Isolation and Structure Determination of Three New Sesquiterpenoids from Achillea millefolium

Abstract

Phytochemical investigation of the whole plant of Achillea millefolium led to the isolation of three new sesquiterpenes which were trivially named as sesquiterpene lactone-esters A and B (1 and 2), and sesquiterpene lactone-diol (3). The structures of these compounds were determined with the help of one-and two-dimensional (1D and 2D) NMR techniques including 1 H NMR, 13 C NMR, HMQC, HMBC, COSY, and NOESY experiments.

Pharmacognosy, Phytochemistry and Pharmacological Properties ofAchillea millefoliumL.: A Review

“…The sesquiterpenoids identified in A. millefolium are sesquiterpene lactone ester A, sesquiterpene lactone ester B and sesquiterpene lactone‐diol (Farooq et al, ), seco‐pseudo guaianolides viz., paulitin, isopaulitin, psilostachyin C, desacetylmatricarin and sintenin (Csupor et al , ), achimillic acids A, B and C (Tozyo et al, ), isoachifolidiene (Rucker et al, ), 8‐acetyl egelolide and 8‐angeloyl egelolide (Ochir et al , ), austricin (deacetylmatricarin), millefin, 8‐hydroxyachillin and artelesin (Konovalov and Chelombit'ko, ), α‐peroxyachifolid, β‐peroxyisoachifolid (Hausen et al, 199; Rucker et al, ), achillifolin, dihydroparthenolide and dihydroreynosin (Ulubelen et al , ), azulenogene sesquiterpene lactones viz., 8‐acetoxy‐artabsine, 8‐angeloxy‐artabsine and 2, 3‐dihydro‐desavetoxy‐matricin (Verzar‐Petri et al, ), acetylbalchanolide and millefolide (Hochmannová et al , ). The sterols identified include, β‐sitosterol, stigmasterol, campesterol and cholesterol while triterpenes identified are α‐amyrin, β‐amyrin, taraxasterol and pseudotaraxasterol (Chandler et al , ).…”

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

“…millefolium L. Three flavones: 5-Hydroxy-3,6,7,4′-tetramethoxyflavone, artemetin, and casticin (Falk et al, 1975) A. millefolium L. Two sesquiterpene lactone-esters, and one sesquiterpene lactone-diol (Farooq et al, 2012) A. millefolium L. Guaianolides: Leucodin, 8α-angeloxy-leucodin, achillin, 8α-angeloxy-achillin, and desacetylmatricarin (Glasl et al, 2003) A. millefolium L. Santolinoidol, a bisabolene sesquiterpene (Fahed et al, 2016) A. setacea Waldst. & Kit.…”

Neurite Outgrowth-Inducing Drimane-Type Sesquiterpenoids Isolated from Cultures of the Polypore Abundisporus violaceus MUCL 56355

“…Compound 8 was purified as a brown solid, and its molecular formula was established to be C 15 H 18 O 5 based on HRESIMS, displaying a protonated molecule and a sodium adduct at m / z 279.1229 [M + H] + (calculated 279.1227) and at m / z 301.1047 [M + Na] + (calculated 301.1046), respectively, indicating seven degrees of unsaturation. The UV spectrum of 8 revealed a maximal absorption (λ max ) at 248 nm, suggesting a possible lactone moiety in its structure . The 13 C NMR data of 8 (Table ) revealed the presence of a ketocarbonyl carbon (δ C 196.8, C-7) along with a second carbonyl carbon at δ C 172.9 (C-11), two deshielded olefinic quaternary carbons at δ C 152.1 (C-9) and δ C 151.3 (C-8) together with the common carboxylic acid carbon at δ C 181.2 (C-13).…”

“…The UV spectrum of 8 revealed a maximal absorption (λ max ) at 248 nm, suggesting a possible lactone moiety in its structure. 25 The 13 C NMR data of 8 ( Table 2 ) revealed the presence of a ketocarbonyl carbon (δ C 196.8, C-7) along with a second carbonyl carbon at δ C 172.9 (C-11), two deshielded olefinic quaternary carbons at δ C 152.1 (C-9) and δ C 151.3 (C-8) together with the common carboxylic acid carbon at δ C 181.2 (C-13). The 1 H NMR, HMBC, and HSQC spectra of 8 ( Figure 4 ) revealed the presence of a deshielded diastereotopic methylene group at δ H 4.85/δ H 4.89 (H 2 -12) with the characteristic large geminal coupling constant ( J value) of 17.5 Hz and directly correlated to a carbon peak at δ C 68.8 ppm.…”