6-Hydroxymellein

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]

6-Hydroxymellein
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
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

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]

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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
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