Lycibarbarspermidines A–O, New Dicaffeoylspermidine Derivatives from Wolfberry, with Activities against Alzheimer’s Disease and Oxidation

Abstract

Fifteen new dicaffeoylspermidine derivatives, lycibarbarspermidines A-O (1-15), were isolated from the fruit of Lycium barbarum (wolfberry). The structures were unambiguously determined by spectroscopic analyses and chemical methods. Dicaffeoylspermidine derivatives, a rare kind of plant secondary metabolites, are primarily distributed in the family of Solanaceae. Only six compounds were structurally identified, and all of them are acyclic aglycones. Compounds 1-15 are the first glycosidic products of dicaffeoylspermidine derivatives, and compounds 14-15 are the first cyclization products of dicaffeoylspermidine derivatives. Moreover, dicaffeoylspermidine derivatives were first isolated and identified from wolfberry. The short-term memory assay on a transgenic fly Alzheimer's disease (AD) model showed that 1-15 exhibited different levels of anti-AD activity. The oxygen radical absorbance capacity assay revealed that 1-15 all displayed antioxidant capacity. Both anti-AD and antioxidant functions are related to the effects of wolfberry. Therefore, dicaffeoylspermidine derivatives are considered beneficial constituents responsible for the antiaging, neuroprotective, anti-AD, and antioxidant effects of wolfberry.

Systematic Review of Chemical Constituents in the Genus Lycium (Solanaceae)

“…Kukoamines A ( 185 ) and kukoamines B ( 186 ) are from the root bark of L. chinense [ 97 , 98 ], while N 1-caffeoyl- N 3-dihydrocaffeoyl spermidine ( 187 ) and lyrium spermidine A ( 188 ) are from the fruits of L. ruthenicum [ 62 , 99 ], listed in Figure 13 . Another 15 spermine alkaloids, lycibarbarspermidine A–O ( 189 – 203 ), listed in Table 9 and Table 10 and Figure 13 , Figure 14 and Figure 15 , are from L. barbarum [ 100 ].…”

Characterization of tropane and cinnamamide alkaloids from Scopolia tangutica by high‐performance liquid chromatography with quadrupole time‐of‐flight tandem mass spectrometry

“…Tropane compounds are strong natural antagonists of muscarinic acetylcholine receptor, among which hyoscyamine and scopolamine are famous in the clinic for the treatment of spasm and ulcer. Cinnamamide alkaloids have drawn increasing attention in recent years due to their relationship with Alzheimer's disease, sepsis, anti-oxidation and analgesia [5][6][7][8]. However, F I G U R E 1 Chemical structures of 13 reference alkaloids isolated from S. tangutica is feasible and practical to identify more potential alkaloids including tropanes and cinnamamide ones from S. tangutica.…”

In search for potential antidiabetic compounds from natural sources: docking, synthesis and biological screening of small molecules from Lycium spp. (Goji)

“…Based on the in vivo results, it can be inferred that the tyramine derivative 9 and the enriched extract TEE, do not possess significant antidiabetic activities. However, it should be noted that several novel phytochemicals were later reported (and not included in these docking studies) to be isolated form Goji and were reported to possess myriad of bioactivities including activities against Alzheimer's disease with lycibarbarsermidines A-O, dicaffeoylspermidine derivatives [29].…”

“…Plants such as Lycium barbarum and L. chinense, also known as gou qi zi or Goji, wolfberry, Chinese wolfberry or matrimony wine, have been widely used in Asian countries for the treatment of a number of symptoms related to [12,19] diabetes, inflammation and as a tonic for well-being. The phytochemicals reported from Goji were claimed to exhibit antioxidant, antitumor, immunomodulatory, cardioprotective, antidiabetic and neuroprotective activities [19,20,21,22,23,24,25,26,27,28,29,30,31,32]. The dried root bark of L. barbarum, has been shown to produce long-term hypoglycemic effects and reduced body weight in diabetic mice [23].…”