Chemical Constituents of the Fruits of Lycium barbarum and their Neuroprotective Activity
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CHEMICAL CONSTITUENTS OF THE FRUITS OF Lycium barbarum AND THEIR NEUROPROTECTIVE ACTIVITY
Songsong Wen,1 Yuwen Xu,1 Chong Niu,1 Qi Liu,1 Lei Zhang,1 Yu Xiang,1 Weijian Wang,1* and Zhenliang Sun2*
Lycium barbarum is a Solanaceae defoliated shrub, which is widely distributed in arid and semi-arid regions of northwestern China, southeastern Europe, and Mediterranean areas [1]. The fruits of L. barbarum, also called wolfberry, have been used for thousands of years in traditional Chinese medicines and nowadays are widely used as a popular functional food. It is reported to exhibit a variety of beneficial effects, such as reducing blood glucose and serum lipids; it has also anti-aging, immune-modulating, anticancer, anti-fatigue, and male fertility-promoting properties [2, 3]. Previous phytochemical studies on L. barbarum showed the presence of phenolic amides, lignans, flavonoids, coumarins, polyphenols, and polysaccharides [4–9]. As part of our research on bioactive compounds from the fruits of L. barbarum, 20 compounds were isolated and identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. To the best of our knowledge, 11 compounds were isolated from this plant for the first time. Bioactivity evaluation showed that three compounds exhibited potential neuroprotective activities. The fruits of L. barbarum were collected from Zhongning, Ningxia Province, China in August 2018 and identified by Dr. Yuwen Xu. A voucher specimen (20180811) was deposited at Shandong Institute for Food and Drug Control. The air-dried fruits of L. barbarum (5.0 kg) were extracted with 80% ethanol three times for 2 h under reflux. After filtration, the filtrate was concentrated under reduced pressure and successively partitioned with petroleum ether, ethyl acetate (EtOAc), and n-butanol. After removal of the solvent, the EtOAc fraction (36.3 g) was subjected to silica gel column chromatography. Successive elution with a gradient of increasing acetone (0–100%) in petroleum ether yielded five fractions (F1–F5) on the basis of TLC analysis. Fraction F3 was separated by semipreparative HPLC to afford compounds 1 (15.0 mg), 2 (7.0 mg), 3 (5.0 mg), 4 (3.0 mg), 5 (15.0 mg), 6 (1.0 mg), 7 (3.0 mg), 8 (10.0 mg), 9 (5.0 mg), 10 (3.0 mg), 11 (2.0 mg), 12 (4.0 mg), 14 (2.0 mg), 15 (2.0 mg), 16 (3.0 mg), 17 (1.0 mg), 18 (40.0 mg), and 19 (3.5 mg). Fraction F4 was isolated in a similar manner to obtain compounds 13 (14.5 mg) and 20 (3.0 mg). These isolated compounds were identified as cannabisin F (1) [10], N1,N5,N10-tri-p-(E)-coumaroylspermidine (2) [11], cannabisin G (3) [10], cannabisin E (4) [10], N-trans-grossamide (5) [12], N-cis-grossamide (6) [13], 7-hydroxy-1(4-hydroxy-3-methoxyphenyl)-N2,N3-bis(4-hydroxyphenethyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxamide (7) [14], N-trans-feruloyltyramine (8) [15], N-trans-coumaroyltyramine (9) [15], lyicumamide C (10) [4], syringaresinol (11) [16], mediaresinol (12) [17], syringaresinol-β-D-glucoside (13) [18], salicifoliol (14) [19], zhebei
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