PubMed · 419342
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M de la Brassinne, F Cornet. 1979-01-15. [Photochemotherapy (PUVA)].. https://pubmed.ncbi.nlm.nih.gov/419342/
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Furanocoumarins are specialized defense compounds in Apiaceae, but the evolutionary path of their biosynthesis is not well understood. We generated a telomere-to-telomere (T2T) genome for Sanicula chinensis, an early-diverging species within the Saniculoideae subfamily, to explore its evolution. Comparative genomics revealed that S. chinensis and Apioideae species each underwent unique whole-genome duplication (WGD). Unlike most species in the Apioideae subfamily, S. chinensis produces a limited diversity and content of furanocoumarins but shows high esculetin levels. This metabolic profile likely stems from three genetic factors: elevated expression of p-Coumaroyl ester 3'-hydroxylase (C3'H) and hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HCT), which shift the metabolic pathway toward simple coumarins; the absence of a key biosynthetic gene cluster, including prenyltransferase (PT) and p-coumaroyl-CoA 2'-hydroxylase (C2'H), found in Apioideae; and incomplete or inactive PT enzymes in S. chinensis. Our results not only shed light on the evolutionary history of furanocoumarin biosynthesis in Apiaceae, but also provide avenues for tailoring furanocoumarin content for agricultural or medical applications in plants.
Time-dependent density functional theory calculations have been performed for the excited states of psoralen, 5-methoxypsoralen, and 8-methoxypsoralen in systems and furan and pyrone monoadducts bonded to a thymine residue. The theoretical assignments to ultraviolet (UV) absorption spectra of isolated systems have been performed. The present calculations have clarified that the excitation energies of the first singlet excited (S1) state of monoadducts are blue-shifted compared with the isolated systems. It is shown that, in particular, the S1 excitation energy of the pyrone monoadduct is significantly blue-shifted and, therefore, the pyrone monoadduct is not excited by UV-A light (300-400 nm), which is used in the photochemotherapy.
The inverse electron-demand Diels-Alder reaction between furocoumarinones and 3,6-bis(methoxycarbonyl)-1,2,4,5-tetrazine was used to give pyridazinofurocoumarins in good yields. The structural characterisation of the synthesised compounds was achieved by NMR spectroscopy. The mass spectrometric behaviour was studied under electron ionisation conditions via sequential product ion fragmentation experiments (MS(n)). This study allowed the evaluation of the role played by the methyl substituent on the benzene ring of pyridazinofurocoumarins in their fragmentation pathways.