Benvitimod

Last updated
Benvitimod
Benvitimod.svg
Names
Preferred IUPAC name
5-[(E)-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1,3-diol
Other names
  • (E)-3,5-Dihydroxy-4-isopropyl-trans-stilbene
  • 3,5-Dihydroxy-4-isopropylstilbene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
    Key: ZISJNXNHJRQYJO-CMDGGOBGSA-N
  • CC(C)c1c(cc(cc1O)/C=C/c2ccccc2)O
Properties
C17H18O2
Molar mass 254.329 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benvitimod (also known as tapinarof or 3,5-dihydroxy-4-isopropyl-trans-stilbene) is a bacterial stilbenoid produced in Photorhabdus bacterial symbionts of Heterorhabditis nematodes. It is a product of an alternative ketosynthase-directed stilbenoids biosynthesis pathway. It is derived from the condensation of two β-ketoacyl thioesters . [1] It is produced by the Photorhabdus luminescens bacterial symbiont species of the entomopathogenic nematode, Heterorhabditis megidis . Experiments with infected larvae of Galleria mellonella , the wax moth, support the hypothesis that the compound has antibiotic properties that help minimize competition from other microorganisms and prevents the putrefaction of the nematode-infected insect cadaver. [2]

Contents

Entomopathogenic nematodes emerging from a wax moth cadaver Entomopathogenic nematode (Heterorhabditis bacteriophora ) Poinar, 1975.jpg
Entomopathogenic nematodes emerging from a wax moth cadaver

Medical research

Benvitimod is being studied in clinical trials for the treatment of plaque psoriasis. [3]

See also

Related Research Articles

<i>Pseudomonas fluorescens</i> Species of bacterium

Pseudomonas fluorescens is a common Gram-negative, rod-shaped bacterium. It belongs to the Pseudomonas genus; 16S rRNA analysis as well as phylogenomic analysis has placed P. fluorescens in the P. fluorescens group within the genus, to which it lends its name.

Waxworm Caterpillar larvae of wax moths

Waxworms are the caterpillar larvae of wax moths, which belong to the family Pyralidae. Two closely related species are commercially bred – the lesser wax moth and the greater wax moth. They belong to the tribe Galleriini in the snout moth subfamily Galleriinae. Another species whose larvae share that name is the Indian mealmoth, though this species is not available commercially.

<i>Heterorhabditis</i> Genus of roundworms

Heterorhabditis is a genus of nematodes belonging to the order Rhabditida. All species of this genus are obligate parasites of insects, and some are used as biological control agents for the control of pest insects.

<i>Pseudomonas aeruginosa</i> Species of bacterium

Pseudomonas aeruginosa is a common encapsulated, Gram-negative, facultatively aerobic, rod-shaped bacterium that can cause disease in plants and animals, including humans. A species of considerable medical importance, P. aeruginosa is a multidrug resistant pathogen recognized for its ubiquity, its intrinsically advanced antibiotic resistance mechanisms, and its association with serious illnesses – hospital-acquired infections such as ventilator-associated pneumonia and various sepsis syndromes.

Stilbenoid

Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are produced by plants, and the only known exception is the antihelminthic and antimicrobial stilbenoid, 2-isoprpyl-5-[(E)-2-phenylvinyl]benzene-1,3-diol, biosynthesized by the Gram-negative bacterium Photorhabdus luminescens.

Entomopathogenic nematode Group of thread worms that attack insects

Entomopathogenic nematodes (EPN) are a group of nematodes, causing death to insects. The term entomopathogenic has a Greek origin, with entomon, meaning insect, and pathogenic, which means causing disease. They are animals that occupy a bio control middle ground between microbial pathogens and predator/parasitoids, and are habitually grouped with pathogens, most likely because of their symbiotic relationship with bacteria. Although many other parasitic thread worms cause diseases in living organisms, entomopathogenic nematodes, are specific in only infecting insects. Entomopathogenic nematodes (EPNs) live parasitically inside the infected insect host, and so they are termed as endoparasitic. They infect many different types of insects living in the soil like the larval forms of moths, butterflies, flies and beetles as well as adult forms of beetles, grasshoppers and crickets. EPNs have been found in all over the world and a range of ecologically diverse habitats. They are highly diverse, complex and specialized. The most commonly studied entomopathogenic nematodes are those that can be used in the biological control of harmful insects, the members of Steinernematidae and Heterorhabditidae. They are the only insect-parasitic nematodes possessing an optimal balance of biological control attributes..

Pinosylvin Chemical compound

Pinosylvin is a pre-infectious stilbenoid toxin that is synthetized in plants during fungal infections, ozone induced stress and physical damage for example. It is a fungitoxin protecting the wood from fungal infection. It is present in the heartwood of Pinaceae and also found in Gnetum cleistostachyum.

<i>Photorhabdus luminescens</i>

Photorhabdus luminescens is a Gammaproteobacterium of the family Morganellaceae, and is a lethal pathogen of insects.

<i>Galleria mellonella</i> Species of moth

Galleria mellonella, the greater wax moth or honeycomb moth, is a moth of the family Pyralidae. G. mellonella is found throughout the world. It is one of two species of wax moths, with the other being the lesser wax moth. G. mellonella eggs are laid in the spring, and they have four life stages. Males are able to generate ultrasonic sound pulses, which, along with pheromones, are used in mating. The larvae of G. mellonella are also often used as a model organism in research.

Moraxella osloensis is a Gram-negative oxidase-positive, aerobic bacterium within the family Moraxellaceae in the gamma subdivision of the purple bacteria.

Naturally occurring phenols

In biochemistry, naturally occurring phenols refers to phenol functional group that is found in natural products. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<i>Heterorhabditis bacteriophora</i> Species of roundworm

Heterorhabditis bacteriophora is a species of entomopathogenic nematode known commonly as beneficial nematodes. They are microscopic and are used in gardening as a form of biological pest control. They are used to control ants, fleas, moths, beetles, flies, weevils, and other pests. They are also amenable to in vitro culture, making them also of interest to evolutionary and molecular biologists who investigate parasitic and symbiotic systems. Heterorhabditis bacteriophora was selected by the National Human Genome Research Institute as a sequencing target, the inbred strain H. bacteriophora TTO1 was sequenced using Roche 454 technology, and a high-quality 77 Mb draft genome assembly was produced in 2013. To reproduce the nematodes release Photorhabdus bacteria from their digestive tract thus killing these pests, then using the cadaver to grow and reproduce.

Xenorhabdus is a genus of motile, gram-negative bacteria from the family of the Morganellaceae. All the species of the genus are only known to live in symbiosis with soil entomopathogenic nematodes from the genus Steinernema.

The biosynthesis of phenylpropanoids involves a number of enzymes.

Photorhabdus is a genus of bioluminescent, gram-negative bacilli which lives symbiotically within entomopathogenic nematodes, hence the name photo and rhabdus. Photorhabdus is known to be pathogenic to a wide range of insects and has been used as biopesticide in agriculture.

Photorhabdus temperata is a species of bacteria. It has been divided into 6 subspecies. It is pathogenic to certain insects.

<i>Heterorhabditis megidis</i> Species of roundworm

Heterorhabditis megidis is a species of nematodes in the genus Heterorhabditis. All species of this genus are obligate parasites of insects, and some are used as biological control agents for the control of pest insects.

Xenorhabdus ehlersii is a bacterium from the genus of Xenorhabdus which has been isolated from the nematode Steinernema serratum in China.

<i>Steinernema carpocapsae</i> Species of roundworm

Steinernema carpocapsae is an entomopathogenic nematode and a member of the family Steinernematidae. It is a parasitic roundworm that has evolved an insect-killing symbiosis with bacteria, and kills its hosts within a few days of infection. This parasite releases its bacterial symbiont along with a variety of proteins into the host after infection, and together the bacteria and nematode overcome host immunity and kill the host quickly. As a consequence, S. carpocapsae has been widely adapted for use as a biological control agent in agriculture and pest control. S. carpocapsae is considered a generalist parasite and has been effectively used to control a variety of insects including: Webworms, cutworms, armyworms, girdlers, some weevils, and wood-borers. This species is an example of an "ambush" forager, standing on its tail in an upright position near the soil surface and attaching to passing hosts, even capable of jumping. As an ambush forager, S. carpocapsae is thought to be especially effective when applied against highly mobile surface-adapted insects. S. carpocapsae can sense carbon dioxide production, making the spiracles a key portal of entry into its insect hosts. It is most effective at temperatures ranging from 22–28 °C (72–82 °F).

<i>Drosophila quinaria</i> species group Species group of the subgenus Drosophila

The Drosophila quinaria species group is a speciose lineage of mushroom-feeding flies studied for their specialist ecology, their parasites, population genetics, and the evolution of immune systems. Quinaria species are part of the Drosophila subgenus.

References

  1. Joyce SA; Brachmann AO; Glazer I; Lango L; Schwär G; Clarke DJ; Bode HB (2008). "Bacterial biosynthesis of a multipotent stilbene". Angew Chem Int Ed Engl. 47 (10): 1942–5. CiteSeerX   10.1.1.603.247 . doi:10.1002/anie.200705148. PMID   18236486.
  2. Hu, K; Webster, JM (2000). "Antibiotic production in relation to bacterial growth and nematode development in Photorhabdus--Heterorhabditis infected Galleria mellonella larvae". FEMS Microbiology Letters. 189 (2): 219–23. doi: 10.1111/j.1574-6968.2000.tb09234.x . PMID   10930742.
  3. "New Topical for Mild to Moderate Psoriasis in the Works". Medscape. March 5, 2017.