Studies on the Constituents of Ligustrum Species. XIII. : Structures of Phenylethanoid Glycosides from the Leaves of Ligustrum obtusifolium SIEB. et ZUCC.

Kikuchi, Masao; Yamauchi, Yoko; Nagaoka, Ichiro; Sugiyama, Masataka; Takahashi, Yuka

doi:10.1248/yakushi1947.108.7_647

Cited by 6 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hydroxytyrosol has been frequently reported in the literature , and is one of the major constituents in olive oil and contributes to the antioxidant behavior of olive oil products; − its bioavailability was also demonstrated in vitro . Compound 7 has previously been isolated from C. racemosa , but NMR data sufficient for the dereplication of 7 , and distinction of the 4- O - vs the 8- O -glycosylated regioisomers , are unavailable. NMR data for the aglycone show significant differences in chemical shift values as compared with the NMR data for the glycoside.…”

Section: Resultsmentioning

confidence: 99%

Guanidine Alkaloids and Pictet−Spengler Adducts from Black Cohosh (Cimicifuga racemosa)

et al. 2009

View full text Add to dashboard Cite

As an extension of work on the recently discovered nitrogenous metabolites from Cimicifuga/ Actaea species, three new guanidine alkaloids have been isolated and characterized from C. racemosa (syn. A. racemosa) roots. Of these, cyclo-cimipronidine (1) and cimipronidine methyl ester (2) are congeners of cimipronidine (3), whereas dopargine (5) is a derivative of dopamine. By employing NMR-and MS-guided chemodiversity profiling of a polar serotonergic (5-HT 7 ) fraction, the guanidine alkaloids were initially detected in a clinical extract of black cohosh and were isolated along with a congener of salsolinol 4, 5, and 3-hydroxytyrosol 3-O-glucoside (7). The structures of 1, 2, and 5 were confirmed by 1D and 2D NMR spectroscopy as well as LC-MS and HRMS spectroscopy. A plausible biosynthetic relationship may be inferred between the homoprolineanalogue cimipronidines and the dopamine-derived Cimicifuga alkaloids. These strongly basic and frequently zwitterionic nitrogenous metabolites contribute considerable chemical diversity to the polar serotonergic fraction of black cohosh.Black cohosh (Cimicifuga racemosa (L.) Nutt., syn. Actaea racemosa L.), historically referred to as "black snakeroot", is a Native American botanical, for which a monograph was included in the first U.S. Pharmacopoeia in 1820. During the 19th century, black cohosh emerged as an important treatment for a variety of female-related health conditions. Recent clinical trials have evaluated its efficacy for the alleviation of menopausal symptoms, such as hot flashes, night sweats, and various psychological complaints. [1][2][3][4][5] In spite of the known beneficial effects of C. racemosa root extract, the bioactive constituent(s) still need to be conclusively identified, especially for the development of a meaningful standardization procedure that is based on both the biological activity of the active principal(s) and the currently practiced chemical standardization protocol related to the content of certain abundant triterpenes. Competitive binding to the dopamine D 2 receptor by an ethanolic (70% v/v) extract was observed 6 as well as binding to the serotonin 5-HT 1A , 5-HT 1D , and 5-HT 7 receptors by isopropanolic (40% v/ v), ethanolic (75% v/v), and methanolic (100%) extracts. 7 The 5-HT receptor subtypes, 5-HT 1A and 5-HT 7 , of the hypothalamus have been shown to be associated with the generation of hot flashes, 7,8 and in several clinical trials the efficacy of selective serotonin reuptake inhibitors (SSRIs) was demonstrated for the treatment of hot flashes (for reviews see ref [9][10][11] ). In addition, scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals has been reported for a methanolic root extract of C. racemosa. 12 † Dedicated to Dr. David G. I. Kingston of Virginia Polytechnic Institute and State University for his pioneering work on natural products. Upon initial detection by LC-MS analysis, cyclo-cimipronidine (1) was isolated and, along with cimipronidine methyl ester (2), characterized as a congener of the previo...

show abstract

Section: Resultsmentioning

confidence: 99%

Guanidine Alkaloids and Pictet−Spengler Adducts from Black Cohosh (Cimicifuga racemosa)

et al. 2009

View full text Add to dashboard Cite

show abstract

“…Figure 10 shows the representative MS/MS spectrum of a potential marker of m/z 577. 15. The adduct ion [M+Na] + , in positive mode, suggests that the empirical molecular formula is most likely C 25 H 30 O 14 (with mass accuracy 1.0 ppm).…”

Section: Identity Assignment and Confirmation Of Chemical Markersmentioning

confidence: 99%

“…[2][3][4] Moreover, it is used as an important component in some traditional Chinese patent medicines. Many components have been successively identified from the fruits of L. lucidum Ait, such as triterpenes; [5,6] oleanolic acid, which is one of the representative compounds, and has generally been considered to be the main biologically active compound and whose content has often been used as one of the criteria to evaluate the quality of this crude drug; [1,7,8] secoiridoid; [9][10][11][12] and phenylethane, [13][14][15][16] which have been isolated and identified from the water-soluble portion of L. lucidum Ait extracts and have proved to have strong biological effects; and finally furfural derivatives [11] (Fig. 1).…”

mentioning

confidence: 99%

Seasonal variations in metabolite profiling of the fruits of Ligustrum lucidum Ait

Guo

Ablajan

et al. 2011

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

The metabolite profiling of fruits of the herb Ligustrum lucidum Ait collected during different months has been performed using ultra-performance liquid chromatography with quadrupole time-of-flight mass spectrometry (UPLC/QTOFMS) and multivariate statistical analysis techniques. The markers such as oleuropein acid, neonuezhenide, specnuezhenide, oleuropein and ligustrosidic acid accountable for such variations were identified through the loadings plot of principal component analysis (PCA), and the tentative identification of the markers is completed by comparing the mass spectra and retention times with those of reference compounds and/or tentatively assigned by matching empirical molecular formulae and MS/MS data with those of the known compounds published. Furthermore, one of the chemical markers, such as specnuezhenide, which is water-soluble, biologically active and also the predominant compound in this crude drug, was quantified by ultra-performance liquid chromatography coupled with a tunable UV detector (UPLC-TUV). The developed UPLC method provides good linearity (r(2)=0.9991), repeatability (RSD=2.96%), intra- and inter-day precisions (RSD=0.21%, 0.96%), with accuracies of 99.18-100.26% and a recovery of specnuezhenide of 97.57%. The fruits of L. lucidum Ait collected from August to December were tested. The results clearly show that the fruits of L. lucidum Ait harvested in October have the highest yields of specnuezhenide. It is also noted that the variations of content of specnuezhenide obtained by both methods have a strong correlation. This suggests that the newly proposed strategy is a reliable and simple method for the rapid discrimination of subtle variations, within the same plant species or strains, due to different seasonal collection times.

show abstract

“…Previous phytochemical investigations on L. obtusifolium re ported the isolation of secoiridoid glycosides, phenolic glycosides, and lignans. [6][7][8] In particular, several secoiridoid glycosides isolated from L. obtusifolium were associated with lysine decreasing activity and anti-hyperglycemic activities. 9,10) However, only a few phytochemical studies on L. obtusifolium have been reported.…”

mentioning

confidence: 99%

Secoiridoid Glycosides from the Twigs of <i>Ligustrum obtusifolium</i> Possess Anti-inflammatory and Neuroprotective Effects

et al. 2018

View full text Add to dashboard Cite

Key words Ligustrum obtusifolium; secoiridoid glycoside; anti-inflammation; nerve growth factor (NGF) regulation Glial cells are major defence cells present in the central nervous system (CNS). Microglia and astrocytes are major defending glia cells. In normal condition microglia gets activated and tries to protect the neuron from hazardous conditions or specially pathogens and CNS injury etc. However, under pathological conditions, microglia cells are over-activated and produce a variety of proinflammatory mediators, including nitric oxide (NO). Lipopolysaccharide (LPS) is being used as a neuroinflammation inducer for in vitro experiments. 1) LPS induced neuroinflammation is also responsible for the induction of neuronal apoptosis characterized by neurodegeneration. LPS is a toll like receptor 4 (TLR4) agonist, that can initiate the TLR4 mediated inflammatory cascades during inflammation as well as neuroinflammation. LPS-TLR4 mediated neuroinflammation induce the expression of inducible nitric oxide synthase (iNOS) protein which is responsible to increase the production of nitric oxide.2) NO is a major biomarker against inflammatory conditions, so we did the screening of the compound to inhibit the nitrite production that proves the antiinflammatory activity of our compounds. Additionally, nerve growth factor (NGF) is an important neurotrophin that helps neuron to survive and differentiate during brain development. It is also believed that, NGF helps to improve neurodegeneration and shows its neuroprotective role in the developing brain. It protects neuron against toxin induced neuronal death and cholinergic cell loss. Hence in this study we screened our compounds to increase NGF production through astrocyte. In this way inhibition of NO production and increased NGF production are responsible for anti-inflammatory and neuroprotective effects. 3)Ligustrum obtusifolium, known as Ibota privet, is a shrub that is widely distributed in East Asia. 4) L. obtusifolium has been used as a Korean traditional medicine, and it has been known that fruits have a cardiac and roborant effect, and the trunks have been used for the treatment of diabetes, and hypertension. Additionally, leaves of this plant have been used for oropharyngeal inflammation, rheumatic condition and diuretic conditions in the traditional medicine of southern Europe.5) Taken together we hypothesized that, the compounds present in this plant may play important role in the treatment of neuroinflammation as well as neurodegenerative conditions. Previous phytochemical investigations on L. obtusifolium re ported the isolation of secoiridoid glycosides, phenolic glycosides, and lignans. [6][7][8] In particular, several secoiridoid glycosides isolated from L. obtusifolium were associated with lysine decreasing activity and anti-hyperglycemic activities. 9,10) However, only a few phytochemical studies on L. obtusifolium have been reported. As a part of our continuing search for bioactive constituents from Korean medicinal plants, we investigated methanol (MeOH) ...

show abstract

Studies on the Constituents of Ligustrum Species. XIII. : Structures of Phenylethanoid Glycosides from the Leaves of Ligustrum obtusifolium SIEB. et ZUCC.

Cited by 6 publications

References 0 publications

Guanidine Alkaloids and Pictet−Spengler Adducts from Black Cohosh (Cimicifuga racemosa)

Guanidine Alkaloids and Pictet−Spengler Adducts from Black Cohosh (Cimicifuga racemosa)

Seasonal variations in metabolite profiling of the fruits of Ligustrum lucidum Ait

Secoiridoid Glycosides from the Twigs of <i>Ligustrum obtusifolium</i> Possess Anti-inflammatory and Neuroprotective Effects

Contact Info

Product

Resources

About