The antioxidant activity of Scorzonera parviflora Jacq. roots were assessed by measuring their ability to scavenge ABTS and DPPH radicals. Bioactivity-guided fractionation was utilized to identify the compound(s) responsible for this activity. The most active phase, ethyl acetate, was isolated using column chromatography. The resulting fractions were then purified using preparative TLC on reverse phase and semi-preparative HPLC. The structures of the pure compounds were elucidated by spectral analysis (MS and 1H, 13C, 2D-NMR). Three undescribed phenolic acid derivatives, namely parvifloric acid A (1), B (2), and C (3), and one new sesquiterpene lactone, parviflorin (4) together with seven known compounds were isolated and identified as scopolin (5), scopoletin (6), caffeic acid (7), protocatechuic acid (8), 4,5-O-dicaffeoylquinic acid (9) 3,5-O-dicaffeoylquinic acid (10), and 3,5-O-dicaffeoylquinic acid methyl ester (11). Finally, the pure compounds obtained were tested to evaluate their antioxidant capacities, using ABTS and DPPH radical scavenging potencies. The highest activity was observed with 3,5-O-dicaffeoylquinic acid (10), followed by its methyl ester.

• Klíčová slova
• Antioxidant activity, Asteraceae, Phenolic acids, Scorzonera parviflora, Sesquiterpene lactone,
• MeSH
• antioxidancia * farmakologie   izolace a purifikace   chemie   MeSH
• fytonutrienty farmakologie   izolace a purifikace   MeSH
• hydroxybenzoáty * izolace a purifikace   farmakologie   chemie   MeSH
• kořeny rostlin * chemie   MeSH
• molekulární struktura MeSH
• Scorzonera * chemie   MeSH
• seskviterpeny farmakologie   izolace a purifikace   chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antioxidancia * MeSH
• fytonutrienty MeSH
• hydroxybenzoáty * MeSH
• phenolic acid MeSH Prohlížeč
• seskviterpeny MeSH

Global agricultural production is significantly hampered by insect pests, and the demand for natural pragmatic pesticides with environmental concern remains unfulfilled. Ageratina adenophora (Spreng.) also known as Crofton weed, is an invasive perennial herbaceous plant that is known to possess multiple bioactive compounds. In our study, two isomers of ageraphorone metabolites i.e, 10 Hα-9-oxo-ageraphorone (10HA) and 10 Hβ-9-oxo-ageraphorone (10HB), were identified from Crofton weed, exhibiting potent antifeedant and larvicidal activities against Plutella xylostella. For antifeedant activity, the median effective concentration (EC50) values for 10HA and 10HB in the choice method were 2279 mg/L and 3233 mg/L, respectively, and for the no choice method, EC50 values were 1721 mg/L and 2394 mg/L, respectively. For larvicidal activity, lethal concentration (LC50) values for 10HA and 10HB were 2421 mg/L and 4109 mg/L at 48 h and 2101 mg/L and 3550 mg/L at 72 h. Furthermore, both in- vivo and in-vitro studies revealed that the isomers 10HA and 10HB exhibited potent detoxifying enzymes inhibition activity such as carboxylesterase and glutathione S-transferases. Molecular docking and MD simulation analysis provide insight into the possible interaction between isomers of ageraphorone metabolites and Carboxylic Ester Hydrolase protein (Gene: pxCCE016b) of P. xylostella, which led to a finding that CarEH protein plays a significant role in the detoxification of the two compounds in P. xylostella. Finally, our findings show that the primary enzymes undergoing inhibition by isomers of ageraphorone metabolites, causing toxicity in insects, are Carboxylesterase and glutathione S-transferase.

• Klíčová slova
• Crofton weed, Detoxifying enzymes, Insect pest, Molecular docking,
• MeSH
• Ageratina * chemie   MeSH
• esterasy chemie   metabolismus   MeSH
• glutathiontransferasa chemie   metabolismus   MeSH
• insekticidy chemie   farmakologie   MeSH
• isomerie MeSH
• larva účinky léků   MeSH
• molekulární konformace MeSH
• můry * účinky léků   MeSH
• rostlinné extrakty chemie   farmakologie   MeSH
• seskviterpeny * chemie   farmakologie   MeSH
• simulace molekulového dockingu MeSH
• stravovací zvyklosti účinky léků   MeSH
• vazebná místa MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• esterasy MeSH
• glutathiontransferasa MeSH
• insekticidy MeSH
• rostlinné extrakty MeSH
• seskviterpeny * MeSH

A sesquiterpenic alkaloid dendrobine is the major bioactive compound extracted from Dendrobium nobile Lindl. This compound was structurally very similar to picrotoxinin (neurotoxin) containing bicyclic or tricyclic ring while dendrobine containing tetracyclic rings with up to 7 stereogenic centers showing numerous neuroprotective effects. Several sesquiterpenic alkaloids such as (+)-(1R,5R,6S,8R,9R)- 8,12-dihydroxy-copacamphan-3-en-2-one, dendrobine, denrine B, (+)- (1R,2S,3R,4S,5R,6S,9R)-3,11,12-trihydroxypicrotoxane-2(15)-lactone, dendroxine B, nobilonine, 13-Hydroxy-14-oxodendrobine, 6-Hydroxy-nobilonine and (-)-(1S,2R,3S,4R,5S,6R,9S,12R)- 3,11,13-trihydroxypicrotoxane-2(15)-lactone were isolated from D. nobile This comprehensive review summarizes the necessary information on the morphology, biochemistry and pharmacology of dendrobine. The phytochemical profile had potent in-vivo and in-vitro efficacy in neuroprotection, nerve function, memory enhancement, cognitive disorders, anxiety and depression, anti-oxidant, psychological conditions, increasing serotonin concentration in synapse anxiolytic, tranquilizing, anti-stress, neurodegenerative (Alzheimer's disease and Parkinson), anti-inflammatory and analgesic. The compound dendrobine activates neuro synapses, serotonergic synapse and signaling pathways during neurotransmission playing important role in Alzheimer's disease, Parkinson's disease, anxiety and long-term depression.

• Klíčová slova
• Anxiety, DNLA, autophagy, neuroinflammation, osteoclasts., oxidative stress,
• MeSH
• alkaloidy * chemie   farmakologie   izolace a purifikace   MeSH
• lidé MeSH
• neurodegenerativní nemoci farmakoterapie   MeSH
• neuroprotektivní látky * farmakologie   chemie   izolace a purifikace   MeSH
• seskviterpeny * chemie   farmakologie   izolace a purifikace   MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• přehledy MeSH
• Názvy látek
• alkaloidy * MeSH
• neuroprotektivní látky * MeSH
• seskviterpeny * MeSH

Trilobolide and its analogues belong to the guaianolide type of sesquiterpene lactones, which are characteristic and widely distributed within the families Asteraceae and Apiaceae. Certain guaianolides are receiving continuously increasing attention for their promising sarco-endoplasmic reticulum Ca2+-ATPase (SERCA)-inhibitory activity. However, because of their alkylation capabilities, they are generally toxic. Therefore, the search for compounds with significant immunobiological properties but with decreased cytotoxicities suitable for use in immune-based pharmacotherapy is ongoing. Therefore, we extended our previous investigation of the immunobiological effects of trilobolide to a series of structurally related guaianolides and germacranolides. To evaluate the relationship, we tested a series of selected derivatives containing α-methyl lactone or exomethylene lactone ring. For a wider comparison, we also included some of their glycosidic derivatives. We assessed the in vitro immunobiological effects of the tested compounds on nitric oxide (NO) production, cytokine secretion, and prostaglandin E2 (PGE2) release by mouse peritoneal cells, activated primarily by lipopolysaccharide (LPS), and evaluated their viability. The inhibitory effects of the apparently most active substance, 8-deoxylactucin, seem to be the most promising.

• Klíčová slova
• 8-deoxylactucin, 8-epiisoamberboin, germacranolides, guaianolides, immune-modulatory effects,
• MeSH
• butyráty MeSH
• cytokiny metabolismus   MeSH
• dinoproston metabolismus   biosyntéza   MeSH
• furany MeSH
• laktony * farmakologie   chemie   MeSH
• lipopolysacharidy farmakologie   MeSH
• myši MeSH
• oxid dusnatý * metabolismus   MeSH
• peritoneální makrofágy účinky léků   metabolismus   MeSH
• seskviterpeny germakranové * farmakologie   chemie   MeSH
• seskviterpeny guajanové * farmakologie   chemie   MeSH
• seskviterpeny farmakologie   chemie   MeSH
• zvířata MeSH
• Check Tag
• myši MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• butyráty MeSH
• cytokiny MeSH
• dinoproston MeSH
• furany MeSH
• germacranolide MeSH Prohlížeč
• laktony * MeSH
• lipopolysacharidy MeSH
• oxid dusnatý * MeSH
• seskviterpeny germakranové * MeSH
• seskviterpeny guajanové * MeSH
• seskviterpeny MeSH
• trilobolide MeSH Prohlížeč

Over the last decades, soft corals have been proven a rich source of biologically active compounds, featuring a wide range of chemical structures. Herein, we investigated the chemistry of an alcyonarian of the genus Lemnalia (Neptheidae), specimens of which were collected from the coral reefs near Al Lith, on the south-west coast of Saudi Arabia. A series of chromatographic separations led to the isolation of 31 sesquiterpenes, featuring mainly the nardosinane and neolemnane carbon skeletons, among which three (13, 14 and 28) are new natural products. The metabolites isolated in sufficient amounts were evaluated in vitro in human tumor and non-cancerous cell lines for a number of biological activities, including their cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activities, as well as for their effect on androgen receptor (AR)-regulated transcription. Among the tested metabolites, compound 12 showed comparable neuroprotective activity to the positive control N-acetylcysteine, albeit at a 10-fold lower concentration.

• Klíčová slova
• Lemnalia, androgen receptor-regulated transcription, anti-inflammatory activity, neuroprotective activity, sesquiterpenes,
• MeSH
• korálnatci * chemie   MeSH
• lidé MeSH
• protinádorové látky * farmakologie   metabolismus   MeSH
• seskviterpeny * chemie   MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Geografické názvy
• Indický oceán MeSH
• Saudská Arábie MeSH
• Názvy látek
• protinádorové látky * MeSH
• seskviterpeny * MeSH

Cystic echinococcosis (CE) remains an important challenge both in humans and animals. There is no safe and suitable remedy for CE, so the discovery of new compounds with promising scolicidal effects, particularly from herbal sources, is of great importance for therapeutic uses in the treatment and prevention of CE reappearance. Sesquiterpenes are C15 organic compounds made up of three isoprene units and mostly occurring as fragrant components of essential oils. They are of economic importance for the cosmetic and pharmaceutical industry, and recently attracted the attention of the scientific community for their remarkable parasiticidal properties. In the present study, we have focused on three known sesquiterpenes, isofuranodiene (IFD), α-bisabolol (BSB), and farnesol (FOH), as important phytoconstituents of the essential oils of wild celery (Smyrnium olusatrum), chamomile (Matricaria chamomilla), and acacia farnese (Vachellia farnesiana), respectively. Protoscoleces were recovered from fertile hydatid cysts and were exposed to different concentrations of the three tested compounds for different exposure times. The viability of protoscoleces was confirmed by 0.1% eosin staining. Results of scolicidal activity evaluations showed that IFD possessed the best effect against Echinococcus granulosus protoscoleces (LC50 and LC90 values of 8.87 and 25.48 µg/mL, respectively), followed by BSB (LC50 of 103.2 µg/mL) and FOH (LC50 of 113.68 µg/mL). The overall toxicity of IFD differed significantly from those of FOH and BSB, while there was no significant difference in toxicity between the latter compounds (p > 0.05). The present study showed that IFD seems to be a promising scolicidal agent and can be further tested to become a candidate for CE treatment.

• Klíčová slova
• cystic echinococcosis, farnesol, isofuranodiene, protoscolex, α-bisabolol,
• MeSH
• antiparazitární látky farmakologie   MeSH
• Echinococcus granulosus účinky léků   MeSH
• farnesol farmakologie   MeSH
• furany chemie   farmakologie   MeSH
• LD50 MeSH
• monocyklické seskviterpeny farmakologie   MeSH
• seskviterpeny chemie   MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antiparazitární látky MeSH
• bisabolol MeSH Prohlížeč
• farnesol MeSH
• furany MeSH
• isofuranodiene MeSH Prohlížeč
• monocyklické seskviterpeny MeSH
• seskviterpeny MeSH

Juvenile hormones (JHs) are sesquiterpenoids synthesized by the corpora allata (CA). They play critical roles during insect development and reproduction. The first JH was described in 1934 as a "metamorphosis inhibitory hormone" in Rhodnius prolixus by Sir Vincent B. Wigglesworth. Remarkably, in spite of the importance of R. prolixus as vectors of Chagas disease and model organisms in insect physiology, the original JH that Wigglesworth described for the kissing-bug R. prolixus remained unidentified. We employed liquid chromatography mass spectrometry to search for the JH homologs present in the hemolymph of fourth instar nymphs of R. prolixus. Wigglesworth's original JH is the JH III skipped bisepoxide (JHSB3), a homolog identified in other heteropteran species. Changes in the titer of JHSB3 were studied during the 10-day long molting cycle of 4th instar nymph, between a blood meal and the ecdysis to 5th instar. In addition we measured the changes of mRNA levels in the CA for the 13 enzymes of the JH biosynthetic pathway during the molting cycle of 4th instar. Almost 90 years after the first descriptions of the role of JH in insects, this study finally reveals that the specific JH homolog responsible for Wigglesworth's original observations is JHSB3.

• MeSH
• biologická proměna * MeSH
• corpora allata chemie   MeSH
• epoxidové sloučeniny chemie   MeSH
• hemolymfa chemie   MeSH
• kukla chemie   fyziologie   MeSH
• nymfa chemie   fyziologie   MeSH
• Rhodnius chemie   fyziologie   MeSH
• seskviterpeny chemie   MeSH
• shazování tělního pokryvu fyziologie   MeSH
• zvířata MeSH
• Check Tag
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Research Support, N.I.H., Extramural MeSH
• Názvy látek
• epoxidové sloučeniny MeSH
• juvenile hormone III MeSH Prohlížeč
• seskviterpeny MeSH

Application of the superficially porous particles (SPPs) grafted with chiral selectors can substantially improve resolution in chromatographic techniques. In this work, we carried out a deeper study on supercritical fluid chromatography systems with 2.7 µm SPPs bonded with teicoplanin and vancomycin. Fast separations of the majority of enantiomers of phytoalexins, substituted tryptophans, and ketamine derivatives, as representatives of important biologically active and structurally diverse chiral compounds have been achieved. The chromatographic behavior of the structurally different analytes served to characterize these separation systems. The influence of separation conditions, namely mobile phase composition, i.e. type of co-solvent and additive on retention, enantioselective resolution and enantioselectivity was examined. The success rate of baseline and partial separations in individual groups of compounds differed with the chiral stationary phase and also with mobile phase composition. The best, baseline separations for the phytoalexins were achieved on the TeicoShell column using methanol as a co-solvent and trifluoroacetic acid as an additive if used. Mostly partial separations were achieved on the vancomycin-based column for all groups of analytes. Complementary separation behavior of these CSPs was confirmed for the majority of the chiral compounds examined in this work.

• Klíčová slova
• Chiral stationary phase, Enantioseparation, Supercritical fluid chromatography, Superficially porous particles, Teicoplanin, Vancomycin,
• MeSH
• alkaloidy chemie   MeSH
• fytoalexiny MeSH
• ketamin chemie   MeSH
• kyselina trifluoroctová chemie   MeSH
• poréznost MeSH
• rozpouštědla chemie   MeSH
• seskviterpeny chemie   MeSH
• stereoizomerie MeSH
• superkritická fluidní chromatografie metody   MeSH
• teikoplanin chemie   MeSH
• vankomycin chemie   MeSH
• vodíková vazba MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• alkaloidy MeSH
• cathinone MeSH Prohlížeč
• fytoalexiny MeSH
• ketamin MeSH
• kyselina trifluoroctová MeSH
• rozpouštědla MeSH
• seskviterpeny MeSH
• teikoplanin MeSH
• vankomycin MeSH

Seven previously undescribed sesquiterpene lactones, three known sesquiterpene lactones (ixerin D, 15-p-hydroxyphenylacetyllactucin, and 15-p-hydroxyphenylacetyllactucin-8-sulfate), and two known quinic acid derivatives (3-O-feruloylquinic acid and 3,5-di-O-caffeoylquinic acid) were isolated from Sonchus palustris L. roots. Four formerly undescribed compounds were elucidated to be 3β,14-dihydroxycostunolide-3-O-β-D-glucopyranosyl-(2-O-p-hydroxyphenylacetyl)-14-O-p-hydroxyphenylacetate, 15-p-methoxyphenylacetyllactucin, 15-p-methoxyphenylacetyllactucin-8-sulfate, and 8-p-hydroxyphenylacetyllactucin-15-sulfate. Additionally, three undescribed conjugates of lactucin and a eudesmanolide type sesquiterpenic acid, sonchpalustrin, 4″-O-methylsonchpalustrin, and isosonchpalustrin, were characterized. The structures of the newly discovered natural products were elucidated using 1D and 2D NMR spectroscopy and UHPLC-HRMS. 15-p-Hydroxyphenylacetyllactucin and 15-p-methoxyphenylacetyllactucin showed significant in vitro cytotoxicity against CEM and BJ cells with IC50 values ranging from 3.9 to 9.8 μM. Compounds 3 and 4 showed also strong anti-inflammatory activity in vitro.

• Klíčová slova
• Biological activities, Chemophenetics, Quinic acid derivatives, Schleswig-Holstein, Sesquiterpene lactones, Sonchus palustris,
• MeSH
• Asteraceae chemie   MeSH
• fytogenní protinádorové látky chemie   izolace a purifikace   farmakologie   MeSH
• fytonutrienty chemie   izolace a purifikace   farmakologie   MeSH
• kultivované buňky MeSH
• laktony chemie   izolace a purifikace   farmakologie   MeSH
• lidé MeSH
• proliferace buněk účinky léků   MeSH
• screeningové testy protinádorových léčiv MeSH
• seskviterpeny chemie   izolace a purifikace   farmakologie   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• fytogenní protinádorové látky MeSH
• fytonutrienty MeSH
• laktony MeSH
• seskviterpeny MeSH

Evaluation of possible interactions with enzymes of drug metabolism is an important part of studies on safety and, in general, on the properties of any drug or biologically active compound. Here, focus is given on interactions of three sesquiterpenes (beta-caryophyllene oxide (CAO), trans-nerolidol (tNER) and farnesol (FAR)) with CYP3A4. To determine the CYP3A4 activity, specific substrates testosterone (TES) and midazolam (MDZ) were used. In human liver microsomes, the CAO inhibited the MDZ 1´-hydroxylation by mixed type inhibition and K(i) 46.6 microM; TES 6beta-hydroxylation was inhibited more strongly by tNER by the same mechanism and with K(i) of 32.5 microM. Results indicated a possibility of different mode of interaction of both compounds within the active site of CYP3A4 and this was why the molecular docking study was done. The docking experiments showed that the studied sesquiterpenes (CAO and tNER) bound to the CYP3A4 active site cause a significant decrease of binding affinity of substrates tested which corresponded well to the inhibition studies. The inhibition observed, however, most probably does not pose a real harm to microsomal drug metabolism as the levels of sesquiterpenes in plasma (assuming the use of these compounds as spices or flavoring additives) does not usually exceed micromolar range. Hence, the interaction of drugs metabolized by CYP3A4 with sesquiterpenes is less probable.

• MeSH
• cytochrom P-450 CYP3A chemie   účinky léků   metabolismus   MeSH
• farnesol chemie   farmakologie   MeSH
• inhibitory cytochromu P450 CYP3A farmakologie   MeSH
• jaterní mikrozomy enzymologie   MeSH
• katalytická doména MeSH
• lidé MeSH
• molekulární modely MeSH
• molekulární struktura MeSH
• polycyklické seskviterpeny chemie   farmakologie   MeSH
• seskviterpeny chemie   farmakologie   MeSH
• simulace molekulového dockingu MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• caryophyllene oxide MeSH Prohlížeč
• CYP3A4 protein, human MeSH Prohlížeč
• cytochrom P-450 CYP3A MeSH
• farnesol MeSH
• inhibitory cytochromu P450 CYP3A MeSH
• nerolidol MeSH Prohlížeč
• polycyklické seskviterpeny MeSH
• seskviterpeny MeSH