6-Methoxymellein

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6-Methoxymellein
6-methoxymellein.PNG
Names
Other names
3-methyl-6-methoxy-8-hydroxy-3,4-dihydroisocoumarin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
Properties
C11H12O4
Molar mass 208.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

6-Methoxymellein is a dihydroisocoumarin, a phenolic compound found in carrots and carrot purées. It is responsible for bitterness in carrots. [1] [2] It is a phytoalexin, induced in carrot slices by UV-C, [3] that allows resistance to Botrytis cinerea [4] and other microorganisms. [5]

Contents

Biosynthesis

6-Methoxymellein is formed from S-adenosyl methionine and 6-hydroxymellein by the enzyme 6-hydroxymellein O-methyltransferase with secondary production of S-adenosylhomocysteine. [6]

Related Research Articles

Phytoalexin class of chemical compounds

Phytoalexins are antimicrobial and often antioxidative substances synthesized de novo by plants that accumulate rapidly at areas of pathogen infection. They are broad spectrum inhibitors and are chemically diverse with different types characteristic of particular plant species. Phytoalexins tend to fall into several classes including terpenoids, glycosteroids and alkaloids; however, researchers often find it convenient to extend the definition to include all phytochemicals that are part of the plant's defensive arsenal.

Stilbenoid class of chemical compounds

Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Stilbenoids can be produced by plants and bacteria.

Pterostilbene chemical compound

Pterostilbene (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role.

Damascone chemical compound

Damascones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascones belong to a family of chemicals known as rose ketones, which also includes damascenones and ionones. beta-Damascone is a contributor to the aroma of roses, despite its relatively low concentration, and is an important fragrance chemical used in perfumery.

Momilactone B chemical compound

Momilactone B is an allelopathic agent produced from the roots of rice. It has been shown to be produced in high concentrations by the roots of rice seedlings. The production of momilactone B has also been induced in response to infection by blast fungus or irradiated with UV light. More recently it has been shown to be a potential chemotherapeutic agent against human colon cancer.

Tricetin chemical compound

Tricetin is a flavone, a type of flavonoid. It is a rare aglycone found in the pollen of members of the Myrtaceae, subfamily Leptospermoideae, such as Eucalyptus globulus. This compound shows anticancer effects on human breast adenocarcinoma MCF-7 cells.

Procyanidin B5 chemical compound

Procyanidin B5 is a B type proanthocyanidin.

2,4,6-Tribromoanisole chemical compound

2,4,6-Tribromoanisole (TBA) is a chemical compound that is a brominated derivative of anisole. It is one of the chemicals responsible for cork taint.

Protocatechuic aldehyde chemical compound

Protocatechuic aldehyde is a phenolic aldehyde, a compound released from cork stoppers into wine.

Naturally occurring phenols group of chemical compounds

In biochemistry, naturally occurring phenols refers to phenol functional group that is found in natural products. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

Grape reaction product chemical compound

The grape reaction product is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing. It is also found in aged red wines. Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts, especially in white wine production. The product can be recreated in model solutions.

Wine chemistry

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4.

<i>delta</i>-Viniferin chemical compound

δ-Viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine leaves. It is also found in plant cell cultures and wine. It can also be found in Rheum maximowiczii.

Mellein chemical compound

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

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.

Oxovitisin group of chemical compounds

Oxovitisins are a type of pyranoanthocyanin with a pyranone (2-pyrone) component found in aged Port wines. They do not contain an oxonium ion component, as anthocyanins do. Therefore, they do not have an absorption maximum at 520 nm. Oxovitisins are stable yellowish pigments with similar unique spectral features, displaying only a pronounced broad band around 370 nm in the UV−vis spectrum.

Falcarindiol chemical compound

Falcarindiol is a polyacetylene found in carrot roots which has antifungal activity. Falcarindiol is the main compound responsible for bitterness in carrots. Falcarindiol and other falcarindiol-type polyacetylenes are also found in many other plants of the family Apiaceae, including some commonly used seasonings such as dill and parsley. A variety of bioactivities have been reported so far for falcaridiol and the falcarindiol-type polyacetylenes, and because of potential health-promoting metabolic effects these compounds are studied as potential nutraceuticals. It is the most-active among several polyynes with potential anticancer activity found in Devil's Club, a medicinal plant used by many indigenous peoples in Alaska and the Pacific Northwest.

Catechin-5-<i>O</i>-glucoside chemical compound

Catechin 5-O-glucoside is a flavanol glucoside. It can be found in rhubarb and in the bark of Rhaphiolepis umbellata. It can also be formed from (+)-catechin by plant-cultured cells of Eucalyptus perriniana.

Ideain chemical compound

Ideain, the cyanidin 3-O-galactoside, is an anthocyanin, a type of plant pigment.

Tellimagrandin I Chemical compound

Tellimagrandin I is an ellagitannin found in plants, such as Cornus canadensis, Eucalyptus globulus, Melaleuca styphelioides, Rosa rugosa, and walnut. It is composed of two galloyl and one hexahydroxydiphenyl groups bound to a glucose residue. It differs from Tellimagrandin II only by a hydroxyl group instead of a third galloyl group. It is also structurally similar to punigluconin and pedunculagin, two more ellagitannin monomers.

References

  1. Structural and Sensory Characterization of Compounds Contributing to the Bitter Off-Taste of Carrots (Daucus carota L.) and Carrot Puree. Andreas Czepa and Thomas Hofmann, J. Agric. Food Chem., 2003, 51, pages 3865-3873, doi : 10.1021/jf034085+ PMID   12797757
  2. Determination and Distribution of 6-Methoxymellein in Fresh and Processed Carrot Puree by a Rapid Spectrophotometric Assay. S.T. Talcott and L.R. Howard, J. Agric. Food Chem., 1999, 47 (8), pages 3237–3242, doi : 10.1021/jf990288f
  3. Induction of 6-Methoxymellein and Resistance to Storage Pathogens in Carrot Slices by UV-C. J. Mercier, J. Arul, R. Ponnampalam and M. Boulet, Journal of Phytopathology, Volume 137, Issue 1, pages 44–54, January 1993, doi : 10.1111/j.1439-0434.1993.tb01324.x
  4. Cell death, 6-methoxymellein accumulation, and induced resistance to Botrytis cinerea in carrot root slices. R. Hoffman and J.B. Heale, Physiological and Molecular Plant Pathology, Volume 30, Issue 1, January 1987, Pages 67–75, doi : 10.1016/0885-5765(87)90083-X
  5. Isolation and antimicrobial activity of the phytoalexin 6-methoxymellein from cultured carrot cells. Fumiya Kurosaki and Arasuke Nishi, Phytochemistry, Volume 22, Issue 3, 1983, Pages 669–672, doi : 10.1016/S0031-9422(00)86959-9
  6. 6-methoxymellein biosynthesis pathway on www.biocyc.org