Induction of Caspase-8 and Death Receptors by a New Dammarane Skeleton from the Dried Fruits of Forsythia koreana

2013 ◽  
Vol 68 (1-2) ◽  
pp. 29-38 ◽  
Author(s):  
Usama W. Hawas ◽  
Amira M. Gamal-Eldeen ◽  
Samy K. El-Desouky ◽  
Young-Kyoon Kim ◽  
Antje Huefner ◽  
...  
Keyword(s):  
Ursolic Acid ◽  
Methyl Ether ◽  
Methanolic Extract ◽  
2D Nmr ◽  
Death Receptors ◽  
Caspase 8 ◽  
2D Nmr Spectroscopy ◽  
Naturally Occurring ◽  
Forsythia Koreana ◽  
Mcf 7

A new naturally occurring compound based on the dammarane skeleton, i.e. cabralealactone 3-acetate-24-methyl ether, was isolated from the aqueous methanolic extract of Forsythia koreana fruits, along with eight known compounds: cabralealactone 3-acetate, ursolic acid, arctigenin, arctiin, phillyrin, rutin, caffeic acid, and rosmarinic acid. The identifi cation of the isolated compounds was based on their spectral analysis including: HREI-MS, 1D and 2D NMR spectroscopy. The selected compounds and the aqueous methanolic extract were evaluated for their cytotoxic activity against human solid tumour cell lines. Cabralealactone 3-acetate-24-methyl ether and ursolic acid were found to be active against human breast cancer cells (MCF-7). The cytotoxicity was associated with the activation of caspase-8, the induction of the death receptors DR4 and DR5, as well as DNA fragmentation, and was thus due to apoptosis rather than necrosis

Antiproliferative Effects of Ocimum basilicum Methanolic Extract and Fractions, Oleanolic Acid and 3-epi-Ursolic Acid

2020 ◽  
Vol 6 (2) ◽  
pp. 134-146 ◽  
Author(s):  
Kehkashan Arshad Qamar ◽  
Ahsana Dar Farooq ◽  
Bina S. Siddiqui ◽  
Nurul Kabir ◽  
Sabira Begum
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Mitotic Spindle ◽  
Immunofluorescence Microscopy ◽  
Methanolic Extract ◽  
Folk Medicine ◽  
Ocimum Basilicum ◽  
Antiproliferative Effects ◽  
Ancient Times ◽  
Mcf 7

Aims: The aim of the current study was to identify active compound(s) responsible for the antiproliferative effects of O. basilicum and explore their underlying mechanism/s. Background: Plants have been the source of medicines for the treatment of various diseases since ancient times. Ocimum basilicum (Sweet Basil, Bobai Tulsi) has been used in the folk medicine for the treatment of human liver, spleen and stomach cancers. Background: Plants have been the source of medicines for the treatment of various diseases since ancient times. Ocimum basilicum (Sweet Basil, Bobai Tulsi) has been used in the folk medicine for the treatment of human liver, spleen and stomach cancers. Objective: To emphasize the importance of O. basilicum as a potential novel non-toxic alternative to the conventional anticancer therapy. Method: O. basilicum (aerial parts) methanolic extract and fractions were screened against HT-144, MCF-7, NCI-H460 and SF-268 human cancer cell lines using sulforhodamine B assay. The more active Petroleum Ether Insoluble (PEI) fraction was fractionated into six sub-fractions (OB-1 to OB-6). Four pure compounds (3-O-methyl ursolic acid, oleanolic acid, 3-epi-ursolic acid and ursolic acid) were isolated from the more potent sub-fraction OB- 6. Triple channel immunofluorescence microscopy was employed to observe the effects of methanolic extract, PEI fraction, sub-fractions OB-5 and OB-6, 3-epi-ursolic acid and oleanolic acid on the cytoskeleton and nuclei of MCF-7 cells. Result: The methanolic extract and the PEI fraction exhibited selectively greater growth inhibition against MCF-7 cell line (TGI: 56 and 36.2 µg/ml, respectively). By using triple channel immunofluorescence microscopy, it was observed that the methanolic extract, PEI fraction, sub-fraction OB-5 and 3-epi-ursolic acid induced irregular mitotic spindle formation and slowing of mitotic progression in MCF-7 cells while sub-fraction OB-6 induced mitotic arrest in the prophase stage. F-actin aggregation was also visible in PEI fraction, subfraction OB-5 and 3-epi-ursolic acid treated MCF-7 cells. Conclusion: These results emphasize the importance of O. basilicum as a potential novel non-toxic alternative to the conventional anticancer therapy and suggest that it inhibits the growth of MCF-7 cancer cells via multiple mechanisms such as interaction with the microtubules and mitotic spindle apparatus, and F-actin aggregation.

scholarly journals Exploration of Hepatoprotective Potential and Phytochemicals of Ziziphus oxyphylla Edgew

2020 ◽  
Vol 40 (04) ◽  
pp. 431-436
Author(s):  
Abdullah .
Keyword(s):  
Superoxide Dismutase ◽  
Methanolic Extract ◽  
Histopathological Examination ◽  
Liver Weight ◽  
2D Nmr ◽  
Chloroform Fraction ◽  
Hypotonic Solution ◽  
2D Nmr Spectroscopy ◽  
Hepatic Diseases ◽  
Antihepatotoxic Activity

Ziziphus oxyphylla Edgew (ZO) has been traditionally used for the treatment of hepatic diseases in Pakistan. The current study was carried out to investigate the effectiveness and mechanism underlying hepatoprotective effect of ZO. Hepatoprotective potential of root extracts (crude methanolic extract and subsequent fractions) was investigated against carbon tetrachloride (CCl4) induced hepatotoxicity in BALB/c mice via determination of serum biomarkers, antioxidant enzymes (catalase, superoxide dismutase), lipid peroxidation and histopathology. Membrane stabilizing activity was determined via inhibition of hypotonic solution and heat-induced hemolysis. Crude methanolic extract and chloroform fraction ameliorated CCl4 induced elevated levels of alanine transaminase (ALT), alkaline phosphatase (ALP), total proteins (TP), total bilirubin (TB) and reversed the antioxidants imbalance in terms of catalase (CAT), superoxide dismutase (SOD) and reduced malondialdehyde (MDA) level. Crude methanol extract inhibited hemolysis induced by hypotonic solution and heat. Histopathological examination of liver specimens of extracts administered mice exhibited recovery from CCl4 induced pathological changes. Moreover, CCl4 induced alteration in body and liver weight was countered by the administration of ZO. Compounds betulinic acid (AZO1), ceanothic acid (AZO2) and zizybrenalic acid (AZO3) were isolated from chloroform fraction of the plant. The structures of compounds were deduced using 1D-and 2D-NMR spectroscopy techniques. The results show that Ziziphus oxyphylla roots extract possess antihepatotoxic activity mediated by the protection of anti-oxidant defense system and membrane-stabilizing activity, probably due to the presence of pentacyclic triterpenes

scholarly journals Diterpenoid Alkaloids from Delphinium aemulans

2018 ◽  
Vol 13 (11) ◽  
pp. 1934578X1801301
Author(s):  
Nurfida Ablajan ◽  
Bo Zhao ◽  
Wenjuan Xue ◽  
Zukela Ruzi ◽  
Jiangyu Zhao ◽  
...  
Keyword(s):  
2D Nmr ◽  
Diterpenoid Alkaloids ◽  
Diterpenoid Alkaloid ◽  
Esi Ms ◽  
Mtt Method ◽  
Naturally Occurring ◽  
Spectroscopic Analyses ◽  
Type C ◽  
Mcf 7

A new naturally occurring lycoctonine-type C19-diterpenoid alkaloid aemulansine (1), together with ten known alkaloids (2–11), were isolated from the whole herb of Delphinium aemulans Navski. Their structures were elucidated by extensive spectroscopic analyses, including 1D, 2D NMR and HR-ESI-MS. Compounds 1–10 were also evaluated in vitro for cytotoxicity against A549, Hela and MCF-7 cells using the MTT method.

New polysubstituted monoterpenic thiazolidinones: synthesis, spectroscopic and crystal structure studies

2018 ◽  
Vol 74 (12) ◽  
pp. 1629-1634 ◽  
Author(s):  
Abdellah N'ait Ousidi ◽  
Moulay Youssef Ait Itto ◽  
Aziz Auhmani ◽  
Abdelkhalek Riahi ◽  
Anthony Robert ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Nmr Spectroscopy ◽  
2D Nmr ◽  
Asymmetric Unit ◽  
2D Nmr Spectroscopy ◽  
X Ray ◽  
X Ray Crystallography ◽  
Naturally Occurring ◽  
Spectroscopic Analyses ◽  
Graph Set

The synthesis of three new polysubstituted monoterpenic thiazolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C14H21N3OS (2), (2Z,5Z)-5-[(dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C16H24N4OS (3), and (2Z,5Z)-5-[(dimethylamino)methylidene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C17H26N4OS (4), is reported, starting from the corresponding thiosemicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thiazolidin-4-ones have been fully characterized by HRMS and 1H and 13C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical molecules within the asymmetric unit with the same absolute configuration. These two molecules are linked through N—H...O hydrogen bonds, building an R 2 2(8) graph-set motif.

Iridoid and Bisiridoid Glycosides from Globularia cordifolia

2003 ◽  
Vol 58 (5-6) ◽  
pp. 337-341 ◽  
Author(s):  
Hasan Kirmizibekmez ◽  
Ihsan Çaliş ◽  
Pinar Akbay ◽  
Otto Sticher
Keyword(s):  
Nmr Spectroscopy ◽  
Methanolic Extract ◽  
Iridoid Glycosides ◽  
2D Nmr ◽  
Iridoid Glycoside ◽  
2D Nmr Spectroscopy

Abstract From the methanolic extract of the underground parts of Globularia cordifolia, a new iridoid glycoside, 5-hydroxydavisioside (1) and a new bisiridoid glycoside, globuloside C (2) were isolated along with six known iridoid glycosides, aucubin, melampyroside, monomelittoside, globularifolin, alpinoside and asperuloside. The structures of the isolates were established by 1D and 2D NMR spectroscopy in combination with IR, UV and MS analyses.

A New Sesquiterpene Lactone Sulfate from Reichardia gaditana (Asteraceae)

2007 ◽  
Vol 62 (1) ◽  
pp. 132-134 ◽  
Author(s):  
Christian Zidorn ◽  
Ernst-Peter Ellmerer ◽  
Werner Heller ◽  
Richard Greil ◽  
Manuela Guggenberger ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
High Resolution ◽  
Structure Elucidation ◽  
Methanolic Extract ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Asteraceae Family ◽  
Resolution Mass

The new sesquiterpenoid 8-deoxy-15-(3′-hydroxy-2′-methyl-propanoyl)-lactucin 3′-sulfate (1) was isolated from the methanolic extract of roots of Reichardia gaditana L. The compound was isolated by silica gel column chromatography (CC) and repeated Sephadex LH-20 CC. Structure elucidation was accomplished by high-resolution mass spectrometry and by 1D- and 2D-NMR spectroscopy. The chemosystematic significance of the new compound is discussed in the context of sesquiterpenoids from other members of the Lactuceae tribe of the Asteraceae family.

scholarly journals Anti-allergic and Cytotoxic Effects of Sesquiterpenoids and Phenylpropanoids Isolated from Magnolia biondii

2017 ◽  
Vol 12 (10) ◽  
pp. 1934578X1701201 ◽  
Author(s):  
Thi Tuyet Mai Nguyen ◽  
Thi Thu Nguyen ◽  
Hyun-Su Lee ◽  
Bomi Lee ◽  
Byung Sun Min ◽  
...  
Keyword(s):  
T Cells ◽  
Optical Rotation ◽  
Interleukin 2 ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
2D Nmr Spectroscopy ◽  
Jurkat T Cells ◽  
Cytotoxic Effects ◽  
D 12 ◽  
Mcf 7

Ten sesquiterpenoids (1-10) and six phenylpropanoid derivatives (11-16) were isolated from the flower buds of Magnolia biondii Pamp. Their structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, and optical rotation. To evaluate their anti-allergic properties, the inhibitory effect of each isolate (1-16) on interleukin-2 (IL-2) gene expression was examined in Jurkat T cells. Among the isolated compounds, three sesquiterpenoids (2, 5, and 7) and two monoterpenoids (12 and 13) strongly inhibited IL-2 production in Jurkat T cells. Four compounds, (-)-parthenolide (2), eudesm-4(15)-eno-1β,6α-diol (5), biondinin D (12), and tiliroside (16), showed cytotoxicity against Jurkat T cells. In addition, (-)-parthenolide (2) exhibited cytotoxicity against the human cervical cancer HeLa cell line, the human breast cancer MCF-7, and human promyelocytic leukemia HL-60 cell lines.

A New Eudesmane Derivative from Leontodon tuberosus

2004 ◽  
Vol 59 (1) ◽  
pp. 95-99 ◽  
Author(s):  
Renate Spitaler ◽  
Ernst-P. Ellmerer ◽  
Christian Zidorn ◽  
Hermann Stuppner
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Phenolic Acids ◽  
Methanolic Extract ◽  
2D Nmr ◽  
The Novel ◽  
2D Nmr Spectroscopy

Abstract Besides the known compounds 2,4,6-trihydroxyacetophenone 4-O-β -D-glucopyranoside and syringaresinol 4’-O-β -D-glucopyranoside, the novel sesquiterpenoid 1,2-dehydro-3-oxocostic acid β - D-glucopyranoside ester was isolated from Leontodon tuberosus L. and its structure established by mass spectrometry and 1D- and 2D-NMR spectroscopy. Additionally, a number of fatty and phenolic acids was identified in the crude methanolic extract by HPLC-DAD and HPLC-MS. The chemosystematic impact of the new sesquiterpenoid is discussed briefly.

scholarly journals Sugar Containing Compounds and Biological Activities of Lagochilus setulosus

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1755
Author(s):  
Davlat Kh. Akramov ◽  
Nilufar Z. Mamadalieva ◽  
Andrea Porzel ◽  
Hidayat Hussain ◽  
Mthandazo Dube ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
Biological Activities ◽  
2D Nmr ◽  
Septoria Tritici ◽  
2D Nmr Spectroscopy ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
Phytochemical Investigation ◽  
Diphenyl Tetrazolium Bromide

Phytochemical investigation of the methanolic extract obtained from the aerial parts of Lagochilus setulosus (Lamiaceae) afforded the new compound 1-methoxy-3-O-β-glucopyranosyl-α-l-oliose (1) together with five known glycosides, namely sitosterol-3-O-β-glucoside (2), stigmasterol-3-O-β-glucoside (3), pinitol (4), 6β-hydroxyl-7-epi-loganin (5), and chlorotuberoside (6). The structures of these compounds were elucidated by extensive spectroscopic analyses, especially HR-MS, 1D and 2D NMR spectroscopy. The in vitro cytotoxic activity of the methanolic extract and the isolated compounds was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and crystal violet (CV) staining assays. In addition, the antifungal activities of the components were evaluated against Botrytis cinerea, Septoria tritici, and Phytophthora infestans. The anthelmintic potential was determined against Caenorhabditis elegans nematodes. Neither the extract nor the isolated compounds showed promising activity in all the bioassays.

scholarly journals A New Flavone from the Leaves of Astronia formosana

2018 ◽  
Vol 13 (6) ◽  
pp. 1934578X1801300
Author(s):  
Yu-Chang Chen ◽  
Jing-Ru Weng
Keyword(s):  
Cell Lines ◽  
Ursolic Acid ◽  
Spectroscopic Data ◽  
Methanolic Extract ◽  
Data Analyses ◽  
Mcf 7

A new flavone, 5,4′-dihydroxy-7,3′-dimethoxy-6,8-dimethylflavone (1), together with four known compounds, ursolic acid (2), β-sitosterol-β-D-glucoside (3), β-sitosterol (4) and lupeol (5) were isolated from the methanolic extract of the leaves of Astronia formosana. The structures were elucidated on the basis of physical and spectroscopic data analyses. Compound 1 showed the slight cytotoxicity against MCF-7, SCM-1, and SCC2095 cell lines with IC50 values of 29.3 ± 9.2, 20.5 ± 10.2, and 25.7 ± 2.9 μM, respectively.

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