scholarly journals Two New Triterpenes and Other Compounds from Mentha aquatica (Lamiaceae)

2017 ◽  
Vol 12 (4) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Maria Ferhat ◽  
Zahia Kabouche ◽  
Yoshinori Fujimoto ◽  
Hiroshi Araya
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Maslinic Acid ◽  
Mentha Aquatica ◽  
Pomolic Acid ◽  
First Time ◽  
Tormentic Acid ◽  
Plant Compounds

Two new triterpenoids, maquatic acid (1), a 2,3- seco-triterpene having an acetal in its A-ring, and 3- O-benzoyltormentic acid (2), were isolated from underground parts of Mentha aquatica, in addition to twelve known compounds, tormentic acid (3), 1- O-benzoylhyptadienic acid (4), 3- epi-ursolic acid (5), hyptadienic acid (6), 3- epi-maslinic acid (7), 3- epi-tormentic acid (8), ursolic acid (9), β-sitosterol (10), oleanolic acid (11), pomolic acid (12), micromeric acid (13) and 21α-hydroxyursolic acid (14) from aerial and underground parts of the plant. Compounds 4-6, 8, 13 and 14 have been isolated from the genus Mentha for the first time.

scholarly journals TRITERPENES FROM DOCYNIA INDICA FRUITS AND THEIR CYTOTOXIC ACTIVITY

2018 ◽  
Vol 56 (4A) ◽  
pp. 199 ◽  
Author(s):  
Lê Xuân Duy
Keyword(s):  
Cytotoxic Activity ◽  
Ursolic Acid ◽  
Ethyl Acetate Fraction ◽  
Cytotoxic Activities ◽  
Hep G2 ◽  
Mass Spectral Data ◽  
Maslinic Acid ◽  
Mass Spectral ◽  
Pomolic Acid ◽  
First Time

Five triterpenes were isolated from the ethyl acetate fraction of methanolic extract of Docynia indica fruits. Their structures were determined to be pomolic acid (1), maslinic acid (2), ursolic acid (3), 23-hydroxy ursolic acid (4) and euscaphic acid (5) by comparison of physicochemical, NMR and mass spectral data with those reported in the literature. All triterpenes (1 – 5) were isolated for the first time from Docynia indica. Compounds 1 – 5 were evaluated for their cytotoxic activity using MTT assay, of which 23-hydroxy ursolic acid (3) and ursolic acid (4) showed cytotoxic activities against HeLa and Hep-G2 cancer cell lines. 

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 Bioassay-guided Isolation of Antiproliferative Triterpenoids from Euonymus alatus Twigs

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Hee Rae Kang ◽  
Hee Jeong Eom ◽  
Seoung Rak Lee ◽  
Sang Un Choi ◽  
Ki Sung Kang ◽  
...  
Keyword(s):  
Cell Lines ◽  
Ursolic Acid ◽  
Anticancer Agent ◽  
Meoh Extract ◽  
Isolation And Identification ◽  
Maslinic Acid ◽  
Euonymus Alatus ◽  
Anticancer Effects ◽  
Korean Traditional Medicine ◽  
First Time

Euonymus alatus (Celastraceae) has been used as an anticancer agent in Korean traditional medicine. However, the potential bioactive contributors to the anticancer effects have not been thoroughly studied. Our screening test revealed that the MeOH extract of E. alatus twigs exhibited significant cytotoxicity against A549, SK-OV-3, and SK-MEL-2 cell lines. A bioassay-guided separation of the MeOH extract of E. alatus twigs resulted in the isolation and identification of 14 triterpenes as main phytochemicals. The structures of the compounds were elucidated on the basis of spectroscopic evidence as lupeol (1), betulin (2), 3β,28,30-lup-20(29)-ene triol (3), lupenone (4), betulone (5), 28,30-dihydroxy-3-oxolup-20(29)-ene (6), messagenin (7), glut-5-en-3β-ol (8), maslinic acid (9), hederagenin (10), 3-oxo-11α-methoxyolean-12-ene (11), 3β-hydroxy-1-oxo-olean-12-en-28-oic acid (12), ursolic acid (13), and 2α-hydroxy-ursolic acid (14). Of these compounds, 3, 6–8, and 10–14 were isolated for the first time from this plant. All isolated triterpenoids had consistent antiproliferative activities against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines. Compounds 2, 5, and 7 showed significant cytotoxicity against all four cell lines tested, with IC50 values of 3.26–8.61 μM.

Chemical Constituents of Corchorus capsularis and C.olitorius (Jute Plant), Part IV Isolation of Corosolic Acid, Ursolic Acid and corosin and Correlation of Corosin with Tormentic Acid

1979 ◽  
Vol 34 (9) ◽  
pp. 1320-1325 ◽  
Author(s):  
M. Manzoor-i-Khuda ◽  
Gerhard Habermehl
Keyword(s):  
Ursolic Acid ◽  
Chemical Constituents ◽  
Plant Part ◽  
Methyl Group ◽  
Corchorus Capsularis ◽  
Acetate Methyl ◽  
Corosolic Acid ◽  
Acid Lactone ◽  
First Time ◽  
Tormentic Acid

Abstract Three triterpenoids have for the first time been isolated from fresh undried jute root, ursolic acid as its acetate, corosolic acid as its acetate and indicated to be urs-2a,2β-diol-12-en-28-oic-acid and oxo-corosin isolated as its acetate-methyl-ester, C36H54O10, m.p. 160 °C, aD-15° (c 0.435%). The 24-carboxyl in corosin-anhydro-lactone-acetate has been reduced to the methyl group and the resultant lactone on acetylation indicated to be identical with tormentic acid lactone acetate.

Chemical Constituents of Nepeta Distans

2010 ◽  
Vol 5 (11) ◽  
pp. 1934578X1000501 ◽  
Author(s):  
Javid Hussain ◽  
Nausheen Bukhari ◽  
Hidayat Hussain ◽  
Najeeb U Rehman ◽  
Syed Murtaza Hussain
Keyword(s):  
Spectral Data ◽  
Phenolic Compound ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Phytochemical Investigation ◽  
Reported Data ◽  
First Time

Phytochemical investigation of Nepeta distans Raul resulted in the isolation of a new phenolic compound, nepatanol (1), and eight known compounds, markhamioside F, netidiol, nepedinol, thymoquinone, eugenol, oleanolic acid, ursolic acid, and β-sitosterol, which have been isolated for the first time from this source. Structures of all the isolates were established on the basis of MS, and 1D and 2D NMR spectral data and by comparison with reported data.

scholarly journals A New C-methyl Isoflavone and Other Compounds from the Roots of Amphiblemma monticola(Melastomataceae)

2017 ◽  
Vol 12 (11) ◽  
pp. 1934578X1701201
Author(s):  
Fabrice S. T. Ndjateu ◽  
Mathieu Tene ◽  
Pierre Tane ◽  
Muhammad I. Choudhary
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Ellagic Acid ◽  
Phytochemical Study ◽  
First Report ◽  
Etoh Extract ◽  
Spectroscopic Analyses ◽  
First Time

The phytochemical study of the EtOH extract of the roots of Amphiblemma monticola Jacq.-Fél. led to the isolation of a new C-methyl isoflavone, amphiblemmone A (1), along with ten known compounds, including 3,4’-di- O-methylellagic acid (2), dimethyl 4,4’,5,5’,6,6’- hexahydroxybiphenyl-2,2’-dicarboxylate (3), lupeol (4), ellagic acid (5), β-sitosterol (6), sitosterol 3- O-β-D-glucopyranoside (7), 3-hydroxy-4,5-dimethoxybenzoic acid (8), 3- O-methylellagic acid 4′- O-β-D-xylopyranoside (9), and a mixture of oleanolic acid (10) and ursolic acid (11). The structures were elucidated using spectroscopic analyses (IR, UV, NMR and MS) and comparison with literature data. Compounds 2-11 were isolated for the first time from the genus Amphiblemma. This is the first report of compounds 2-4, 8 and 9 from the Melastomataceae family.

scholarly journals A New Hyptadienic Acid Derivative from Hyptis Verticillata (Jacq.) with Insecticidal Activity

2008 ◽  
Vol 3 (11) ◽  
pp. 1934578X0800301
Author(s):  
Duanne A. C. Biggs ◽  
Roy B. R. Porter ◽  
William F. Reynolds ◽  
Lawrence A. D. Williams
Keyword(s):  
Acid Derivative ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Insecticidal Activity ◽  
Betulinic Acid ◽  
Spectroscopic Analysis ◽  
Cylas Formicarius ◽  
Sweet Potato Weevil ◽  
Cylas Formicarius Elegantulus ◽  
Tormentic Acid

A new triterpene, A(1)-1-benzoate-19α-hydroxy-urs-2(3),12(13)-dien-28-oic acid (1), was isolated from Hyptis verticillata, in addition to the known triterpenes tormentic acid, isolated as the diacetate (2), betulinic acid (3), α- and β-amyrin, oleanolic acid and ursolic acid. The structure of 1 was elucidated by spectroscopic analysis. Compounds 1–3 exhibited insecticidal activity against the sweet potato weevil Cylas formicarius elegantulus (Summers).

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

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.

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