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 Establishment and triterpenoid production of Ocimum basilicum cambial meristematic cells

2020 ◽  
Vol 143 (3) ◽  
pp. 573-581
Author(s):  
Alexander Mehring ◽  
Janik Haffelder ◽  
Jonas Chodorski ◽  
Judith Stiefelmaier ◽  
Dorina Strieth ◽  
...  
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Biomass Accumulation ◽  
Ocimum Basilicum ◽  
Meristematic Cells ◽  
Cultivation Period ◽  
Shake Flasks ◽  
Valuable Compounds ◽  
Whole Plants ◽  
First Time

AbstractThe application of plant suspension culture to produce valuable compounds, such as the triterpenoids oleanolic acid and ursolic acid, is a well-established alternative to the cultivation of whole plants. Cambial meristematic cells (CMCs) are a growing field of research, often showing superior cultivation properties compared to their dedifferentiated cell (DDC) counterparts. In this work, the first-time establishment of O. basilicum CMCs is demonstrated. DDCs and CMCs were cultivated in shake flasks and wave-mixed disposable bioreactors (wDBRs) and evaluated regarding triterpenoid productivity and biomass accumulation. CMCs showed characteristic small vacuoles and were found to be significantly smaller than DDCs. Productivities of oleanolic and ursolic acid of CMCs were determined at 3.02 ± 0.76 mg/(l*d) and 4.79 ± 0.48 mg/(l*d) after 19 days wDBR cultivation, respectively. These values were consistently higher than any productivities determined for DDCs over the observed cultivation period of 37 days. Elicitation with methyl jasmonate of DDCs and CMCs in shake flasks resulted in increased product contents up to 48 h after elicitor addition, with the highest increase found in CMCs at 232.30 ± 19.33% (oleanolic acid) and 192.44 ± 18.23% (ursolic acid) after 48 h.

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.

scholarly journals Oleanolic Acid, Ursolic Acid and Apigenin from Ocimum basilicum as Potential Inhibitors of the SARS-CoV-2 Main Protease: A Molecular Docking Study

2021 ◽  
pp. 1-16
Author(s):  
Aristote Matondo ◽  
Jason T. Kilembe ◽  
Etienne M. Ngoyi ◽  
Carlos N. Kabengele ◽  
Giresse N. Kasiama ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Biological Activities ◽  
Ocimum Basilicum ◽  
In Vivo Studies ◽  
Molecular Docking Study ◽  
Docking Score ◽  
Main Protease ◽  
Potential Inhibitors

Aim: The present study aims at identifying potential inhibitors from a set of ten compounds from Ocimum basilicum against the SARS-CoV-2 main protease, the chymotrypsin-like protease (3CLpro). Materials and Methods: Computational studies by molecular docking (Autodock tool) were used to obtain the scoring function of ten phytochemicals in interaction with the SARS-CoV-2 main protease. The pharmacokinetic behavior of the high-docking score compounds was addressed by using SwissADME and pkCSM webservers. Results: Three high-docking score ligands were identified as hit compounds mainly the oleanolic acid (-8.55 kcal/mol), the ursolic acid (-8.21 kcal/mol) and apigenin (-7.52 kcal/mol). Their pharmacokinetic profile revealed that they have good therapeutic profile of druggability and safe. The biological activities of the three compounds especially their anti-inflammatory properties in relation with the excessive production of proinflammatory cytokines in the most severe form of the COVID-19 were also highlighted.  Conclusion: COVID-19 outbreak is a serious public health threat that requires immediate action. In order to combat this pandemic, several strategies are used and the identification of potential inhibitors of the main protease of the virus is one of the widely used strategies. Here, three potential inhibitors from Ocimum basilicum plant (leaves) were pinpointed. Further in-vitro and in-vivo studies are needed that will clarify the role of Ocimum basilicum for the management of COVID-19 disease.

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

Bis (Isothiocyanatomethyl) Benzene, A Plant Derived Anti-Neoplastic Compound: Purified from Moringa Oleifera Leaf Extract

2019 ◽  
Vol 19 (5) ◽  
pp. 677-686 ◽  
Author(s):  
Samrat Paul ◽  
Piyali Basak ◽  
Namrata Maity ◽  
Chayan Guha ◽  
Nandan Kumar Jana
Keyword(s):  
Anticancer Activity ◽  
Leaf Extract ◽  
Moringa Oleifera ◽  
Folk Medicine ◽  
Drug Formulation ◽  
Indigenous Species ◽  
Cancer Cell Growth ◽  
Apoptotic Pathway ◽  
Dimeric Form ◽  
Mcf 7

Background: Moringa oleifera lam, commonly known as “Sajina”, is an indigenous species to India. In our folk medicine, it is used for the treatment of Canker (cancer). The Moringa oleifera leaf extract contains many phyto-compounds, with some being anti-neoplastic in nature. Objective: Our preliminary study showed that the leaf extract significantly kills cancer cells compared to normal cells. On searching for the new phyto-compound, Bis-isothiocyanatomethyl) benzene was purified and isolated. Methods: The sequential process of fractional distillation, column chromatography, followed by TLC and HPLC is performed for purification. Every fraction from each step was tested on HeLa cell line for evaluating the presence of the phyto-compound. Results and Conclusion: FTIR peak analysis of a single phyto-compound shows the presence of thiocyanate group, aromatic carbon group. 1H & 13C NMR peak analysis along with High-resolution mass spectroscopy (HRMS) calculation confirm the chemical structure with IUPAC name [Bis (Isothiocyanatomethyl) benzene]. Previously, Isothiocyanatomethyl- benzene solely or in conjugation with sugar molecule has been reported, but its dimeric form in nature hasnot yet been published anywhere. It shows anticancer activity by retarding cancer cell growth & inhibits carcinogenesis on HeLa, MCF-7, and MDA-MB-231 cell lines by caspase 3 apoptotic pathway and showed comparatively less cytotoxicity to PBMC cell. It shows anticancer activity almost the same as the market available drug Cis-Platin. Therefore, further extrapolating its activity with different concentrations may result in its use as a drug formulation for the treatment of cancer.

Apoptosis Caused by Triterpenes and Phytosterols and Antioxidant Activity of an Enriched Flavonoid Extract from Passiflora mucronata

2019 ◽  
Vol 18 (10) ◽  
pp. 1405-1416 ◽  
Author(s):  
Isabel C.V. da Silva ◽  
Goran N. Kaluđerović ◽  
Pollyana F. de Oliveira ◽  
Denise O. Guimarães ◽  
Carla H. Quaresma ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Cell Lines ◽  
Oleanolic Acid ◽  
Folk Medicine ◽  
Hexane Fraction ◽  
Cytotoxicity Test ◽  
B16f10 Cell ◽  
Dpph Method ◽  
Melanoma B16f10 ◽  
First Time

Background: P. mucronata (Pm) comes from South America, Brazil and is characterized as “Maracujá de Restinga”. It is used in folk medicine for its soothing properties and in treating insomnia. Objective: The present study for the first time analyzed the antioxidant and cytotoxicity of the hydroalcoholic leaves extract and fractions from Pm. Method: The cytotoxicity test will be evaluated by different assays (MTT and CV) against human prostate cancer (PC3) and mouse malignant melanoma (B16F10) cell lines, and the antioxidant test by DPPH method. Results: β-Amyrin, oleanolic acid, β-sitosterol and stigmasterol were isolated of the most active, hexane fraction. These substances were tested against the tumor cell lines: β-sitosterol and stigmasterol showed the most relevant activity to PC3 in CV assay and, oleanolic acid to B16F10 by the MTT assay. In addition, it was possible to indicate that the mode of cell death for stigmasterol, presumably is apoptosis. In terms of antioxidant activity, the hydroalcoholic leaves extract presented higher activity (EC50 133.3 µg/mL) compared to the flower (EC50 152.3 µg/mL) and fruit (EC50 207.9 µg/mL) extracts. By the HPLC-MS, it was possible to identify the presence of flavones in the leaf extract (isoschaftoside, schaftoside, isovitexin, vitexin, isoorientin, orientin). Conclusions: P. mucronata hexane fraction showed promising cytotoxic effect against cancer cell lines, and stigmasterol contributes to this activity, inducing apoptosis of these cells. Furthermore, as other Passiflora species, Pm extract showed antioxidant activity and flavones are its major phenolic compounds.

Ursolic Acid and Oleanolic Acid: Pentacyclic Terpenoids with Promising Anti-Inflammatory Activities

2016 ◽  
Vol 10 (1) ◽  
pp. 21-33 ◽  
Author(s):  
Dharambir Kashyap ◽  
Ajay Sharma ◽  
Hardeep S. Tuli ◽  
Sandeep Punia ◽  
Anil K. Sharma
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Anti Inflammatory

scholarly journals Potential Application of Some Lamiaceae Species in the Management of Diabetes

Plants ◽  
2021 ◽  
Vol 10 (2) ◽  
pp. 279
Author(s):  
Ninon G.E.R. Etsassala ◽  
Ahmed A. Hussein ◽  
Felix Nchu
Keyword(s):  
Metabolic Disorders ◽  
Review Paper ◽  
Chemical Constituents ◽  
Folk Medicine ◽  
Therapeutic Agents ◽  
Antidiabetic Activity ◽  
Adverse Side Effects ◽  
Potential Source ◽  
Ancient Times ◽  
Phytochemical Constituents

Diabetes is one of the most dangerous metabolic disorders, with high rates of mortality worldwide. Since ancient times, medicinal plants have been used in traditional medicine to treat many diseases, including diabetes and its related complications. Plants are widely accepted, affordable, and perceived to have minimal adverse side effects. The Lamiaceae family is a potential source of therapeutic agents for the management of metabolic disorders, including diabetes. Hence, this review paper summarizes the antidiabetic use of Lamiaceae species in folk medicine globally. Furthermore, we present the antidiabetic activities and phytochemical constituents of twenty-three (23) Lamiaceae species and the antidiabetic activity of some notable chemical constituents isolated from some of these Lamiaceae species.

scholarly journals Lupeol acetate as a potent antifungal compound against opportunistic human and phytopathogenic mold Macrophomina phaseolina

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Shabnam Javed ◽  
Zaid Mahmood ◽  
Khalid Mohammed Khan ◽  
Satyajit D. Sarker ◽  
Arshad Javaid ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Ethyl Acetate ◽  
Oleanolic Acid ◽  
Vanillic Acid ◽  
Fungal Biomass ◽  
Protocatechuic Acid ◽  
Methanolic Extract ◽  
Antifungal Compound ◽  
Chloroform Fraction ◽  
Lupeol Acetate

AbstractAntifungal activity of Monothecabuxifolia methanolic extract and its various fractions were assessed against Macrophominaphaseolina, a soil-borne fungal pathogen of more than 500 vegetal species as well as rare and emerging opportunistic human pathogen. Different concentrations of methanolic extract (3.125 to 200 mg mL−1) inhibited fungal biomass by 39–45%. Isolated n-hexane, chloroform and ethyl acetate fractions suppressed fungal biomass by 32–52%, 29–50% and 29–35%, respectively. Triterpenes lupeol and lupeol acetate (1, 2) were isolated from n-hexane while betulin, β-sitosterol, β-amyrin, oleanolic acid (3–6) were isolated from chloroform fraction. Vanillic acid, protocatechuic acid, kaempferol and quercetin (7–10) were isolated from the ethyl acetate fraction and identified using various spectroscopic techniques namely mass spectroscopy and NMR. Antifungal activity of different concentrations (0.0312 to 2 mg mL−1) of the isolated compounds was evaluated and compared with the activity of a broad spectrum fungicide mancozeb. Different concentrations of mencozeb reduced fungal biomass by 83–85%. Among the isolated compounds lupeol acetate (2) was found the highest antifungal against M.phaseolina followed by betulin (3), vanillic acid (7), protocatechuic acid (8), β-amyrin (5) and oleanolic acid (6) resulting in 79–81%, 77–79%, 74–79%, 67–72%, 68–71% and 68–71%, respectively. Rest of the compounds also showed considerable antifungal activity and reduced M.phaseolina biomass by 41–64%.

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