Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
 
The structure was elucidated in this paper
Publication DOI: 10.1002/hlca.201500218
Journal NLM ID: 2985094R
Publisher: Verlag Helvetica Chimica Acta
Correspondence: Bechthold A <andreas.bechtholdpharmazie.uni-freiburg.de>
Institutions: Institut für pharmazeutische Biologie und Biotechnologie, Albert-Ludwigs Universität, Freiburg, Germany, Department of Natural Products Chemistry, School of Pharmacy, China Medical University, Shenyang, China, Institute of Applied Ecology, Chinese Academy of Sciences, Shenyang, China, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China

Based on the chemical analysis and targeted bioactivity screening, a new polyketide glycoside, myrothecoside, was isolated from a terrestrial halotolerant fungus, Myrothecium sp. GS-17. The structure of myrothecoside was elucidated on the basis of extensive spectroscopic analysis including 1D- and 2D-NMR (1H,1H-COSY, HSQC, HMBC, and NOESY) experiments, combined with mass spectroscopic data and physicochemical properties. This compound exhibited weak cytotoxicity against human leukemia (HL-60) cancer cell with an IG50 value of 63.61 μm, and also antifungal activities against plant pathogenic fungi Rhizoctonia solani and Fusarium oxysporum using standard agar diffusion tests at 20 μg/disk.

antibacterial activity, fungi, secondary metabolites, Myrothecium, glycosylated polyketides

Structure type: monomer ; 512.3221 [M+H]+
C₂₇H₄₅NO₈
Location inside paper: fig. 2, Table, myrothecoside
Compound class: terpene glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
 
Methods: 13C NMR, 1H NMR, FTIR, UV, optical rotation measurement, RP-HPLC, HR-ESI-MS, HMBC, HMQC, COSY, HSQC, HCl hydrolysis, HPLC/ESI-MS
Biological activity: Myrothecoside shows a weak activity against human leukemia (HL-60) cancer cell with an IG50 value of 63.61 μM. Myrothecoside was active against plant pathogenic fungi Rhizoctonia solani and Fusarium oxysporum using standard agar diffusion tests at 20 μg/disk.
Biosynthesis and genetic data: genetic data
Comments, role: NMR temperature was not specificied
 
NCBI Taxonomy refs (TaxIDs): 1821730
Show glycosyltransferases
 
NMR conditions: in C5D5N        [as TSV]

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 H21 H22 H23 5,4 Me 3.77   5 bDManp 4.99 4.44 4.15 4.07 3.70 4.20 4.34     Subst 3.01 2.83 4.79 2.04 2.34 4.95 5.39 5.94 2.30 2.10 5.59 2.30 2.10 5.59 5.43 1.71 0.64 1.56 1.36 0.57 1.44 1.22 0.76 0.98 0.82 0.95

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 5,4 Me 60.9   5 bDManp 98.5 73.1 76.1 79.1 78.3 62.9     Subst 175.6 44.0 67.0 43.7 76.7 128.5 140.8 49.3 37.8 133.0 132.9 43.2 42.2 32.9 47.1 37.0 47.1 17.1 22.9 23.3

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