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The investigation of a dichloromethane extract of flower heads of a Hungarian taxon of the Achillea millefolium group led to the isolation of three flavonoid aglycones, one triterpene, one germacranolide and five guaianolides. Their structures were elucidated by UV-VIS, EI- and CI-MS, 1H NMR and 13C NMR spectroscopic methods as well as by 2D-NMR studies and by selective 1D-NOE experiments. Besides apigenin, luteolin and centaureidin, β-sitosterol, 3β-hydroxy-11α,13-dihydro-costunolide, desacetylmatricarin, leucodin, achillin, 8α-angeloxy-leucodin and 8α-angeloxy-achillin were isolated. Both latter substances are reported here for the first time. Their NMR data were compared with those of the other guaianolides. The stereochemistry of 3β-hydroxy-11α,13-dihydro-costunolide was discussed and compared with data of the literature.

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After extraction of coarsely ground seeds of AESCULUS GLABRA Willd. with 80% methanol the saponin fraction was submitted to enzymatic and acid hydrolysis, giving qualitatively identical TLC-spectra of the sapogenins. For separation of the obtained sapogenins silica gel-columns with chloroform-methanol-water mixtures as mobile phases were employed. Five main components (genins G-A to G-E), identified as 21,22-diangeloyl-barringtogenol C, 21,22-diangeloyl-R (1)-barrigenol, 21-angeloyl-barringtogenol C, 22-angeloyl-R (1)-barrigenol and 21-angeloyl-R (1) barrigenol have been isolated. Structure elucidation was accomplished by (1)H-NMR and mass spectrometry of the genins, their acetates and several isopropyliden derivatives. The acid free sapogenins barringtogenol C and R (1) barrigenol (G-F and G-G) were found and identified by thin layer chromatography.