A Validated HPLC-PDA-HRMS Method to Investigate the Biological Stability and Metabolism of Antiparasitic Triterpenic Esters (original) (raw)
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Molecules
The antioxidant and enzyme inhibitory potential of fifteen cycloartane-type triterpenes’ potentials were investigated using different assays. In the phosphomolybdenum method, cycloalpioside D (6) (4.05 mmol TEs/g) showed the highest activity. In 1,1-diphenyl-2-picrylhydrazyl (DPPH*) radical and 2,2′-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) cation radical scavenging assays, cycloorbicoside A-7-monoacetate (2) (5.03 mg TE/g) and cycloorbicoside B (10) (10.60 mg TE/g) displayed the highest activities, respectively. Oleanolic acid (14) (51.45 mg TE/g) and 3-О-β-d -xylopyranoside-(23R,24S)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol 7-monoacetate (4) (13.25 mg TE/g) revealed the highest reducing power in cupric ion-reducing activity (CUPRAC) and ferric-reducing antioxidant power (FRAP) assays, respectively. In metal-chelating activity on ferrous ions, compound 2 displayed the highest activity estimated by 41.00 mg EDTAE/g (EDTA equivalents/g). The tested triterpene...
The antibacterial activities of some plant-derived triterpenes
African Journal of Traditional, Complementary and Alternative Medicines, 2015
Background: The increase in the prevalence of multi-drug resistant bacteria has necessitated the search for new antimicrobials from alternative sources such as traditional medicinal plants. Materials and Methods: The agar well diffusion method was employed to determine the susceptibilities of four plant derived triterpenes namely, 3β-hydroxylanosta-9, 24-dien-21-oic acid (RA5), and methyl-3β-hydroxylanosta-9, 24-dien-21oate (RA3), a mixture of oleanolic acid and betulinic acid (SF1) and a mixture of 3β-acetonyloleanolic acid and 3β-acetonylbetulinic acid (SF2), at a concentration of 10 mg/ml against seven Escherichia coli, one Bacillus cereus, five Enterococcus and nine Vibrio bacteria. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were determined through the micro-broth dilution assay. The checkerboard method was used to determine the antibiotictriterpene interactions while the cytosolic lactate dehydrogenase test was used to determine the membrane damaging potentials of the triterpenes in comparison to 3% Triton X-100. Results: The triterpenes RA3, RA5, SF1 and SF2 had activities against 86.4%, 54.6%, 22.7% and 9.09% of the test bacteria respectively. SF1 had the lowest MIC values ranging 0.625-10 mg/ml with lower MIC values being noted against Gram negative bacteria in comparison to Gram positive bacteria; this trend was also noted among the activities of RA3 and RA5 although they had higher MIC value ranges of 1.25-10 mg/ml and 5-10 mg/ml respectively. MBC studies proved the triterpenes to be mostly bacteriostatic. The interaction studies with ciprofloxacin were mainly ranging between indifference and antagonism. RA3 alone showed minimal membrane damaging potential with the levels of cytosolic lactate dehydrogenase released ranging from 1-36% in comparison to 3%Triton X-100 against E.coli (DSM-8695) and V. vulnificus (AL 042). Conclusion: The results hereby show the potential that the test triterpenes have as antibacterial agents, especially against the Gram negative bacteria namely E. coli and Vibrio bacteria.
Pharmacological Property of Pentacyclic Triterpenoids
Egyptian Journal of Chemistry, 2019
P LANT terpenoids are utilized generally for their aromatic behaviour. They act as conventional herbal remedies and are under research for antineoplastic activity, antibacterial activity, antidiabetic activity, anti-inflammatory activity, anti-platelet aggregate activity, antiviral activity, antioxidative activity, antiallergic, antihypertensive activity and additional pharmaceutical actions. Plants not only just deposit terpenes for herbariums defence yet in addition emanate essential mixtures in response to herbivory and numerous different abiotic and biotic stresses. Now a day, there is a phenomenal developing enthusiasm for natural triterpenes over the most recent couple of decades because of the revelation of their potential biological and pharmacological activities. Pentacyclic triterpenes are ancillary plant elements broadly spread in stem, leaves, bark and fruit peel. Specifically, the ursane, lupane and oleanane pentacyclic triterpenes show different pharmacological impact. Subsequently, these triterpenes are offering key components for the improvement of novel multi-targeted bioactive agents.
Journal of Pharmacognosy and Phytochemistry, 2019
Trichodesma indicum (Linn.) R.Br. is traditionally used folk medicine, having a lot of pharmacological bustles. The current study is focused on investigating the phytochemical and biological evaluation of T. indicum. Quantification of oleanolic acid, lupeol, and linolic acid is done by using a tertiary mobile phase consisting of toluene: ethyl acetate: formic acid (7: 2.5: 0.5 v/v). Oleanolic acid, lupeol, and linolic acid were resolved at Rf 0.46 ± 0.04, 0.55 ± 0.04 and 0.62 ± 0.05 respectively and it was quantified at its wavelength of maximum absorbance of 600nm after derivatization with anisaldehyde sulphuric acid reagent. The limits of detection and limit of quantification were found to be 662.4, 665.18 and 660.26ng per ml and 2007.4, 2015.7 and 2000.78 ng per ml for linolic acid lupeol, and oleanolic acid, respectively. The linear regression data for the calibration plot showed a good linear relationship between peak area and concentration in the range of 200-600ng/Spot. The developed HPTLC method is accurate, precise and has been successfully applied for the assay of this bioactive molecule in Trichodesma indicum. The pharmacological potential of the extract is dependent on the contents of active secondary metabolites present in the plants. The antioxidant potential was studied by using DPPH and 2-deoxyribose assay. Antioxidant potential was observed showing IC50 values (326.82±1.21µg/ml) and (449.62±2.01µg/ml) by DPPH and 2-deoxyribose method respectively. In vitro antidiabetic potential of the plant were also assessed by starch iodine assay and DNS method. IC50 was observed (86.57 ± 2.57µg/ml) in 3, 5 DNS assay and (222.86 ± 3.36 mg/ml) in starch iodine assay. Results are promising; this work forms a firm base for further research to explore the lead compound which is responsible for the medicinal value of this plant.
State-of-the-Art and Opportunities for Bioactive Pentacyclic Triterpenes from Native Mexican Plants
Plants
Native Mexican plants are a wide source of bioactive compounds such as pentacyclic triterpenes. Pentacyclic triterpenes biosynthesized through the mevalonate (MVA) and the 2-C-methyl-D-erythritol-phosphate (MEP) metabolic pathways are highlighted by their diverse biological activity. Compounds belonging to the oleanane, ursane, and lupane groups have been identified in about 33 Mexican plants, located geographically in the southwest of Mexico. The works addressing these findings have reported 45 compounds that mainly show antimicrobial activity, followed by anti-inflammatory, cytotoxic, anxiolytic, hypoglycemic, and growth-stimulating or allelopathic activities. Extraction by maceration and Soxhlet with organic solvents and consecutive chromatography of silica gel have been used for their whole or partial purification. Nanoparticles and nanoemulsions are the vehicles used in Mexican formulations for drug delivery of the pentacyclic triterpenes until now. Sustainable extraction, form...
International Journal of Biochemistry Research & Review, 2017
Triterpenoids are the most promising plant secondary metabolites. Several triterpenoids, including ursolic acid, oleanolic acid, betulinic acid, celastrol, pristimerin, lupeol and avicins are representative group of phytochemicals possesses biological properties. Anti-tumor, anti-cancer, antibiotic , cytotoxic, anti-inflammatory, anti-HIV, acetyl cholinesterase, anti-wrinkle and antifeedant activities of these compounds is measured. Role for triterpenes in the cancer setting is also gradually emerging. Triterpenoids are highly multifunctional and structurally diverse organic compounds, characterized by a basic backbone modified in multiple ways, allowing the formation of more than 20,000 naturally occurring triterpenoid varieties. Fusidic acid is a representative member of terpenes, which has found clinical applications. It is nonallergic, has relatively low toxicity and has little cross-resistance with other clinically used antibiotics and it remains a unique and promising agent due to the significant potencies against Staphylococci.
Biosynthetic pathways of triterpenoids and strategies to improve their Biosynthetic Efficiency
Plant Growth Regulation
2016). The biosynthesis of isoprenoids/terpenoids is important for living organisms and for agriculture and industry. To date, approximately 80,000 terpenoid compounds are found naturally, which perform various (structural and functional) roles as secondary metabolites (Pemberton et al. 2017). Triterpenoids are biosynthesized in the endoplasmic reticulum and cytoplasm via the combination of two molecules of farnesyl diphosphate to form a C30 precursor (squalene), which is known as the mevalonate/acetate pathway (Yan et al. 2014). Squalene epoxide is the precursor of 3-hydroxytriterpenes, whereas all 3-deoxytriterpenes are directly derived from the cyclization of squalene, and it leads to the biosynthesis of the triterpenoids (Sawai and Saito 2011). Triterpenoids are divided into different subgroups, such as acyclic, monocyclic, bicyclic, tricyclic, tetracyclic and pentacyclic compounds according to the diverse features in their structures (Nguyen et al. 2015). However, the major types of triterpenoids are the tetracyclic derivatives of lanostane, dammarane, sprotostane, cucurbitane, apotirucallane, tirucallane, euphane and cycloartane; the pentacyclic derivatives of baccharenyl cation-type animals, plants, bacteria and fungi (Muffler et al. 2011). Plant terpenoids have important functions in the fluidity of the membrane, respiration, photosynthesis and growth regulation and development (Tholl 2015), and are present in different parts of plants, such as the aerial parts of Lantana camara L. (Abdjul et al. 2017), the leaves of Campsis grandiflora and the cuticle waxes of apple peel (Abdjul et al. 2017). They are also found in marine algae (Laurencia sp) (Singh et al. 2020) and the endophytic fungus of Huperzia serata (Cui et al. 2021) and Fusarium sp. (Ibrahim et al. Communicated by Mohsin Tanveer.
Production of triterpenoids with cell and tissue cultures
Acta biochimica Polonica, 2013
Triterpenes are group of biologically active compounds which can be found in higher plants. Their main source are plants bark, leaves, twigs, fruits, resins or oils. The biological activity of triterpens is very diversified and many studies have already confirmed the following therapeutic effects: anti-inflammatory, antimicrobial, antiviral, antifungial, immunomodulatory, and hepatoprotective. Synthesis of triterpenes derivates can be performed by chemical or enzymatic reactions, however biotransformation is more specific and eliminates the side products and the molecule alterations. These processes use isolated enzymes or microorganisms. Cell culture in vitro eliminates problems like extract variability as well as instability of the compounds being obtained during the extraction process. What is more, it ensures high reproducibility and optimal regio- and enantioselectivity. The most widely used technique is a classical screening of a series of microbial strains. Studies on triterp...
Biomedical Chromatography, 2005
Pistacia species contain oleoresins with bioactive triterpenes. In this study triterpenes, including minor components, were identified and quantified in both neutral and acidic fraction of Pistacia lentiscus var. Chia resin, grown exclusively in Chios island (Greece), collected traditionally, as well as by the use of stimulating agents (liquid collection). It was proved that these two resin samples were composed of several different minor triterpenes. In the traditional collection of the resin, 36 triterpenes were identified, 23 of which are new minor compounds (five in the acidic and eighteen in the neutral fraction). In the liquid collection resin eight compounds were identified in the acidic and 11 in the neutral fraction, while seven compounds were not contained in resin traditionally collected. The main triterpenes in both resin samples collected traditionally and by use of stimulating agents were in the following order: isomasticadienonic acid (24 and 22.5% w/w of triterpenic fraction respectively), masticadienonic acid (9.3 and 14.7% w/w of triterpenic fraction) and 28-norolean-17-en-3-one (19 and 36% w/w of triterpenic fraction respectively). The aim of this study was to compare the qualitative and quantitative composition of triterpenes in the resin samples collected using the traditional and new liquid techniques, and examine whether the collection technique influences the contained triterpenes in P. lentiscus var. Chia resin samples. Finally, since there is confusion on interpreting mass spectra of triterpenes we present an analytical review on the base peaks, main fragments and fragmentation mechanism/pattern of several skeleton penta-and tetracyclic triterpenes reported in P. lentiscus resin. Also, a biosynthetic route for triterpene skeletons contained in P. lentiscus resin was approached. EXPERIMENTAL Materials and methods. Pistacia lentiscus var. Chia resin, collected both traditionally and using ethrel (liquid collection) were kindly provided by the Chios Mastic Gum Growers Association (Chios, Greece). Both resins were fractionated to acidic and neutral fractions according to . Methylation of the acidic fraction was performed in order to improve its chromatographic behaviour as follows: 800 mg of each acidic fraction was mixed with 9 mL iodomethane 10% in AcCN in the presence of 1.5 g potassium carbonate at 60°C for 3 h (Katritzky, 1995). All samples were diluted in chloroform. All solvent used were Merck products.