Constituents of Paramichelia baillonii. Three New Germacranolides

Journal of Natural Products
1988.0

Abstract

In a previous report, we described the isolation and identification of four components from the bark of Paramichelia baillonii (Pierre) Hu (Magnoliaceae), a medicinal plant used by natives of northern Thailand, including the germacranolide epoxides (-)-dihydroparthenolide and (-)-parthenolide, the oxoaporphinoid alkaloid liriodenine, and a new germacranolide alkaloid (-)-bisparthenolidine. In this paper, we describe the structural elucidation of three new germacranolides isolated from the bark of P. baillonii. A chromatographic fraction mentioned in the previous study (eluted after bisparthenolidine and not further investigated) was analyzed by ¹H-nmr and found to be a 2:1:1 mixture of components 1, 2, and 3, which were separated by flash chromatography. Compound 1 was identified as (-)-9α-hydroxydihydroparthenolide, a new germacranolide, based on ir, ms, and ¹H- and ¹³C-nmr spectra. Compound 2 was determined to be 8α-acetoxy-2α-hydroxydihydroparthenolide (named paramicholide) using ir, ms, and nmr data. Compound 3 was concluded to be 2α-hydroxydihydroparthenolide based on ir and ¹H-nmr spectra. To our knowledge, none of these three substituted dihydroparthenolides (1-3) have been isolated from natural sources before. Biosynthetically, although the oxygenation of the parent dihydroparthenolide occurred at three different positions, all substituents were introduced on the α face of the molecule.

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