Hemisynthesis and absolute configuration of novel 6-pentyl-2H-pyran-2-one derivatives from Trichoderma spp

نویسندگان

  • Mourad Daoubi
  • Cristina Pinedo-Rivilla
  • Belén Rubio
  • Rosa Hermosa
  • Enrique Monte
  • Josefina Aleu
  • Isidro G. Collado
چکیده

A comparative study of the secondary metabolism of two Trichoderma spp. with that of the Thctf1 transcription factor gene null mutant of Trichoderma harzianum 34 was carried out in order to deepen our knowledge of the biosynthetic pathway and mode of action of 6-pentyl-2H-pyran-2-one (1) and its derivatives as biocontrol agents. New isolated metabolites have shed light on the detoxification mechanism of 6-pentyl-pyranone by Trichoderma spp. All new compounds were synthesized and their stereoisomer characterized. The absolute configuration of 6-[(10R,20S)-dihydroxypentyl]-2H-pyran-2-one and 6-((10S,20R)-20-propyloxiran-1-yl)-2H-pyran-2-one was determined by NMR analysis of the corresponding Mosher’s esters. 2009 Elsevier Ltd. All rights reserved.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Association Phase Transfer Catalyst with Electro-organic Synthesis of 4-(Dihydroxyphenylthio)-6-methyl-2H-pyran- 2-One Derivatives

Introduction The number of natural and synthetic 2H-pyran-2-one derivatives has been reported to exert notably the potential biological activity [1] and medicinal application such as: anticancer activity [2] hepatoprotective activity [3]. On the other hand, catechol derivatives are promising group of compounds worthwhile for further investigation, which may lead to the discovery of selective ac...

متن کامل

Comparative chemical analysis of the essential oil constituents in the bark, heartwood and fruits of Cryptocarya massoy (Oken) Kosterm. (Lauraceae) from Papua New Guinea.

Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-2-one) and C-12 (5,6-dihydro-6-heptyl-2H-pyran-...

متن کامل

Metabolomics by Proton High-Resolution Magic-Angle-Spinning Nuclear Magnetic Resonance of Tomato Plants Treated with Two Secondary Metabolites Isolated from Trichoderma.

Trichoderma fungi release 6-pentyl-2H-pyran-2-one (1) and harzianic acid (2) secondary metabolites to improve plant growth and health protection. We isolated metabolites 1 and 2 from Trichoderma strains, whose different concentrations were used to treat seeds of Solanum lycopersicum. The metabolic profile in the resulting 15 day old tomato leaves was studied by high-resolution magic-angle-spinn...

متن کامل

Alkyl-Substituted δ-Lactones Derived from Dihydrojasmone and Their Stereoselective Fungi-Mediated Conversion: Production of New Antifeedant Agents.

A chemoenzymatic method was applied to obtain optically pure alkyl-substituted δ-lactones. First, chemical Baeyer-Villiger oxidation of dihydrojasmone (1) was carried out, affording two new alkyl-substituted δ-lactones: 3,4-dihydro-5-methyl-6-pentyl-2H-pyran-2-one (2) and 5-methyl-6-pentyl-1,13-dioxabicyclo[4.1.0]heptan-2-one (3). In the next step, fungal strains were investigated as biocatalys...

متن کامل

Synthesis and estimations of antimicrobial properties of novel pyrazoline derivatives

Chalcones are the condensation product of acetophenone in combination with aromatic aldehydes in the presence of strong base. Chalcones and their metal complexes having prominent role in modern coordination chemistry. These compounds possessing novel structural features, interesting spectral and magnetic properties, have been the subject of intensive research due to their importance in medical,...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2015