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

Marmesin plays a central role in the biosynthesis of furocoumarins in the plant Ruta graveolens, more commonly known as rue. It is the biosynthetic precursor for psoralen and other furocoumarins present in rue. It also a constituent of Aegle marmelos, Ammi majus, Poncirus trifoliata and Prangos bucharica and others Chatterjee, A. et al, J. Am. Chem. Soc., 1949, 71, 606-609

Spectra

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

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.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.

UV-Vis UV: [neutral]λmax  217 (ε7420); 338 (ε17700)( MeOH)   [neutral]λmax  332( EtOH).Anonymous Dictionary of natural products; Chapman & Hall: London, 1994.

Laboratory synthesis 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.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.

Metabolism in plants (+)-Marmesin is converted to psoralen by the enzyme psoralen synthase.

This is part of the pathway to a group of natural products called furanocoumarins.

References