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  • Article: In Vitro Acanthamoebicidal Activity of Fusaric Acid and Dehydrofusaric Acid from an Endophytic Fungus Fusarium sp. Tlau3.
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    ABSTRACT: Acanthamoeba is a genus of free-living protozoa that can cause sight- and life-threatening diseases in man. Its control is still problematic due to the lack of effective and nontoxic acanthamoebicidal agents. Herein, we report the first finding of an in vitro killing effect of fusaric acid and dehydrofusaric acid, isolated from metabolites of the Fusarium fujikuroi species complex Tlau3, on Acanthamoeba trophozoites isolated from two clinical (AS, AR) and two soil (S3, S5) samples. AS, AR, and S3 were classified as members of the T4 genotype, whereas S5 belongs to T5. The fungal extract was found to exhibit acanthamoebicidal activity, and activity-guided fractionation led to the isolation and identification of active principles, fusaric acid and dehydrofusaric acid. Their effects were in concentration- and time-dependent manners. Fusaric acid and dehydrofusaric acid showed IC50 values against AS trophozoites of 0.31 and 0.34 µM, respectively. Commercial fusaric acid displayed the same acanthamoebicidal activity as that of the isolated fusaric acid, and therefore, commercial fusaric acid was used throughout this study. IC50 values of commercial fusaric acid against AR, S3, and S5 trophozoites were 0.33, 0.33, and 0.66 µM, respectively. Fusaric acid calcium salt has a history of usage as a hypotensive agent in humans with no observed toxicity. The present study suggests that fusaric acid may serve as a starting point for the development towards therapeutic and environmental acanthamoebicides with low toxicity to humans.
    Planta Medica 08/2012; 78(14):1562-7. · 2.15 Impact Factor
  • Article: A novel tricyclic polyketide and its biosynthetic precursor azaphilone derivatives from the endophytic fungus Dothideomycete sp.
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    ABSTRACT: Azaphilone derivatives 1 and 2 and a novel tricyclic polyketide 3, together with a known azaphilone, austdiol (4), were isolated from the endophytic fungus Dothideomycete sp., which was isolated from a Thai medicinal plant, Tiliacora triandra. Compound 3 is the first polyketide having a tricyclic 6,6,6 ring system, which is similar to that of a terpenoid skeleton. The absolute configurations of stereogenic centers in 1-3 were addressed by Mosher's method and biosynthetic analogy with a known azaphilone isolated from the same fungus. Cytotoxic and antimicrobial activities of the isolated compounds were evaluated.
    Organic & Biomolecular Chemistry 07/2012; 10(35):7220-6. · 3.70 Impact Factor
  • Article: Paraherquamide E
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    ABSTRACT: In the title compound, C28H35N3O4, also known as 14-deoxyparaherquamide A,the two pyrrolidine rings adopt envelope conformations. The piperazine ring of the diazabicyclo[2.2.2]octan-3-one unit adopts a boat conformation whereas the two piperidine rings are in distorted boat conformations. Intramolecular C—H...O hydrogen bonds are observed. In the crystal, the molecules are linked into chains along the b axis by intermolecular N—H...O hydrogen bonds.
    Acta Crystallographica Section E. 01/2010;
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    Article: Roles of key residues specific to cyclooxygenase II: an ONIOM study
    Darinee Sae-Tang, Prasat Kittakoop, Supa Hannongbua
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    ABSTRACT: AbstractBinding energy calculations of flurbiprofen to the binding pocket of the cyclooxygenase (COX) enzyme were performed based on quantum chemical calculations. The interaction energies between flurbiprofen and two types of COX binding sites were studied. Quantum chemical calculations were used, based on the B3LYP hybrid functional and the MP2 method, with 6-31G(d) and 6-31G(d,p) basis sets. The results show that the main interaction between flurbiprofen and two COX isozymes (COX-1 and COX-2) is due to Arg120. In addition, selective SC558 COX-2 inhibitor was also compared. It was found that repulsive interaction plays a significant role in its inhibition of COX-2. ONIOM2(B3LYP/6-31G(d):PM3) calculations indicate that flurbiprofen interacts via moderate hydrogen bonding with Arg120 in the COX-2 binding site, while no hydrogen bond was detected with either Tyr355 or Val523. The ONIOM2 method can be used to describe the specific interaction of the inhibitor and is helpful in designing a specific COX inhibitor. Graphical Abstract
    Monatshefte fuer Chemie/Chemical Monthly 04/2012; 140(12):1533-1541. · 1.53 Impact Factor
  • Article: Antimycobacterial activity of bisbenzylisoquinoline alkaloids from Tiliacora triandra against multidrug-resistant isolates of Mycobacterium tuberculosis.
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    ABSTRACT: Bisbenzylisoquinoline alkaloids, tiliacorinine (1), 2'-nortiliacorinine (2), and tiliacorine (3), isolated from the edible plant, Tiliacora triandra, as well as a synthetic derivative, 13'-bromo-tiliacorinine (4), were tested against 59 clinical isolates of multidrug-resistant Mycobacterium tuberculosis (MDR-MTB). The alkaloids 1-4 showed MIC values ranging from 0.7 to 6.2 μg/ml, but they exhibited the MIC value at 3.1 μg/ml against most MDR-MTB isolates. The present work suggests that bisbenzylisoquinoline alkaloids are potential new chemical scaffolds for antimycobacterial activity.
    Bioorganic & medicinal chemistry letters 02/2012; 22(8):2902-5. · 2.65 Impact Factor

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