Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Sedum sediforme
Organ / tissue: stem
The structure was elucidated in this paperNCBI PubMed ID: 16183294Publication DOI: 10.1016/j.bmc.2005.08.046Journal NLM ID: 9413298Publisher: Elsevier
Correspondence: Vicente F <francisca_vicente
merck.com>
Institutions: Infectious Diseases, Merck Research Laboratories, Rahway, USA, Centro de Investigación Básica, Merck Research Laboratories, Merck, Sharp and Dohme de España, Madrid, Spain, Department of Molecular Biology, Aarhus University, Arhus, Denmark
A novel sordarin derivative, moriniafungin (1), containing a 2-hydroxysebacic acid residue linked to C-3' of the sordarose residue of sordarin through a 1,3-dioxolan-4-one ring was isolated from the fungus Morinia pestalozzioides. Isolation of moriniafungin employed a highly specific bioassay consisting of a panel of Saccharomyces cerevisiae strains containing chimeric eEF2 for Candida glabrata, Candida krusei, Candida lusitaniae, Crytpococcus neoformans, and Aspergillus fumigatus as well as wild type and human eEF2. Moriniafungin exhibited an MIC of 6 microg/mL versus Candida albicans and IC(50)'s ranging from 0.9 to 70 microg/mL against a panel of clinically relevant Candida strains. Moriniafungin was shown to inhibit in vitro translation in the chimeric S. cerevisae strains at levels consistent with the observed IC(50). Moriniafungin has the broadest antifungal spectrum and most potent activity of any natural sordarin analog identified to date
natural products, taxonomy, antifungal compound, sordarin, Morinia, fungal protein synthesis
Structure type: monomer ; 691.3705 [M+H]+
C
37H
54O
12Location inside paper: Fig. 1, Table 2
Trivial name: moriniafungin
Compound class: glycoside
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, extraction, optical rotation measurement, column chromatography, cell growth, centrifugation, antifungal activity test, countercurrent chromatography, ESI-FTMS
Biological activity: moriniafungin shows antifungal activity against the ascomycetous yeasts, S. cerevisiae, C. albicans, and C. glabrata, but displays no antifungal activity against the basidiomycetous yeast Cr. neoformans and the ascomycetous yeasts C. parapsilosis, C. krusei, and C. lusitaniae. Moriniafungin has acquired significant activity against the C. krusei chimeric construct, against which sordarin is completely inactive
Comments, role: atom enumeration is according to the Fig. 1 in the paper
Related record ID(s): 49729
NCBI Taxonomy refs (TaxIDs): 323524
Show glycosyltransferases
NMR conditions: in CD2Cl2
[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
17,3 Subst 172.9 76.2 32.5 25.0-29.3 25.0-29.3 25.0-29.3 25.0-29.3 25.0-29.3 34.2 178.9
17,4 Me 62.1
17 bDSugp 98.7 74.1 108.2 83.0 70.1 17.7
Subst1 148.8 131.1 46.9 29.8 59.2 72.9 65.9 29.5 41.6 31.4 32.4 26.6 42.1 28.0 21.3 22.8 205.1 176.2 74.9 17.5
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
17,3 Subst - 4.594 1.65-1.83 1.26-1.6 1.26-1.6 1.26-1.6 1.26-1.6 1.26-1.6 2.353 -
17,4 Me 3.473
17 bDSugp 4.562 3.709 - 3.321 3.540 1.316
Subst1 - 6.089 2.698 1.25-1.95 - - - 1.80-1.94 1.77 2.07 1.22-2.05 0.99-1.86 1.994 2.318 1.032 0.970 - - 3.716-3.996 0.808
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
17,3 Subst 76.2/4.594 32.5/1.65-1.83 25.0-29.3/1.26-1.6 25.0-29.3/1.26-1.6 25.0-29.3/1.26-1.6 25.0-29.3/1.26-1.6 25.0-29.3/1.26-1.6 34.2/2.353
17,4 Me 62.1/3.473
17 bDSugp 98.7/4.562 74.1/3.709 83.0/3.321 70.1/3.540 17.7/1.316
Subst1 131.1/6.089 46.9/2.698 29.8/1.25-1.95 29.5/1.80-1.94 41.6/1.77 31.4/2.07 32.4/1.22-2.05 26.6/0.99-1.86 42.1/1.994 28.0/2.318 21.3/1.032 22.8/0.970 74.9/3.716-3.996 17.5/0.808
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 |
|---|
| 17,3 | Subst |
| 4.594 | 1.65
1.83 | 1.26
1.6 | 1.26
1.6 | 1.26
1.6 | 1.26
1.6 | 1.26
1.6 | 2.353 |
| |
| 17,4 | Me | 3.473 | |
| 17 | bDSugp | 4.562 | 3.709 |
| 3.321 | 3.540 | 1.316 | |
| | Subst1 |
| 6.089 | 2.698 | 1.25
1.95 |
|
|
| 1.80
1.94 | 1.77 | 2.07 | 1.22
2.05 | 0.99
1.86 | 1.994 | 2.318 | 1.032 | 0.970 |
|
| 3.716
3.996 | 0.808 |
|
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 |
|---|
| 17,3 | Subst | 172.9 | 76.2 | 32.5 | 25.0
29.3 | 25.0
29.3 | 25.0
29.3 | 25.0
29.3 | 25.0
29.3 | 34.2 | 178.9 | |
| 17,4 | Me | 62.1 | |
| 17 | bDSugp | 98.7 | 74.1 | 108.2 | 83.0 | 70.1 | 17.7 | |
| | Subst1 | 148.8 | 131.1 | 46.9 | 29.8 | 59.2 | 72.9 | 65.9 | 29.5 | 41.6 | 31.4 | 32.4 | 26.6 | 42.1 | 28.0 | 21.3 | 22.8 | 205.1 | 176.2 | 74.9 | 17.5 |
|
There is only one chemically distinct structure:
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Halymenia dilatata
The structure was elucidated in this paperNCBI PubMed ID: 8968393Publication DOI: 10.7164/antibiotics.49.998Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Institutions: Marine Biotechnology Institute, Shimizu Laboratories, Shimizu, Japan
Novel antimicroalgal substances halymecins A (1), B (2) and C (3) were isolated from the fermentation broth of a Fusarium sp. and halymecins D (4) and E (5) from an Acremonium sp. The structures of these halymecins, Fig. 1, were determined based on extensive 2D NMR studies as well as mass spectral data. These chemical structures are conjugates of di- and trihydroxydecanoic acid. Halymecin A showed antimicroalgal activity against Skeletonema costatum
glycolipid, antimicrobial activity, Acremonium sp., Fusarium sp., halymecins
Structure type: monomer ; 965.5701 [M-H]-
C
48H
86O
19Location inside paper: Fig. 1, structure 2, Table 1, 2
Trivial name: halymecin B
Compound class: glycolipid
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, acid hydrolysis, methanolysis, HPLC, UV, extraction, optical rotation measurement, column chromatography, cell growth, centrifugal partition chromatography, centrifugation, countercurrent chromatography
Comments, role: atom enumeration is according to the IUPAC
Related record ID(s): 48029
NCBI Taxonomy refs (TaxIDs): 5506
Show glycosyltransferases
NMR conditions: in 50%CDCl3 / 50%CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10
5,3 Ac 171.59 21.28
5,5,5,3 bDManp 101.15 72.12 75.87 68.26 77.47 62.67
5,5,5 Subst 172.91 41.62 75.57 41.87 69.67 38.47 25.92 23.17-34.87 23.17-34.87 14.40
5,5 Subst 172.62 42.62 66.50 42.49 73.39 23.17-34.87 23.17-34.87 23.17-34.87 23.17-34.87 14.42
5 Subst 171.12 39.80 69.00 38.82 72.24 23.17-34.87 23.17-34.87 23.17-34.87 23.17-34.87 14.42
Subst 174.94 43.15 66.20 41.70 73.61 23.17-34.87 23.17-34.87 23.17-34.87 23.17-34.87 14.42
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10
5,3 Ac - 2.01
5,5,5,3 bDManp 4.57 3.87 3.45 3.62 3.45 3.62
5,5,5 Subst - 2.56-2.75 4.28 1.56 3.63 1.41 1.41 1.32 1.32 0.86
5,5 Subst - 2.45 4.07 1.70-1.80 5.04 1.60 1.32 1.32 1.32 0.86
5 Subst - 2.55-2.65 5.21 1.85-1.95 4.93 1.60 1.32 1.32 1.32 0.86
Subst - 2.35-2.45 3.95 1.65-1.81 5.01 1.60 1.32 1.32 1.32 0.86
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
5,3 Ac 21.28/2.01
5,5,5,3 bDManp 101.15/4.57 72.12/3.87 75.87/3.45 68.26/3.62 77.47/3.45 62.67/3.62
5,5,5 Subst 41.62/2.56-2.75 75.57/4.28 41.87/1.56 69.67/3.63 38.47/1.41 25.92/1.41 23.17-34.87/1.32 23.17-34.87/1.32 14.40/0.86
5,5 Subst 42.62/2.45 66.50/4.07 42.49/1.70-1.80 73.39/5.04 23.17-34.87/1.60 23.17-34.87/1.32 23.17-34.87/1.32 23.17-34.87/1.32 14.42/0.86
5 Subst 39.80/2.55-2.65 69.00/5.21 38.82/1.85-1.95 72.24/4.93 23.17-34.87/1.60 23.17-34.87/1.32 23.17-34.87/1.32 23.17-34.87/1.32 14.42/0.86
Subst 43.15/2.35-2.45 66.20/3.95 41.70/1.65-1.81 73.61/5.01 23.17-34.87/1.60 23.17-34.87/1.32 23.17-34.87/1.32 23.17-34.87/1.32 14.42/0.86
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 |
|---|
| 5,3 | Ac |
| 2.01 | |
| 5,5,5,3 | bDManp | 4.57 | 3.87 | 3.45 | 3.62 | 3.45 | 3.62 | |
| 5,5,5 | Subst |
| 2.56
2.75 | 4.28 | 1.56 | 3.63 | 1.41 | 1.41 | 1.32 | 1.32 | 0.86 |
| 5,5 | Subst |
| 2.45 | 4.07 | 1.70
1.80 | 5.04 | 1.60 | 1.32 | 1.32 | 1.32 | 0.86 |
| 5 | Subst |
| 2.55
2.65 | 5.21 | 1.85
1.95 | 4.93 | 1.60 | 1.32 | 1.32 | 1.32 | 0.86 |
| | Subst |
| 2.35
2.45 | 3.95 | 1.65
1.81 | 5.01 | 1.60 | 1.32 | 1.32 | 1.32 | 0.86 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 |
|---|
| 5,3 | Ac | 171.59 | 21.28 | |
| 5,5,5,3 | bDManp | 101.15 | 72.12 | 75.87 | 68.26 | 77.47 | 62.67 | |
| 5,5,5 | Subst | 172.91 | 41.62 | 75.57 | 41.87 | 69.67 | 38.47 | 25.92 | 23.17
34.87 | 23.17
34.87 | 14.40 |
| 5,5 | Subst | 172.62 | 42.62 | 66.50 | 42.49 | 73.39 | 23.17
34.87 | 23.17
34.87 | 23.17
34.87 | 23.17
34.87 | 14.42 |
| 5 | Subst | 171.12 | 39.80 | 69.00 | 38.82 | 72.24 | 23.17
34.87 | 23.17
34.87 | 23.17
34.87 | 23.17
34.87 | 14.42 |
| | Subst | 174.94 | 43.15 | 66.20 | 41.70 | 73.61 | 23.17
34.87 | 23.17
34.87 | 23.17
34.87 | 23.17
34.87 | 14.42 |
|
There is only one chemically distinct structure:
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