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Structure of the coumarin glycoside reoselin from the roots ofFerula kirialovii

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Abstract

The structure of terpenoid and carbohydrate moieties of the molecule of reoselin have been confirmed by the use of13C NMR spectra, and the position of the carbohydrate moiety has been corrected. Reoselin is S-(−)-karatavikinol β-sophoroside at the tertiary hydroxy group (S-(−)-karativikinol tertiary-O-β-D-sophoroside) and not at the secondary hydroxy group, as was previously assumed. The absolute configuration of the single asymmetric center, the carbon atom to which the secondary hydroxy group is attached, has been assigned by analogy with S-(−)-epoxysqualene and S-(−)-epoxyfarnesol. S-(−)-Karatavikinol tertiary O-β-D-sophoroside has been isolated from giant fennels, a characteristic feature of which is the biosynthesis via direct antiparallel cyclization of bicyclic sesquiterpenoid derivatives of umbelliferone with the configuration of the ring linkage enantiometric to the linkage of rings A and B of triterpenoids.

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Additional information

V. L. Komarov Botanical Institute, Academy of Sciences of the USSR, Leningrad. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 62–66, January–February, 1987.

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Bukreeva, T.V. Structure of the coumarin glycoside reoselin from the roots ofFerula kirialovii . Chem Nat Compd 23, 51–54 (1987). https://doi.org/10.1007/BF00602458

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Keywords

  • Carbohydrate
  • Carbon Atom
  • Glycoside
  • Characteristic Feature
  • Coumarin