Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 01:21:27 UTC
Update Date2025-10-07 16:05:29 UTC
Metabolite IDMMDBc0008529
Metabolite Identification
Common NameFeigrisolide C
DescriptionFeigrisolide C is a secondary metabolite belonging to the class of macrotetrolide antibiotics. It is extracted from marine bacteria of the genus Streptomyces and has been studied for its bioactive properties. Notably, Feigrisolide C, alongside bonactin, has demonstrated the ability to inhibit the growth of the pathogenic fungus Magnaporthe oryzae, which is responsible for wheat blast disease. In experimental settings, Feigrisolide C was shown to reduce mycelial growth in a dose-dependent manner, although it was less effective than bonactin, with minimal inhibitory concentrations of 0.025 µg/disk. This represents the first report of Feigrisolide C's role in inhibiting mycelial development, conidia production, and morphological changes in germinated conidia of the fungus, effectively controlling wheat blast disease in vivo (PMID:36015411 ). The structural identity of Feigrisolide C has been confirmed as (2'S,3'S,6'R,8'R)-homononactoyl (2R,3R,6S,8S)-nonactic acid through total synthesis, correcting earlier misconceptions about its macrodiolide structure (PMID:16277346 ).
Structure
SynonymsNot Available
Molecular FormulaC21H36O7
Average Mass400.512
Monoisotopic Mass400.246103499
IUPAC Name(1S,2S,5S,8R,9R,12S,14R)-8-hydroxy-5-[(2R)-2-hydroxybutyl]-2,9,12-trimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione
Traditional Name(1S,2S,5S,8R,9R,12S,14R)-8-hydroxy-5-[(2R)-2-hydroxybutyl]-2,9,12-trimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CC)C[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C)C(=O)O[C@@]([H])(C)C[C@@]2([H])CC[C@]([H])(O2)[C@]([H])(C)C(=O)O1
InChI Identifier
InChI=1S/C21H36O7/c1-5-15(22)11-17-6-8-18(23)13(3)20(24)26-12(2)10-16-7-9-19(27-16)14(4)21(25)28-17/h12-19,22-23H,5-11H2,1-4H3/t12-,13+,14-,15+,16+,17-,18+,19-/m0/s1
InChI KeyHQBGZNNKSCTNKH-JWFKEXIPSA-N