Abstract
A sesquiterpene lactone of the germacrane type, salonitenolide, has been isolated for the first time from the epigeal part ofCentaurea pseudomaculosa Dobrocz (spotted centaurea) and has been identified. The structures of the germacranolides and hanphyllin have been determined by the method of x-ray structural analysis: salonitenolide is 8-hydroxy-6β,8β(H)7α(H)-germacra-1(10),4,11(13)-trien-6,12-olide and hanphyllin is 3-hydroxy-3α,7α(H),6β(H)-germacra-1(10),4,11(13)-trien-6,12-olide. It has been established that the ten-membered rings of salonitenolide and hanphyllin are of the chair-chair type,1D14,15D5. On the basis of the results of CD spectroscopy, the chiral centers in the hanphyllin molecule have been assigned the 3S, 6R, and 7S configurations.
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Additional information
Institute of Organic Synthesis and Coal Chemistry, Kazakh SSR Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Heteroorganic Compounds, USSR Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 781–785, November–December, 1989.
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Turdybekov, K.M., Adekenov, S.M., Timofeeva, T.V. et al. Molecular and crystal structure of the germacranolides salonitenolide and hanphyllin. Chem Nat Compd 25, 662–665 (1989). https://doi.org/10.1007/BF00598260
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DOI: https://doi.org/10.1007/BF00598260