scholarly journals Triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle Lonicera caerulea var. kamtschatica

2017 ◽  
Vol 86 (1) ◽  
Author(s):  
Rafał Becker ◽  
Cezary Pączkowski ◽  
Anna Szakiel
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Fruit Ripening ◽  
Cuticular Waxes ◽  
Lonicera Caerulea ◽  
Pentacyclic Triterpenes ◽  
Pests And Diseases ◽  
Leaf Waxes ◽  
Compositional Study

Edible honeysuckle (honeyberry) <em>Lonicera caerulea</em> is becoming popular as a novel berry crop with several useful features such as early fruit ripening and exceptional hardiness, particularly resistance to pests and diseases as well as severe frosts in winter and droughts in summer. The triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle (a Russian cultivar Chernichka) was analyzed by GC-MS. The major compounds identified were the tetracyclic triterpenoids campesterol, cholesterol, cycloartanol, cycloart-23-ene-3,25-diol, 24-methylenecycloartanol (only in leaves), sitosterol, stigmasta-3,5-dien-7-one, and stigmasterol; and the pentacyclic triterpenes: <em>α</em>-amyrin, <em>β</em>-amyrin, hop-22(29)-en-3-one, oleanolic acid, and ursolic acid. Several remarkable features of the analyzed triterpenoid contents were revealed, including the relatively low abundance of triterpenoids in fruit waxes (6.5% of wax extract) compared to leaf waxes (22%), and a particularly high proportion of tetracyclic triterpenoids (tetracyclic to pentacyclic compound ratios of 4:1 in fruits and almost 7:1 in leaves). These rare features distinguish the triterpenoid profile of the cuticular waxes of <em>L. caerulea</em> var. <em>kamtschatica</em> from the majority of triterpenoid profiles in plant cuticular waxes investigated to date. To our knowledge, this is the first quantitative compositional study on triterpenoid compounds in the cuticular waxes of edible honeysuckle, supplementing the knowledge of cuticular triterpenoid diversity and distribution.

scholarly journals Synthesis and antitumor activity of fluorouracil – oleanolic acid/ursolic acid/glycyrrhetinic acid conjugates

MedChemComm ◽  
2019 ◽  
Vol 10 (8) ◽  
pp. 1370-1378 ◽  
Author(s):  
Chun-Mei Liu ◽  
Jia-Yan Huang ◽  
Li-Xin Sheng ◽  
Xiao-An Wen ◽  
Ke-Guang Cheng
Keyword(s):  
Antitumor Activity ◽  
Adverse Effects ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Biological Activities ◽  
Glycyrrhetinic Acid ◽  
Antitumor Activities ◽  
Pentacyclic Triterpene ◽  
Pentacyclic Triterpenes

Due to the obvious adverse effects of 5-fluorouracil and considering the diverse biological activities of pentacyclic triterpenes, twelve pentacyclic triterpene-5-fluorouracil conjugates were synthesized and their antitumor activities were evaluated.

Sterols and Triterpenes in Cell Culture of Hyssopus officinalis L.

2003 ◽  
Vol 58 (5-6) ◽  
pp. 308-312 ◽  
Author(s):  
Zuzanna Skrzypek ◽  
Halina Wysokińska
Keyword(s):  
Cell Culture ◽  
Cell Suspension ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Cell Suspension Cultures ◽  
Suspension Cultures ◽  
Pentacyclic Triterpenes ◽  
Hyssopus Officinalis

Abstract Cell suspension cultures from hypocotyl-derived callus of Hyssopus officinalis were found to produce two sterols i. e. β-sitosterol (1) and stigmasterol (2), as well as several known pentacyclic triterpenes with an oleanene and ursene skeleton. The triterpenes were identified as oleanolic acid (3), ursolic acid (4), 2α, 3β-dihydroxyolean-12-en-28-oic acid (5), 2α, 3β- dihydroxyurs-12-en-28-oic acid (6), 2α, 3β, 24-trihydroxyolean-12-en-28-oic acid (7), and 2α,3β, 24-trihydroxyurs-12-en-28-oic acid (8). Compounds 5-8 were isolated as their acetates (6, 8) or bromolactone acetates(5, 7)

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.

Changes in the Triterpenoid Content of Cuticular Waxes during Fruit Ripening of Eight Grape (Vitis vinifera) Cultivars Grown in the Upper Rhine Valley

2014 ◽  
Vol 62 (32) ◽  
pp. 7998-8007 ◽  
Author(s):  
Flora Pensec ◽  
Cezary Pączkowski ◽  
Marta Grabarczyk ◽  
Agnieszka Woźniak ◽  
Mélanie Bénard-Gellon ◽  
...  
Keyword(s):  
Vitis Vinifera ◽  
Fruit Ripening ◽  
Cuticular Waxes ◽  
Rhine Valley ◽  
Upper Rhine

scholarly journals Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells

2008 ◽  
Vol 100 (1) ◽  
pp. 36-43 ◽  
Author(s):  
M. Emília Juan ◽  
Joana M. Planas ◽  
Valentina Ruiz-Gutierrez ◽  
Hannelore Daniel ◽  
Uwe Wenzel
Keyword(s):  
Colon Cancer ◽  
Cancer Cells ◽  
Oleanolic Acid ◽  
Caspase 3 ◽  
Hydroxyl Group ◽  
Colon Cancer Cells ◽  
Maslinic Acid ◽  
Olive Fruit ◽  
Pentacyclic Triterpenes ◽  
Ht 29

We have previously reported the anticarcinogenic effects of an olive fruit extract composed of pentacyclic triterpenes, the main components of which are maslinic acid (73·25 %) and oleanolic acid (25·75 %). Here we examined the effects of the individual components on proliferation, necrosis and apoptosis rates by fluorescence-based techniques in human HT-29 colon cancer cells. Oleanolic acid showed moderate antiproliferative activity, with an ec50 of 160·6 (se 10·6) μmol/l, and moderate cytotoxicity at high concentrations ( ≥ 250 μmol/l). On the other hand, maslinic acid inhibited cell growth with an ec50 of 101·2 (se 7·8) μmol/l, without necrotic effects. Oleanolic acid, which lacks a hydroxyl group at the carbon 2 position, failed to activate caspase-3 as a prime apoptosis protease. In contrast, maslinic acid increased caspase-3-like activity at 10, 25 and 50 μmol/l by 3-, 3·5- and 5-fold over control cells, respectively. The detection of ROS in the mitochondria, which serve as pro-apoptotic signal, evidenced the different bioactivity of the two triterpenes. Confocal microscopy analysis revealed that maslinic acid generated superoxide anions while oleanolic acid-treated cells did not differ from the control. Completion of apoptosis by maslinic acid was confirmed microscopically by the increase in plasma membrane permeability, and detection of DNA fragmentation. In conclusion, the anticancer activity observed for olive fruit extracts seems to originate from maslinic acid but not from oleanolic acid. Maslinic acid therefore is a promising new compound for the chemoprevention of colon cancers.

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