Chemical Constituents of the Leaves of Diospyros kaki (Persimmon)

Diospyros kaki (persimmon) leaves have long been utilized as traditional medicine for the treatment of ischemic stroke, angina, and hypertension and as a healthy beverage and cosmetic for anti-aging. This study aimed to isolate as many compounds as possible from an ethanol extract of the persimmon leaves to identify the biologically active compounds. The antioxidative effect of the ethyl acetate layer from the ethanol extract of the persimmon leaves was demonstrated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and online high-performance liquid chromatography-2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (HPLC-ABTS) analysis. A new flavonoid, kaempferol-3-O-β-d-2″-coumaroylgalactoside (1), and a new natural compound, kaempferol-3-O-β-d-2″-feruloylglucoside (3) were isolated from the ethyl acetate layer, along with 25 previously known compounds, including fourteen flavonoids, one ionone, two coumarins, seven triterpenoids, and one acetophenone. Their structures were determined by the interpretation of spectrometric and spectroscopic data. All isolated compounds were rapidly evaluated using an online HPLC-ABTS assay, and of these, compounds 4–8, 11, 13, 15, and 16 clearly showed antioxidative effects. The amount of these compounds was 0.3–0.65% of the extract.

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Identification of Biflavones in Ethyl Acetate Fraction from Ethanol Extract of Selaginella doederleinii Hieron

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.550-553.1862 ◽

2012 ◽

Vol 550-553 ◽

pp. 1862-1865

Author(s):

Yan Zhang ◽

Li Yang ◽

Lin Wang

Keyword(s):

Physicochemical Properties ◽

Ethyl Acetate ◽

Dimethyl Ether ◽

Spectroscopic Data ◽

Chemical Constituents ◽

Ethanol Extract ◽

Ethyl Acetate Fraction ◽

Chemical Structures ◽

Trimethyl Ether ◽

First Time

The chemical constituents were isolated from the ethyl acetate fraction from ethanol extract of Selaginella doederleinii Hieron by column chromatography on silica gel and Sephadex LH-20. The chemical structures of six biflavones were elucidated on the basis of physicochemical properties and spectroscopic data as amentoflavone (1), robustaflavone 7,4',7''-o-trimethyl ether (2), heveaflavone (3), podocarpusflavone A (4), robustaflavone 4',4'''-o-dimethyl ether (5) and robustaflavone 4'-o-methyl ether (6). Biflavones 2, 4 and 5 were obtained from Selaginella doederleinii Hieron for the first time.

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High-Throughput Identification of Organic Compounds from Polygoni Multiflori Radix Praeparata (Zhiheshouwu) by UHPLC-Q-Exactive Orbitrap-MS

Molecules ◽

10.3390/molecules26133977 ◽

2021 ◽

Vol 26 (13) ◽

pp. 3977

Author(s):

Shaoyun Wang ◽

Xiaozhu Sun ◽

Shuo An ◽

Fang Sang ◽

Yunli Zhao ◽

...

Keyword(s):

High Performance ◽

Chemical Constituents ◽

Water Extract ◽

Ethanol Extract ◽

In Vivo Studies ◽

Polygonum Multiflorum ◽

Q Exactive ◽

Orbitrap Ms

Polygoni Multiflori Radix Praeparata (PMRP), as the processed product of tuberous roots of Polygonum multiflorum Thunb., is one of the most famous traditional Chinese medicines, with a long history. However, in recent years, liver adverse reactions linked to PMRP have been frequently reported. Our work attempted to investigate the chemical constituents of PMRP for clinical research and safe medication. In this study, an effective and rapid method was established to separate and characterize the constituents in PMRP by combining ultra-high performance liquid chromatography with hybrid quadrupole-orbitrap mass spectrometry (UHPLC-Q-Exactive Orbitrap-MS). Based on the accurate mass measurements for molecular and characteristic fragment ions, a total of 103 compounds, including 24 anthraquinones, 21 stilbenes, 15 phenolic acids, 14 flavones, and 29 other compounds were identified or tentatively characterized. Forty-eight compounds were tentatively characterized from PMRP for the first time, and their fragmentation behaviors were summarized. There were 101 components in PMRP ethanol extract (PMRPE) and 91 components in PMRP water extract (PMRPW). Simultaneously, the peak areas of several potential xenobiotic components were compared in the detection, which showed that PMRPE has a higher content of anthraquinones and stilbenes. The obtained results can be used in pharmacological and toxicological research and provided useful information for further in vitro and in vivo studies.

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Cycloartane-Type Triterpenes and Botanical Origin of Propolis of Stingless Indonesian Bee Tetragonula sapiens

Plants ◽

10.3390/plants8030057 ◽

2019 ◽

Vol 8 (3) ◽

pp. 57 ◽

Cited By ~ 6

Author(s):

Niken Pujirahayu ◽

Toshisada Suzuki ◽

Takeshi Katayama

Keyword(s):

High Performance ◽

Chemical Constituents ◽

Mangifera Indica ◽

Ethanol Extract ◽

Gas Chromatography Mass Spectrometry ◽

Botanical Origin ◽

Characteristic Peak ◽

Hplc Chromatogram ◽

Main Components ◽

Layer Chromatography

This study clarifies the chemical constituents and botanical origin of Tetragonula sapiens Cockerell bee propolis collected from Southeast Sulawesi, Indonesia. Propolis samples and resin of Mangifera indica were extracted with 99% ethanol to obtain an ethanol extract of propolis (EEP) and an ethanol extract of M. indica resin (EEM). Column chromatography, thin-layer chromatography (TLC), and high-performance liquid chromatography (HPLC) were developed and used for the separation and isolation of compounds from the ether-soluble fraction. The structure of the compounds was determined by nuclear magnetic resonance (NMR) spectroscopic analysis, and their molecular weight analyzed by gas chromatography–mass spectrometry (GC–MS). The HPLC chromatogram of the EEP was then compared with the HPLC chromatogram of EEM to investigate the botanical origin of propolis. Five compounds were isolated from the EEP, and their structures were determined as mangiferolic acid, cycloartenol, ambonic acid, mangiferonic acid, and ambolic acid, which are cycloartane-type triterpenes. The characteristic peak of the HPLC chromatograms of EEP and EEM showed a similar pattern, which is that the main components of propolis were also found in M. indica resin. These results suggested that the propolis from Southeast Sulawesi was rich in cycloartane-type triterpenes, and the plant source of the propolis could be Mangifera indica (mango).

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Phytoconstituents Isolation and Hepatoprotective Activity Potential of Averrhoa bilimbi Leaf Extract

Journal of Pharmaceutical Research International ◽

10.9734/jpri/2021/v33i58b34239 ◽

2021 ◽

pp. 573-581

Author(s):

Raghavendra Prabhu ◽

Ronald Fernandes ◽

K. Adarsha Govinda

Keyword(s):

Ethyl Acetate ◽

Leaf Extract ◽

Histopathological Examination ◽

Chemical Constituents ◽

Ethanol Extract ◽

Tween 80 ◽

Hepatoprotective Activity ◽

Albino Rats ◽

Standard Drug ◽

Plant Chemical

Objective: To isolate and evaluate the hepatoprotective activity of the crude ethanolic leaf extract of Averrhoa bilimbi Methods: The leaves of Averrhoa bilimbi were extracted by cold maceration using ethanol as a solvent, and the solvent fractions were obtained with petroleum ether and ethyl acetate. Preliminary phytochemical tests were performed for the presence or absence of secondary metabolites. Plant chemical constituents were isolated using column chromatography and characterized by IR,1HNMR,13CNMR and mass spectroscopic values. Albino rats were treated with the vehicles (distilled water or 2% Tween 80), three different doses (100, 200 and 400 mg/kg) of the crude ethanol extract and the standard drug (silymarin 100 mg/kg), and the hepatotoxicant paracetamol. Then, the levels of biomarkers of liver injury – such as alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) – and liver function such as bilirubin were measured along with histopathological examination. Results: Preliminary phytochemical studies shown the presence of n-docosanoic acid and beta sitosterol from petroleum extract and from ethyl acetate a flavonoid apigenin.The ethanol extract suppressed the plasma levels of AST, ALT and ALP (P=0.05) in the aforementioned doses. Maximum hepatoprotective activity was observed at the dose of 400 mg/kg body weight. Conclusion: Averrhoa bilimbi is endowed with hepatoprotective activity, probably with the presence its chemical constituents like sterols,flavonoids and terpenoids.

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Chemical Constituents of the Insecticidal Active Extract of Tinospora crispa

Scientific Research Journal ◽

10.24191/srj.v10i1.5408 ◽

2019 ◽

Vol 10 (1) ◽

pp. 23

Author(s):

Nor Aziyah Bakhari ◽

Siti Nur Amirah Diana Fadzillah ◽

Norain Isa

Keyword(s):

Blood Pressure ◽

Petroleum Ether ◽

Silica Gel ◽

1H Nmr ◽

Column Chromatography ◽

Mobile Phase ◽

Spectroscopic Data ◽

Chemical Constituents ◽

Ethanol Extract ◽

First Time

Tinospora crispa Miers (Menispermaceae) is a climbing vine with stems rich in warts. The plant is called Akar Seruntum or Patawali in Malaysia and is widely used for treating skin complaints, malaria, bacterial abscess, high blood pressure and diabetes. In the present study, the stems of T. crispa were collected from the locality and succesively extracted with petroleum ether, followed by chloroform and ethanol. The insecticidal active extract (ethanol extract) was subjected to column chromatography of silica gel eluted with a gradient mobile phase containing hexane, chloroform and ethanol. Among the chemical constituents isolated are n-tetracosyl trans-ferulate and n-octacosyl alcohol, along with three known aporphine alkaloids; N-formylnornuciferine, N-acetylnornuciferine and lysicamine. All compounds were identified by comparing their spectroscopic data (UV, IR, 1H NMR, MS) with data from corresponding values in the literature. Isolation of n-tetracosyl trans-ferulate and n-octacosyl alcohol is reported the first time for T. crispa.

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ANTIOXIDANT ACTIVITY OF TARENNA POLYCARPA (MIQ.) KOORD. LEAF

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2018.v11i4.21929 ◽

2018 ◽

Vol 11 (4) ◽

pp. 224

Author(s):

Rika Puspita Sari ◽

Marline Nainggolan ◽

Rosidah Rosidah

Keyword(s):

Antioxidant Activity ◽

Ethyl Acetate ◽

Leaf Extract ◽

Inhibitory Concentration ◽

Ethanol Extract ◽

Ethyl Acetate Fraction ◽

Antioxidant Potential ◽

Hexane Fraction ◽

Dpph Assay

Objective: The objective of this study is to evaluate the antioxidant activity of Tarenna polycarpa (Miq.) koord. Ex Valenton. Leaf extract and fractions.Methods: Antioxidant activity was examined by DPPH method.Results: Ethanol extract, n-hexane fraction, and ethyl acetate fraction with DPPH assay measured as half maximal inhibitory concentration were 55.21, 109.73, and 42.04 μg/mL, respectively.Conclusions: The results reveal that T. polycarpa extract and fractions have strong antioxidant potential. Our further study is to isolate compounds responsible for antioxidant components.

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A New Optical Biflavonoid, (2″R)-2″,3″-Dihydrorobustaflavone 7,4′-Dimethyl Ether, and Other Constituents from Selaginella trichoclada Alsto

Natural Product Communications ◽

10.1177/1934578x19887885 ◽

2019 ◽

Vol 14 (12) ◽

pp. 1934578X1988788

Author(s):

Peng Yang ◽

Mei-Long Lu ◽

Ke Li ◽

Qun Zhou

Keyword(s):

Dimethyl Ether ◽

Spectroscopic Data ◽

High Performance ◽

Human Cancer ◽

Ethanol Extract ◽

Racemic Compound ◽

Chiral Phase ◽

Human Cancer Cell Lines ◽

First Time ◽

Mcf 7

A new optical biflavonoid, (2” R)-2″,3″-dihydrorobustaflavone 7,4′-dimethyl ether (1), and 6 known compounds (2-7) were isolated for the first time from the 70% ethanol extract of Selaginella trichoclada Alsto. The structures of the compounds were confirmed by extensive spectroscopic data analyses. Racemic compound 1 was separated by chiral-phase high-performance liquid chromatography, and the absolute configurations of (±)-1 were defined by circular dichroism spectroscopic data. Compound 1 exhibited moderate cytotoxicity against MCF-7, A549, and HepG2 human cancer cell lines.

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UJI SENYAWA FLAVONOID TOTAL DARI EKSTRAK ETANOL HERBA BINARA (Artemisia annua) MENGGUNAKAN HIGH PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC) TAHUN 2019

JURNAL FARMASIMED (JFM) ◽

10.35451/jfm.v2i1.323 ◽

2019 ◽

Vol 2 (1) ◽

pp. 16-20

Author(s):

Jhon Patar Sinurat ◽

Novandi Purba ◽

Romauli Anna Teresia Marbun

Keyword(s):

High Performance Liquid Chromatography ◽

Liquid Chromatography ◽

Ethyl Acetate ◽

High Performance ◽

Artemisia Annua ◽

Ethanol Extract ◽

Partial Structure ◽

Water Solvent ◽

Fat Removal ◽

Two Stages

ABSTRAK Herba binara (Artemisia Annua) is one of the plants that contains flavonoids which are efficacious as antioxidants and anticancer. The purpose of this study was to determine the total flavonoid compounds contained in ethanol extract of binara herbs (Artemisia Annua). Compounds in ethanol extract of binara herbs were identified by phytochemical screening. The results showed that the ethanol extract of binara herbs contained alkaloids, flavonoids, saponins, and tannins. Extraction was carried out in two stages, namely maceration stage with 96% ethanol and fat removal stage by hydrolysis using distilled water solvent. The extract was partitioned with ethyl acetate and n-hexane solvents, then the partitions were examined by TLC using the mobile phase of chloroform and ethyl acetate (7: 3). Ribbon patches that have the same Rf and color prices as the initial detection are taken and searched. Then analyzed using High Performance Liquid Chromatography (HPLC). Based on the wavelength as well as the TLC test, a partial structure which was strongly suspected of total flavonoids was 0.93 g. Kata Kunci :Herba Binara (Artemisia Annua), flavonoid, KLT, High Performance Liquid Chromatography(HPLC).

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ANTIOXIDATIVE ACTIVITIES AND CHEMICAL CONSTITUENTS OF THE ETHYL ACETATE EXTRACT FROM JASMINUM UNDULATUM KER-GAWL

Science and Technology Development Journal ◽

10.32508/stdj.v14i2.1943 ◽

2011 ◽

Vol 14 (2) ◽

pp. 50-57

Author(s):

Anh Thi Tran ◽

Binh Thanh Nguyen ◽

Hoai Thi Cam Ho ◽

Huong Dang Thien Bui ◽

Mai Thi Thanh Nguyen

Keyword(s):

Nitric Oxide ◽

Ethyl Acetate ◽

Petroleum Ether ◽

Antioxidative Activity ◽

Chemical Constituents ◽

Radical Scavenging ◽

Ethanol Extract ◽

Ethyl Acetate Fraction ◽

Dpph Radical ◽

Dpph Radical Scavenging

From the total crude ethanol extract of Jasminum undulatum Ker Gawl.’s leaves and stems, five fractionss were obtained by partitioning with petroleum ether, chloroform, ethyl acetate and n-butanol solvents. These five fractions were investigated for antioxidative activity using the DPPH radical scavenging and nitric oxide-inhibitory assay. All the fractions showed antioxidative activity except the petroleum ether fraction. Among the fractionss, the ethyl acetate fraction was the most potent fraction in both assays with the SC50 values of 5.30 μg/ml and 80.90 μg/ml, respectively. Further investigation on the eight sub-fractions isolated and extracted from the ethyl acetate fraction showed that one of these sub-fractions, the TE6 sub-fraction, showed the most significant antioxidative activity with the SC50 values of 3.15 μg/ml and 61.83 μg/ml respectively in the DPPH radical scavenging and nitric oxide-inhibitory assay. From the TE4 and TE6 sub-fractions, three compounds were isolated, including p-tyrosol (1), protocatechuic acid (2) and hydroxytyrosol (3). The structure of those compounds were elucidated by spectrometric methods IR, MS, 1D-NMR, and 2D-NMR.

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Biologically Active Terpenoids fromTamarix Species

Eurasian Chemico-Technological Journal ◽

10.18321/ectj225 ◽

2013 ◽

Vol 15 (3) ◽

pp. 219 ◽

Cited By ~ 2

Author(s):

N.А. Sultanova ◽

Zh.А. Abilov ◽

А.K. Umbetova ◽

M.I. Choudhary

Keyword(s):

Enzyme Activity ◽

Ethyl Acetate ◽

Antioxidant Activities ◽

Radical Scavenging ◽

Ethanol Extract ◽

Biologically Active ◽

Bioactive Substances ◽

Aerial Parts ◽

Ethanol Extracts ◽

Ethyl Acetate Extracts

We carried out research of bioactive substances obtained from ethanol extract (70%). This ethanol extract (70%) was obtained by us from the aerial parts of Tamarix plants (Т.laxa Willd., T.hispida Willd., T.ramosissima Ledeb. and Т.еlongatа Ledeb.). These plants belong to the family of Tamaricaceae which grow on the territory of Kazakhstan. For the preliminary separation of bioactive substances, the fractional extraction of ethanol extracts (70%) of Tamarix species was carried out using chloroform and ethyl acetate. Chloroform and ethyl acetate extracts contained terpenoids (positive reactions with Lieberman-Burchard reagent and cerium sulfate). Isolation of terpenoids from chloroform and ethyl acetate extracts was achieved by a series of separations on chromatography column over silica gel and these terpenoids were eluted with gradient mixture of hexaneethylacetate (0-100%). From the aerial parts of Tamarix (Т.laxa Willd., T.hispida Willd., T.ramosissima Ledeb., Т.еlongatа Ledeb) five terpenoids were isolated. Their structures of 1-5 were found using alkaline hydrolysis and UV, IR, 1H and 13C NMR, COSY-45°, HMQC, HMBC, EIMS, FABMS (-ve) spectral analyses. Pentacyclic triterpenoids: ursolic acid (1), 3β-al-D- friedoolean-14-en-28-oic acid methyl ether (2), 3-α-[3´´,4´´-dihydroxy-trans-cinnamoyloxy]-D-friedoolean-14-en-28-oic acids (isotamarixen) (3), 3-α-hydroxy-D-friedoolean-14-en-28-oic acid (4) and 3-α-[4´´-dihydroxy-trans-cinnamoyloxy]-Dfriedoolean -14-en-28-oic acid (5) were isolated from the aerial parts of Tamarix. Ethanol extracts (70%), chloroform, ethylacetate extracts from Tamarix laxa, Tamarix elongata showed antioxidant activity. Antioxidant activities were determined using the DPPH (1, 1-diphenyl-2-picrylhydrazyl radical) scavenging method. Ethanol extracts from Tamarix hispida (50%) were found to contain the triterpenoid: 3-α-[3´´, 4´´-dihydroxy-trans-cinnamoyloxy]-D-friedoolean-14-en-28-oic acids (isotamarixen), which were tested in vitro for their effect on the α-glycosidase enzyme activity. 3-α-[3´´, 4´´-dihydroxy-trans-cinnamoyloxy]-D-friedoolean-14-en-28-oic showed inhibiting effect on the α-glycosidase enzyme activity and was found to be a potent antioxidant.

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