3-O-Methylfunicone

Last updated
3-O-Methylfunicone
3-O-methylfunicone.svg
Names
Preferred IUPAC name
Methyl 3,5-dimethoxy-2-{5-methoxy-4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-carbonyl}benzoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C20H20O8/c1-6-7-14-19(26-4)18(22)13(10-28-14)17(21)16-12(20(23)27-5)8-11(24-2)9-15(16)25-3/h6-10H,1-5H3/b7-6+
    Key: WGLRJONCGNNMKL-VOTSOKGWSA-N
  • InChI=1/C20H20O8/c1-6-7-14-19(26-4)18(22)13(10-28-14)17(21)16-12(20(23)27-5)8-11(24-2)9-15(16)25-3/h6-10H,1-5H3/b7-6+
    Key: WGLRJONCGNNMKL-VOTSOKGWBV
  • C/C=C/c1c(c(=O)c(co1)C(=O)c2c(cc(cc2OC)OC)C(=O)OC)OC
Properties
C20H20O8
Molar mass 388.368 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-O-Methylfunicone is a chemical compound isolated from Penicillium pinophilum . [2] It inhibits the growth of phytopathogenic fungi. [3]

Related Research Articles

<span class="mw-page-title-main">Penicillin</span> Group of antibiotics derived from Penicillium fungi

Penicillins are a group of β-lactam antibiotics originally obtained from Penicillium moulds, principally P. chrysogenum and P. rubens. Most penicillins in clinical use are synthesised by P. chrysogenum using deep tank fermentation and then purified. A number of natural penicillins have been discovered, but only two purified compounds are in clinical use: penicillin G and penicillin V. Penicillins were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today for various bacterial infections, though many types of bacteria have developed resistance following extensive use.

<i>Penicillium</i> Genus of fungi

Penicillium is a genus of ascomycetous fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production.

<i>Penicillium roqueforti</i> Species of fungus

Penicillium roqueforti is a common saprotrophic fungus in the genus Penicillium. Widespread in nature, it can be isolated from soil, decaying organic matter, and plants.

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

Mevastatin is a hypolipidemic agent that belongs to the statins class.

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

Citrinin is a mycotoxin which is often found in food. It is a secondary metabolite produced by fungi that contaminates long-stored food and it can cause a variety of toxic effects, including kidney, liver and cell damage. Citrinin is mainly found in stored grains, but sometimes also in fruits and other plant products.

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

Cyclopiazonic acid (α-CPA), a mycotoxin and a fungal neurotoxin, is made by the molds Aspergillus and Penicillium. It is an indole-tetramic acid that serves as a toxin due to its ability to inhibit calcium-dependent ATPases found in the endoplasmic and sarcoplasmic reticulum. This inhibition disrupts the muscle contraction-relaxation cycle and the calcium gradient that is maintained for proper cellular activity in cells.

<span class="mw-page-title-main">Desmetramadol</span> Opioid painkiller medication

Desmetramadol, also known as O-desmethyltramadol (O-DSMT), is an opioid analgesic and the main active metabolite of tramadol. Tramadol is demethylated by the liver enzyme CYP2D6 to desmetramadol in the same way as codeine, and so similarly to the variation in effects seen with codeine, individuals who have a less active form of CYP2D6 will tend to have reduced analgesic effects from tramadol. Because desmetramadol itself does not need to be metabolized to induce an analgesic effect, it can be used in individuals with low CYP2D6 activity unlike tramadol.

Penicillium aurantiogriseum is a plant pathogen infecting asparagus and strawberry. Chemical compounds isolated from Penicillium aurantiogriseum include anicequol and auranthine.

Penicillium griseofulvum is a species of the genus of Penicillium which produces patulin, penifulvin A, cyclopiazonic acid, roquefortine C, shikimic acid, griseofulvin, and 6-Methylsalicylic acid. Penicillium griseofulvum occurs on cereals and nuts.

<span class="mw-page-title-main">Snow Mountain garlic</span> Himalayan mountain garlic

Snow Mountain garlic, is a subspecies of garlic found in mountainous Jammu and Kashmir. It grows well in the western Himalayas at altitudes of up to 1,800 m (6,000 ft), in temperatures as low as −10 °C (14 °F), and with very little oxygen. In Hindi, it is known as ek pothi lahsun.

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

Cerevisterol (5α-ergosta-7,22-diene-3β,5,6β-triol) is a sterol. Originally described in the 1930s from the yeast Saccharomyces cerevisiae, it has since been found in several other fungi and, recently, in deep water coral. Cerevisterol has some in vitro bioactive properties, including cytotoxicity to some mammalian cell lines.

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

Andrastin A is a farnesyltransferase inhibitor isolate of Penicillium species including Penicillium albocoremium and Penicillium roqueforti. It has been produced bio-synthetically by porting the relevant gene sequence into Aspergillus oryzae.

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

Vermistatin is an organic compound and a metabolite of mine-dwelling Penicillium vermiculatum found in Berkeley Pit Lake, Butte, Montana. Penisimplicissin is a vermistatin analog with anticancer activity.

Medicinal fungi are fungi that contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or under research include antibiotics, anti-cancer drugs, cholesterol and ergosterol synthesis inhibitors, psychotropic drugs, immunosuppressants and fungicides.

Penicillium citrinum is an anamorph, mesophilic fungus species of the genus of Penicillium which produces tanzawaic acid A-D, ACC, Mevastatin, Quinocitrinine A, Quinocitrinine B, and nephrotoxic citrinin. Penicillium citrinum is often found on moldy citrus fruits and occasionally it occurs in tropical spices and cereals. This Penicillium species also causes mortality for the mosquito Culex quinquefasciatus. Because of its mesophilic character, Penicillium citrinum occurs worldwide. The first statin (Mevastatin) was 1970 isolated from this species.

Penicillium herquei is an anamorph, filamentous species of the genus of Penicillium which produces citreorosein, emodin, hualyzin, herquline B, janthinone, citrinin and duclauxin,.

Penicillium pinophilum is a species of fungus in the genus Penicillium which was isolated from a radio set in Papua New Guinea. Penicillium pinophilum produces 3-O-methylfunicone and mycophenolic acid

<span class="mw-page-title-main">Griseoxanthone C</span> Chemical compound found in some lichens

Griseoxanthone C is an organic compound in the structural class of chemicals known as xanthones. Its chemical formula is 1,6-dihydroxy-3-methoxy-8-methylxanthen-9-one, and its molecular formula is C15H12O5. It is found in a plant and some fungi, including a lichen.

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

Epanorin is a lichen secondary metabolite with the molecular formula C25H25NO6. Epanorin inhibits the proliferation of MCF-7 cancer cells.

References

  1. "KNApSAcK Metabolite Information - C00038270". www.knapsackfamily.com.
  2. Buommino, E; Tirino, V; De Filippis, A; Silvestri, F; Nicoletti, R; Ciavatta, ML; Pirozzi, G; Tufano, MA (2011). "3-O-methylfunicone, from Penicillium pinophilum, is a selective inhibitor of breast cancer stem cells". Cell Proliferation. 44 (5): 401–9. doi:10.1111/j.1365-2184.2011.00766.x. PMC   6495666 . PMID   21951283.
  3. De Stefano, Salvatore; Nicoletti, Rosario; Milone, Alfredo; Zambardino, Salvatore (December 1999). "3-o-Methylfunicone, a fungitoxic metabolite produced by the fungus Penicillium pinophilum". Phytochemistry. 52 (8): 1399–1401. Bibcode:1999PChem..52.1399D. doi:10.1016/S0031-9422(99)00320-9.