A. Z. Abyshev

A new coumarin, pranferol, from the roots ofPrangos ferulacea

SummaryA new coumarin, pranferol C16H16O5, has been isolated from the roots ofPrangos ferulacea (L.) Lindl.The structure 5-(2′-hydroxy-3′-methylbutoxy)furo-2′,3′:7,6-coumarin has been proposed for pranferol.

The structure of alatol

SummaryFrom the roots ofPrangos alata Grossh (Prangos biebersteinii Karjag) a new furocoumarin (I), C17H18O6, mp 125–127°C (from benzene), which has been called alatol, has been isolated.On the basis of the results of IR and NMR spectra and chemical properties, the structure of 5-(2″-hydroxy-3″-methoxy-3″-methylbutoxy)-furo-2′,3′:7,6-coumarin has been proposed for (I). This structure has been confirmed by the partial synthesis and by the mass spectra of alatol and of its acetate.

The structure of ulopterol

ConclusionsA new coumarin C15H18O5 with mp 141.5–142.5° C (from benzene) has been isolated from the roots and fruit ofPrangos uloptera D. C., and it has been called “ulopterol.” On the basis of UV, IR, NMR, and mass spectra it has been found to have the structure of 6-(2′,3′-dihydroxy-3′-methylbutyl)-7-methoxy-coumarin and is a geometrical isomer of meranzin hydrate.

Natural (−)-7-methoxy-8-(β, γ-dihydroxyisopentyl)-coumarin

SummaryThe roots ofPrangos ferulaceae (L.) Lindl. have yielded (−)-7-methoxy-8-(β, γ-dihydroxyisopentyl)-coumarin, composition C15H18O5, with mp 128°. [α]D20-53.03°, identical with a synthetic hydrate of meransin and found by us in nature for the first time. Various coumarin derivatives are present in the roots ofPrangos ferulaceae (L.): osthole, oxypeucedanin, oxypeucedanin hydrate, and isoimperatorin.

Gosferol — A new furocoumarin from the roots of Prangos ferulacea

SummaryFrom the roots ofPrangos ferulacea (L.) Lindl. has been isolated a new furocoumarin (I), C10H14O5, with mp 136.5–138.5°C (from ethanol), [α]D20 ± 0° (chloroform), which we have calledgosferol.On the basis of a study of the UV, IR, NMR, and mass spectra and the chemical properties of gosferol, the structure 5-(2″-hydroxy-3″-methylbutenyloxy)furo-2′,3′:7,6-coumarin has been proposed for it.

Pranferin — A new coumarin from the roots of Prangos ferulacea

SummaryFrom the roots ofPrangos ferulacea (L) Lindl. a new coumarin has been isolated, C18H22O5, mp 167.5–169°C (from benzene) [α]16D ± 0° (c 3.88; chloroform), and it has been called pranferin.By a study of its UV, IR, NMR, and mass spectra and chemical properties, its structure has been established as 8-(2′-acetyl-2′-tert-butoxyethyl)-7-methoxycoumarin.

Pranferol from the roots of Prangos ferulacea

ConclusionsFrom the roots ofPrangos ferulacea (L.) Lindl. growing in Armenia an optically inactive furocoumarin C16H16O5, an isomer of pranferol, has been isolated.

Structure of polymeric coumarins. I. Determination of the double bonds in copolymers and the initial coumarins by ozonization

The paper gives the results obtained in a study of the structure of coumarin derivatives by the following metheds: ozonization of the double bonds in the monomeric and polymeric coumarins, and also in mixtures of polyvinylpyrrolidone with monomeric coumarins, and the treatment of the monomeric coumarins under the conditions of radical copolymerization but without the participation of N-vinylpyrrolidone.

Polymeric coumarin derivatives

SummaryCopolymers of vinylpyrrolidone with coumarin, umbelliferone, esculetin, osthole, ostholic acid, meranzin hydrate, isoimperatorin, oxypeucedanin hydrate, isooxypeucedanin, gosferol, pranchimgin, and marmesin have been synthesized and their structures have been studied.On the basis of a study of UV, IR, and NMR spectra, and also of chemical properties, it has been established that copolymerization takes place at the 3,4 double bond of the lactone ring and side chains do not participate in polymerization.In a pharmacological study of monomeric coumarins and their copolymers it was found that they all possess well-defined spasmolytic and hypotensive properties.

Furocoumarins of the roots of Prangos ferulacea

SummaryIt has been established that the treatment of oxypeucedanin and oxypeucedanin hydrate with 20% sulfuric acid in ethanol forms, in addition to known substances, a new coumarin derivative (VI), C18H20O6, with mp 93–94.5°C, for which the structure of 5-(3″-ethoxy-2″-hydroxy-3″methylbutoxy)furo-2′,3′:7,6-coumarin has been proposed. On the basis of the investigation performed and the similarity of the structures of the compounds isolated, a hypothetical scheme of the biogenesis of furocoumarins inPrangos ferulacea (L.) Lindl. has been put forward.