oleanane
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Lupane derivatives containing an electronegative substituent in the position 2 of the skeleton are often cytotoxic, however, the most active compounds are not selective enough. To further study the influence of a substituent in the position 2 in lupane and 18α-oleanane derivatives on their biological properties, we prepared a set of 38 triterpenoid compounds, 19 of them new, most of them substituted in the position 2. From betulin, we obtained 2-bromo dihydrobetulonic acid and 2-bromo allobetulon and their substitutions yielded derivatives with various substituents in the position 2 such as amines, amides, thiols, and thioethers. Nitration of allobetulon and dihydrobetulonic acid gave 2-nitro and 2,2-dinitro derivatives. Fifteen derivatives had IC50 < 50 μM on a chemosensitive CCRF-CEM (acute lymphoblastic leukemia) cell line and were tested on another seven cancer cell lines including resistant and two non-cancer lines. 2-Amino allobetulin had IC50 4.6 μM and caused significant block of the tumor cells in S and slightly in G2/M transition and caused strong inhibition of DNA and RNA synthesis at 5 × IC50. 2-Amino allobetulin is the most active derivative of 18α-oleanane skeletal type prepared in our research group to date.
- MeSH
- cytotoxiny chemie farmakologie MeSH
- inhibiční koncentrace 50 MeSH
- kontrolní body buněčného cyklu účinky léků MeSH
- kyselina olenalová analogy a deriváty chemie farmakologie MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- nukleové kyseliny antagonisté a inhibitory biosyntéza MeSH
- protinádorové látky chemie farmakologie MeSH
- screeningové testy protinádorových léčiv MeSH
- triterpeny chemie farmakologie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
1,10-Phenanthroline was decorated with triterpenoid-based substituents bearing additional spermine units to form amphiphilic molecules. The synthetic procedure designed for the new phenanthroline-triterpenoid amphiphiles is described in detail. Besides 1,10-phenanthroline, all target structures bear 1,4-disubstituted 1,2,3-triazole rings. The target compounds self-assembled into either helical-like or sheet-like nanostructures, depending on the structure of the target molecule, either based on betulinic acid or oleanolic acid, and on the way of binding spermine subunits to the rest of the molecules. They also proved their ability to coordinate 64Cu(II) ions. Finally, the target compounds showed cytotoxicity that was partly dependent on the formation of nanostructures.
- MeSH
- fenantroliny chemie MeSH
- kyselina olenalová * MeSH
- spermin MeSH
- triazoly MeSH
- triterpeny * MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Článek navazuje na předchozí část zaměřenou na protinádorové účinky triterpenoidů a podává podrobným způsobem přehled dalších farmakologických aktivit, které se často mezi sebou překrývají. Protizánětlivé, antiulcerózní, antimikrobiální, antiprotozoální, ale také virostatické a analgetické patří mezi ty nejvýznamnější. Vlastní mechanizmus působení je různorodý, přes ovlivnění prozánětlivých enzymů, transkripčních faktorů, blokádu uvolnění histaminu, až k inhibici enzymů důležitých pro replikaci virionu, či patogenitu baktérie. Pokročilé metody izolace a přesná identifikace přírodních triterpenoidů otevírá cestu k syntetickým modifikacím a screeningu semisyntetických sloučenin s potenciálně vyšším žádoucím a nižším nežádoucím účinkem.
This article is the second part of the review about triterpenoids and their biological activities. The first part focuses on the anticancer effects and the second part is about other pharmacological activities. These effects have been found to often overlap. Antiinflammatory, antiulcerogenic, antimicrobial, antiprotozoal, virostatic and analgestic activity are the most significant effects. The mechanism of action is heterogenous over inhibition of pro-inflammatory enzymes, transcriptional factors to inhibition of release of histamine, and inhibition of enzymes important for the replication of viroids or pathogenicity of bacteria. Isolation and precise identification of triterpenoids occurring in nature is ongoing. Advanced analysis opens up new ways to other synthetic modifications and to the screening of more effective semi-synthetic compounds with higher activity and eliminated adverse reactions.
Medicinal plants have been used to treat different diseases throughout the human history namely in traditional medicine. Most of the plants mentioned in this review article belong among them, including those that are widely spread in the nature, counted frequently to be food and nutrition plants and producing pharmacologically important secondary metabolites. Triterpenoids represent an important group of plant secondary metabolites displaying emerging pharmacological importance. This review article sheds light on four selected triterpenoids, oleanolic, ursolic, betulinic and platanic acid, and on their amide derivatives as important natural or semisynthetic agents in cancer treatment, and, in part, in pathogenic microbe treatment. A literature search was made in the Web of Science for the given key words covering the required area of secondary plant metabolites and their amide derivatives. The most recently published findings on the biological activity of the selected triterpenoids, and on the structures and biological activity of their relevant amide derivatives have been summarized therein. Mainly anti-cancer effects, and, in part, antimicrobial and other effects of the four selected triterpenoids and their amide derivatives have also been reviewed. A comparison of the effects of the parent plant products and those of their amide derivatives has been made.
The aim of our study was to increase the extraction efficiency of carvacrol, rosmarinic, oleanolic and ursolic acid from the different species of oregano herbs (Origanum onites L., Origanum vulgare spp. hirtum and Origanum vulgare L.). Various extraction methods (ultrasound-assisted, heat-reflux, continuous stirring, maceration, percolation) and extraction conditions (different solvent, material:solvent ratio, extraction temperature, extraction time) were used, and the active substances were determined by HPLC. The lowest content of carvacrol, rosmarinic, oleanolic and ursolic acid was obtained by percolation. During heat-reflux extraction, the content of active substances depended on the solvent used: ethanol/non-aqueous solvent (glycerol or propylene glycol) mixture was more effective compared with ethanol alone. The results showed that for each species of oregano the most optimal extraction method should be selected to maximize the content of biologically active substances in the extracts.
- MeSH
- cinnamáty izolace a purifikace MeSH
- depsidy izolace a purifikace MeSH
- dobromysl (rod) chemie klasifikace MeSH
- kyselina olenalová izolace a purifikace MeSH
- molekulární struktura MeSH
- monoterpeny izolace a purifikace MeSH
- rostlinné extrakty chemie MeSH
- rozpouštědla MeSH
- triterpeny izolace a purifikace MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
Leaf extracts of Hedera helix L. are widely used in the treatment of upper respiratory diseases. The saponins a-hederin and hederacoside C are considered to be the main compounds responsible for the biological activity. a-Hederin and hederacoside C were determined in H. helix leaf extracts using a fast, simple and validated HPLC method. An XTerra MS C18 column and mobile phase composed of 10 mM ammonium acetate at pH 8.5 (adjusted with triethylamine) and acetonitrile were used for the chromatography at 1.2 mL min(-1). The column was kept at 30°C. Detection was performed at 220 nm. An approach utilizing a basic pH of the aqueous part of the mobile phase enabled analysis in 5 minutes in isocratic mode. The method was validated and used for the quality control of H. helix leaf ethanolic extracts.
- MeSH
- břečťan chemie MeSH
- kyselina olenalová analogy a deriváty chemie MeSH
- listy rostlin chemie MeSH
- reprodukovatelnost výsledků MeSH
- rostlinné extrakty chemie MeSH
- saponiny chemie MeSH
- vysokoúčinná kapalinová chromatografie metody MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Geografické názvy
- Česká republika MeSH
- Polsko MeSH
Gymnema sylvestre, známá pod jménem gurmar, je stálezelená liána původem z tropických oblastí Asie, Afriky a Austrálie. Odedávna se používá v tradiční ájurvédské medicíně k léčbě mnoha onemocnění, jako je cukrovka, obezita, malárie, kožní onemocnění, astma, kašel, záněty, infekce a hadí uštknutí. Jako hlavní účinné látky byly identifikovány triterpenické saponiny oleananového a dammaranového typu (gymnemové kyseliny, gymnemasaponiny a gymnemosidy). Antidiabetický a hypolipidemický účinek byl potvrzen v experimentech na zvířatech i v klinických studiích, další výzkum pokračuje.
Gymnema sylvestre, also known as gurmar, is an evergreen climber originated in tropical Asia, Africa and Australia. It has been usedfor centuries in traditional ayurvedic medicine for treatment of many illnesses, such as diabetes, obesity, malaria, skin diseases,asthma, cough, inflammations, infections, and snakebite. The research has identified the main active components as oleanan- anddammarane‑typetriterpenic saponins (gymnemic acids, gymnemasaponins, and gymnemosides). Antidiabetic and hypolipidemiceffects were confirmed in animal studies and clinical trials, further research continues.
- MeSH
- ájurvéda MeSH
- antibakteriální látky terapeutické užití MeSH
- diabetes mellitus * terapie MeSH
- dvojitá slepá metoda MeSH
- fytoterapie * MeSH
- Gymnema sylvestre * chemie MeSH
- hypoglykemika MeSH
- hypolipidemika MeSH
- klinické zkoušky jako téma MeSH
- kombinovaná farmakoterapie MeSH
- léčivé rostliny MeSH
- lidé MeSH
- potravní doplňky MeSH
- saponiny klasifikace škodlivé účinky terapeutické užití MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
Oleanolic acid (OA) is a pentacyclic triterpenoid with favourable physiological activity. It is widely distributed in more than 200 species of plants. OA has garnered significant interest because of its potential biological activities, such as antioxidant, bacteriostatic, and hair growth-promoting effects. To study the effect of OA on hair growth and related mechanisms, we investigated hair growth in mice with testosterone-induced androgenetic alopecia (AGA) that were treated with three different concentrations of OA. The antioxidant, bacteriostatic, and cytotoxic effects of OA were evaluated. We found that mice with testosterone-induced AGA treated with 1% or 0.5% OA showed significantly enhanced hair growth and increased vascular endothelial growth factor/glyceraldehyde-3-phosphate dehydrogenase ratio and levels of fibroblast growth factor receptor and insulin-like growth factor 1. Using an immunofluorescence staining assay, we demonstrated that β-catenin, a key Wnt signalling transducer, was highly expressed in the OA-treated groups. These results suggest that OA may promote hair growth by stimulating hair matrix cell proliferation via the Wnt/β-catenin pathway and lowering the levels of tumour necrosis factor-alpha, and transforming growth factor-beta 1, dihydrotestosterone, and 5α-reductase.
- MeSH
- alopecie chemicky indukované farmakoterapie metabolismus MeSH
- antioxidancia MeSH
- beta-katenin * metabolismus MeSH
- cytokiny MeSH
- kyselina olenalová * farmakologie MeSH
- myši MeSH
- testosteron MeSH
- vaskulární endoteliální růstový faktor A metabolismus MeSH
- vlasový folikul metabolismus patologie MeSH
- zvířata MeSH
- Check Tag
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
