Bioactive Constituents from the Aerial Parts of Lippia triphylla

Yi Zhang, Yue Chen, Shiyu Wang, Yongzhe Dong, Tingting Wang, Lu Qu, Nan Li, Tao Wang
2015 Molecules  
Five new compounds, lippianosides A (1), B (2), C (3), D (4), and E (5), along with 26 (6-31) known ones were obtained from the 95% EtOH extract of Lippia triphylla (L. triphylla) aerial parts collected from Rwanda, Africa. Among the known compounds, 11 and 17-30 were isolated from the Lippia genus for the first time. In addition, 12, 13, and 16 were firstly obtained from this species. The structures of them were elucidated by chemical and spectroscopic methods. The antioxidant and triglyceride
more » ... accumulation inhibition effects of the 31 compounds were examined in L6 cells and HepG2 cells, respectively. L. triphylla (L 1 HER.) O. Kuntze (syn. L. citrodora (ORT.) HBK) is a perennial, bushy plant of Verbenaceae family, commonly named lemon verbena. It grows spontaneously in many countries in South America, such as Brazil, Chile, Argentina, and Peru, had been introduced into Europe by the end of the 17th century, and has since been cultivated in North Africa and Southern Europe [8] . It contains special lemon-like fragrance, and is used against vertigo, nausea, and headaches in Greece [9] . During the course of our studies, we identified five new compounds, lippianosides A-E (1-5), along with 26 known ones (6-31) from the 95% EtOH extract of L. triphylla aerial parts collected from Rwanda. Their structures were elucidated by chemical and spectroscopic methods. Based on previous Lippia genus activity reports evidence, the antioxidant and TG accumulation inhibitory effects of the isolates were examined. Results and Discussion The 95% EtOH extract of L. triphylla was subjected to solvent partition, chromatographic isolation, and chemical and spectral analyses. As a result, five new compounds, lippianosides A-E (1-5) (Figure 1 ), together with 26 known ones (Figure 2 ), jionoside C (6) [10], trans-acteoside (7) [11], isoverbascoside (8) [12], cis-acteoside (9) [13], martynoside (10) [14], isomartynoside (11) [14], β-hydroxyacteoside (12) [15], campneoside I (13) [16], cistanoside F (14) [17], jaceosidin (15) [18], nepetin (16) [19], nepitrin (17) [20], dehydrodiconiferyl glucoside D (18) [21], dehydrodiconiferyl glucoside E (19) [21], (+)-lariciresinol-9-O-β-D-glucopyranoside (20) [22], (+)-pinoresinol 4-O-β-D-glucoside (21) [23,24], dihydrovomifoliol-O-β-D-glucopyranoside (22) [25,26], turpinionoside D (23) [27], 9-hydroxymegastigm-5-en-4-one (24) [28], (´)-loliolide (25) [29,30], eudesm-4(15)-ene-1β,6α-diol (26) [31], (6S)-3,7-dimethyl-7-hydroxy-2(Z)-octen-6-olide (27) [32], ursolic acid (28) [33], avicennone A (29) [34], benzyl alcohol O-β-D-glucopyranoside (30) [35], and icariside H 1 (31) [36] were yielded and identified. Among the known ones, 11 and 17-30 were isolated from the Lippia genus for the first time, and 12, 13, and 16 were obtained from this species for the first time. Lippianoside A (1), rαs 25 D +7.9˝(in MeOH), white powder. Its molecular formula, C 27 H 36 O 12 , was determined from the molecular ion peak at m/z 575.2113 [M + Na] + by HR-Q-TOF-ESI-MS measurement. Acid hydrolysis of 1 with 1 M HCl yielded D-glucose, which was identified on the basis of retention time (HPLC) and optical rotation [37, 38] .
doi:10.3390/molecules201219814 pmid:26670227 fatcat:xp7ui56xrfelxhc6nwdyz6bz7u