Structure elucidation and NMR assignments of a new sesquiterpene of volatile oil from Artemisia frigida Willd.

Abstract

A new sesquiterpene, artefrigin (5), together with four known sesquiterpenes were isolated from the volatile oil of Artemisia frigida Willd. The structure of 5 was elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.

Neutrophil Immunomodulatory Activity of Farnesene, a Component of Artemisia dracunculus Essential Oils

“…Artemisia exhibits significant intraspecies variations in terpenes present in their essential oils [ 16 , 26 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 ]. For example, the variation in volatile components of these plants may occur during plant maturation at different altitudes.…”

Structure determination of liquid molecules by encapsulation in an aromatic cavity with hydrogen bonding and enhanced C–H⋯π interactions

“…For example, the volatile sesquiterpene artefrigin, isolated from the oil of Artemisia frigida , was elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D- and 2D-NMR techniques. 6 However, the spectroscopic analyses often provide subjective structures, and are incorrect sometimes. 7…”

“…For example, the volatile sesquiterpene artefrigin, isolated from the oil of Artemisia frigida, was elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D-and 2D-NMR techniques. 6 However, the spectroscopic analyses often provide subjective structures, and are incorrect sometimes. 7 The single-crystal X-ray diffraction (SCD) technique provides definite structural information at the atomic level and is recognized as the most reliable method for structure determination.…”

Chemical Constituents from the Fruits of Amomum kravanh and Their Role in Activating Alcohol Dehydrogenase

“…235.1693). The NMR data of 2 ( Table 1 ) were similar to those of (-)-(6 R )-11-hydroxybisabol-2,7(14)-dien-4-one, a bisabolane sesquiterpenoid isolated from the aerial parts of Mikania shushunensis [ 18 ], except for that an additional double bond [ δ H 5.61 (1H, t, J = 20.1 Hz, H-9), 5.65 (1H, t, J = 5.9 Hz, H-10); δ C 199.7 (C-9), 111.1 (C-9)] in 2 was observed. The double bond was assigned at C9-C10 based on the HMBC correlations from H-12/H-13 to C-10 and 1 H- 1 H COSY correlations of H-8/H-9/H-10 ( Figure 2 ).…”

“…Thirty-five known compounds were identified based on their MS and NMR data (11-45): 2-methyl-6-(4-methyl-3-cyclohexen-1-yl)-6-heptene-2,3-diol (11) [25], stigmasta-4,22-dien-3-one (12) [11], stigmasta-1,5-dien-3-one (13) [11], stigmast-4-en-3-one ( 14) [11], stigmasta-4,6-dien-3-one (15) [11], β-rosasterol (16) [26], ergosta-4,24(28)-dien-3-ol (17) [27], ergosterol peroxide (18) [28], 5,8-epidioxyergost-6-en-3-ol (19) [29], 5,8-epidioxy-23-methyle rgosta-6,22-dien-3-ol (20) [30], olean-12-ene (21) [31], 2,3-dihydro-5,7-dihydroxy-2-(4-hydrox yphenyl)-3-methoxy-4H-1-benzopyran-4-one (22) [32], kumatakenin (23) [33], ermanin (24) [34], 5-hydroxy-3,7,4 -trimethoxyflavone (25) [11], isokaempferide (26) [11], (4S,6R)-4-hydroxy-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one (27) [11], (4R,6R)-4-hydroxy-3methyl-6-(1-methylethyl)-2-cyclohexen-1-one (28) [11], 4-hydroxy-2-methyl-5-(1-methylethy l)cyclohexanone (29) [11], rel-(+)-(4R,6R,7R)-7-hydroxy-3,4,6-trimethyl-2-cyclohepten-1-one (30) [35], rel-(+)-(4R,5S)-5-hydroxy-4,5-dimethyl-1-cycloheptene-1-carboxylic acid (31) [36], p-menth-1-ene-7,8-diol (32) [37], cinnamic acid (33) [37], kravanol B (34) [12], tifentai (35) [38], ...…”