Marmesin

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Marmesin
Marmesin.png
Names
Preferred IUPAC name
(2S)-2-(2-Hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one
Other names
Nodakenetin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • CC(C)([C@@H]1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
Properties
C14H14O4
Molar mass 246.262 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Marmesin (nodakenetin) is a chemical compound precursor in psoralen and linear furanocoumarins biosynthesis. [1]

Marmesin plays a central role in the biosynthesis of furocoumarins in the plant Ruta graveolens , more commonly known as rue. It acts as the natural intermediate in the formation of the furan ring that leads to a 4’,5’-dihydro furocoumarin-derivative. This substance can then be transformed into psoralen and other furocoumarins present in rue. Upon feeding the herb a dose of marmesin, radioactivity became strongly incorporated into psoralen and thus the plant itself. [2] [ clarification needed ] It is constituent of Aegle marmelos , Ammi majus , Poncirus trifoliata and Prangos bucharica and others [3]

Spectra

IR Spectra

IR (ATR): νmax 3480, 2971, 1699, 1631, 1488 cm-1. [4]

Proton-NMR

1H-NMR (300 MHz, CDCl3): δ 7.59 (d, J = 9.5 Hz, 1H, aromatic), 7.22 (s, 1H, aromatic), 6.75 (d, J = 21.6 Hz, 1H, aromatic), 6.20 (d, J = 9.5 Hz, 1H, aromatic), 4.74 (t, J = 8.8 Hz, 1H, CH), 3.28-3.15 (m, 2H, CH2), 1.87 (s, 1H, OH), 1.37 (s, 3H, CH3), 1.24 (s, 3H, CH3) ppm. [5]

UV-Vis

UV: [neutral]λmax  217 (ε7420); 338 (ε17700)( MeOH)   [neutral]λmax  332( EtOH). [6]

Production

Synthesis of marmesin has been successfully conducted in the laboratory on multiple occasions. One way of doing so is by a strategy based on the palladium-catalyzed intramolecular coupling reaction. This reaction would construct the dihydropyran ring and synthesize the compound from the intermediate (-)-peucedanol. The key step in the overall synthesis uses catalytic asymmetric epoxidation of an enone. [7]

References

  1. ↑ Steck, Warren; Brown, Stewart A. (1971). "Comparison of (+)- and (−)-Marmesin as Intermediates in the Biosynthesis of Linear Furanoconmarins". Biochemistry and Cell Biology . 49 (11): 1213–1216. doi:10.1139/o71-174. ISSN   1208-6002. PMID   5134594.
  2. ↑ Caporale, G.; Dall’Acqua, F.; Capozzi, A.; Marciani, S.; Crocco, R. Studies on the biosynthesis of some furocoumarins present in Ruta graveolens. Zeitschrift für Naturforschung B 1971, 26, 1256-1259.
  3. ↑ Chatterjee, A. et al, J. Am. Chem. Soc., 1949, 71, 606-609
  4. ↑ Ando, T.; Nagumo, M.; Ninomiya, M.; Tanaka, K.; Linhardt, R. J.; Koketsu, M. Synthesis of coumarin derivatives and their cytoprotective effects on t-BHP-induced oxidative damage in HepG2 cells. Bioorg. Med. Chem. Lett. 2018, 28, 2422-2425.
  5. ↑ Kommera, R.; Bhimapaka, C. R. A simple and efficient approach for the preparation of dihydroxanthyletin, xanthyletin, decursinol and marmesin. Synthetic Communications 2020, 50, 3204-3211.
  6. ↑ Anonymous Dictionary of natural products; Chapman & Hall: London, 1994.
  7. ↑ Nemoto, T.; Ohshima, T.; Shibasaki, M. Enantioselective total syntheses of novel PKC activator (+)-decursin and its derivatives using catalytic asymmetric epoxidation of an enone. Tetrahedron Lett. 2000, 41, 9569-9574.
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