Lignan glycosides from the Rhizomes of Smilax trinervula and their Biological activities

Phytochemical investigation of the rhizomes of Smilax trinervula led to isolation and structure elucidation of eight lignan glycosides, including five new lignans, namely, (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4′-O-β-d-glucopyranoside (1), (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4-O-β-d- glucopyranoside (2) (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-4′, 7-epoxy-8, 5′-neolignan 9′-O-β-d-glucopyranoside (3), (7R, 8R)-4, 9, 9′-trihydroxy-3, 5-dimethoxy-7.O.4′, 8.O.3′- neolignan 9′-O-β-d-glucopyranoside (4), and (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-8, 4′-oxy-neolignan 4-O-β-d-glucopyranoside (5), along with three known compounds (6-8). Their structures were established mainly on the basis of 1D and 2D NMR spectral data, ESI–MS and comparison with the literature. Compounds 1-8 were tested in vitro for their cytotoxic activity against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Compounds 3 and 5 exhibited cytotoxic activity against Lovo cells, with IC₅₀ value of 10.4 μM and 8.5 μM, respectively.     

Flavonol glycosides from the leaves of Boldoa purpurascens and their anti-inflammatory properties

Boldoa purpurascens is used in Latin America and the Caribbean as a potent diurectic. Phytochemical analysis has shown the presence of flavonoids and other active compounds. In the present work, three flavonol glycosides were isolated from the leaves of the plant. Their structures have been determined by mass spectrometry and by 1D and 2D NMR analysis as 6-methoxykaempferol-3-O-[α-l-rhamnopyranosyl-(1”’ → 2”)]-β-d-xylopyranoside (1); 3,4′,5-trihydroxy-6,7-methylenedioxyflavone-3-O-[α-l-rhamnopyranosyl-(1”’ → 2”)]-β-d-glucopyranoside (2); and 3,4′,5′,5-tetrahydroxy-6,7-methylenedioxyflavone-3-O-[α-l-rhamnopyranosyl-(1”’ → 2”)]-β-d-xylopyranoside (3). Compounds 1 and 3 are reported for the first time from nature. The NF-κB luciferase assay showed that these compounds have a partial inhibitory effect on NF-κB activation, compound 2 being the most potent one. In the carrageenan induced paw oedema assay in rats, the flavonoid fraction showed acute anti-inflammatory activity, with the highest percentage of inhibition (75.8%) at a dose of 40 mg/kg.     

Constituents of the leaves of Pseuderanthemum carruthersii (Seem.) Guill. var. atropurpureum (Bull.) Fosb.

A new iridoid, 5β,6β-dihydroxyantirrhide (1) was isolated from the dried leaves of Pseuderanthemum carruthersii (Seem.) Guill. var. atropurpureum (Bull.) Fosb. (Acanthaceae), together with 13 known compounds, including two iridoids, linarioside and antirrhinoside; five phenylethanoids, echipuroside A, verbascoside, isoverbascoside, isomartynoside and osmanthuside B; and six flavonoids, luteolin 7-O-β-d-glucopyranoside, luteolin 7-O-rutinoside, apigenin 7-O-rutinoside, apigenin 6-C-α-l-arabinopyranosyl–8-C-β-l-arabinopyranoside, apigenin 6,8-di-C-α-l-arabinopyranoside and apigenin 6-C-β-d-xylopyranosyl–8-C-α-l-arabinopyranoside. Their chemical structures were elucidated by 1D and 2D NMR as well as HR-ESI-MS spectroscopic analysis. Some purified compounds were evaluated the acetylcholinesterase inhibition and cytotoxic activities against the HeLa cervical cancer cell line and the MCF-7 breast cancer cell line at the concentration of 100 μg/mL. Luteolin 7-O-β-d-glucopyranoside exhibited cytotoxic activities against both the HeLa cervical cancer cell line and the MCF-7 breast cancer cell line. Verbascoside and isoverbascoside showed strong cytotoxic activity against the MCF-7 breast cancer cell line. The tested compounds showed the AChE inhibitory activity fairly weak.     

Two new guaiane sesquiterpenes from Datura metel L. with anti-inflammatory activity

Chemical investigation of an acidic methanol extract of the whole plants of Datura metel resulted in the isolation of two new guainane sesquiterpenes, 1β,5α,7β-guaiane-4β,10α,11-triol (1) and 1α,5α,7α-11-guaiene-2α,3β,4α,10α,13-pentaol (2), along with eight known compounds: pterodontriol B (3), disciferitriol (4), scopolamine (5), kaempferol 3-O-β-d-glucosyl(1 → 2)-β-d-galactoside 7-O-β-d-glucoside (6), kaempferol 3-O-β-glucopyranosyl(1 → 2)-β-glucopyranoside-7-O-α-rhamnopyranoside (7), pinoresinol 4′′-O-β-d-glucopyranoside (8), (7R,8S,7′S,8′R)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxy-lignan-4-O-β-d-glucopyranoside (9), and (7S,8R,7′S,8′S)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4-O-β-d-glucopyranoside (10). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. Compounds 2-4 and 6-10 were shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells.     

Cytotoxic glucosydic iridoids from Veronica americana

Fractionation guided by the cytotoxic activity of the methanolic extract of Veronica americana led to the isolation of two new iridoids identified as 4β-hydroxy-6-O-(p-hydroxybenzoyl)-tetrahydrolinaride (1) and 10-O-protocatechuyl-catalpol (2), together with four known aromatic acids, veratric acid (3) p-methoxybenzoic acid (4), p-hydroxybenzoic acid (5) and protocatechuic acid (6). The structure of these compounds was determined by spectroscopic analysis. Iridoid glycosides 1 and 2 showed selective cytotoxic activity against the human cancer cell lines HF-6 (IC₅₀ = 0.031 and 0.066 μM, respectively) and PC-3 (IC₅₀ = 0.721 and 0.801 μM, respectively), with less sensitivity in normal MRC-5 cells (IC₅₀ = 77.103 and 1451.562 μM, respectively). Compound 1 was 9.9 times more potent than camptothecin against HF-6 cell line, while compound 2 was 4.7 times, more potent, against the same cell line, than camptothecin. The found biological efficacy of 1 and 2 allow us to propose these compounds as candidates for the development of effective anticancer therapeutic agents.     

Two new penterpenoid saponins and a new diterpenoid glycoside from Hemsleya chinensis

Two new penterpenoid saponins, hemsloside-Ma4 (1) hemsloside-Ma5 (2), and a new diterpenoid glycoside, hemsloside-Ma6 (3), were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra and chemical methods, the structures of new compounds were determined to be 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside (1), 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopy-ranoside (2), and 13ϵ-hydroxylabda-8(17), 14-dien-18-oic acid-18-O-α-l-rhamnopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-O-α-l-rhamnopyranoside (3). Diterpenoid-type compound (3) was isolated from Hemsleya genus for the first time.     

Ellagitannin and flavonoid constituents from Agrimonia pilosa Ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities

A new ellagitannin, agritannin (1), a new flavone glycoside, agriflavone (2), and another flavone glycoside with spectroscopic data reported for the first time, kaempferol-3-O-[(S)-3-hydroxy-3-methylglutaryl (1→6)]-β-d-glucoside (3), along with 16 known compounds were isolated from the aerial parts of Agrimonia pilosa Ledeb. These compounds were evaluated for PTP1B inhibitory activity. Among them, compounds 9 and 18 displayed potential inhibitory activity against PTP1B with IC₅₀ values of 7.14 ± 1.75 and 7.73 ± 0.24 μM, respectively. In addition, compound 1 showed significant inhibitory effect with an IC₅₀ value of 17.03 ± 0.09 μM. Furthermore, these compounds were tested in AChE inhibitory assays. Most of them were found to have moderate inhibitory effects, with IC₅₀ values ranging from 60.20 ± 1.09 to 92.85 ± 1.12 μM. Except compounds 3, 8, and 18 were inactive.     

Novel dammarane saponins from Gynostemma pentaphyllum and their cytotoxic activities against HepG2 cells

Two new dammarane saponins, 2α,3β,12β-trihydroxydammar-20(22),24-diene-3-O-[β-d-glucopyranoxyl(1→2)-β-d-6″-O-acetylglucopyranoside (1, namely damulin C) and 2α,3β,12β-trihydroxydammar-20(21),24-diene-3-O-[β-d-glucopyranoxyl(1→2)-β-d-6″-O-acetylglucopyranoside (2, namely damulin D), were isolated from the ethanol extract of Gynostemma pentaphyllum, which had been heat processed by steaming at 125 °C. The NMR spectroscopic data of the novel saponins were completely assigned by using a combination of 2D NMR experiments including ¹H–¹H COSY, HSQC, and HMBC. Their cytotoxic activities of human liver adenocarcinoma HepG2 cells were evaluated in vitro. They showed cytotoxicities against HepG2 cell line with IC₅₀ of 40 ± 0.7 and 38 ± 0.5 μg/ml, respectively.     

Acylated pregnane glycosides from Caralluma quadrangula

In a previous study, the methanolic extract as well as the chloroform fraction of the aerial parts of Caralluma quadrangula (Forssk.) N.E.Br. indigenous to Saudi Arabia showed significant in vitro cytotoxic activity against breast cancer (MCF7) cell line. In a biologically-guided fractionation approach, four acylated pregnane glycosides were isolated from the chloroform fraction of C. quadrangula. The structures of the isolated compounds were elucidated by the analysis of their MS and NMR data. The compounds were identified as 12,20-di-O-benzoylboucerin 3-O-β-d-digitoxopyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-cymaropyranoside (1), 12,20-di-O-benzoylboucerin 3-O-β-d-cymaropyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-cymaropyranoside (2), 12,20-di-O-benzoylboucerin 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-digitoxopyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-cymaropyranoside (3) and 12,20-di-O-benzoyl-3β,5α,12β,14β,20-pentahydroxy-(20R)-pregn-6-ene 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-digitoxopyranosyl-(1 → 4)-β-d-canaropyranosyl-(1 → 4)-β-d-cymaropyranoside (4). The isolated compounds were tested for their cytotoxic activity against breast cancer (MCF7) cell line.     

New cytotoxic dihydrochalcone and steroidal saponins from the aerial parts of Sansevieria cylindrica Bojer ex Hook

A new dihydrochalcone, 2‘,4‘-dihydroxy-3‘-methoxy-3,4-methylenedioxy-8-hydroxymethylene dihydrochalcone 1 and two new steroidal saponins, (25S)-ruscogenin-1-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranoside 2, (25S)-ruscogenin-3-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside 3, together with three known steroidal saponins (25S)-ruscogenin-3-O-β-d-glucopyranoside 4, (25S)-ruscogenin-1-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-α-l-arabinopyranoside 5 and (25R)-26-O-β-d-glucopyranosyl-furost-5-ene-1β,3β,22α,26-tetrol-1-O-α-L-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-α-l-arabinopyranoside 6 were isolated from the aerial parts of Sansevieria cylindrica. The structures of the new compounds were established by UV, IR, EI-MS, HR-ESI–MS as well as 1D (¹H,¹³C and DEPT-135) and 2D (HSQC, HMBC and TOCSY) NMR spectral analysis. The isolated compounds 1-6 were assayed for in vitro cytotoxicities against the three human tumor cell lines HT116, MCF7 and HepG2. Compound 1 showed a moderate cytotoxicity against MCF7. Compounds 2, 3 and 6 exhibited moderate cytotoxicities against the three used cell lines and compound 5 showed marked cytotoxicities against all used cell lines.     

New triterpene saponins from Phryna ortegioides

Four new and three known oleanane-type saponins have been isolated from the methanolic extract of Phryna ortegioides, a monotypic and endemic taxon of Caryophyllaceae.The structures of the new compounds were determined as gypsogenic acid 28-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (2), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-]-β-d-glucopyranosyl ester (3), 3-O-α-l-arabinofuranosyl-16α-hydroxyolean-12-en-23,28-dioic acid-28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (4). Their structures were established by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. Noteworthy, none of isolated compounds possesses as aglycone moiety gypsogenin, considered a marker of Caryophyllaceae family.The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. Only compound 6 showed a weak activity against A375 and DeFew cell lines with IC₅₀ values of 77 and 52 μM, respectively. None of the other tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number.     

Cytotoxic pterosins from Pteris multifida roots against HCT116 human colon cancer cells

Two new pterosin glycosides, (2S,3S)-pterosin C 3-O-β-d-(4′-(E)-caffeoyl)-glucopyranoside (1) and (2S,3S)-pterosin C 3-O-β-d-(6′-(E)-p-coumaroyl)-glucopyranoside (2), were isolated from Pteris multifida (Pteridaceae) roots along with ten known pterosin compounds (3–12). The chemical structures of the isolated compounds were elucidated by extensive analysis of the 1D, 2D NMR, HRESIMS, and CD spectroscopic data. The cytotoxicities of 1–12 against HCT116 human colorectal cancer cell line were evaluated. Among the isolates, compound 1 showed moderate antiproliferative activity in HCT116 cells with an IC₅₀ value of 8.0 ± 1.7 μM. Additionally, 1 induced the upregulation of the caspase-9 and procaspase-9 levels in Western blots and increased the annexin V/propidium iodide (PI)-positive cell population in flow cytometry.     

Three new glycosides from the whole plant of Clematis lasiandra Maxim and their cytotoxicity

Phytochemical investigation on the whole plant of Clematis lasiandra Maxim led to the isolation of two new phenolic glycosides (1 and 2), one new lignanoid glycoside (3), together with three known lignanoid glycosides (4–6). The structures of the new compounds were elucidated as 4-O-β-d-galactopyranosyl-ethyl-E-caffeate (1), 4-O-β-d-galactopyranosyl-3-hydroxyl-phenylethene (2) and (8R)-3,3′-dimethoxy-4,4′,9,9′-tetrahydroxy-5′,8-lignan 3′-O-β-d-glucopyranoside (3), on the basis of extensive spectral analysis and chemical evidence. The characteristic of the polymerized C-5′–C-8 type lignanoid aglycone in glycoside 3 was found from genus Clematis for the first time. Compounds 1–6 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, the new glycosides 1 and 2 showed significant cytotoxicity against those three tumor cell lines with IC₅₀ in the range from 9.73 to 22.31 μM, while lignanoid glycosides 3–6 showed weak cytotoxicity to those test cell lines with IC₅₀ value more than 52.71 μM.     

Triterpenoid saponins and C-glycosyl flavones from stem bark of Erythrina abyssinica Lam and their cytotoxic effects.

Six new compounds including two oleanane-type triterpenoid saponins (1, 2) and four C-glycosyl flavones (3–6), along with a known saponin (7), three di-C-glycosyl flavones (8–10) and a glycosyl auronol (11), were isolated from the stem bark of Erythrina abyssinica Lam. The structures of the new compounds, identified as 3-O-[α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl]-22-O-β-d-glucopyranosyl sophoradiol (1), 3-O-[α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 2)-β-d-glucuronopyranosyl]-22-O-β-d-glucopyranosyl sophoradiol (2), 6-C-β-glucopyranosyl-8-C-β-quinovopyranosyl apigenin (3), 6-C-β-quinovopyranosyl-8-C-β-glucopyranosyl apigenin (4), 8-C-[6″-O-α-l-rhamnopyranosyl-(1‴ → 6″)]-β-glucopyranosyl 7,4′-dihydroxyflavone (5) and 8-C-[6″-O-β-d-xylopyranosyl-(1‴ → 6″)]-β-glucopyranosyl 7,4′-dihydroxyflavone (6), were determined by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and acid hydrolysis. These new compounds together with the known saponins 7 were evaluated for their cytotoxic activity against MCF-7 (estrogen dependent) and MDA-MB-231 (estrogen independent) cell lines. The new saponin 2 exhibited the highest cytotoxic activity among tested compounds, exerting a selective inhibitory effect against the proliferation of MCF-7 cells, with lower IC₅₀ value (12.90 μM) than that of the positive control, resveratrol (13.91 μM). Structure–activity relationship of these compounds is also discussed.     

Rheediinosides A and B,two antiproliferative and antioxidant triterpene saponins from Entada rheedii

Two triterpenoid saponins have been isolated from the seed kernels of Entada rheedii. Their structures have been established using 1D- and 2D-NMR and mass spectrometry as 3-O-β-d-xylopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl-(1 → 6)-2-acetylamino-2-deoxy-β-d-glucopyranosylentagenic acid 28-O-β-apiofuranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranoside (Rheediinoside A, 1) and 3-O-β-d-glucopyranosyl-(1 → 3)-O-[β-d-xylopyranosyl-(1 → 3)-α-l-arabinopyranosyl-(1 → 6)]-2-acetylamino-2-deoxy-β-d-glucopyranosylentagenic acid 28-O-β-apiofuranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranoside (Rheediinoside B, 2). Compounds 1 and 2 were tested for their antiproliferative activity against T98G, A431, PC3 and B16-F1 cell lines, and further for their antioxidant properties. Moderate cytotoxic potency and antioxidant properties were found for these compounds whereas Rheediinoside B was in all assays more active than Rheediinoside A.     

Two secopregnane-type steroidal glycosides from Cynanchum stauntonii (Decne.) Schltr.ex Levl.

Two new steroid glycosides, stauntosaponins A (1) and B (2), were isolated from Cynanchum stauntonii (Decne.) Schltr.ex Levl. (Asclepiadaceae) together with five known compounds, anhydrohirundigenin monothevetoside, glaucogenin C mono-d-thevetoside, hirundoside A, cynatratoside A, and glaucogenin C. Stauntosaponins A and B were formulated as 3-O-β-d-oleandropyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (1) and 3-O-β-d-thevetopyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (2). Compounds 1 and 2 showed moderate inhibitory activities against Na⁺/K⁺-ATPase with IC₅₀ values of 21 and 29 μM, respectively, whereas ouabain as a positive control displayed an IC₅₀ value of 3.5 μM.     

Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity

A pentacyclic triterpene, oleanderocioic acid, two flavonoidal glycosides, quercetin-5-O-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside and kaempferol-5-O-[α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside, and a cardenolide, oleandigoside, together with 11 known compounds, were isolated from the leaves of Nerium oleander. Their structures were elucidated on the basis of spectroscopic analysis. The growth inhibitory and cytotoxic activities of eight compounds were evaluated against the MCF-7 human breast cancer cell line using a sulforhodamine B assay. Three compounds, oleandrin, odoroside A and B were further assayed using a panel of 57 human cancer cell lines.     

Two new spirostanol saponins from the the roots and rhizomes of Tupistra chinensis

Two new spirostanol saponins (1) and (2), together with three known saponins (3–5), were isolated from the roots and rhizomes of Tupistra chinensis, and their structures were determined as (20S, 22R)-spirost-25(27)-en-1β, 3β, 4β, 5β-tetraol-5-O-β-d-glucopyranoside (1) and (20S, 22R)-spirost-25(27)-en-1β, 3β, 5β-triol-5-O-β-d-glucopyranoside (2), (20S, 22R)-spirost-25(27)-en-1β, 2β, 3β, 4β, 5β-pentaol-5-O-β-d-glucopyranoside (3), Δ²⁵⁽²⁷⁾-pentrogenin (4) and ranmogenin A (5) on the basis of physicochemical properties and spectral analysis. The isolated compounds were evaluated for their cytotoxic activities against A549 and H1299 tumor cell lines in vitro. Among them, compound 2 showed cytotoxicities against A549 cells (IC₅₀ 52.66 ± 3.12 μmol L⁻¹) and H1299 cells (IC₅₀ 57.29 ± 2.51 μmol L⁻¹), respectively.     

Phytochemical screening of flavonoids with their antioxidant activities from rapeseed (Brassica napus L.)

Ten flavone compounds, including three new flavonoid glycosides, were isolated from defatted rapeseed, and their protective antioxidant effect on H₂O₂-induced oxidative damage in human umbilical vein endothelial cells (ECV-304) was investigated. Three new flavonoid glycosides were identified as kaempferol-3-O-[(6-O-sinapoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside]-7-O-β-d-glucopyranoside (8), kaempferol-3,7-di-O-β-d-glucopyranoside-4'-O-(6-O-sinapoyl)-β-d-glucopyranoside (9), and kaempferol-3-O-[(3-O-sinapoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside]-7-O-β-d-glucopyranoside (10). The protective effects of all of the isolated compounds on H₂O₂-induced oxidative damage were assessed, and the activities of superoxide dismutase (SOD) and lactate dehydrogenase (LDH) were measured. All of compounds had a protective effect on H₂O₂-induced oxidative damage in ECV-304 cells and the presence of a substituted sinapoyl group and its position in the structures were used to elucidate the activity differences.     

Novel 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-one derivatives as potential anti-cancer agents

A novel series of 3,5,6-trisubstituted pyrazolo[4,3-d]pyrimidin-7-one derivatives, especially 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-ones were synthesized and evaluated for their in vitro anticancer activities against various human cancer cell lines. The inhibitory activities for several kinases have also been tested. The prepared compounds library exhibited significant anticancer activity towards HT-29 colon and DU-145 prostate cancer cell lines. The structure–activity relationships of the 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-one scaffold at R¹, R² and R³ have been elucidated. Among the synthesized compounds, 12b was the most active compound with GI₅₀ value of 0.44 μM and 1.07 μM against HT-29 and DU-145 cell lines, respectively, and 13a was the most selective compound towards colon cancer cell line.