Secondary metabolites of Tanacetopsis karataviensis plant
Authors
Dilnoza E. Dusmatova, Kambarali K. Turgunov, Bakhodir Tashkhodzhaev, Rimma F. Mukhamatkhanova, Ildar D. Shamyanov
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As part of the ongoing study of the plant Tanacetopsis karataviensis, this article presents the results of the isolation of the sesquiterpene lactone ridentin and the flavonoids eupatilin and luteolin from its aerial parts. The ¹H NMR spectrum of ridentin, recorded in DMSO-d6 + CCl4, did not provide complete information on the splitting patterns and coupling constants of certain protons. The X-ray crystallographic analysis confirmed the spatial structure of ridentin, which contains a 10-membered labile germacranolide macrocycle. The macrocyclic conformation of ridentin differs from that observed in the known compound subchrysine, particularly in the syn-orientation of the exo-bonds at C14 and C15. The conditional macrocycle form of subchrysine (udCT) differs from the uuCC conformation observed in ridentin crystals. These energetically favorable conformations undergo mutual interconversion in solution at room temperature. However, the absolute configuration of the ridentin molecule, according to X-ray crystallographic data, remains 1R, 3S, 6R, 7S, with an endo double bond configuration of 4E in the macrocycle.
Ridentin, eupatilin and luteolin have been isolated from Tanacetopsis karataviensis for the first time.
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Authors
Dilnoza E. Dusmatova, Kambarali K. Turgunov, Bakhodir Tashkhodzhaev, Rimma F. Mukhamatkhanova, Ildar D. Shamyanov
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