Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
Organ / tissue: root
 
The structure was elucidated in this paper
Publication DOI: 10.1021/ol9905295
Journal NLM ID: 100890393
Publisher: American Chemical Society
Correspondence: Nikaido T <nikaidophar.toho-u.ac.jp>
Institutions: School of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba, 274-8510, Japan, School of Pharmaceutical Sciences, Beijing Medical University, Beijing 100083, China

The structure of echinothiophene, the β-D-glucoside of a benzo[b]thiophene lactone bearing a novel skeleton, has been deduced from extensive NMR and MS studies. The compound undergoes facile epimerization at the C-6 center, perhaps through the enol 2. Molecular mechanics and dynamics calculations indicated that the structure 1 (C-6, R) is more stable than 3 (C-6, S).

Echinops grijissii, benzothiophene glycoside, echinothiophene

Structure type: monomer ; 495 [M+Na]+
C₂₃H₂₆O₁₀S
Location inside paper: echinothiophene, compound 1, table 1, fig. 1
Trivial name: echinothiophene
Compound class: benzothiophene glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
 
Methods: 13C NMR, 1H NMR, IR, HPLC, UV, molecular modeling, molecular mechanics, RP-HPLC, HMBC, DEPT, COSY, NOESY, HOHAHA, HSQC, HR-FAB-MS, molecular dynamics
Comments, role: echinothiophene in MeOH solution exists as a inseparatable mixture of (C-6, R) and (C-6, S) epimers with molar ratio of ca. 2:3, compound 1 was obtained via crystallization from aqueous MeOH
3D data: conformation data
 
NCBI Taxonomy refs (TaxIDs): 1804979
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NMR conditions: in DMSO-d6 at 353 K       [as TSV]

1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 5 bDGlcp 4.96 3.32 3.36 3.24 3.37 3.53 3.75     Subst 7.36 7.88 6.28 6.02 6.39 6.10 5.79 2.21 3.44 4.80

13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 5 bDGlcp 102.2 73.1 76.5 69.7 76.9 60.7     Subst 142.6 119.1 127.8 116.3 149.3 137.4 79.9 168.3 119.0 154.4 124.6 131.8 129.9 133.1 35.5 60.1 58.5

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