Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Six New Coumarin Glycosides from the Aerial Parts of Gendarussa vulgaris.

ABSTRACT: Six new coumarin glycosides, genglycoside A-F (1-6), were isolated from the aerial parts of Gendarussa vulgaris, along with ten known analogues (7-16). Their structures were unambiguously established on the basis of extensive spectroscopic data and HPLC analysis. The cytotoxic activities of all isolated compounds were evaluated by MTT assay. Compound 12 showed the most potent cytotoxicity in Eca-109, MCF-7, and HepG2 cell lines. By the preliminary structure-activity relationships, it was firstly discovered that the glycosylation or esterification at 7,8-dihydroxy or 7-hydroxy drastically reduced the cytotoxic activity of the parent coumarin.

SUBMITTER: Sun Y

PROVIDER: S-EPMC6514664 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Six New Coumarin Glycosides from the Aerial Parts of Gendarussa vulgaris.

Sun Yanjun Y Gao Meiling M Chen Haojie H Han Ruijie R Chen Hui H Du Kun K Zhang Yanli Y Li Meng M Si Yingying Y Feng Weisheng W

Molecules (Basel, Switzerland) 20190412 8

Six new coumarin glycosides, genglycoside A-F (1-6), were isolated from the aerial parts of Gendarussa vulgaris, along with ten known analogues (7-16). Their structures were unambiguously established on the basis of extensive spectroscopic data and HPLC analysis. The cytotoxic activities of all isolated compounds were evaluated by MTT assay. Compound 12 showed the most potent cytotoxicity in Eca-109, MCF-7, and HepG2 cell lines. By the preliminary struct ...[more]

PMID: 31013828

Similar Datasets

New flavonolignan glycosides from the aerial parts of Zizania latifolia.

Project description:Two new flavonolignan glycosides, tricin-4'-O-(threo-?-guaiacylglyceryl) ether 7''-O-?-D-glucopyranose (4) and tricin-4'-O-(erythro-?-guaiacylglyceryl) ether 7''-O-?-D-glucopyranose (5) were isolated from the roots of Zizania latifolia, together with tricin-7-O-?-D-glucopyranose (1), tricin-4'-O-(threo-?-guaiacylglyceryl) ether 7-O-?-D-glucopyranose (2), and tricin-4'-O-(erythro-?-guaiacylglyceryl) ether 7-O-?-D-glucopyranose (3). Their structures were identified on the basis of spectroscopic techniques, including HR-ESI/MS, 1D-NMR (1H, 13C, DEPT), 2D-NMR (gCOSY, gHSQC, gHMBC), and IR spectroscopy.

| S-EPMC6272199 | biostudies-literature

Two new phenylpropanoid glycosides from the aerial parts of Lespedeza cuneata.

Project description:Two new phenylpropanoid glycosides named cuneataside E (1) and cuneataside F (2), were isolated from the aerial parts of Lespedeza cuneata (Dum. Cours.) G. Don, whose structures were E and Z isomer, respectively. Their structures were elucidated on the basis of comprehensive spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR). In in vitro bioassays at 10 μmol/L, compound 1 showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HeG2 cells.

| S-EPMC5071639 | biostudies-literature

Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris).

Project description:While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-?-D-glucopyranosyl(1?2)-?-D-galactopyranoside-7-O-?-D-glucuropyranoside (1), kaempferol 3-O-?-D-glucopyranosyl(1?2)-?-D-galacto-pyranoside-7-O-?-D-glucuropyranoside (3), their derivatives 4-10,12-15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-{[(6-O-E-p-coumaroyl)-?-D-glucopyranosyl(1?2)]-?-L-rhamnopyranosyl(1?6)}-?-D-galactopyranoside-7-O-?-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.

| S-EPMC6270693 | biostudies-literature

New tetranorlabdanoic acid from aerial parts of Salvia aethiopis.

Project description:Salvia aethiopis is a perennial plant native to Eurasia and known by the common names Mediterranean sage or African sage. This plant has been used in Iranian medicine as a carminative and tonic. The ethanolic extract of aerial part of S. aethiopis exhibited moderate to weak activity towards delta and kappa opioid receptors (46.3 and 45.3% displacement, respectively). Chromatographic purification of the ethanolic extract on silica gel column led to isolation of one new: 3α-hydroxy-8α-acetoxy-13,14,15,16-tetranorlabdan-12-oic acid (I) and three known compounds: sesquiterpene spathulenol (II), β-sitosterol (III) and β-sitosterol-3-O-glucoside (IV). The structures of all isolated compounds were elucidated by their NMR (1D and 2D) and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding assays.

| S-EPMC5671917 | biostudies-literature

Prenylated Flavonoid Glycosides with PCSK9 mRNA Expression Inhibitory Activity from the Aerial Parts of Epimedium koreanum.

Project description:Phytochemical investigation on the n-BuOH-soluble fraction of the aerial parts of Epimedium koreanum using the PCSK9 mRNA monitoring assay led to the identification of four previously undescribed acylated flavonoid glycosides and 18 known compounds. The structures of new compounds were elucidated by NMR, MS, and other chemical methods. All isolated compounds were tested for their inhibitory activity against PCSK9 mRNA expression in HepG2 cells. Of the isolates, compounds 6, 7, 10, 15, and 17-22 were found to significantly inhibit PCSK9 mRNA expression. In particular, compound 7 was shown to increase LDLR mRNA expression. Thus, compound 7 may potentially increase LDL uptake and lower cholesterol levels in the blood.

| S-EPMC8230864 | biostudies-literature

Plectrabarbene, a New Abietane Diterpene from Plectranthus barbatus Aerial Parts.

Project description:A new abietane diterpene namely plectrabarbene (2), together with two known compounds: sugiol (1) and 11,14-dihydroxy-8,11,13-abietatrien-7-one (3) have been isolated from the aerial parts of Plectranthus barbatus Andr. (Labiatae). The structures of these compounds were determined by various spectral techniques (e.g., UV, IR, NMR, and FAB) and by comparison with the literature data. A molecular docking study of the isolated diterpenes (1-3) was performed with AChE to gain an insight into their AChE inhibition mechanism. The results of docking experiments revealed that the all tested compounds showed binding affinity at the active site of AchE in comparison to donepezil.

| S-EPMC7288077 | biostudies-literature

Two New Stilbenoids from the Aerial Parts of Arundina graminifolia (Orchidaceae).

Project description:Two new phenanthrene derivatives, a phenanthrenequinone named arundiquinone (1) and a 9,10-dihydrophenanthrene named arundigramin (2) together with a known lignin dimer (3) and seven known stilbenoids (4-10) were isolated from the aerial parts of the Asian orchid Arundina graminifolia. The structures of the isolated compounds were elucidated by spectroscopic methods, including extensive 1D, 2D NMR (heteronuclear single quantum coherence (HSQC), heteronuclear multiple-bond correlation spectroscopy (HMBC), and HR-ESI-MS techniques, as well as comparison with respective literature reports. The cytoprotective activity of the isolated compounds were evaluated for their ability to reduce beta amyloid induced toxicity on undifferentiated PC12 cells. Compound 8 showed moderate cytoprotective activity at 0.5 µmol/L (71% of cell viability) while the other compounds showed no significant activity at the highest concentration tested.

| S-EPMC6273616 | biostudies-literature

Three new tetranorditerpenes from aerial parts of acerola cherry (Malpighia emarginata).

Project description:Acerola cherry is a world famous fruit which contains abundant antioxidants such as vitamin C, anthocyanins, flavonoids, and phenolics. However, studies concerning bioactivity components from aerial parts of acerola (Malpighia emarginata) are scarce. In view of this, we have examined the constituents of aerial parts of acerola, and three new tetranorditerpenes acerolanins A-C (1-3) with a rare 2H-benz[e]inden-2-one substructure were isolated. Their structures were determined on the basis of spectral studies and acerolanin C was confirmed by X-ray crystallographic analysis. Furthermore, three new compounds have been studied for their cytotoxic activity.

| S-EPMC6270683 | biostudies-literature

New Phenylpropanoid and Coumarin Glycosides from the Stems of Hydrangea paniculata Sieb.

Project description:A new phenylpropanoid glycoside (1), and two new coumarin glycosides (2, 3), together with two known compounds (4, 5), have been isolated from the stems of Hydrangea paniculata Sieb. Their structures have been determined by spectroscopic and chemical methods. Furthermore, compound 1 (50 μM) exhibited significant hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays.

| S-EPMC6155810 | biostudies-literature

Six New Diterpene Glycosides from the Soft Coral Lemnaliabournei.

Project description:A chemical study on the extracts of soft coral Lemnalia bournei resulted in the isolation and identification of six new bicyclic diterpene glycosides including three new lemnaboursides E-G (1-3), and three new lemnadiolboursides A-C (4-6), along with three known lemnaboursides (7-9). Their structures were elucidated by detailed spectroscopic analysis, ECD analysis, chemical methods, and comparison with the literature data. Lemnadiolboursides A-C (4-6) contained a lemnal-1(10)-ene-7,12-diol moiety compared with the lemnaboursides. All these compounds were evaluated for antibacterial activity; cell growth inhibition of A549, Hela, HepG2, and CCRF-CEM cancer cell lines; and inhibition of LPS-induced NO production in RAW264.7 macrophages. The results indicated that compounds 1, 2, and 4-6 exhibited antibacterial activity against Staphylococcus aureus and Bacillus subtilis (MIC 4-16 μg/mL); compounds 1-9 displayed low cytotoxicity on the CCRF-CEM cell lines (IC50 10.44-27.40 µM); and compounds 1, 2, and 5 showed weak inhibition against LPS-induced NO production (IC50 21.56-28.06 μM).

| S-EPMC8231804 | biostudies-literature