Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Hevea brasiliensis
Organ / tissue: leaf
The structure was elucidated in this paperNCBI PubMed ID: 26626161Publication DOI: 10.1016/j.phytochem.2015.11.009Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Rukachaisirikul V <vatcharin.r
psu.ac.th>
Institutions: National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, Klong Luang, Thailand, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Thailand, Natural Products Research Center of Excellence and Department of Microbiology, Faculty of Science, Prince of Songkla University, Hat Yai, Thailand, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok, Thailand
Investigation of the fungus Phoma herbarum PSU-H256 isolated from a leaf of Hevea brasiliensis resulted in the isolation of eight terezine derivatives (E-L) together with four known compounds. Their structures were established by analysis of spectroscopic evidence. For terezines E and H, their structures were confirmed by single-crystal X-ray diffraction crystallography. In addition, the absolute configuration at C-7 in terezine E was established by Mosher's method. Terezines K and L were tested for antibacterial, antimalarial, antimycobacterial and cytotoxic activities, but were inactive.
Phoma herbarum, Euphorbiaceae, Hevea brasiliensis, pyrazine, pyrazinone
Structure type: monomer ; 473.1532 [M+Na]+
C
21H
26N
2O
9Location inside paper: Fig. 1, 8, Table 3
Trivial name: terezine L
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, TLC, biological assays, UV, extraction, microscopy, optical rotation measurement, CC, cell growth, melting point determination, antibacterial assay, cytotoxicity assay, evaporation, ECD, antimalarial assay
NCBI Taxonomy refs (TaxIDs): 73001Reference(s) to other database(s): GenDB:KP184332
Show glycosyltransferases
NMR conditions: in (CD3)2CO
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
2 bDGlcp 97.9 74.3 78.2 71.6 77.9 62.8
Subst 149.8 150.4 154.8 132.7 189.6 129.3 133.8 116.2 163.3 116.2 133.8 30.0 20.8 21.0 54.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
2 bDGlcp 5.76 3.54 3.50 3.46 3.37 3.68-3.83
Subst - - - - - - - 7.90 6.97 - 6.97 7.90 3.46 1.31 1.29 3.93
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
2 bDGlcp 97.9/5.76 74.3/3.54 78.2/3.50 71.6/3.46 77.9/3.37 62.8/3.68-3.83
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 |
|---|
| 2 | bDGlcp | 5.76 | 3.54 | 3.50 | 3.46 | 3.37 | 3.68
3.83 | |
| | Subst |
|
|
|
|
|
|
| 7.90 | 6.97 |
| 6.97 | 7.90 | 3.46 | 1.31 | 1.29 | 3.93 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 2 | bDGlcp | 97.9 | 74.3 | 78.2 | 71.6 | 77.9 | 62.8 | |
| | Subst | 149.8 | 150.4 | 154.8 | 132.7 | 189.6 | 129.3 | 133.8 | 116.2 | 163.3 | 116.2 | 133.8 | 30.0 | 20.8 | 21.0 | 54.1 |
|
There is only one chemically distinct structure:
Found 
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