Acetylstachyflin

Acetylstachyflin

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Category Antibiotics
Catalog number BBF-00008
CAS
Molecular Weight 427.53
Molecular Formula C25H33NO5

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Description

Stachyflin and acetylstachyflin, produced by Stachybotrys sp. RF-7260, were found to have potent anti-influenza A virus activity.

Specification

Synonyms 3H-Naphtho[1',8a':5,6]pyrano[2,3-e]isoindol-3-one, 11-(acetyloxy)-1,2,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5-hydroxy-6a,7,10,10-tetramethyl-, (6aR,7S,9aS,11S,13aS)-
IUPAC Name [(1S,13R,14S,17S,19S)-10-hydroxy-13,14,18,18-tetramethyl-7-oxo-2-oxa-6-azapentacyclo[11.8.0.01,17.03,11.04,8]henicosa-3,8,10-trien-19-yl] acetate
Canonical SMILES CC1CCC2C(C(CCC23C1(CC4=C(C=C5C(=C4O3)CNC5=O)O)C)OC(=O)C)(C)C
InChI InChI=1S/C25H33NO5/c1-13-6-7-19-23(3,4)20(30-14(2)27)8-9-25(19)24(13,5)11-16-18(28)10-15-17(21(16)31-25)12-26-22(15)29/h10,13,19-20,28H,6-9,11-12H2,1-5H3,(H,26,29)/t13-,19-,20-,24+,25-/m0/s1
InChI Key PYXJLZDIRGAZQG-RGXVLITJSA-N

Properties

Appearance Colorless needle Crystal
Antibiotic Activity Spectrum viruses
Melting Point >300°C

Reference Reading

1. Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp. RF-7260. I. Isolation, structure elucidation and biological activities
Kazuyuki Minagawa, Shuichi Kouzuki, Jun Yoshimoto, Yoshimi Kawamura, Hiroyoshi Tani, Tatsuo Iwata, Yoshihiro Terui, Hiroshi Nakai, Shigenori Yagi, Naohiko Hattori, Tamio Fujiwara, Toshiyuki Kamigauchi J Antibiot (Tokyo). 2002 Feb;55(2):155-64. doi: 10.7164/antibiotics.55.155.
Two novel compounds, stachyflin and acetylstachyflin, have been isolated by solid-state fermentation of Stachybotrys sp. RF-7260. The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decalin. The absolute stereochemistry of stachyflins was determined by circular dichroism analysis. Stachyflin showed antiviral activity against influenza A virus (H1N1) in vitro with an IC50 value of 0.003 microM. Acetylstachyflin was about 77-fold less active than stachyflin.
2. Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp. RF-7260. II. Synthesis and preliminary structure-activity relationships of stachyflin derivatives
Kazuyuki Minagawa, Shuichi Kouzuki, Toshiyuki Kamigauchi J Antibiot (Tokyo). 2002 Feb;55(2):165-71. doi: 10.7164/antibiotics.55.165.
Stachyflin and acetylstachyflin, produced by Stachybotrys sp. RF-7260, were found to have potent anti-influenza A virus activity. Stachyflin is a new class of hemagglutinin fusion inhibitors of influenza A virus. Several derivatives were synthesized from acetylstachyflin and subjected to preliminary examination of their structure-activity relationships. Among them, the 3-oxo and 3,8'-dioxo derivatives showed potent antiviral activity similar to stachyflin. The 3-epi derivative was four times less active than stachyflin. Modification of the 6'-hydroxy group and the C-5' position markedly diminished the antiviral activity.
3. Novel stachyflin derivatives from Stachybotrys sp. RF-7260. Fermentation, isolation, structure elucidation and biological activities
Kazuyuki Minagawa, Shuichi Kouzuki, Hiroyoshi Tani, Kikuo Ishii, Tatsuo Tanimoto, Yoshihiro Terui, Toshiyuki Kamigauchi J Antibiot (Tokyo). 2002 Mar;55(3):239-48. doi: 10.7164/antibiotics.55.239.
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.

Bio Calculators

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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