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Tenuazonic acid

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Tenuazonic acid
Category Antibiotics
Catalog number BBF-03498
CAS 610-88-8
Molecular Weight 197.23
Molecular Formula C10H15NO3
Purity >98%

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Tenuazonic acid is a nitrogen-containing heterocyclic antibiotic produced by Alternaria tenuis Auct 430 and Asp. sp. 1404. It has inhibitory effect on enterovirus, respiratory virus, vaccinia virus and herpes simplex virus. It can inhibit KB cells and amoeba in dysentery.

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Synonyms 3-acetyl-5-(butan-2-yl)-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one
Storage Store at -20°C
IUPAC Name 4-acetyl-2-butan-2-yl-3-hydroxy-1,2-dihydropyrrol-5-one
Canonical SMILES CCC(C)C1C(=C(C(=O)N1)C(=O)C)O
InChI InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)
InChI Key CEIZFXOZIQNICU-UHFFFAOYSA-N
Source Alternaria sp
Appearance Light Yellow Oil
Antibiotic Activity Spectrum viruses; parasites
Boiling Point 401.068°C at 760 mmHg
Melting Point 117°C
Flash Point 196.4±28.7 °C
Density 1.178 g/cm3
Solubility Soluble in DMSO
1. Mycotoxins: occurrence, toxicology, and exposure assessment
A J Ramos, S Marin, V Sanchis, G Cano-Sancho Food Chem Toxicol . 2013 Oct;60:218-37. doi: 10.1016/j.fct.2013.07.047.
Mycotoxins are abiotic hazards produced by certain fungi that can grow on a variety of crops. Consequently, their prevalence in plant raw materials may be relatively high. The concentration of mycotoxins in finished products is usually lower than in raw materials. In this review, occurrence and toxicology of the main mycotoxins are summarised. Furthermore, methodological approaches for exposure assessment are described. Existing exposure assessments, both through contamination and consumption data and biomarkers of exposure, for the main mycotoxins are also discussed.
2. Deacetyl- tenuazonic acid
David Siegel, Matthias Koch, Irene Nehls, Franziska Emmerling Acta Crystallogr Sect E Struct Rep Online . 2009 May 7;65(Pt 6):o1201. doi: 10.1107/S1600536809015372.
The heterocycle in the title compound {systematic name: (5S)-5-[(1S)-1-methyl-prop-yl]pyrrolidine-2,4-dione}, C(8)H(13)NO(2), is planar (r.m.s. deviation for all non-H atoms = 0.008 Å). The crystal structure is stabilized by N-H⋯O hydrogen bonding.
3. Tenuazonic acid production is dispensable for virulence, but its biosynthetic gene expression pattern is associated with the infection of Pyricularia oryzae
Choong-Soo Yun, Kazuko Yoshida, Takayuki Motoyama, Takeshi Kashiwa, Hiroyuki Osada Biosci Biotechnol Biochem . 2021 Dec 22;86(1):135-139. doi: 10.1093/bbb/zbab195.
Tenuazonic acid (TeA) is a toxin produced by the rice blast fungus Pyricularia oryzae. Although knockout of the TeA biosynthetic gene TAS1 did not affect the virulence of P. oryzae, constitutive TAS1 expression suppressed its infection. TAS1 expression was induced alongside transition of P. oryzae infection behavior. The results suggested that controlling TeA biosynthesis is important for P. oryzae infection.

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