A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of Atractylodes lancea DC

Abstract

A new prenylated dihydrobenzofuran derivative (1), was isolated from the rhizomes of Atractylodes lancea DC (Asteraceae), along with ten known compounds, including atractylenolide II (2), phi-taraxasteryl acetate (3), taraxerol acetate (4), beta-sitosterol (5), stigmasterol (6), beta-eudesmol (7), atractylenolide III (8), atractylenolide IV (9), daucosterol (10), and stigmasterol 3-O-beta-D-glucopyranoside (11). The structure of the new compound (1) was elucidated as trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid by the combination of 1D, 2D NMR analysis and mass spectrometry, and it was the first reported 2,3-dihydrobenzofuran derivative having a carboxyl residue at C-5 and an isopentene moiety at C-7 contemporaneously. In addition, compound 1 exhibited significant cytotoxicity against cancer cell lines HCT-116 and MKN-45.

Jasmonic acid is involved in the signaling pathway for fungal endophyte-induced volatile oil accumulation of Atractylodes lancea plantlets

“…Atractylodes lancea , a member of the Compositae family, is a traditional Chinese medicinal plant [1,2]. Volatile oils from A. lancea show antimicrobial activities as well.…”

New eudesmane-type sesquiterpenoids from the processed rhizomes of Atractylodes macrocephala

“…In the current project, we examined the chemical ingredients of AMR processed with wheat bran. As a result, two new eudesmane-type sesquiterpenoid, namely eudesma-4(15),7(11)-dien-8a,12-ether (atractylenother, 1) and 8a-hydroxyeudesma-4(15),7(11)-dien-8b,12-olide (8-epiatractylenolide III, 2), one new natural product named 4(R),15-epoxy-8b-hydroxyatractylenolide II (3) [14], together with four known eudesmanolidetype sesquiterpenoid lactones, atractylenolides I (4) [15], II (5) [16], III (6) [16], and IV (7) [16] (Figure 1), were isolated. Their structures were determined by combination analysis based on NMR and mass spectra.…”

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

“…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).…”