Sesquiterpene lactone dimers from the fruit of Carpesium abrotanoides L

NMR-Guided Isolation of Anti-inflammatory Carabranolides from the Fruits of Carpesium abrotanoides L.

“…Carabranolides present two NMR signals of characteristic methines at δ H ∼0.44 and ∼0.34 (H-1 and H-5) as well as a quaternary carbon at δ C ∼17.1 (C-10) in their 1 H and 13 C NMR spectra for the cyclopropane moiety. 4,6,15 Chemical shifts of H-4 and C-4 in these compounds shifted downfield from δ H ∼3.8 to ∼4.9 and from δ C ∼68 to ∼71, respectively, due to the esterification of the hydroxy group at C-4 of carabrol.…”

“…16 Therefore, an NMR-guided isolation method for carabranolide derivatives was established in this study. Signals for H-1, H-4, H-5, C-4, and C-10 were observed in 1 H and 13 C NMR spectra (Figure 1) of the ethanolic extract of C. abrotanoides fruits. A series of fractionation steps were then performed and monitored by NMR analyses.…”

“…The 1 H NMR spectrum of 1 (Table 2) exhibited 1 H signals for two methyl groups at δ H 1.06 (s, H-14) and 1.21 (d, J = 6.2 Hz, H-15), one exocyclic olefinic methylene at δ H 5.56 (d, J = 2.5 Hz, H-13a) and 6.24 (d, J = 2.5 Hz, H-13b), and two methines of a characteristic cyclopropane moiety at δ H 0.34 (ddd, J = 9.1, 7.0, 4.1 Hz, H-5) and 0.44 (td, J = 7.2, 4.1 Hz, H-1). The 13 C NMR and DEPT135 spectra showed signals for 27 carbons (Table 1), including two methyl groups (δ C 18.3 and 20.0, C-14 and C-15, respectively), 13 methylenes (one exocyclic methylene at δ C 122.7, C-13), seven methines (four oxygenated methines at δ C 69.0, 70.6, 75.8, and 84.7; C-10′, C-4, C-8, and C-9′), and five quaternary carbons (three carbonyl carbons at δ C 170.6, 173.5, and 175.4, C-12, C-1′, and C-12′). 1 H and 13 C NMR spectroscopic data of 1 suggested the presence of a carabranolide unit and a furanoctanoic acid group in 1.…”

“…The 13 C NMR and DEPT135 spectra showed signals for 27 carbons (Table 1), including two methyl groups (δ C 18.3 and 20.0, C-14 and C-15, respectively), 13 methylenes (one exocyclic methylene at δ C 122.7, C-13), seven methines (four oxygenated methines at δ C 69.0, 70.6, 75.8, and 84.7; C-10′, C-4, C-8, and C-9′), and five quaternary carbons (three carbonyl carbons at δ C 170.6, 173.5, and 175.4, C-12, C-1′, and C-12′). 1 H and 13 C NMR spectroscopic data of 1 suggested the presence of a carabranolide unit and a furanoctanoic acid group in 1.…”

Lipskynoids A–G, New Acyclic Diterpenes from the Flowers ofCarpesium lipskyi

“…The genus Carpesium (Asteraceae family) has 24 species distributed in Asia and Eurasia, among which 18 species are mainly found in Gansu and Qinghai provinces of China. [1] There are many reports on the chemical constituents of this genus, including sesquiterpenes, diterpenoids, and lignan glycopyranosides, [2][3][4][5][6][7] and its anti-inflammatory, cytotoxicity, and anti-tumor activity. [8,9] Carpesium lipskyi is an endemic species in China, with the efficacy of clearing heat and detoxifying.…”