From a Multipotent Stilbene to Soluble Epoxide Hydrolase Inhibitors with Antiproliferative Properties

Buscató, Estel la; Büttner, Dominik; Brüggerhoff, Astrid; Klingler, Franca‐Maria; Wéber, Júlia; Scholz, Bastian; Živković, Aleksandra; Marschalek, Rolf; Stark, Holger; Steinhilber, Dieter; Bode, Helge B.; Proschak, Ewgenij

doi:10.1002/cmdc.201300057

Cited by 28 publications

(22 citation statements)

References 41 publications

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“…Six isolates produced xenocoumacin derivatives (Reimer et al, 2009) or amicoumacin derivatives (Park et al, 2016) being potent antibiotics, while all of the Photorhabdus spp. produced isopropylstilbene that has multiple biological activities including antibiotic activity (Li et al, 1995; Buscató et al, 2013). All Xenorhabdus isolates produced xenoamicin derivatives showing weak antiprotozoal activity (Zhou et al, 2013).…”

Section: Discussionmentioning

confidence: 99%

Screening of the Antimicrobial Activity against Drug Resistant Bacteria of Photorhabdus and Xenorhabdus Associated with Entomopathogenic Nematodes from Mae Wong National Park, Thailand

et al. 2017

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Photorhabdus and Xenorhabdus are symbiotic with entomopathogenic nematodes (EPNs) of the genera Heterorhabditis and Steinernema, respectively. These bacteria produce several secondary metabolites including antimicrobial compounds. The objectives of this study were to isolate and identify EPNs and their symbiotic bacteria from Mae Wong National Park, Thailand and to evaluate the antibacterial activities of symbiont extracts against drug resistant bacteria. A total of 550 soil samples from 110 sites were collected between August 2014 and July 2015. A total of EPN isolates were obtained through baiting and White trap methods, which yielded 21 Heterorhabditis and 3 Steinernema isolates. Based on molecular identification and phylogenetic analysis, the most common species found in the present study was P. luminescens subsp. akhurstii associated with H. indica. Notably, two species of EPNs, H. zealandica and S. kushidai, and two species of symbiotic bacteria, X. japonica and P. temperata subsp. temperata represented new recorded organisms in Thailand. Furthermore, the association between P. temperata subsp. temperata and H. zealandica has not previously been reported worldwide. Disk diffusion, minimal inhibitory concentration, and minimal bactericidal concentration analyses demonstrated that the crude compound extracted by ethyl acetate from P. temperata subsp. temperata could inhibit the growth of up to 10 strains of drug resistant bacteria. Based on HPLC-MS analysis, compound classes in bacterial extracts were identified as GameXPeptide, xenoamicin, xenocoumacin, mevalagmapeptide phurealipids derivatives, and isopropylstilbene. Together, the results of this study provide evidence for the diversity of EPNs and their symbiotic bacteria in Mae Wong National Park, Thailand and demonstrate their novel associations. These findings also provide an important foundation for further research regarding the antimicrobial activity of Photorhabdus bacteria.

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Section: Discussionmentioning

confidence: 99%

Screening of the Antimicrobial Activity against Drug Resistant Bacteria of Photorhabdus and Xenorhabdus Associated with Entomopathogenic Nematodes from Mae Wong National Park, Thailand

et al. 2017

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“…However, this traditional process of drug development takes many years, and none of sEH inhibitors are in clinical use yet. Alternatively, sEH inhibitors derived from natural products, especially edible vegetables, could provide a shorter path to treating patients and companion animals, offering inexpensive therapeutics to patients that will not require the same regulatory barriers as pharmaceuticals [15,16]. In addition, study of these natural products will explain the modes of action of some natural remedies.…”

Section: Introductionmentioning

confidence: 99%

Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales

et al. 2017

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Recently, dibenzylurea-based potent soluble epoxide hydrolase (sEH) inhibitors were identified in Pentadiplandra brazzeana, a plant in the order Brassicales. In an effort to generalize the concept, we hypothesized that plants that produce benzyl glucosinolates and corresponding isothiocyanates also produce these dibenzylurea derivatives. Our overall aim here was to examine the occurrence of urea derivatives in Brassicales, hoping to find biologically active urea derivatives from plants. First, plants in the order Brassicales were analyzed for the presence of 1, 3-dibenzylurea (compound 1), showing that three additional plants in the order Brassicales produce the urea derivatives. Based on the hypothesis, three dibenzylurea derivatives with sEH inhibitory activity were isolated from maca (Lepidium meyenii) roots. Topical application of one of the identified compounds (compound 3, human sEH IC50 = 222 nM) effectively reduced pain in rat inflammatory pain model, and this compound was bioavailable after oral administration in mice. The biosynthetic pathway of these urea derivatives was investigated using papaya (Carica papaya) seed as a model system. Finally, a small collection of plants from the Brassicales order was grown, collected, extracted and screened for sEH inhibitory activity. Results show that several plants of the Brassicales order could be potential sources of urea-based sEH inhibitors.

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“…It is produced by all strains of Photorhabdus , which are entomopathogenic bacteria that live in symbiosis with nematodes of the genus Heterorhabditis . It is crucial for nematode development,2 shows insecticidal and antibiotic activity,3 and is also an inhibitor of the human soluble epoxide hydrolase (sEH) 4. Owing to its multiple activities, it has also been called the “Swiss army knife” of P. luminescens 5.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Cyclohexanediones and Dialkylresorcinols – Bioactive Natural Products from Entomopathogenic Bacteria

et al. 2014

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A synthesis for the recently identified, widespread bacterial natural product classes of dialkylresorcinols and cyclohexanediones was developed. The synthesis route is similar to the biosynthesis route in that the formation of the cyclohexanedione ring results from two parts, as exemplified by the synthesis of the multifunctional isopropylstilbenes identified in Photorhabdus luminescens. Testing of these compounds revealed good bioactivity against Trypanosoma brucei rhodesiense and T. cruzi, the causative agents of sleeping sickness and Chagas disease, respectively.

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From a Multipotent Stilbene to Soluble Epoxide Hydrolase Inhibitors with Antiproliferative Properties

Cited by 28 publications

References 41 publications

Screening of the Antimicrobial Activity against Drug Resistant Bacteria of Photorhabdus and Xenorhabdus Associated with Entomopathogenic Nematodes from Mae Wong National Park, Thailand

Screening of the Antimicrobial Activity against Drug Resistant Bacteria of Photorhabdus and Xenorhabdus Associated with Entomopathogenic Nematodes from Mae Wong National Park, Thailand

Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales

Facile Synthesis of Cyclohexanediones and Dialkylresorcinols – Bioactive Natural Products from Entomopathogenic Bacteria

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