6-Hydroxymellein

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6-Hydroxymellein
6-Hydroxymellein.PNG
Names
IUPAC name
(3R)-6,8-dihydroxy-3-methyl-3,4-dihydroisochromen-1-one
Other names
(R)-6-hydroxymellein
(−)-6-Hydroxymellein
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
Properties
C10H10O4
Molar mass 194.18 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-Hydroxymellein is a dihydroisocoumarin, a phenolic compound found in carrots. [1] It has also been isolated in Aspergillus terreus and shows an inhibition of pollen development in Arabidopsis thaliana . [2]

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. [3]

Related Research Articles

<i>Arabidopsis</i> genus of plants

Arabidopsis (rockcress) is a genus in the family Brassicaceae. They are small flowering plants related to cabbage and mustard. This genus is of great interest since it contains thale cress, one of the model organisms used for studying plant biology and the first plant to have its entire genome sequenced. Changes in thale cress are easily observed, making it a very useful model.

<i>Arabidopsis thaliana</i> species of flowering plant in the cabbage family Brassicaceae

Arabidopsis thaliana, the thale cress, mouse-ear cress or arabidopsis, is a small flowering plant native to Eurasia and Africa. A. thaliana is considered a weed; it is found by roadsides and in disturbed land.

Self-pollination when pollen from one flower pollinates the same flower or other flowers of the same individual

Self-pollination is when pollen from the same plant arrives at the stigma of a flower or at the ovule. There are two types of self-pollination: in autogamy, pollen is transferred to the stigma of the same flower; in geitonogamy, pollen is transferred from the anther of one flower to the stigma of another flower on the same flowering plant, or from microsporangium to ovule within a single (monoecious) gymnosperm. Some plants have mechanisms that ensure autogamy, such as flowers that do not open (cleistogamy), or stamens that move to come into contact with the stigma. The term selfing that is often used as a synonym, is not limited to self-pollination, but also applies to other types of self-fertilization.

Cytokinin class of chemical compounds

Cytokinins (CK) are a class of plant growth substances (phytohormones) that promote cell division, or cytokinesis, in plant roots and shoots. They are involved primarily in cell growth and differentiation, but also affect apical dominance, axillary bud growth, and leaf senescence. Folke Skoog discovered their effects using coconut milk in the 1940s at the University of Wisconsin–Madison.

<i>Aspergillus</i> Genus of fungi

Aspergillus is a genus consisting of a few hundred mould species found in various climates worldwide.

ABC model of flower development

The ABC model of flower development is a scientific model of the process by which flowering plants produce a pattern of gene expression in meristems that leads to the appearance of an organ oriented towards sexual reproduction, a flower. There are three physiological developments that must occur in order for this to take place: firstly, the plant must pass from sexual immaturity into a sexually mature state ; secondly, the transformation of the apical meristem's function from a vegetative meristem into a floral meristem or inflorescence; and finally the growth of the flower's individual organs. The latter phase has been modelled using the ABC model, which aims to describe the biological basis of the process from the perspective of molecular and developmental genetics.

Nottingham Arabidopsis Stock Centre Arabidopsis resource center at the University of Nottingham

The Nottingham Arabidopsis Stock Centre (NASC) provides seed and information resources to the International Arabidopsis Genome Project and the wider research community. It is based in the School of Biosciences at the University of Nottingham's Sutton Bonington Campus, in the English county of Nottinghamshire.

Carrot Root vegetable, usually orange in color

The carrot is a root vegetable, usually orange in colour, though purple, black, red, white, and yellow cultivars exist. They are a domesticated form of the wild carrot, Daucus carota, native to Europe and Southwestern Asia. The plant probably originated in Persia and was originally cultivated for its leaves and seeds. The most commonly eaten part of the plant is the taproot, although the stems and leaves are eaten as well. The domestic carrot has been selectively bred for its greatly enlarged, more palatable, less woody-textured taproot.

Pectinesterase class of enzymes

Pectinesterase (PE) is a ubiquitous cell-wall-associated enzyme that presents several isoforms that facilitate plant cell wall modification and subsequent breakdown. It is found in all higher plants as well as in some bacteria and fungi. Pectinesterase functions primarily by altering the localised pH of the cell wall resulting in alterations in cell wall integrity.

Superman is a plant gene in Arabidopsis thaliana, that plays a role in controlling the boundary between stamen and carpel development in a flower. It is named for the comic book character Superman, and the related genes kryptonite (gene) and clark kent were named accordingly. It encodes a transcription factor. Homologous genes are known in the petunia and snapdragon, which are also involved in flower development, although in both cases there are important differences from the functioning in Arabidopsis. Superman is expressed early on in flower development, in the stamen whorl adjacent to the carpel whorl. It interacts with the other genes of the ABC model of flower development in a variety of ways.

<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.

mir-160 microRNA precursor family

In molecular biology, mir-160 is a microRNA that has been predicted or experimentally confirmed in a range of plant species including Arabidopsis thaliana and Oryza sativa (rice). miR-160 is predicted to bind complementary sites in the untranslated regions of auxin response factor genes to regulate their expression. The hairpin precursors are predicted based on base pairing and cross-species conservation; their extents are not known. In this case, the mature sequence is excised from the 5' arm of the hairpin.

mir-172 microRNA precursor family

The mir-172 microRNA is thought to target mRNAs coding for APETALA2-like transcription factors. It has been verified experimentally in the model plant, Arabidopsis thaliana. The mature sequence is excised from the 3' arm of the hairpin.

Mellein chemical compound

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

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.

Methyl halide transferase is an enzyme with systematic name S-adenosylmethionine:iodide methyltransferase. This enzyme catalyses the following chemical reaction

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

Aspergillus alabamensis is a soil fungus in the division Ascomycota first described in 2009 as a segregated taxon of A. terreus. Originally thought to be a variant of A. terreus, A. alabamensis is situated in a distinctive clade identified by genetic analysis. While A. alabamensis has been found to be morphologically similar to Aspergillus terreus by morphological studies, the two differ significantly in active metabolic pathways, with A. alabamensis producing the mycotoxins citrinin and citreoviridin but lacking mevinolin.

Feronia, also known as FER or protein Sirene, is a recognition receptor kinase found in plants. FER plays a significant part in the plant immune system as a receptor kinase which assists in immune signaling within plants, plant growth, and plant reproduction. FER is regulated by the Rapid Alkalinization Factor (RALF). FER regulates growth in normal environments but it is most beneficial in stressful environments as it helps to initiate immune signaling. FER can also play a role in reproduction in plants by participating in the communication between the female and male cells. FER is found in and can be studied in the organism Arabidopsis thaliana.

Sexual selection in Arabidopsis thaliana

Sexual selection in Arabidopsis thaliana is a mode of natural selection by which the flowering plant Arabidopsis thaliana selects mates to maximize reproductive success.

Cysteine-rich proteins are small proteins that contain multiple internal disulphide bonds that cross-link them into their tertiary structure. CRPs include a highly conserved secretion peptide signal at the N-terminus and a cysteine-rich region at the C-terminus.

References

  1. Kurosaki, F.; Nishi, A. (1988). "A methyltransferase for synthesis of the phytoalexin 6-methoxymellein in carrot cells". FEBS Letters. 227 (2): 183. doi:10.1016/0014-5793(88)80894-9.
  2. Shimada, A.; Kusano, M.; Takeuchi, S.; Fujioka, S.; Inokuchi, T.; Kimura, Y. (2002). "Aspterric acid and 6-hydroxymellein, inhibitors of pollen development in Arabidopsis thaliana, produced by Aspergillus terreus". Zeitschrift für Naturforschung C. 57 (5–6): 459–464. doi:10.1515/znc-2002-5-610. PMID   12132685.
  3. 6-Hydroxymellein biosynthesis pathway on www.biocyc.org