Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1016/j.tetlet.2019.151227Journal NLM ID: 2984819RPublisher: Elsevier
Correspondence: Jang J-H <jangjh
kribb.re.kr>; Ahn JS <jsahn
kribb.re.kr>
Institutions: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan, Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea, Department of Biomolecular Science, KRIBB School of Bioscience, Korea University of Science and Technology (UST), Daejeon, South Korea, Chemical Biology Research Group, RIKEN Center for Sustainable Resource Science (CSRS), Saitama, Japan, Advanced Elements Chemistry Laboratory, RIKEN, Cluster for Pioneering Research (CPR), Saitama, Japan, Korean Collection for Type Cultures, Korea Research Institute of Bioscience and Biotechnology, Jeongeup, South Korea, Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea, RIKEN-KRIBB Joint Research Unit, RIKEN Center for Sustainable Resource Science (CSRS), Saitama, Japan
LC/MS-based chemical screening of fungal extract fraction library led to identification of three 2,3-aryl substituted furanone metabolites (1–3), including one known butenolide glycoside (1) whose stereochemistry remained unsolved and two new compounds gotjawaside and gotjawalide (2 and 3), from Auxarthron sp. KCB15F070, a fungus isolated from a soil sample of the volcanic island Jeju, Korea. Their planar structures were elucidated by 1D- and 2D-NMR spectroscopic and HRESIMS spectrometric techniques, and the absolute configurations of three compounds were solved using a combination of chemical derivatizations and computational analysis of vibrational circular dichroism (VCD) spectra.
secondary metabolites, ascomycetes, butenolide glycosides, vibrational circular dichroism
Structure type: monomer ; 522.1739 [M+Na]+
C
26H
29NO
9Location inside paper: structure 1
Trivial name: malfilamentoside B
Compound class: glycoside
Contained glycoepitopes: IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, NMR-2D, IR, extraction, LC-MS, column chromatography, antibacterial assay, HR-ESI-MS, cytotoxicity assay, derivatization, ECD, antifungal assay, VCD
Related record ID(s): 49711
NCBI Taxonomy refs (TaxIDs): 33185
Show glycosyltransferases
There is only one chemically distinct structure:
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1016/j.tetlet.2019.151227Journal NLM ID: 2984819RPublisher: Elsevier
Correspondence: Jang J-H <jangjh
kribb.re.kr>; Ahn JS <jsahn
kribb.re.kr>
Institutions: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan, Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea, Department of Biomolecular Science, KRIBB School of Bioscience, Korea University of Science and Technology (UST), Daejeon, South Korea, Chemical Biology Research Group, RIKEN Center for Sustainable Resource Science (CSRS), Saitama, Japan, Advanced Elements Chemistry Laboratory, RIKEN, Cluster for Pioneering Research (CPR), Saitama, Japan, Korean Collection for Type Cultures, Korea Research Institute of Bioscience and Biotechnology, Jeongeup, South Korea, Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea, RIKEN-KRIBB Joint Research Unit, RIKEN Center for Sustainable Resource Science (CSRS), Saitama, Japan
LC/MS-based chemical screening of fungal extract fraction library led to identification of three 2,3-aryl substituted furanone metabolites (1–3), including one known butenolide glycoside (1) whose stereochemistry remained unsolved and two new compounds gotjawaside and gotjawalide (2 and 3), from Auxarthron sp. KCB15F070, a fungus isolated from a soil sample of the volcanic island Jeju, Korea. Their planar structures were elucidated by 1D- and 2D-NMR spectroscopic and HRESIMS spectrometric techniques, and the absolute configurations of three compounds were solved using a combination of chemical derivatizations and computational analysis of vibrational circular dichroism (VCD) spectra.
secondary metabolites, ascomycetes, butenolide glycosides, vibrational circular dichroism
Structure type: monomer ; 508.1583 [M+Na]+
C
25H
27NO
9Location inside paper: structure 2, Table 1, 2
Trivial name: gotjawaside
Compound class: glycoside
Contained glycoepitopes: IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, NMR-2D, IR, extraction, LC-MS, column chromatography, antibacterial assay, HR-ESI-MS, cytotoxicity assay, derivatization, ECD, antifungal assay, VCD
Comments, role: NMR temperature was not specified; Atom enumeration is according to the structure 1 in the paper
Related record ID(s): 49710
NCBI Taxonomy refs (TaxIDs): 33185
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17
4,2 Ac 173.7 23.0
4 aDGlcpN 101.7 55.3 73.2 71.6 75.3 62.1
Subst 172.0 131.4 160.4 103.4 130.5 130.3 129.5 130.4 129.5 130.3 71.1 142.7 128.8 130.1 129.6 130.1 128.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17
4,2 Ac - 1.74
4 aDGlcpN 5.23 3.91 3.38 3.49 3.77 3.79-3.85
Subst - - - 6.31 - 7.34-7.35 7.34-7.35 7.34-7.35 7.34-7.35 7.34-7.35 5.95 - 7.46 7.41 7.34-7.35 7.41 7.46
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
4,2 Ac 23.0/1.74
4 aDGlcpN 101.7/5.23 55.3/3.91 73.2/3.38 71.6/3.49 75.3/3.77 62.1/3.79-3.85
Subst 103.4/6.31 130.3/7.34-7.35 129.5/7.34-7.35 130.4/7.34-7.35 129.5/7.34-7.35 130.3/7.34-7.35 71.1/5.95 128.8/7.46 130.1/7.41 129.6/7.34-7.35 130.1/7.41 128.8/7.46
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 |
|---|
| 4,2 | Ac |
| 1.74 | |
| 4 | aDGlcpN | 5.23 | 3.91 | 3.38 | 3.49 | 3.77 | 3.79
3.85 | |
| | Subst |
|
|
| 6.31 |
| 7.34
7.35 | 7.34
7.35 | 7.34
7.35 | 7.34
7.35 | 7.34
7.35 | 5.95 |
| 7.46 | 7.41 | 7.34
7.35 | 7.41 | 7.46 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 |
|---|
| 4,2 | Ac | 173.7 | 23.0 | |
| 4 | aDGlcpN | 101.7 | 55.3 | 73.2 | 71.6 | 75.3 | 62.1 | |
| | Subst | 172.0 | 131.4 | 160.4 | 103.4 | 130.5 | 130.3 | 129.5 | 130.4 | 129.5 | 130.3 | 71.1 | 142.7 | 128.8 | 130.1 | 129.6 | 130.1 | 128.8 |
|
There is only one chemically distinct structure:
Found 
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