Mellein

Last updated
Mellein
Mellein.svg
Names
IUPAC name
8-Hydroxy-3-methyl-3,4-dihydroisochromen-1-one
Other names
(−)-Mellein
(R)-(−)-Mellein
Ochracin
3,4-Dihydro-8-hydroxy-3-methyl-1H-2-benzopyran-1-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
Properties
C10H10O3
Molar mass 178.187 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

Mellein is a dihydroisocoumarin, a phenolic compound produced by the mold species Aspergillus ochraceus . [1]

Derivatives

4-Hydroxymellein is also produced by Aspergillus ochraceus . [1]

6-Hydroxymellein, together with S-adenosyl methionine, is a substrate of the enzyme 6-hydroxymellein O-methyltransferase to form 6-methoxymellein and S-adenosylhomocysteine in Apiaceae. [2] 6-Methoxymellein is one of the compounds responsible for bitterness in carrots.

Related Research Articles

<i>Penicillium</i> Genus of fungi

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

<i>Aspergillus niger</i> species of fungus

Aspergillus niger is a fungus and one of the most common species of the genus Aspergillus.

<i>Aspergillus flavus</i> aspergillus flavus

Aspergillus flavus is a saprotrophic and pathogenic fungus with a cosmopolitan distribution. It is best known for its colonization of cereal grains, legumes, and tree nuts. Postharvest rot typically develops during harvest, storage, and/or transit. Its specific name flavus derives from the Latin meaning yellow, a reference to the frequently observed colour of the spores. A. flavus infections can occur while hosts are still in the field (preharvest), but often show no symptoms (dormancy) until postharvest storage and/or transport. In addition to causing preharvest and postharvest infections, many strains produce significant quantities of toxic compounds known as mycotoxins, which, when consumed, are toxic to mammals. A. flavus is also an opportunistic human and animal pathogen, causing aspergillosis in immunocompromised individuals.

Ochratoxin group of chemical compounds

Ochratoxins are a group of mycotoxins produced by some Aspergillus species and some Penicillium species, especially P. verrucosum. Ochratoxin A is the most prevalent and relevant fungal toxin of this group, while ochratoxins B and C are of lesser importance.

Gliotoxin chemical compound

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin. It is the most prominent member of the epipolythiopiperazines, a large class of natural products featuring a diketopiperazine with di- or polysulfide linkage. These highly bioactive compounds have been the subject of numerous studies aimed at new therapeutics. Gliotoxin was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite.

Mycotoxicology is the branch of mycology that focuses on analyzing and studying the toxins produced by fungi, known as mycotoxins. In the food industry it is important to adopt measures that keep mycotoxin levels as low as practicable, especially those that are heat-stable. These chemical compounds are the result of secondary metabolism initiated in response to specific developmental or environmental signals. This includes biological stress from the environment, such as lower nutrients or competition for those available. Under this secondary path the fungus produces a wide array of compounds in order to gain some level of advantage, such as incrementing the efficiency of metabolic processes to gain more energy from less food, or attacking other microorganisms and being able to use their remains as a food source.

<i>Aspergillus terreus</i> species of fungus

Aspergillus terreus, also known as Aspergillus terrestris, is a fungus (mold) found worldwide in soil. Although thought to be strictly asexual until recently, A. terreus is now known to be capable of sexual reproduction. This saprotrophic fungus is prevalent in warmer climates such as tropical and subtropical regions. Aside from being located in soil, A. terreus has also been found in habitats such as decomposing vegetation and dust. A. terreus is commonly used in industry to produce important organic acids, such as itaconic acid and cis-aconitic acid, as well as enzymes, like xylanase. It was also the initial source for the drug mevinolin (lovastatin), a drug for lowering serum cholesterol.

Aspergillus ochraceus is a mold species in the genus Aspergillus known to produce the toxin ochratoxin A, one of the most abundant food-contaminating mycotoxins, and citrinin. It also produces the dihydroisocoumarin mellein. It is a filamentous fungus in nature and has characteristic biseriate conidiophores. Traditionally a soil fungus, has now began to adapt to varied ecological niches, like agricultural commodities, farmed animal and marine species. In humans and animals the consumption of this fungus produces chronic neurotoxic, immunosuppressive, genotoxic, carcinogenic and teratogenic effects. Its airborne spores are one of the potential causes of asthma in children and lung diseases in humans. The pig and chicken populations in the farms are the most affected by this fungus and its mycotoxins. Certain fungicides like mancozeb, copper oxychloride, and sulfur have inhibitory effects on the growth of this fungus and its mycotoxin producing capacities.

6-Methoxymellein chemical compound

6-Methoxymellein is a dihydroisocoumarin, a phenolic compound found in carrots and carrot purées. It is responsible for bitterness in carrots. It is a phytoalexin, induced in carrot slices by UV-C, that allows resistance to Botrytis cinerea and other microorganisms.

6-Hydroxymellein chemical compound

6-Hydroxymellein is a dihydroisocoumarin, a phenolic compound found in carrots. It has also been isolated in Aspergillus terreus and shows an inhibition of pollen development in Arabidopsis thaliana.

Aspergillus sydowii is a pathogenic fungus that causes several diseases in humans. It has been implicated in the death of sea fan corals in the Caribbean Sea.

Circumdatin H chemical compound

Circumdatin H is an alkaloid. It was isolated, along with related compounds, from the fungus Aspergillus ochraceus.

<i>Aspergillus parasiticus</i> species of fungus

Aspergillus parasiticus is a fungus belonging to the genus Aspergillus. This species is an unspecialized saprophytic mold, mostly found outdoors in areas of rich soil with decaying plant material as well as in dry grain storage facilities. Often confused with the closely related species, A. flavus, A. parasiticus has defined morphological and molecular differences. Aspergillus parasiticus is one of three fungi able to produce the mycotoxin, aflatoxin, one of the most carcinogenic naturally occurring substances. Environmental stress can upregulate aflatoxin production by the fungus, which can occur when the fungus is growing on plants that become are damaged due to exposure to poor weather conditions, during drought, by insects, or by birds. In humans, exposure to A. parasiticus toxins have potential to cause delayed development in children and produce serious liver diseases and/or hepatic carcinoma in adults. The fungus is also able to cause the infection known as aspergillosis in humans and other animals. A. parasiticus is of agricultural importance due to its ability to cause disease in corn, peanut, and cottonseed.

Aspergillus campestris is a species of fungus in the genus Aspergillus. The species was first described in 1982. It is from the Candidi section. The fungi in the Candidi section are known for their white spores. It has been shown to produce a high number of secondary metabolites.

Aspergillus robustus is a species of fungus in the genus Aspergillus. It has phototropic conidiophores. The species was first described in 1978. The genome of A. robustus was in 2016 sequenced as a part of the Aspergillus whole-genome sequencing project - a project dedicated to performing whole-genome sequencing of all members of the Aspergillus genus. The genome assembly size was 33.14 Mbp.

Aspergillus nakazawae is a species of fungus in the genus Aspergillus. It is from the Circumdati section. The species was first described in 1950. It has been reported to produce aspergamide A, aspergamide B, notoamides, penicillic acid, mellein, 4-hydroxy mellein, xanthomegnin, viomellein, aspyrone, and neoaspergillic acid.

Aspergillus christenseniae is a species of fungus in the genus Aspergillus. It is from the Cervini section. The species was first described in 2016. It has been reported to produce 4-hydroxymellein, terremutin, orange-red anthraquinone, and chlorflavonin. The species was named for Martha Christensen.

Aspergillus subnutans is a species of fungus in the genus Aspergillus. It is from the Cervini section. The species was first described in 2016. It has been reported to produce 4-hydroxymellein.

Aspergillus transcarpathicus is a species of fungus in the genus Aspergillus. It is from the Cervini section. The species was first described in 2016. It has been reported to produce asparvenones, terremutin, 4-hydroxymellein, and xanthocillin.

Aspergillus wisconsinensis is a species of fungus in the genus Aspergillus. It is from the Cervini section. The species was first described in 2016. It has been reported to produce an asparvenone, 4-hydroxymellein, sclerotigenin, two territrems, and cycloaspeptide.

References

  1. 1 2 Moore, J. H.; Davis, N. D.; Diener, U. L. (1972). "Mellein and 4-hydroxymellein production by Aspergillus ochraceus Wilhelm". Applied Microbiology. 23 (6): 1067–1072. PMC   380508 . PMID   5064985.
  2. 6-methoxymellein biosynthesis pathway on www.biocyc.org