Betaenone C

Last updated
Betaenone C
Betaenone C skeletal.svg
Names
IUPAC name
(2S,3R,4R,4aS,5R,7R,8aS)-3-[(2R)-butan-2-yl]-2,7-dihydroxy-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C21H34O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h8-9,12-14,16-17,22,25-26H,7,10-11H2,1-6H3/b9-8-/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1 Yes check.svgY
    Key: YRYPVWAJOMXOHH-ITBWMFDCSA-N Yes check.svgY
  • InChI=1S/C21H34O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h8-9,12-14,16-17,22,25-26H,7,10-11H2,1-6H3/b9-8-/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1
    Key: YRYPVWAJOMXOHH-ITBWMFDCSA-N
  • CC2CC(C)(O)CC(C(=O)C1(C)O)C2C(C)(C(=O)\C=C/O)C1C(C)CC
Properties
C21H34O5
Molar mass 366.498 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Betaenone C, like other betaenones (A and B), is a secondary metabolite isolated from the fungus Pleospora betae , a plant pathogen. [1] Of the seven phytotoxins isolated in fungal leaf spots from sugar beet (Beta vulgaris), it showed 89% growth inhibition. Betaenone C has been shown to act by inhibiting RNA and protein synthesis. [2]

Betaenone ABC skeletal.svg

Related Research Articles

<span class="mw-page-title-main">Thymine</span> Chemical compound of DNA

Thymine is one of the four nucleobases in the nucleic acid of DNA that are represented by the letters G–C–A–T. The others are adenine, guanine, and cytosine. Thymine is also known as 5-methyluracil, a pyrimidine nucleobase. In RNA, thymine is replaced by the nucleobase uracil. Thymine was first isolated in 1893 by Albrecht Kossel and Albert Neumann from calf thymus glands, hence its name.

DnaG is a bacterial DNA primase and is encoded by the dnaG gene. The enzyme DnaG, and any other DNA primase, synthesizes short strands of RNA known as oligonucleotides during DNA replication. These oligonucleotides are known as primers because they act as a starting point for DNA synthesis. DnaG catalyzes the synthesis of oligonucleotides that are 10 to 60 nucleotides long, however most of the oligonucleotides synthesized are 11 nucleotides. These RNA oligonucleotides serve as primers, or starting points, for DNA synthesis by bacterial DNA polymerase III. DnaG is important in bacterial DNA replication because DNA polymerase cannot initiate the synthesis of a DNA strand, but can only add nucleotides to a preexisting strand. DnaG synthesizes a single RNA primer at the origin of replication. This primer serves to prime leading strand DNA synthesis. For the other parental strand, the lagging strand, DnaG synthesizes an RNA primer every few kilobases (kb). These primers serve as substrates for the synthesis of Okazaki fragments.

<span class="mw-page-title-main">Cytarabine</span> Chemical compound (chemotherapy medication)

Cytarabine, also known as cytosine arabinoside (ara-C), is a chemotherapy medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and non-Hodgkin's lymphoma. It is given by injection into a vein, under the skin, or into the cerebrospinal fluid. There is a liposomal formulation for which there is tentative evidence of better outcomes in lymphoma involving the meninges.

Reverse-transcriptase inhibitors (RTIs) are a class of antiretroviral drugs used to treat HIV infection or AIDS, and in some cases hepatitis B. RTIs inhibit activity of reverse transcriptase, a viral DNA polymerase that is required for replication of HIV and other retroviruses.

An antimetabolite is a chemical that inhibits the use of a metabolite, which is another chemical that is part of normal metabolism. Such substances are often similar in structure to the metabolite that they interfere with, such as the antifolates that interfere with the use of folic acid; thus, competitive inhibition can occur, and the presence of antimetabolites can have toxic effects on cells, such as halting cell growth and cell division, so these compounds are used as chemotherapy for cancer.

Topoisomerase inhibitors are chemical compounds that block the action of topoisomerases, which are broken into two broad subtypes: type I topoisomerases (TopI) and type II topoisomerases (TopII). Topoisomerase plays important roles in cellular reproduction and DNA organization, as they mediate the cleavage of single and double stranded DNA to relax supercoils, untangle catenanes, and condense chromosomes in eukaryotic cells. Topoisomerase inhibitors influence these essential cellular processes. Some topoisomerase inhibitors prevent topoisomerases from performing DNA strand breaks while others, deemed topoisomerase poisons, associate with topoisomerase-DNA complexes and prevent the re-ligation step of the topoisomerase mechanism. These topoisomerase-DNA-inhibitor complexes are cytotoxic agents, as the un-repaired single- and double stranded DNA breaks they cause can lead to apoptosis and cell death. Because of this ability to induce apoptosis, topoisomerase inhibitors have gained interest as therapeutics against infectious and cancerous cells.

Phytotoxins are substances that are poisonous or toxic to the growth of plants. Phytotoxic substances may result from human activity, as with herbicides, or they may be produced by plants, by microorganisms, or by naturally occurring chemical reactions.

<span class="mw-page-title-main">Rhizoxin</span> Chemical compound

Rhizoxin is an antimitotic agent with anti-tumor activity. It is isolated from a pathogenic plant fungus which causes rice seedling blight.

<span class="mw-page-title-main">Hygromycin B</span>

Hygromycin B is an antibiotic produced by the bacterium Streptomyces hygroscopicus. It is an aminoglycoside that kills bacteria, fungi and higher eukaryotic cells by inhibiting protein synthesis.

<span class="mw-page-title-main">Ganoderic acid</span> Chemical compound

Ganoderic acids are a class of closely related triterpenoids found in Ganoderma mushrooms. For thousands of years, the fruiting bodies of Ganoderma fungi have been used in traditional medicines in East Asia. Consequently, there have been efforts to identify the chemical constituents that may be responsible for the putative pharmacological effects. There are dozens of ganoderic acids that have been isolated and characterized, of which ganoderic acid A and ganoderic acid B are the most well characterized. Some ganoderic acids have been found to possess biological activities including hepatoprotection, anti-tumor effects, and 5-alpha reductase inhibition.

<span class="mw-page-title-main">Aminocoumarin</span>

Aminocoumarin is a class of antibiotics that act by an inhibition of the DNA gyrase enzyme involved in the cell division in bacteria. They are derived from Streptomyces species, whose best-known representative – Streptomyces coelicolor – was completely sequenced in 2002. The aminocoumarin antibiotics include:

In organic chemistry, an intramolecular Diels-Alder cycloaddition is a Diels–Alder reaction in which the diene and a dienophile are both part of the same molecule. The reaction leads to the formation of the same cyclohexene-like structure as usual for a Diels–Alder reaction, but as part of a more complex fused or bridged cyclic ring system. This reaction gives rise to various natural derivatives of decalin.

<span class="mw-page-title-main">Indolocarbazole</span>

Indolocarbazoles (ICZs) are a class of compounds that are under current study due to their potential as anti-cancer drugs and the prospective number of derivatives and uses found from the basic backbone alone. First isolated in 1977, a wide range of structures and derivatives have been found or developed throughout the world. Due to the extensive number of structures available, this review will focus on the more important groups here while covering their occurrence, biological activity, biosynthesis, and laboratory synthesis.

<span class="mw-page-title-main">Betaenone B</span> Chemical compound

Betaenone B, like other betaenones, 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, 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.

Streptomyces scabies or Streptomyces scabiei is a streptomycete bacterium species found in soils around the world. Unlike most of the 500 or so Streptomyces species it is a plant pathogen causing corky lesions to form on tuber and root crops as well as decreasing the growth of seedlings. Along with other closely related species it causes the potato disease common scab, which is an economically important disease in many potato growing areas. It was first described in 1892, being classified as a fungus, before being renamed in 1914 and again in 1948. Several other species of Streptomyces cause similar diseases to S. scabies but other, more closely related species, do not.

<span class="mw-page-title-main">Lupeol</span> Chemical compound

Lupeol is a pharmacologically active pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.

<span class="mw-page-title-main">Betaenone A</span> Chemical compound

Betaenone A, like other betaenones, is a secondary metabolite isolated from the fungus Pleospora betae, a plant pathogen. Of the seven phytotoxins isolated in fungal leaf spots from sugar beet, it showed 73% growth inhibition.

<span class="mw-page-title-main">Betaenone</span> Phytotoxin

Betaenones are phytotoxins found in the fungus Pleospora betae. The compounds were found to inhibit a variety of protein kinases.

<span class="mw-page-title-main">Tagetitoxin</span> Chemical compound

Tagetitoxin (TGT) is a bacterial phytotoxin produced by Pseudomonas syringae pv. tagetis.

Bradyrhizobium betae is a species of legume-root nodulating, microsymbiotic nitrogen-fixing bacterium first isolated from the roots of Beta vulgaris, hence its name. It is slow-growing an endophytic. The type strain is PL7HG1T.

References

  1. Ichihara A.; Oikawa, Hideaki; Hayashi, Kazuko; Sakamura, Sadao; Furusaki, Akio; Matsumoto, Takeshi (1983). "Structures of Betaenones A and B, Novel Phytotoxins from Phoma betae Fr". J. Am. Chem. Soc. 105 (9): 2907–2908. doi:10.1021/ja00347a070.
  2. Haraguchi, T.; Oguro, Mieko; Nagano, Hiroshi; Ichihara, Akitami; Sakamura, Sadao (1983). "Specific inhibitors of eukaryotic DNA synthesis and DNA polymerase α, 3-deoxyaphidicolin and aphidicolin-17-monoacetate". Nucleic Acids Res. 11 (4): 1197–2000. doi:10.1093/nar/11.4.1197. PMC   325786 . PMID   6402759.