Pulvinone

• 5 - phenylmethylene -4-hydroxy -3- phenylfuran -2 (5H )-one ( IUPAC)

• 4941-88-2 ( E and Z mixture)
• 78376-10-0 (Z)
• 100074-80-4 (S)

Fixed

243-247 ° C

Template: Infobox chemical / molecular formula search available

The pulvinone is an organic chemical compound that is one of the lactones, esters, enols and the group of Pulvinsäure dyes. Although the pulvinone is not a natural substance, various naturally occurring hydroxylated derivatives are known which are produced by fungi, such as the Goldröhrling (Boletus elegans, grevillei also known as Suillus ), or by molds such as Aspergillus Terreus. Compared to Vulpinsäure and Pulvinsäure the pulvinone has a low toxicity.

History and habitat

In fungi and lichens Dickröhrlingsverwandten as the many different dyes are present which are either derivatives of Pulvinsäure (about Gomphidsäure ) or composed of a plurality Pulvinsäure - units ( for example, two units: Badione ). 1831 Pulvinsäure methyl ester Vulpinsäure was in the study of lichens ( Cetraria vulpina ) discovered by the French pharmacist and chemist Antoine Bebert, but in 1860 investigated and described in detail by Franz Möller and Adolph Strecker. In an attempt to clarify the structure of the Vulpinsäure, Adolf levels found in 1880 that the Vulpinsäure could be hydrolyzed to a diacid. He called the diacid obtained Pulvinsäure. 1894, the constitution of the Pulvinsäure of Jacob Volhard was clarified by he could make Pulvinsäure synthetically by basic hydrolysis of a corresponding dinitrile. He was also small amounts of by-product, which has been shown separately a year later by Ludwig and Claisen Th Ewan and 5- benzylidene -4-hydroxy -3- phenylfuran -2 ( 5H)-one characterized.

Claisen and Ewan described it as the Pulvinsäure the underlying lactone this developed shortly after the name pulvinone.

Biological Significance

Interestingly, the name pulvinone was not until a century after the discovery of Urpulvinons become a generic term, namely as 1973 by Edwards and Gill, the first natural hydroxylated derivative was isolated. It was a trihydroxyliertes pulvinone, which as a yellow pigment in the European Goldröhrling mushroom (Boletus elegans, also known as Suillus grevillei ) was found. In the same year 1973, Seto and his staff have been found in cultures of Aspergillus terreus Pulvinone. To distinguish these from which Suillus grevillei isolated natural products, these compounds were called Aspulvinone and named alphabetically after the chromatographic elution. ( The least polar Aspulvinon thus became the Aspulvinon A, the closest eluting the Aspulvinon B, etc ... ).

Like many other yellow dyes in fungi and lichens derives the pulvinone on the Pulvinsäure. Thus, the pulvinone structural motif is present in many natural products. All derivatives of Pulvinsäuremonomers as the Pulvinsäure itself and about the Gomphidsäure that Vulpinsäure that Aspulvinone, and derivatives of Pulvinsäuredimers such as the Badione, Norbadione or Pulvinondimers as the Aurantricholon contain this motif. In general, all naturally occurring Pulvinonderivate Z - configured.

Biosynthesis

In fungi, the biosynthesis of aromatic amino acids such as phenylalanine over tyrosine and runs; it arises after Oxidesaminierung to Arylbrenztraubensäure, dimerization, ring cleavage and decarboxylation finally Pulvinongerüst.

Chemical Properties

The pulvinone is a lactone, so an intramolecular ester of trans-1 ,4 -diphenyl- 2 ,3- dihydroxy- 1 ,3-butadiene -1 -carboxylic acid and is produced from this by elimination of water:

Pharmacological activity

• Rehse et al demonstrated that representatives of the family of Pulvinone exhibit anticoagulant activity in rats.
• Early 80s were purchased from ICI and Smith Kline & French, many derivatives of Vulpinsäure patented due to anti-inflammatory, antipyretic and analgesic properties. However Vulpinsäure, as well as many of its derivatives, a cytotoxin. As Pulvinone showed lower cytotoxicity compared to the corresponding Vulpinsäurederivaten, the anti-inflammatory potential of more than 100 Pulvinonen was examined by Organon. To date, little is known about the results of this study.
• The company Wyeth in 2005 patented biphenyl Pulvinone because of their excellent activity against Gram- positive bacteria. However, based antibiotics have been used so far only in animals on the Pulvinongerüst.

Representation

Jacob Volhard synthesized as the first Vulpinsäure that Pulvinsäure and pulvinone. To date, 10 total syntheses of Pulvinonen have been published: