Octadecyl Silica Gel Research Articles

Postmortem distribution of ropivacaine and its metabolite in human body fluids and solid tissues by GC-MS/MS using standard addition method.

An analytical method was developed for determining ropivacaine and its main metabolite, 3-hydroxyropivacaine in biomedical samples using gas chromatography-tandem mass spectrometry (GC-MS/MS). Then, this established method was applied to investigate the distribution of ropivacaine and its metabolite in human fluids and solid tissues obtained from an authentic case ropivacaine involved. The fluid sample was added acetonitrile, and solid tissue was homogenized using a freezer mill and then added into acetonitrile. Then, an internal standard solution was added to the mixtures. The mixture was centrifuged at 12,000 × g for 5min, and the upper layer of acetonitrile was transferred to magnesium sulfate and octadecyl silica (C18) gel for cleaning up the sample. After centrifugation, the upper layer was then evaporated to dryness with nitrogen, and dissolved with methanol, then injected into the GC-MS/MS system. The coefficients of determination (r2) of constructed calibration curves were all greater than 0.999. The limits of detection for ropivacaine and 3-hydroxyropivacaine in target samples were 15ng/mL and 10ng/mL, respectively. The recovery rates of ropivacaine and 3-hydroxyropivacaine ranged from 97.6% to 103% and from 96.5% to 104%, respectively. The inter-day precision values of ropivacaine and 3-hydroxyropivacaine were not greater than 6.25% and 7.98%, respectively, and the inter-day trueness values were not greater than 6.90% and 8.33%, respectively; the intra-day precision and trueness values of ropivacaine and 3-hydroxyropivacaine were not greater than 3.20%, 6.78%, 7.84% and 8.99%, respectively. GC-MS/MS method for simultaneous detection and quantification of ropivacaine and 3-hydroxyropivacaine in biological samples was successfully developed. The method could also be applied to samples obtained from an authentic case; their distribution among tested fluids and solid tissues were also measured. This is the first report on the distribution of ropivacaine and its major metabolite 3-hydroxyropivacaine in a human case.

The retention features of nitrogen-containing heterocyclic compounds in reversed-phase and hydrophilic HPLC-MS modes

Aromatic five- and six-membered nitrogen-containing heterocyclic compounds are biologically active substances and are widely used in biochemistry and medicine. In addition, such compounds are known as ecotoxicants formed during oxidation processes in industrial wastewater. High-performance liquid chromatography-mass spectrometry is widely used to determine nitrogen-containing heterocycles in various complex mixtures. Octadecyl silica gel is the main sorbent for chromatographic separation. However, octadecyl silica gel does not always enable satisfactory separation in the presence of highly polar isomeric molecules, and more selective chromatographic approaches are required. One of these is hydrophilic chromatography, which facilitates the separation of polar compounds. The aim of the study was to comparatively characterize the retention of a number of five- and six-membered nitrogen-containing heterocyclic compounds during reversed-phase and hydrophilic liquid chromatography with mass spectrometric detection. In addition, spectrophotometric detection at a wavelength of 210 nm was carried out. In the study, we used sorbents based on octadecyl silica gel and unmodified silica gel. High-resolution mass spectrometry was used in the electrospray ionization mode. We studied 19 nitrogen-containing heterocyclic compounds. We used aqueous acetonitrile mobile phases with added aqueous solutions of formic acid and diethylamine as acid-base modifiers. An ammonium formate solution was used as a modifier during hydrophilic chromatography. Reversed-phase chromatography showed that the introduction of 0.1% aqueous formic acid solution increased the ionization and the mass spectrometer signal intensity, but did not always result in a satisfactory separation of isomers upon elution from the octadecyl silica gel surface. The introduction of 0.01% diethylamine solution provided no significant improvement in the separation compared to the mobile phase without modifiers. The use of unmodified silica gel in hydrophilic chromatography mode allowed us to separate isomeric five-membered heterocycles, which was demonstrated by narrow symmetric peaks, but did not result in selective separation of isomeric diazines. Thus, we studied the retention of 19 nitrogen-containing heterocyclic compounds using reversed-phase and hydrophilic liquid chromatography with electrospray ionisation. It was determined that hydrophilic chromatography on unmodified silica gel could be used for satisfactory separation of isomeric five-membered heterocyclic compounds of different classes. For six-membered heterocycles, satisfactory separation was achieved by elution from the surface of octadecyl silica gel using aqueous acetonitrile mobile phase without modifiers.

Phenylalkyl Glycosides from the Flowers of Brugmansia arborea L. and Their Radical Scavenging Effect and Protective Effect on Pancreatic Islets Damaged by Alloxan in Zebrafish (Danio rerio) Larvae.

The study aimed to investigate the antioxidant and antidiabetic activity of Brugmansia arborea L. flower extracts, solvent fractions, and isolated compounds. B. arborea L flowers were extracted with aqueous methanol, and concentrated extract was successively partitioned into EtOAc, n-BuOH, and H2O fractions. Repeated silica gel and octadecyl silica gel column chromatographies for EtOAc and n-BuOH fractions led to the isolation of a new phenylalkyl glycoside (6), along with five known ones. Several spectroscopic data led to the structure determination of one new phenylalky glycoside as brugmansioside C (named) (6) and five known ones as benzyl-O-β-D-glucopyranoside (1), benzyl-O-β-D-glucosyl-(1→6)-β-D-glucopyranoside (2), 2-phenylethyl-O-β-D-glucopyranoside (3), 2-phenylethyl-O-β-D-glucosyl-(1→6)-β-D-glucopyranoside (4), and 3-phenylpropyl-O-β-D-glucopyranoside (5). The five known ones (1-5) were isolated from B. arborea flowers for the first time in this study. The extract, solvent fractions, and all isolated compounds showed radical scavenging activities using ABTS radical, and EtOAc fraction showed the highest scavenging capacity, whereas compounds 2, 4, and 6 did not display the capacity to use the DPPH radical. The extract, solvent fractions, and all isolated compounds showed a protective effect on pancreatic islets damaged by alloxan treatment in zebrafish larvae. The pancreatic islet size treated with EtOAc, n-BuOH fractions, and all compounds significantly increased by 64.0%, 69.4%, 82.0%, 89.8%, 80.0%, 97.8%, 103.1%, and 99.6%, respectively, compared to the alloxan-induced group. These results indicate that B. arborea flowers and their isolated compounds are useful as potential antioxidant and antidiabetic agents.

Total Synthesis of a Reversed-Bacicyclin Using a Combination of Solid- and Solution-Phase Methods

Bacicyclin is a cyclic hexapeptide with antibacterial activity against Enterococcus faecalis and Staphylococcus aureus with minimum inhibition concentration (MIC) values of 8 and 12 µM, respectively. Studies on a reversed sequence of bacicyclin were conducted to investigate how the reversed peptide sequence affects its biological properties. A reversed-bacicylin, cyclo-(Gly-Leu-Val-Ile-Ala-Phe), was successfully synthesized by constructing the linear precursor on 2-chlorotrityl chloride resin using a Fmoc-based strategy. The HATU/HOAt reagent was applied in all peptidic bond formations, and the desired linear hexapeptide (82% yield) was cleaved off the resin using a mixture of trifluoroacetic acid:dichloromethane (2:8). The linear peptide was cyclized using 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxidehexa-fluorophosphate (HATU) as a coupling agent and diisopropylethylamine (DIPEA) as the base in a very dilute solution (0.001 M) in dichloromethane, then purified by octadecyl silica gel (ODS) column chromatography to obtain the reversed-bacicyclin (43.7% yield). The purity of the cyclic product was analyzed using analytical RP-HPLC (tR = 20.01 min), and characterized by HR-TOF-MS, 1H-NMR, and 13C-NMR. The biological activity of the reversed-bacicyclin is much lower compared to bacicyclin, indicating that the amino acid sequence of the cyclopeptide dictates the antibacterial activity. This finding gives additional information on the relationship between peptide sequence and biological properties.

Striatal Isolated from Cyathus striatus Extracts Induces Apoptosis in Human Pancreatic Cancer Cells.

The aim of the present study was to identify the structure of active compounds in Cyathus stratus that previously demonstrated anti-pancreatic cancer activity. The active compounds were purified from a crude extract by a series of RP-18 preparative chromatography using homemade octadecyl silica gel column. HPLC injection of the crude extract revealed a chromatogram with three main peaks with retention times (RT) 15.6, 18.2, and 22.5 min. Each fraction that exhibited promising activity in vitro was further separated using various available chromatographic techniques. The purified compound with the ultimate anti-cancer activity appeared at RT of 15.8 in the HPLC chromatogram with more than 90% purity. The main peak at the mass spectra appeared at m/z = 446.2304 with the calculated molecular formula of C25H34O7. One- and two-dimensional NMR analyses indicated that the structure of the active molecule (peak 15.8 min in HPLC) was identified as striatal C. Exposure of human pancreatic cancer cells to purified striatal C resulted in induction of apoptosis. Further studies are needed in order to develop a method for the synthesis of striatal in order to use it in clinical studies for treatment of cancer.

Simultaneous Determination of Pyridate, Quizalofop-ethyl, and Cyhalofop-butyl Residues in Agricultural Products Using Liquid Chromatography-Tandem Mass Spectrometry.

An analytical method was developed to simultaneously determine pyridate, quizalofop-ethyl, and cyhalofop-butyl in brown rice, soybean, potato, pepper, and mandarin using LC-MS/MS. Purification was optimized using various sorbents: primary–secondary amine, octadecyl (C18) silica gel, graphitized carbon black, zirconium dioxide-modified silica particles, zirconium dioxide-modified silica particles (Z-SEP), and multi-walled carbon nanotubes (MWCNTs). Three versions of QuECHERS methods were then tested using the optimal purification agent. Finally, samples were extracted using acetonitrile and QuEChERS EN salts and purified using the Z-SEP sorbent. A six-point matrix-matched external calibration curve was constructed for the analytes. Good linearity was achieved with a determination coefficient ≥0.999. The limits of detection and quantification were 0.0075 mg/kg and 0.01 mg/kg, respectively. The method was validated after fortifying the target standards to the blank matrices at three concentration levels with five replicates for each concentration. The average recovery was within an acceptable range (70–120%), with a relative standard deviation <20%. The applicability of the developed method was evaluated with real-world market samples, all of which tested negative for these three herbicide residues. Therefore, this method can be used for the routine analysis of pyridate, quizalofop-ethyl, and cyhalofop-butyl in agricultural products.

New phenylalkanoids from the rhizome of Cnidium officinalis Makino

Cnidium officinalis rhizomes were immersed in 80% MeOH. The extract was fractionated to water, n-butanol, and ethyl acetate fractions (Fr). Open column chromatography was repeatedly carried out on n-butanol and ethyl acetate Fr using silica gel, octadecyl silica gel, and Sephadex LH-20 as the stationary phase affording five phenyl alkanoids 1–5 including two new ones. The molecular structures including stereochemistry were decided based on spectroscopic interpretation of nuclear magnetic resonance, mass spectrometry, and infrared spectroscopy as well as chemical reaction. Three known compounds, coniferyl alcohol methyl ether (1), vanillin (2), and coniferyl aldehyde (3), were reported in the beginning for this plant by authors. Two new phenyl alkanoids were named, 7-methoxyeugenol and cnidiumoside.

Influence of ionic liquids’ nature on chromatographic retention of benzimidazoles by RP HPLC

One of the priority tasks of the pharmaceutical industry is to manufacturing high-quality, effective, and safe medicines. Thus, the interest in for searching biologically active compounds perspective for the creation of new drugs is growing. The aim of this work was to study the chromatographic behavior of benzimidazole and its firstly synthesized derivatives by reversed-phase–HPLC (RP-HPLC). The sorption of benzimidazole and its five derivatives from liquid solutions of various qualitative composition on octadecyl silica gel was studied by the method of RP HPLC. Mobile phases contained ionic liquids (IL) as an additive: 1-butyl-2,3-dimethylimidazolium tetrafluoroborate ([BdMIM] [BF4]) and 1-butyl-3 methylimidazolium bromide ([BMIM] [Br]). The effect of eluent’s and ILs’ nature on benzimidazoles’ retention from six compositions of mobile phases at a ratio of H2O (or aqueous solution of IL)/organic modifier (acetonitrile or methanol) of 50/50 vol.% was studied. The standard changes in the enthalpy of the benzimidazoles’ transition from the aqueous-organic eluent to the octadecyl silica gel layer and the entropy components of the process were calculated based on the temperature dependences of the retention factors. A comparative analysis of the enthalpies’ and entropy components’ values of the sorption process for the studied benzimidazoles was carried out. Also the enthalpy–entropy dependences were considered.

Влияние природы ионных жидкостей на сорбцию бензимидазола и некоторых его производных из водно-ацетонитрильных растворов на октадецилсиликагеле

Исследование сорбции биологически активных соединений (БАС) из жидких растворов явля-ется актуальным направлением современной науки и практики, так как касается многих сфер деятель-ности человека, таких как, например, экология и медицина. БАС являются потенциальными активными компонентами лекарственных средств, а изучение их сорбции может помочь в решении проблемы кон-троля качества фармацевтических препаратов и субстанций, разработки российских аналогов зарубеж-ных лекарств, а также проблему очистки природных водоемов и сточных вод. Наиболее подходящим методом исследования лекарственных препаратов является метод обращенно-фазовой высокоэффек-тивной жидкостной хроматографии (ОФ ВЭЖХ). Однако в случае исследования БАС методом ОФ ВЭЖХ возникает ряд проблем, таких как, например, денатурация белков; сложность разделения смесей лекарственных средств, а также проблема сильной зависимости факторов удерживания от свойств сор-бента. Возможным решением этих проблем могут стать ионные жидкости (ИЖ), которые, благодаря своей двойственной природе, позволяют поддерживать ряд важных для хроматографии межмолекуляр-ных взаимодействий как с поверхностью сорбента, так и с аналитами, что делает их перспективными добавками в ОФ ВЭЖХ.В связи с вышесказанным, целью настоящего исследования было изучение влияния природы ИЖ на удерживание октадецилсиликагелем бензимидазола и его впервые синтезированных производ-ных из водно-ацетонитрильных элюентов и элюентов, содержащих растворенный 1-бутил-2,3-димети-лимидазолий тетрафторборат ([BdMIM] [BF4]) и 1-бутил-3-метилимидазолий бромид ([BMIM][Br]). Рассмотрено влияние состава водно-ацетонитрильного раствора на факторы удерживания биологиче-ски активных производных бензимидазола на октадецилсиликагеле в рамках моделей Снайдера-Соче-винского и Сочевинского- Вахмайстера и рассчитаны соответствующие угловые коэффициенты. Пока-зано, что зависимости для некоторых сорбатов не линейные и соответственно, их удерживание не мо-жет быть описано в рамках используемых полуэмпирических моделей.При сравнении величин угловых коэффициентов уравнений Сочевинского- Вахмайстера и Снайдера-Сочевинского показано, что на комплекс межмолекулярных взаимодействий влияет природа ионных жидкостей, а также строение анализируемых соединений. Выявлено, что система с [BdMIM][BF4] характеризуется наименьшими значениями n и S для всех соединений, а также показано, что в этой системе модели Сочевинского-Вахмайстера и Снайдера-Сочевинского не позволяют описать удерживание следующих сорбатов: бензимидазола (сорбат № 1), 1,2-бис-(гидроксиметил)-бензимида-зола (сорбат № 3) и 2-бензил-1-(3-фенилпропил)-1H-бензимидазола (сорбат № 6).

Dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis and their cytotoxicity on human cancer cell lines

Repeated chromatographic separations of the EtOAc fraction of Schisandra chinensis fruits on silica gel, octadecyl silica gel, and Sephadex LH-20 led to the isolation and identification of seven dibenzocyclooctadiene lignans (1–7). The NMR data reported in the literature for angeloyl gomisin H (5) were shown to be incorrect. We unambiguously identified the compounds based on detailed analysis of the 1D and 2D NMR data, especially from HMBC and NOESY experiments. In addition, MTT assays and cell viability experiments verified the cytotoxicity of the isolated dibenzocyclooctadiene lignans against the human cancer cell lines AGS, HeLa, and HT-29.

The Influence of the Surface Chemistry of Sorbents on the Efficiency of Separation of Mixed S,N-Derivatives of 1,1-Dimethylhydrazine

The influence of the surface chemistry of nonpolar sorbents (silica gel C18 and porous graphitized carbon), temperature, and liquid phase composition on the parameters of chromatographic retention of S,N-derivatives of 1,1-dimethylhydrazine (thiosemicarbazides) has been studied under the conditions of liquid chromatography. Experimental data have been compared with the results of preliminary estimates obtained for the adsorption characteristics of thiosemicarbazides using a molecular-statistical approache and determination of lipophility factor. Satisfactory agreement has been revealed between the experimental data and theoretical predictions. It has been shown that mixtures of ethyl-, allyl-, and phenylthiosemicarbazide are most efficiently separated by chromatography with the use of porous graphitized carbon packed into a Hypercarb column. The selectivity of this sorbent is 1.5 times higher than that of octadecyl silica gel packed into a Zorbax Eclipse XDB C18 column.

A New Neolignan Glucoside from the Stems of “Baekma” Cultivar, Chrysanthemum morifolium

A new neolignan glucoside has been isolated from Chrysanthemum morifolium ‘Baekma’ cultivar through repeated silica gel and octadecyl silica gel (ODS) column chromatographies. On the basis of spectroscopic data including NMR, MS, and IR, the chemical structure of the new neolignan glucoside was determined to be (7S,8S)-7-O-[1′-(4′,5′-dihydroxy-3′-methoxyphenyl)propanol]guaiacylglycerol 4-O-β-D-glucopyranoside (1), named baekmaoside A.

Effect of the Nature of the Sorbent on the Retention of 1,2,4-Triazole and 1,2,4-Triazine Derivatives under the Conditions of Reversed-Phase High-Performance Liquid Chromatography

The chromatographic retention of 1,2,4-triazine and 1,2,4-triazole derivatives on octadecyl silica gel, super–cross linked polystyrene, and porous graphitized carbon is studied using water-acetonitrile mobile phase. The effect the structure of sorbate molecules and the nature of the sorbent have on the retention characteristics under conditions of RP HPLC is analyzed. The influence of the acetonitrile concentration in the eluent on the retention of the investigated compounds by sorbents of various nature is illustrated.

Studying the Sorption of Certain Benzimidazoles on Octadecyl Silica Gel from Water–Acetonitrile Solutions via Liquid Chromatography

The effect the composition of a water–acetonitrile eluent has on the sorption of benzimidazoles by octadecyl silica gel is studied using the Snyder–Soczewinski model. Three-parameter equations associating retention factors and certain physicochemical characteristic of the molecules of benzimidazoles are obtained via linear regression analysis. Standard changes in the enthalpy of the transfer of benzimidazoles from the water–acetonitrile phase to the layer of octadecyl silica gel and entropic components of the process are calculated from the temperature dependences of the retention factors. The enthalpy–entropy dependences of sorption are discussed.

Liquid chromatographic ligand-exchange chiral stationary phases based on amino alcohols

Liquid chromatographic ligand-exchange chiral stationary phases (CSPs) have been developed for the resolution of racemic compounds, which can be used as bidentate or tridentate ligands. In this paper, we review the development of liquid chromatographic ligand-exchange CSPs based on amino alcohols or their derivatives coated dynamically on octadecylsilica gel or bonded covalently to silica gel and their applications to the resolution of α-amino acids, β-amino acids, α-hydroxycarboxylic acids and proton pump inhibitors (PPIs). The relationship between the structures of CSPs and chromatographic resolution behaviors is discussed. In particular, a rational approach to the development of improved ligand-exchange CSPs based on amino alcohols derived from α-amino acids is followed.

Thermodynamics of the Sorption of Benzimidazoles on Octadecyl Silica Gel from Water–Methanol Eluents

The standard enthalpy and entropy component of transferring benzimidazoles from water-methanol solutions to surfaces of octadecyl silica gel are determined using reversed-phase high-performance liquid chromatography (RP HPLC). The dependences between the enthalpy and polarizability of the molecules of the studied benzimidazoles, the enthalpy and the entropy factor are studied, and the influence of the quantitative composition of the water-methanol solution on the enthalpy are studied.

The use of the HPLC method for the quantitative determination of cetylpyridinium hexafluorosilicate in a dental gel

Cetylpyridinium hexafluorosilicate has been proposed as a caries preventive and antibacterial agent for use as a gel for oral application, which requires development of quality control methods.Aim. To develop the method for the quantitative determination of cetylpyridinium hexafluorosilicate in a dosage form using HPLC.Materials and methods. The object of the study is the experimental dosage form – a gel proposed for use in dental practice. The research method is HPLC.Results and discussion. The method for the quantitative determination of the active component, which allows determining cetylpyridinium hexafluorosilicate in the gel in the presence of excipients of the dosage form, has been developed. It is recommended to carry out this determination by the HPLC method using the column of 150 × 4.6 mm in size filled with octadecyl silica gel for chromatography, the sorbent particle size of 3.5 μm, a mixture of perchlorate buffer solution (pH 3.0) and acetonitrile (30 : 70) as a mobile phase and UV detection at the wavelength of 254 nm.Conclusions. The conditions of the chromatographic study by the HPLC method proposed provide sufficient selectivity for the quantitative determination of cetylpyridinium hexafluorosilicate in the dosage form, and it has been confirmed by studying the validation characteristics of the method.

Phenylpropanoids from Lilium Asiatic hybrid flowers and their anti-inflammatory activities

Three phenylpropanoids were isolated from the flowers of Lilium Asiatic hybrids through repeated silica gel or octadecyl silica gel column chromatographies. The chemical structures were determined to be 1-O-trans-caffeoyl-β-d-glucopyranoside (1), regaloside A (2), and regaloside B (3), based on spectroscopic data gathered from nuclear magnetic resonance (NMR) spectroscopy, electron ionization mass spectrometry (EI/MS), polarimetry, and infrared spectroscopy (IR) experiments. Compounds 1 and 2 showed significant DPPH radical scavenging activity of 60.1 and 58.0% at 160 ppm, respectively, compared with the 62.0% activity of the positive control, α-tocopherol. At a concentration of 50 μg/mL, compounds 1–3 inhibited the expression of iNOS to 4.1 ± 0.01, 70.3 ± 4.07, and 26.2 ± 0.63, respectively, and decreasing COX-2 expression to 67.8 ± 4.86, 131.6 ± 8.19, and 98.9 ± 4.99. Also, at the same concentration, compounds 1–3 decreased the ratio of p-p65/p-65 to 43.8 ± 1.67, 40.7 ± 1.30, and 43.2 ± 1.60, respectively, and the expression of VCAM-1 to 42.1 ± 2.31, 48.6 ± 2.65, and 33.8 ± 1.74, respectively.

Identification of Pyrogallol in the Ethyl Acetate-Soluble Part of Coffee as the Main Contributor to Its Xanthine Oxidase Inhibitory Activity.

In this study, ethyl acetate-soluble parts of hot-water extracts from roasted coffee beans were found to demonstrate potent xanthine oxidase (XO) inhibition. The XO inhibitory activities and chlorogenic lactone contents (chlorogenic lactones have previously been identified as XO inhibitors in roast coffee) were measured for ethyl acetate-soluble parts prepared from coffee beans roasted to three different degrees. Although chlorogenic lactone contents decreased with higher degrees of roasting, the XO inhibitory activity did not decrease. These data led us to investigate new potent inhibitors present in these ethyl acetate-soluble extracts. Repeated assay-guided purifications afforded a highly potent XO inhibitor, which was eluted before chlorogenic lactones via medium-pressure chromatography using an octadecylsilica gel column. The obtained inhibitor was identified as pyrogallol (1,2,3-trihydroxybenzene), which had an IC50 of 0.73 μmol L-1, much stronger than that of other related polyphenolic compounds. Quantitative analysis of pyrogallol and chlorogenic lactones revealed that pyrogallol (at concentrations of 33.9 ± 4.2 nmol mL-1 in light roast coffee and 39.4 ± 3.9 nmol mL-1 in dark roast coffee) was the main XO inhibitor in hot-water extracts of roasted coffee beans (i.e., drinking coffee).

Phenolic compounds from the leaves of eggplant (Solanum melongenaL.)

The leaves of eggplant (Solanum melongena L.) were extracted with 80 % aqueous MeOH, and the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH, and water fractions. From the n-BuOH fraction, five compounds were isolated through the repeated silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies. On the basis of physic-chemical and spectroscopic data including mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance, they were identified to be caffeic acid (1), chlorogenic acid (2), cryptochlorogenic acid (3), panasenoside (4), and (6R,7E,9R)-4,7-megastigmadien-3-one-9-β-D-glucopyranoside (5). Compounds 3 and 4 were isolated for the first time from the leaves of S. melongena L. in this study.