Guaianolide sesquiterpene lactones from Centaurothamnus maximus

Taha A. Hussien, Tarik A. Mohamed, Abdelsamed I. Elshamy, Mahmoud F. Moustafa, Hesham R. El-Seedi, Paul W. Pare, Mohamed Elamir F. Hegazy

Research output: Contribution to journalArticlepeer-review

Abstract

Centaurothamnus maximus (family Asteraceae), is a leafy shrub indigenous to the south-western Arabian Peninsula. With a paucity of phytochemical data on this species, we set out to chemically characterize the plant. From the aerial parts, two newly identified guaianolides were isolated: 3β-hydroxy-4α(acetoxy)-4β(hydroxymethyl)-8α-(4-hydroxy methacrylate)-1αH,5αH, 6αH-gual-10(14),11(13)-dien-6,12-olide (1) and 15-descarboxy picrolide A (2). Seven previously reported compounds were also isolated: 3β, 4α, 8α-trihydroxy-4-(hydroxymethyl)-lαH, 5αH, 6βH, 7αH-guai-10(14),11(13)-dien-6,12-olide (3), chlorohyssopifolin B (4), cynaropikrin (5), hydroxyjanerin (6), chlorojanerin (7), isorhamnetin (8), and quercetagetin-3,6-dimethyl ether-4’-O-β-D-pyranoglucoside (9). Chemical structures were elucidated using spectroscopic techniques, including High Resolution Fast Atom Bombardment Mass Spectrometry (HR-FAB-MS), 1D NMR;1 H,13 C NMR, Distortionless Enhancement by Polarization Transfer (DEPT), and 2D NMR (1 H-1 H COSY, HMQC, HMBC) anal-yses. In addition, a biosynthetic pathway for compounds 1–9 is proposed. The chemotaxonomic significance of the reported sesquiterpenoids and flavonoids considering reports from other Centaurea species is examined.

Original languageEnglish
Article number2055
JournalMolecules
Volume26
Issue number7
DOIs
StatePublished - Apr 1 2021

Keywords

  • Asteraceae
  • Biosynthesis
  • Centaurothamnus maximus
  • Chemotaxonomy
  • Flavonoids
  • Guaianolides

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