2270-41-9

Usage

Uses

Scirpentriol is a trichothecene mycotoxin.

InChI:InChI=1/C15H22O5/c1-8-3-4-14(6-16)9(5-8)20-12-10(17)11(18)13(14,2)15(12)7-19-15/h5,9-12,16-18H,3-4,6-7H2,1-2H3/t9-,10-,11-,12-,13-,14-,15-/m1/s1

Upstream product

• 2270-40-8 4,15-diacetoxyscirpenol 
• 2270-40-8 ((2S,2'R,3'R,4'S,5'S,5a'R,9a'R)-4'-acetoxy-3'-hydroxy-5',8'-dimethyl-2',3',4',5',7',9a'-hexahydrospiro[oxirane-2,10'-[2,5]methanobenzo[b]oxepin]-5a'(6'H)-yl)methyl acetate 

Downstream Products

• 81331-27-3 3α,15-bis(chloroacetoxy)scirpen-4-one 
• 80178-14-9 15-(chloroacetoxy)scirpene-3α,4β-diol 
• 80178-15-0 3α-(chloroacetoxy)scirpene-4β,15-diol 
• 80178-16-1 3α,15-bis(chloroacetoxy)scirpen-4β-ol 
• 80178-18-3 3α,4β,15-tris(chloroacetoxy)scirpene 
• 80178-17-2 4β-(chloroacetoxy)scirpene-3α,15-diol 
• 81452-35-9 C₁₅H₂₀O₅ 
• 38818-51-8 calonectrin 
• 38818-51-8 calonectrin 

Relevant academic research and scientific papers

Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay

Many Fusarium species produce trichothecenes, sesquiterpene epoxides that differ in patterns of oxygenation and esterification at carbon positions C-3, C-4, C-7, C-8, and C-15. For the first comprehensive and quantitative comparison of the effects of oxygenation and esterification on trichothecene phytotoxicity, we tested 24 precursors, intermediates, and end products of the trichothecene biosynthetic pathway in an Arabidopsis thaliana detached leaf assay. At 100 μM, the highest concentration tested, only the trichothecene precursor trichodiene was nontoxic. Among trichothecenes, toxicity varied more than 200-fold. Oxygenation at C-4, C-8, C-7/8, or C-15 was, on average, as likely to decrease as to increase toxicity. Esterification at C-4, C-8, or C-15 generally increased toxicity. Esterification at C-3 increased toxicity in one case and decreased toxicity in three of eight cases tested. Thus, the increase in structural complexity along the trichothecene biosynthetic pathway in Fusarium is not necessarily associated with an increase in phytotoxicity.

Synthesis of four carbon-13-labeled type A trichothecene mycotoxins and their application as internal standards in stable isotope dilution assays

The first stable isotope dilution assay (SIDA) for the simultaneous quantitation of the most abundant type A trichothecenes in foods and feeds was developed. Synthesis of carbon-13-labeled T2-toxin, HT2-toxin, diacetoxyscirpenol, and monoacetoxyscirpenol was accomplished by [ 13C2]-acetylation of T2-triol and scirpentriol, respectively. Scirpentriol was prepared from diacetoxyscirpenol by complete alkaline hydrolysis and subsequently was converted to [13C 6]-triacetoxyscirpentriol by peracetylation with [13C 4]-acetic anhydride. The latter compound was selectively hydrolyzed using ammonium hydroxide to give [13C4]-diacetoxyscirpenol and [13C2]-monoacetoxyscirpenol in reasonable yields. Analogously, [13C6]-T2-triacetate was prepared from T2-triol and subjected to controlled hydrolysis to yield [13C 4]-T2-toxin and [13C2]-HT2-toxin. All synthesized products were characterized by NMR and MS experiments. Using the prepared isotopically labeled standards, SIDAs were developed for the quantitation of type A trichothecenes in food and feeds. The mycotoxins were quantified by LC-single and tandem MS after cleanup on multifunctional columns. The method revealed good sensitivity with low detection and quantification limits along with excellent recovery and good precision in interassay studies. Food samples were analyzed using the developed SIDA and showed substantial contamination of oat products with T2-toxin and HT2-toxin. Diacetoxyscirpenol was detected on potatoes, whereas monoacetoxyscirpenol was not present in the analyzed samples.

Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene

The partial syntheses of two trichothecenes, calonectrin (4β,15-diacetoxy-12,13-epoxytrichothec-9-ene) and deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (4β,15-diacetoxy-3α-hydroxy-12,13-epoxytrichothec-9-ene) are described. In addition, and in order to provide further insight into the mode of action of the trichothecene mycotoxins, 3α,4β,15-tricetoxy-12,13-epi-epoxytrichothec-9-ene, of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer, epi-epoxide proved to be biologically inactive.

Antitumor agents

Novel 3-oxoscirpen-4β,15-diol esters and derivatives thereof are provided for use as antitumor agents. Also provided are processes for producing the above compounds and methods for using them to inhibit malignant tumors in mammals.

Antitumor agents

Novel mono-, di- and triacylated derivatives of scirpentriol are provided for use as antitumor agents. Also provided are methods for the production of such derivatives.