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- Betaenone_B abstract "Betaenone B, like other betaenones (A and C), is a secondary metabolite isolated from the fungus Pleospora betae, a plant pathogen. Its phytotoxic properties have been shown to cause sugar beet leaf spots, which is characterized by black, pycnidia containing, concentric circles eventually leading to necrosis of the leaf tissue. Of the seven phytotoxins isolated in fungal leaf spots from sugar beet (Beta vulgaris), betaenone B showed the least amount of phytotoxicity showing only 8% inhibition of growth while betaenone A and C showed 73% and 89% growth inhibition, respectively. Betaenone B is therefore not considered toxic to the plant, but will produce leaf spots when present in high concentrations (0.33 µg/µL). While the mechanism of action of betaenone B has yet to be elucidated, betaenone C has been shown to inhibit RNA and protein synthesis. Most of the major work on betaenone B, including the initial structure elucidation of betaenone A, B and C as well as the partial elucidation mechanism of biosynthesis, was presented in three short papers published between 1983–88. The compounds were found to inhibit a variety of protein kinases signifying a possible role in cancer treatment.Molecular structures of betaenone A, B and C.The structure of betaenone B was determined via nuclear magnetic resonance spectroscopy (NMR), CD and optical rotatory dispersion (ORD) measurements. While it was also shown that that betaenone B could be converted to betaenone A by oxidation by PCC followed by exposure to base, it wasn't until 1988 that a semi-complete total synthesis was reported. Using 1,3-butadiene as a starting material, a stereoselective synthesis of (+/-)-4-de(3'-hydroxypropionyl) betanenone B was achieved in a 24-step synthesis. Bioactivity of this synthetic product was not tested and no further work on total synthesis of betaenones has been published since.While a complete de novo synthesis of betaenone B has yet to be reported, Daniel Pratt and Paul Hopkins in 1988 proposed a method for synthesizing a precursor of betaenone B from methoxybenzoquinone and 1,3-butadiene via a Diels–Alder reaction and Claisen chemistry.".
- Betaenone_B atcPrefix "none".
- Betaenone_B casNumber "85269-23-4".
- Betaenone_B iupacName "(2S,3R,4R,4aS,5R,7R,8aS)-3-sec-butyl-2,7-dihydroxy-4-(3-hydroxypropanoyl)-2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one".
- Betaenone_B pubchem "158750".
- Betaenone_B thumbnail Betaenone_B.svg?width=300.
- Betaenone_B wikiPageID "23220304".
- Betaenone_B wikiPageRevisionID "584138470".
- Betaenone_B atcPrefix "none".
- Betaenone_B c "21".
- Betaenone_B casNumber "85269".
- Betaenone_B chemspiderid "139645".
- Betaenone_B date "December 2011".
- Betaenone_B h "36".
- Betaenone_B hasPhotoCollection Betaenone_B.
- Betaenone_B inchi "1".
- Betaenone_B inchikey "PUZNAAVWFXQUDM-HBKHSIGZBL".
- Betaenone_B iupacName "-3".
- Betaenone_B meltingHigh "108".
- Betaenone_B meltingPoint "103.5".
- Betaenone_B molecularWeight "368.508".
- Betaenone_B o "5".
- Betaenone_B pubchem "158750".
- Betaenone_B reason "Claisen condensation or rearrangement, or ?".
- Betaenone_B smiles "O=C[C@]2C".
- Betaenone_B stdinchi "1".
- Betaenone_B stdinchikey "PUZNAAVWFXQUDM-HBKHSIGZSA-N".
- Betaenone_B verifiedrevid "462331618".
- Betaenone_B watchedfields "changed".
- Betaenone_B width "250".
- Betaenone_B subject Category:Alcohols.
- Betaenone_B subject Category:Ketones.
- Betaenone_B subject Category:Tetralins.
- Betaenone_B type Abstraction100002137.
- Betaenone_B type Agent114778436.
- Betaenone_B type Alcohol107884567.
- Betaenone_B type Alcohols.
- Betaenone_B type Beverage107881800.
- Betaenone_B type CausalAgent100007347.
- Betaenone_B type Chemical114806838.
- Betaenone_B type Compound114818238.
- Betaenone_B type Drug103247620.
- Betaenone_B type DrugOfAbuse103248958.
- Betaenone_B type Fluid114939900.
- Betaenone_B type Food100021265.
- Betaenone_B type Ketone114926294.
- Betaenone_B type Ketones.
- Betaenone_B type Liquid114940386.
- Betaenone_B type Material114580897.
- Betaenone_B type Matter100020827.
- Betaenone_B type OrganicCompound114727670.
- Betaenone_B type Part113809207.
- Betaenone_B type PhysicalEntity100001930.
- Betaenone_B type Relation100031921.
- Betaenone_B type Substance100019613.
- Betaenone_B type Substance100020090.
- Betaenone_B type Drug.
- Betaenone_B type DrugProduct.
- Betaenone_B type FunctionalSubstance.
- Betaenone_B comment "Betaenone B, like other betaenones (A and C), is a secondary metabolite isolated from the fungus Pleospora betae, a plant pathogen. Its phytotoxic properties have been shown to cause sugar beet leaf spots, which is characterized by black, pycnidia containing, concentric circles eventually leading to necrosis of the leaf tissue.".
- Betaenone_B label "Betaenone B".
- Betaenone_B sameAs m.065_lrs.
- Betaenone_B sameAs Q4897328.
- Betaenone_B sameAs Q4897328.
- Betaenone_B sameAs Betaenone_B.
- Betaenone_B wasDerivedFrom Betaenone_B?oldid=584138470.
- Betaenone_B depiction Betaenone_B.svg.
- Betaenone_B isPrimaryTopicOf Betaenone_B.