Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: stem
The structure was elucidated in this paperPublication DOI: 10.1002/(SICI)1099-1573(199806)12:4<275::AID-PTR295>3.0.CO;2-IJournal NLM ID: 8904486Publisher: Chichester: Wiley
Institutions: Laboratory of Drug Discovery Research and Development, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, US, University of California Los Angeles LA Biomed, Torrance, US, University of Canterbury, Sch Phys & Chem Sci, Christchurch, New Zealand, ADT Pharmaceut LLC, Orange Beach, AL, USA
A crude aqueous extract of Mentzelia chilensis GAY (Loasaceae), the ethyl acetate extraction thereof as well as the molecular weight fraction <1000 Dalton obtained by ultrafiltration showed antiinflammatory activity on carrageenin induced rat paw oedema. Bioassay guided isolation led to the iridoid glycoside mentzeloside (syn. deutzioside) as an active principle. Mentzeloside showed a marked and significant dose dependent inhibitory activity on carrageenin induced rat paw oedema with an ED50 Of 40.4 μg/kg.
antiinflammatory activity, Iridoids, Mentzelia chilensis, Mentzelia fendleriana, anguarate, mentzeloside, deutzioside
Structure type: monomer ; 346
Location inside paper: p. 276, Scheme, compound 1
Trivial name: mentzeloside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, HPLC, UV, extraction, EI-MS, ultrfiltration, column chromatrography
Biological activity: exhibits strong antiinflamatory activity: ED50 = 40.4μg/kg
NCBI Taxonomy refs (TaxIDs): 228046
Show glycosyltransferases
NMR conditions: in CD3OD at 297 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
1 bDGlcp 100.37 74.78 78.32 71.75 77.97 62.72
Subst 96.40 136.68 112.93 43.56 79.82 55.86 59.19 41.95 16.40
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
1 bDGlcp 4.67 3.23 3.37 3.27 3.27 3.63-3.86
Subst 4.77 6.09 - 2.00 3.96 3.41 3.57 2.44 1.65
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
1 bDGlcp 100.37/4.67 74.78/3.23 78.32/3.37 71.75/3.27 77.97/3.27 62.72/3.63-3.86
Subst 96.40/4.77 136.68/6.09 43.56/2.00 79.82/3.96 55.86/3.41 59.19/3.57 41.95/2.44 16.40/1.65
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 1 | bDGlcp | 4.67 | 3.23 | 3.37 | 3.27 | 3.27 | 3.63
3.86 | |
| | Subst | 4.77 | 6.09 |
| 2.00 | 3.96 | 3.41 | 3.57 | 2.44 | 1.65 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 1 | bDGlcp | 100.37 | 74.78 | 78.32 | 71.75 | 77.97 | 62.72 | |
| | Subst | 96.40 | 136.68 | 112.93 | 43.56 | 79.82 | 55.86 | 59.19 | 41.95 | 16.40 |
|
There is only one chemically distinct structure:
Found 
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(previously named: Mentzelia fendleriana)