivative, icariside A7
Structure type: oligomer
Location inside paper: p. 356, Scheme, compound 4
Trivial name: glycoside
Compound class: epimedin L
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, EI-MS, methylation, FAB-MS, acid hydrolysis, HPLC, UV, extraction, CC, HMBC
Related record ID(s): 61963, 62031
NCBI Taxonomy refs (TaxIDs): 63351
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
3,3,3 Ac 169.7 21.0
3,3,6 Ac 169.5 20.6
3,3 bDGlcp 104.5 70.7 77.6 68.1 73.3 63.4
3,4 Ac 170.2 20.4
3 aLRhap 101.0 69.4 77.1 70.9 68.3 16.9
7 bDGlcp 100.5 73.3 76.5 69.6 77.1 60.6
Subst 157.3 133.8 178.0 159.0 98.2 160.5-161.6 108.4 153.0 105.5 21.3 122.0 131.0 25.4 17.7 122.0 130.4 114.1 161.5 114.1 130.4 55.5
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
3,3,3 Ac - 1.99
3,3,6 Ac - 1.94
3,3 bDGlcp 4.40 ? ? ? ? ?
3,4 Ac - 2.02
3 aLRhap 5.36 ? ? 4.83 ? 0.72
7 bDGlcp 5.04 ? ? ? ? ?
Subst - - - - 6.64 - - - - ? 5.17 - 1.60 1.68 7.89 7.16 - 7.16 7.89 3.88
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
3,3,3 Ac 21.0/1.99
3,3,6 Ac 20.6/1.94
3,3 bDGlcp 104.5/4.40 70.7/? 77.6/? 68.1/? 73.3/? 63.4/?
3,4 Ac 20.4/2.02
3 aLRhap 101.0/5.36 69.4/? 77.1/? 70.9/4.83 68.3/? 16.9/0.72
7 bDGlcp 100.5/5.04 73.3/? 76.5/? 69.6/? 77.1/? 60.6/?
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
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 |
|---|
| 3,3,3 | Ac |
| 1.99 | |
| 3,3,6 | Ac |
| 1.94 | |
| 3,3 | bDGlcp | 4.40 | ? | ? | ? | ? | ? | |
| 3,4 | Ac |
| 2.02 | |
| 3 | aLRhap | 5.36 | ? | ? | 4.83 | ? | 0.72 | |
| 7 | bDGlcp | 5.04 | ? | ? | ? | ? | ? | |
| | Subst |
|
|
|
| 6.64 |
|
|
|
| ? | 5.17 |
| 1.60 | 1.68 | 7.89 | 7.16 |
| 7.16 | 7.89 | 3.88 |
|
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 |
|---|
| 3,3,3 | Ac | 169.7 | 21.0 | |
| 3,3,6 | Ac | 169.5 | 20.6 | |
| 3,3 | bDGlcp | 104.5 | 70.7 | 77.6 | 68.1 | 73.3 | 63.4 | |
| 3,4 | Ac | 170.2 | 20.4 | |
| 3 | aLRhap | 101.0 | 69.4 | 77.1 | 70.9 | 68.3 | 16.9 | |
| 7 | bDGlcp | 100.5 | 73.3 | 76.5 | 69.6 | 77.1 | 60.6 | |
| | Subst | 157.3 | 133.8 | 178.0 | 159.0 | 98.2 | 160.5
161.6 | 108.4 | 153.0 | 105.5 | 21.3 | 122.0 | 131.0 | 25.4 | 17.7 | 122.0 | 130.4 | 114.1 | 161.5 | 114.1 | 130.4 | 55.5 |
|
There is only one chemically distinct structure:
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Displayed record 1
