Chemical Constituents of Luculia pinceana in Vietnam and Evaluation of their Biological Activity

2020 ◽  
Vol 10 (2) ◽  
pp. 163-167
Author(s):  
Phan Minh Giang ◽  
Le Thi Huyen ◽  
Nguyen Van Dau ◽  
Duong Hong Anh ◽  
Pham Hung Viet
Keyword(s):  
Human Cancer ◽  
Chemical Constituents ◽  
Radical Scavenging ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Chemical Studies ◽  
Weak Activity ◽  
Dpph Scavenging ◽  
Dpph Scavenging Assay ◽  
First Time

Background: In the flora of China and Vietnam, Luculia pinceana Hook of the family Rubiaceae is described as a medicinal plant. Prior chemical studies of L. pinceana in China isolated iridois, glycosides of cincholic acid, and kaempferol glycosides from the stem, however, have not been conducted with L. pinceana in Vietnam. Methods: The stem of L. pinceana was extracted with a mixture of 90%EtOH–H2O at room temperature and the extract was further fractionated by using liquid-liquid extraction and repeated column- chromatographic techniques. Spectroscopic data (IR, MS, 1D- and 2D-NMR) were used to determine structures of isolated compounds. Results: Thirteen compounds were isolated and structurally determined. Oleanolic acid (2), scopoletin (3), cleomiscosin A (4), (E)-mappianine E (5a), (Z)-mappianine E (5b), vanillic acid (6), 2-hydroxyacetophenone-4-O-β-D-glucopyranoside (7), sweroside (10), and 4-methoxyacetophenone- 2-O-β-D-glucopyranoside (11) were isolated for the first time from L. pinceana. Compounds 6, 10, 11, loganin (8), 7-ketologanin (9) were not active (IC50 > 300 µg/ml), whereas 7 showed a weak activity (IC50 268.35 µg/ml) in the DPPH (1,1-diphenylpicrazyl) radical scavenging assay. A mixture of 5a/5b was cytotoxic against the human cancer cell line HepG2 (IC50 100.57 µg/ml) in the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Conclusion: L. pinceana in Vietnam was investigated for the first time. We isolated compounds of varied biosynthetic origins including monoterpene indole, iridoid, coumarin, coumaro-lignoid, phytosterol, oleanane triterpenoid, phenolic acid, and acetophenone. Nine of the thirteen compounds are newly isolated from L. pinceana. The study determined weak scavenging activity of acetophenone (7) in the DPPH-scavenging assay and weak cytotoxicity of a mixture of two monoterpene indoles (5a and 5b) against HepG2 cell.

scholarly journals Anticancer Activities of Chemical Constituents from Leaves and Twigs of Mitrephora winitii

2021 ◽  
Vol 21 (3) ◽  
pp. 699
Author(s):  
Sukee Sukdee ◽  
Puttinan Meepowpan ◽  
Narong Nantasaen ◽  
Siriporn Jungsuttiwong ◽  
Sarinya Hadsadee ◽  
...  
Keyword(s):  
Cancer Cell ◽  
Chemical Constituents ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Anticancer Activities ◽  
Chromatographic Separations ◽  
Chemical Structures ◽  
Anti Cancer ◽  
First Time ◽  
Mcf 7

The genus Mitrephora has been investigated and its anti-inflammatory, anti-bacterial and anti-parasitical activities were examined along with its potential as an anti-cancer cell line and inhibitor for platelet aggregation. In this work, air-dried leaves and twigs of M. winitii were grounded and extracted with n-hexane, ethyl acetate and methanol, respectively. Chromatographic separations of these extracts led to the isolation of three known compounds and one new compound (compound 2). The chemical structures of these were identified using spectroscopic investigation of 1D- and 2D-NMR and the resulting data confirmed these as stigmasterol (1), (3,4-dimethoxyphenyl)(5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)methanol (2), diayangambin (3), and methyl-L-inositol (4). The chemical constituents were reported the first time in M. winitii. Compound 2 showed anti-cancer cell lines with ED50 13.07 µg/mL against KB cells and then was tested for cytotoxicity against MCF-7 cells with ED50 11.77 µg/mL.

scholarly journals Chemical Constituents of the Aerial Parts ofDaucus carotasubsp.hispidusGrowing in Tunisia

2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1986351
Author(s):  
Saoussen Hammami ◽  
Abdelsamed I. Elshamy ◽  
Ridha El Mokni ◽  
Ali Snene ◽  
Kanako Iseki ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
Squamous Carcinoma ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
Weak Activity ◽  
Cervical Cells ◽  
Antimicrobial And Antioxidant Activity ◽  
First Time ◽  
High Resolution Mass Spectroscopy

Three known polyol menthane monoterpenoids, namely, (4 R)-1- p-menthen-6,8-diol (1), (4 R)-1- p-menthen-4,7-diol (2), and (1 R,2 R,4 R)- p-menthane-1,2,4-triol (3), and 6 known phenolics (4-9), in addition to β-sitosterol 3- O-glucoside (10), were isolated from the aerial parts of Daucus carota subsp. hispidus (Ball) Heywood (Family: Apiaceae) growing in Tunisia. The structures of the isolated compounds were established depending upon the spectroscopic techniques including one and two-dimensional nuclear magnetic resonance (1D, and 2D NMR) and high resolution mass spectroscopy (HRMS). The absolute configuration of the compounds 1 to 3 was determined using experimental circular dichroism (CD) for the first time. Compounds 1 to 3 were reported for the first time from this plant. Compounds 1 to 3 exhibited no antimicrobial and antioxidant activity using superoxide dismutase-like activities. Compounds 2 and 3 exhibited weak activity, while 1 showed negative cytotoxic activity against human mouth squamous carcinoma (HSC-2) and human cervical cells (HeLa) cancer cells.

scholarly journals Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (2) ◽  
pp. 1934578X2199334
Author(s):  
Do Thi Trang ◽  
Bui Huu Tai ◽  
Dan Thuy Hang ◽  
Pham Hai Yen ◽  
Phan Thi Thanh Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Spectral Data ◽  
Absolute Configuration ◽  
Marine Sponge ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Extensive Analysis ◽  
First Time ◽  
Tddft Method ◽  
Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

scholarly journals Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2772 ◽  
Author(s):  
You-Min Ying ◽  
Lu Huang ◽  
Ting Tian ◽  
Cui-Yu Li ◽  
Shi-Lei Wang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Natural Occurrence ◽  
Fungal Metabolites ◽  
Isolation And Identification ◽  
Late Step ◽  
Neosartorya Fischeri ◽  
The One ◽  
First Time

The One Strain Many Compounds (OSMAC) method was applied to explore the chemical diversities of secondary metabolites produced by Neosartorya fischeri NRRL 181. Four pyripyropenes 1–4, eight steroids 5–11, and four prenylated indole alkaloids 12–15, were obtained from the fungus cultured in petri dishes containing potato dextrose agar (PDA). 1,7,11-trideacetylpyripyropene A (1) and 1,11-dideacetyl pyripyropene A (2) were obtained and spectroscopically characterized (1D, 2D NMR, and HR-ESI-MS) from a natural source for the first time. It offered a sustainable source of these two compounds, which were usually used as starting materials in preparing pyripyropene derivatives. In addition, as compared with all the other naturally occurring pyripyropenes, 1 and 2 possessed unique acetylation patterns that did not follow the established late-step biosynthetic rules of pyripyropenes. The natural occurrence of 1 and 2 in the fungus implied that the timing and order of hydroxylation and acetylation in the late-step biosynthetic pathway of pyripyropenes remained to be revealed. The isolation and identification of 1–15 indicated that the OSMAC method could remarkably alter the metabolic profile and enrich the chemical diversities of fungal metabolites. Compounds 1–4 exhibited no obvious cytotoxicity against the triple-negative breast cancer cell line MDA-MB-231 as compared with taxol.

scholarly journals Chemical Constituents of Eupatorium japonicum and Anti-Inflammatory, Cytotoxic, and Apoptotic Activities of Eupatoriopicrin on Cancer Stem Cells

2021 ◽  
Vol 2021 ◽  
pp. 1-12
Author(s):  
Minh Giang Phan ◽  
Thi Thao Do ◽  
Thi Nga Nguyen ◽  
Thi Viet Huong Do ◽  
Ngoc Phuc Dong ◽  
...  
Keyword(s):  
Anticancer Agents ◽  
Human Cancer ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Sesquiterpene Lactones ◽  
No Production ◽  
Bioactive Constituents ◽  
Anti Inflammatory ◽  
First Time ◽  
Eupatorium Japonicum

Eupatorium japonicum Thunb. of the plant family Asteraceae is a popular traditional herb in Vietnam. However, its chemical constituents as well as bioactive principles have not been investigated yet. We investigated the phytochemistry of E. japonicum in Vietnam and isolated seventeen compounds (1–17) including phytosterols, terpenoids, phenolic acids, flavonoids, fatty alcohols, and fatty acids. They were structurally determined by MS and NMR analysis. Except for compounds 6 and 12, all the other compounds were identified for the first time from E. japonicum. Since many sesquiterpene lactones with α-methylene γ-lactone ring are reported as anti-inflammatory and anticancer agents, eupatoriopicrin (10), 1-hydroxy-8-(4,5-dihydroxytigloyloxy)eudesma-4(15),11(13)-dien-6,12-olide (11) were selected among the isolates for biological assays. Compound 10 was identified as the main bioactive sesquiterpene lactone of E. japonicum showing its potent anti-inflammatory and cytotoxic activity through inhibiting NO production and the growth of HepG2 and MCF-7 human cancer cell lines. For the first time, eupatoriopicrin (10) was demonstrated to strongly inhibit NTERA-2 human cancer stem cell (CSC) line in vitro. It is noticeable that the cytotoxicity of eupatoriopicrin against NTERA-2 cells is mediated by its apoptosis-inducing capability of 10 as demonstrated by the results of Hoechst 33342 staining, flow cytometry apoptosis analysis, and caspase-3 activity assays. The biological activities of the main bioactive constituents 1–7, 10, 12, and 15 supported the reported anti-inflammatory and anticancer properties of extracts from E. japonicum.

scholarly journals CONTRIBUTE TO STUDY ON CHEMICAL CONSTITUENTS OF URENA LOBATA (L.) OF VIETNAM

2019 ◽  
Vol 57 (2) ◽  
pp. 162
Author(s):  
Quan Minh Pham ◽  
Hoai Van Thi Tran ◽  
Lam Tien Do ◽  
Phuong Lan Doan ◽  
Inh Thi Cam ◽  
...  
Keyword(s):  
Mental Disorders ◽  
Ethyl Acetate ◽  
Ethyl Acetate Extract ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Tree Roots ◽  
Chemical Structures ◽  
Phytochemical Investigation ◽  
First Time

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.

scholarly journals Conjugated Polyene Ketones From the Marine Sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110437
Author(s):  
Bui H. Tai ◽  
Dan T. Hang ◽  
Do T. Trang ◽  
Pham H. Yen ◽  
Phan T. T. Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Marine Sponge ◽  
Human Cancer ◽  
2D Nmr ◽  
Ionization Mass ◽  
Hep G2 ◽  
Human Cancer Cells ◽  
Resolution Electron ◽  
New Compounds ◽  
First Time

Five conjugated polyene ketones (1-5) were isolated from the methanol extract of the marine sponge Clathria ( Thalysias) reinwardti (Vosmaer, 1880) living in the coastal waters of Vietnam. Their structures were determined to be 8-(2′,3′,4′-trimethylphenyl)-6-methyl-oct-3( E),5( E),7( E)-trien-2-one (1), 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo- β-ionone (4), and 4-(2′,3′,4′-trimethylphenyl)-but-3( E)-en-2-one (5), by extensive analysis of high-resolution electron spray ionization mass spectrum (HR-ESI-MS), one-dimensional, and two-dimensional (2D) nuclear magnetic resonance (NMR) spectra, as well as by comparison of the spectral data with those reported in the literature. Compound 1 was new, compounds 2 to 4 were isolated from nature for the first time, and the chemical structure as well as the NMR assignments, of 5 were indicated by 2D NMR for the first time. Additionally, compound 5 exhibited cytotoxic activity against the human cancer cells SK-LU-1, SK-Mel-2, MCF-7, and Hep-G2 with half-minimal inhibitory concentration (IC50) values of 15.12 ± 3.43, 17.41 ± 2.83, 33.12 ± 3.39, and 34.38 ± 3.52 µM, respectively, but displayed only a weak cytotoxic effect on the normal HEK-239A cells (IC50 64.67 ± 3.67 µM). Compound 5 also significantly increased Caspase-3 activity in SK-LU-1 cells at concentrations of 10, 15, and 20 µM.

Cytotoxic constituents of Alocasia macrorrhiza

2017 ◽  
Vol 72 (1-2) ◽  
pp. 21-25 ◽  
Author(s):  
Marwa Elsbaey ◽  
Kadria F.M. Ahmed ◽  
Mahmoud F. Elsebai ◽  
Ahmed Zaghloul ◽  
Mohamed M.A. Amer ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Spectroscopic Data ◽  
Human Cancer ◽  
Indole Alkaloid ◽  
Acid Methyl Ester ◽  
2D Nmr ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Acid Methyl ◽  
First Time

AbstractAn indole alkaloid, 2-(5-hydroxy-1H-indol-3-yl)-2-oxo-acetic acid (1) isolated for the first time from nature, in addition to the nine known compounds 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (2), alocasin B (3), hyrtiosin B (4), α-monopalmitin (5), 1-O-β-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (6), 3-epi-betulinic acid (7), 3-epi-ursolic acid (8),β-sitosterol (9) andβ-sitosterol 3-O-β-D-glucoside (10) were isolated from the rhizomes ofAlocasia macrorrhiza(Araceae). Their structures were elucidated by 1D and 2D NMR spectroscopic data. Of these compounds,6exhibited the strongest cytotoxicity against the four tested human cancer cell lines (IC50of about 10 µM against Hep-2 larynx cancer cells).

scholarly journals Chemical Constituents from Farfugium Japonicum Var. formosanum

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Sung-Fei Hsieh ◽  
Tain-Jye Hsieh ◽  
Mohamed El-Shazly ◽  
Ying-Chi Du ◽  
Chin-Chung Wu ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
Cancer Cell Line ◽  
Inflammatory Activity ◽  
Human Neutrophils ◽  
Spectral Techniques ◽  
Methanolic Extracts ◽  
Aerial Parts ◽  
Anti Inflammatory ◽  
Farfugium Japonicum ◽  
First Time

Two new eremophilenolides, 6β8β10β-trihydroxyeremophil-7(11)-en-12,8-olide (1) and 3βacetoxy-8α-hydroxy-6β-methoxyeremophila-7(11),9-dien-12,8-olide (2) along with twenty-nine other compounds were obtained from the methanolic extracts of the aerial parts and rhizomes of Farfugium japonicum (L.) Kitam. v ar. formosanum (Hayata) Kitam. (Compositae = Asteraceae). The structures of the isolated compounds were characterized and identified by spectral techniques. Compounds 5, 6, 10, 12-24, 29, and 30, were reported for the first time from this genus. Cytotoxicity and anti-inflammatory activity of the isolated compounds were evaluated. Compounds 3 and 16 possessed moderate cytotoxicity against human breast cancer cell line (MCF 7). Compounds 3, 16, 25 and 26 exhibited moderate cytotoxicity against hepatoma cells (Hep G2 and Hep 3B). With respect to the anti-inflammatory activity, compounds 15 and 16 (each 10 μg/mL) inhibited superoxide anion generation by human neutrophils in response to fMLP/CB by 92.0% and 87.3%, respectively.

scholarly journals Chemical Constituents and Antioxidant and Biological Activities of the Essential Oil from Leaves of Solanum spirale

2012 ◽  
Vol 7 (7) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Sukanya Keawsa-ard ◽  
Boonsom Liawruangrath ◽  
Saisunee Liawruangrath ◽  
Aphiwat Teerawutgulrag ◽  
Stephen G. Pyne
Keyword(s):  
Antioxidant Activity ◽  
Essential Oil ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Radical Scavenging ◽  
Octadecanoic Acid ◽  
Small Cell Lung ◽  
Hexahydrofarnesyl Acetone ◽  
First Time ◽  
Mcf 7

The essential oil of the leaves Solanum spirale Roxb. was isolated by hydrodistillation and analyzed for the first time using GC and GC-MS. Thirty-nine constituents were identified, constituting 73.36% of the total chromatographical oil components. ( E)-Phytol (48.10%), n-hexadecanoic acid (7.34%), β-selinene (3.67%), α-selinene (2.74%), octadecanoic acid (2.12%) and hexahydrofarnesyl acetone (2.00%) were the major components of this oil. The antioxidant activity of the essential oil was evaluated by using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay. The oil exhibited week antioxidant activity with an IC50 of 41.89 mg/mL. The essential oil showed significant antibacterial activity against both Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus with MIC values of 43.0 μg/mL and 21.5 μg/mL, respectively. It also showed significant cytotoxicity against KB (oral cancer), MCF-7 (breast cancer) and NCI-H187 (small cell lung cancer) with the IC50 values of 26.42, 19.69, and 24.02 μg/mL, respectively.

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