Novel stachyflin derivatives from Stachybotrys sp. RF-7260. Fermentation, isolation, structure elucidation and biological activities.
Stachybotrys sp. RF-7260 was found to produce stachyflins, novel anti-influenza virus agents, under solid-state fermentation conditions. Feeding DL-lysine to a culture of Stachybotrys sp. RF-7260 induced the formation of the novel compounds, SQ-02-S-L2 and -L1, and feeding DL-valine the formation of SQ-02-S-VI and -V2. The structures of these metabolites were determined by detailed 2D NMR analyses in comparison with acetylstachyflin. SQ-02-S-L2 and -L1 have the lysine moiety and SQ-02-S-V1 has the valine moiety. SQ-02-S-V2 has an amidine moiety instead of the lactam moiety in acetylstachyflin. SQ-02-S-L2, -L1 and -V1, substituted on the lactam amide hydrogen, displayed only a low level of the antiviral activity. However, deacetyl SQ-02-S-V2 showed potent antiviral activity similar to stachyflin.
Minagawa
Kazuyuki
K
Shionogi Research Laboratories, Shionogi & Co, Ltd, Osaka, Japan. kazuyuki.minagawa@shionogi.co.jp
Kouzuki
Shuichi
S
Tani
Hiroyoshi
H
Ishii
Kikuo
K
Tanimoto
Tatsuo
T
Terui
Yoshihiro
Y
Kamigauchi
Toshiyuki
T
D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002417:Cattle; D002460:Cell Line; D005285:Fermentation; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009980:Influenza A virus / Q000187:drug effects; D007668:Kidney / Q000166:cytology; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013191:Stachybotrys / Q000378:metabolism*; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D012717:Sesquiterpenes; C120519:stachyflin