Highly oxygenated guaianolides from Otanthus maritimus

Chemical composition and antibacterial activity of Otanthus maritimus (L.) Hoffmanns. & Link essential oils from Corsica

“…3,4 The plant is traditionally employed in folk medicine in decoctions as tonics, dyspeptics and for the treatment of toothache, asthmatic bronchitis, dysentery and inflammation of the urinary bladder. [5][6][7][8] Studies have reported the identification of various components isolated from O. maritimus extracts: polyacetylenes, thiophenamides, highly unsatured amides, 9 piperidine amides 10 and sesquiterpene hydrocarbons 11 from the roots. Sesaminelike compounds and flavonoids, 6,12 also sesquiterpene lactones and oxygenated monoterpenes, 5,7,13 have been isolated from the aerial parts of the plant.…”

“…[5][6][7][8] Studies have reported the identification of various components isolated from O. maritimus extracts: polyacetylenes, thiophenamides, highly unsatured amides, 9 piperidine amides 10 and sesquiterpene hydrocarbons 11 from the roots. Sesaminelike compounds and flavonoids, 6,12 also sesquiterpene lactones and oxygenated monoterpenes, 5,7,13 have been isolated from the aerial parts of the plant. Only one study has described the chemical composition of a Grecian O. maritimus essential oil, obtained from the aerial parts, which exhibited a significant repellency against the ant Monomorius pharaonis.…”

Achillinin A, a Cytotoxic Guaianolide from the Flower of Yarrow,Achillea millefolium

“…The signals at 56.3 and 57.3 were assigned to epoxide carbons, and the protons bonding to these carbons at 3.55 (1H, d, J ¼ 1:1 Hz) and 3.29 (1H, d, J ¼ 1:1 Hz) were assigned to cis-epoxide protons. 20 20) together with the carbon resonance lines at 77.2 (C), 56.2 (CH), 57.3 (CH) and 70.7 (C) in the 13 C-NMR spectrum demonstrate the presence of an 2,3-epoxy-1,4-dihydroxy moiety on a five-membered ring. The chemical shifts and coupling constant further corroborate the structure of ring-A as a cyclopentane ring.…”

“…All these observations suggest that compound 1 was a highly oxygenated guaianolide. 20,21) Furthermore, the signals due to H14 and H15 were exhibited as a pair of three-proton singlets at 1.13 and 1.55, indicating the presence of 4,10-dihydroxy groups.…”

The Aerial Part Headspace Constituents ofOtanthus maritimusL. (Asteraceae)

“…A number of investigations on the chemical composition of Otanthus maritimus L. reported the isolation of thiophene derivatives, guaianolides, sesquiterpene hydrocarbons, sesquiterpene lactones and flavonoids from the root and aerial parts of the plant [5][6][7][8][9] .…”