Eudesmane sesquiterpenoids from the Asteraceae family

Abstract

This review covers the structures and biological activities of eudesmane-type sesquiterpenoids from the plants of the Asteraceae family. Biosynthetic studies or chemical syntheses leading to the revision of structures or stereochemistries have also been included, and 593 references are cited.

Four New Sesquiterpenoids from the Fruits of Alpinia oxyphylla

“…The CH 2 Cl 2 extract was subjected to a silica gel column chromatography (CC) eluted with petroleum ether-acetone in a gradient (1 : 0 to 1 : 1), to afford 14 fractions (Fr. [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Fr.…”

Natural sesquiterpenoids

“…262 The essential oils from the liverwort Plagiochila bifaria 263 264 In this work, the structures of another two metabolites have been revised to 275 and 277. These compounds had been obtained from Bazzania tridens 265 and Lepidozia vitrea, 266 respectively.…”

Inflammatory Inhibitory Activity of Sesquiterpenoids from <i>Atractylodes macrocephala</i> Rhizomes

“…Compound 2 was isolated as a white amorphous powder with a molecular formula of C 14 in HR-EI-MS. The optical rotation of 2 was determined to C-NMR data of 1 and 2 suggested that 2 is an analogue of 1.…”

“…Repeated silica gel and reverse phase column chromatography of the CHCl 3 fraction afforded three new sesquiterpenoids (1-3) and eleven known ones (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). The chemical structures of the known compounds were determined to be atractylenolide II (4), 12) atractylenolide III (5), 13) asterolid (6), 14) 8β-methoxyatractylenolide (7), 15) atractylenolide V (8), 16) atractylenolide I (9), 17) atractylenolactam (10), 5) Z-methyl caffeate (11), 18) ferulic acid (12), 19) Z-5-hydroxy ferulic acid (13), 20) and 2-hydroxy ferulic acid (14) 21) based on an analysis of the 1 H-and 13 C-NMR spectra and confirmed by a comparison with those reported in the literature (Fig. 1 C-NMR spectrum and distortionless enhancement by polarization transfer (DEPT) spectrum of 1 displayed 15 carbon signals, including one methyl, five methylenes, one exocyclic methylene, one hydroxymethyl, one aliphatic methine, one oxygenated methine, one aliphatic quaternary, three olefinics and one carbonyl carbon ( Table 1).…”

“…11) This study examines whether new metabolites also contribute to the biological activity of A. macrocephala. Three new eudesmane-type sesquiterpenoids, i.e., 13-hydroxylatractylenolide II (1), 4-ketone-atractylenolide III (2) and eudesm-4(15)-ene-7β,11-diol (3), together with eleven known compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were isolated. Their structures were elucidated by combination analysis based on their NMR and mass spectra.…”