Pyranocoumarin

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Xanthyletine.svg
Seselin.svg
Chemical structures of xanthyletin (top) and seselin

Pyranocoumarins are a class of chemical compounds that have a core structure that consists of a pyran ring fused to a coumarin. As phytochemicals, pyranocoumarins are uncommon and found mainly the plant families Apiaceae and Rutaceae. [1] For example, Citrus sinensis and Citrus limonia are sources of xanthyletin and seselin. [2]

In the biosyntheses of pyranocoumarins, the pyran ring is formed via the methylerythritol phosphate pathway and the coumarin is derived from the shikimate pathway. [2]

See also

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

Angelicin is the parent compound in a family of naturally occurring organic compounds known as the angular furanocoumarins. Structurally, it can be considered as benzapyra-2-one fused with a furan moiety in the 7,8-position. Angelicin is commonly found in certain Apiaceae and Fabaceae plant species such as Bituminaria bituminosa. It has a skin permeability coefficient (LogKp) of -2.46. The maximum absorption is observed at 300 nm. The 1HNMR spectrum is available; the infrared and mass spectra of angelicin can be found in this database. The sublimation of angelicin occurs at 120 °C and the pressure of 0.13 Pa. Angelicin is a coumarine.

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4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position.

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Marmesin (nodakenetin) is a chemical compound precursor in psoralen and linear furanocoumarins biosynthesis.

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References

  1. Khandy, Maria T.; Sofronova, Anastasia K.; Gorpenchenko, Tatiana Y.; Chirikova, Nadezhda K. (2022). "Plant Pyranocoumarins: Description, Biosynthesis, Application". Plants. 11 (22): 3135. doi: 10.3390/plants11223135 . PMC   9693251 . PMID   36432864.
  2. 1 2 Amaral, Jéssica C.; Da Silva, Michelli M.; Da Silva, M. Fátima G. F.; Alves, Thayana C.; Ferreira, A. Gilberto; Forim, Moacir R.; Fernandes, João B.; Pina, Edieidia S.; Lopes, Adriana A.; Pereira, Ana M. S.; Novelli, Valdenice M. (2020). "Advances in the Biosynthesis of Pyranocoumarins: Isolation and 13C-Incorporation Analysis by High-Performance Liquid Chromatography–Ultraviolet–Solid-Phase Extraction–Nuclear Magnetic Resonance Data". Journal of Natural Products. 83 (5): 1409–1415. doi:10.1021/acs.jnatprod.9b00607. PMID   32372647. S2CID   218519965.