A new guaianolide and other constituents from Achillea ligustica

Addressing the Challenges of Structure Elucidation in Natural Products Possessing the Oxirane Moiety

“…As far as we can tell, the revised guaianolide A is the only example of the formal HCl opening of 1,2-epoxide (i.e., not the 3,4-epoxide) in artecanin or canin (the incorrect structure of chloroklotzchin notwithstanding). However, a related 9-acetate, algerianolide, was isolated from A. ligustica and its structure was established by X-ray analysis . Comparison of the experimental 13 C NMR chemical shifts for guaianolide A and algerianolide reveals a strong similarity.…”

“…However, a related 9acetate, algerianolide, was isolated from A. ligustica and its structure was established by X-ray analysis. 38 Comparison of the experimental 13 C NMR chemical shifts for guaianolide A and algerianolide reveals a strong similarity. In fact, when the carbons proximal to the C9−OAc substitution, i.e., C7−C10 and C14, were omitted from this comparison, the remaining 10 carbons gave a rmsd of 0.37 ppm, Figure 7.…”

Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review

“…An epimeric sesquiterpene lactone + matricarin + 5-hydroxy-5,6-secocaryophyllen-6-one (3) (Mahmoud et al, 2012) A. ligustica All. Piperidine amides, sesquiterpene lactones with rare 5/6/5 skeletons, guaianolides, and flavonoids (Bruno and Herz, 1988;Tzakou et al, 1995a;Ahmed et al, 2003;Boudjerda et al, 2008) A. lingulata Waldst. & Kit.…”

Phytochemical composition, ethnomedicinal uses, and pharmacological properties of Achillea ligustica All.: A review

“…Guaianolide sesquiterpene lactones types are the main sesquiterpenes identified from A. ligustica collected from different countries. Thus, ten guaianolides 22-31 were identified, with four iso-secotanpartholides 32-35, two sesquiterpenes lactones with 5/6/5 skeleton (36 and 37), one eudesmane sesquiterpene lactone 38, one isodaucane sesquiterpene 39, and 5-hydroxy-5,6-seco-caryophellen-6-one 40 (Table 2, Figure 2) [20,25,26,[29][30][31]. The species is characterized by the presence of chlorinated guaianolide sesquiterpenes, three of them chlorinated in position 3 (compounds 22, 27, and 28) and one in position 2 (compound 25), and matricarin 23 was the most guaianolide sesquiterpene cited by the studies.…”