Chemical constituents from the roots of Xanthium sibiricum

Abstract

Xanthium sibiricum patrin ex Widder (Compositae) is an annual herb which grows all around China. Chemical investigations of its roots resulted in the identification of 15 compounds: stigmast-4-en-6β-ol-3-one (1), β-sitostenone (2), β-sitosterol (3), nonadecanoic acid (4), 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol (5), scopoletin (6), Jatrocin B (7), (±)syringaresinol (8), 9,9'-O-di-(E)-feruloyl-(-)-secoisolariciresinol (9), cleomiscosin A (10), cleomiscosin C (11), N-trans-feruloyl tyramine (12), daucosterol (13), 5-methyluracil (14) and uracil (15). Structures were elucidated by spectroscopic (NMR and MS) methods and confirmed by comparing with reference samples and literature data. Compounds 1-2, 4-12, 14, and 15 were isolated from this genus for the first time, while this is the first report of coumarinolignoids in the Compositae family, and coumarinoligoids could be considered as valuable chemotaxonomic markers for the plant.

Cinnamide Derivatives as Mammalian Arginase Inhibitors: Synthesis, Biological Evaluation and Molecular Docking

“…R f = 0.22 (Cyclohexane/EtOAc 5:5); IR (ATR) γ cm −1 : 3287, 3015, 2936, 1651, 1586, 1510; 1 H-NMR (MeOD- d 4 , 300 MHz): δ 7.43 (d, J = 16.0 Hz, 1H), 7.12 (s, 1H), 7.07–7.01 (m, 3H), 6.79 (d, J = 8.1 Hz, 1H), 6.71 (d, J = 8.0 Hz, 2H), 6.40 (d, J = 16.0 Hz, 1H), 3.88 (s, 3H), 3.47 (t, J = 6.9 Hz, 2H), 2.76 (t, J = 6.9 Hz, 2H); HRMS (ESI) m / z calcd for C 18 H 20 NO 4 [M + H] + : 314.1314, found: 314.1396. The analytical data were in line with previously described data [50]. …”

Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum

“…The 1 H NMR and 13 C NMR spectra ( Table 2) of 5 and 6 showed the presence of two methyls, two methylenes, five methines (including one oxygenated and one olefinic carbon), and three quaternary carbons (one olefinic carbon, one carboxylic carbonyl, and one ester carbonyl). The 1 H− 1 H COSY and HSQC spectra demonstrated the occurrence of the following spin system in the structures of 5 and 6: C(2)H 2 Figure 1). In 5 and 6, HMBC correlations from H-2 to C-1/C-7 and from Me-11 to C-1/C-6/C-7 revealed the connectivity of the seven-membered ring A. HMBC correlations from Me-10 to C-4/C-8/C-9, together with the chemical shifts of C-5 (δ C 83.0 in 5 and 82.9 in 6), established the fivemembered ring B.…”

“…Seven new sesquiterpenes (1, 3−8), a new sesquiterpene natural product (2), and two new lignans (9 and 10) were isolated from an EtOAc-soluble fraction of the 95% EtOH extract prepared from the fruits of X. sibiricum by a combination of different chromatographic methods.…”

“…R indices (all data): R 1 = 0.0334, wR 2 = 0.0821, and largest difference peak and hole: 0.172 and −0.156 e Å −3 . The absolute structure was determined using a Flack parameter of 0.2 (2). Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 1017147.…”

Methanol extracts of Xanthium sibiricum roots inhibit inflammatory responses via the inhibition of nuclear factor-κB (NF-κB) and signal transducer and activator of transcription 3 (STAT3) in murine macrophages

“…Xanthium sibiricum (Asteraceae), an annual herbaceous plant, has been used in traditional Chinese medicine for treating inflammatory diseases such as appendicitis, chronic bronchitis, rheumatism and rhinitis (Kan et al, 2011;State Pharmacopoeia Commission of the PRC, 2000). An infusion of the plant is also applied to the treatment of tuberculosis and kidney problems (Chopra et al, 1986).…”