Antioxidant diterpenoids from the roots of <i>Salvia barrelieri</i>

Kolak, Ufuk; Kabouche, Ahmed; Öztürk, Mehmet; Kabouche, Zahia; Topcu, Gülaçtı; Ulubelen, Ayhan

doi:10.1002/pca.1130

Cited by 63 publications

(50 citation statements)

References 24 publications

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“…We have previously described the cytotoxic and apoptogenic properties of three isolated diterpenoids from S. chorassanica including taxodione against the leukemic K562 and HL-60 cancer cells (Tayarani-Najaran et al 2013). Taxodione is also famous for potent antioxidant activity (Kolak et al 2009). Similar to taxodione, former reports show that tanshinone IIA induces mitochondria-dependent apoptosis in prostate cancer cells which is in agreement with diterpenoide cytotoxicity (Won et al 2010).…”

Section: Discussionmentioning

confidence: 97%

“…DNAbinding ability (Zaghloul et al 2008) antimicrobial (Kuzma et al 2012, insecticidal (Fraga et al 2005), and neuronal GABAA receptor blockage effects (Rutherford et al 1994) are among the different biological activities related to taxodione. Taxodione has been also tested for antioxidant activity and exhibited the highest activity among diterpenoids isolated from Salvia genus (Kolak et al 2009). In agreement with these findings, we have previously reported the neural protection effects of Scutellaria litwinowii methanol extract, saffron and its active ingredient crocin and Nigella sativa extract and thymoquinone as potent antioxidants in serum/glucose deprivation (SGD) induced PC12 cell injury via attenuation of ROS (Mousavi et al 2010a, b;Afsharzadeh et al 2012).…”

Section: Introductionmentioning

confidence: 99%

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Anti-apoptotic Effect of Taxodione on Serum/Glucose Deprivation-Induced PC12 Cells Death

et al. 2014

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Taxodione, a diterpenoid from the roots of Salvia chorassanica Bunge, possesses cytotoxic, apoptotic, and antimicrobial activity. This study was designed to investigate the protective effects of taxodione on serum/glucose deprivation-induced ischemic injury in PC12 cells and related mechanisms. In an in vitro model of ischemia, PC12 cells were exposed to serum and glucose deprivation for 6 and 18 h. The protective effects of the methanol extract of S. chorassanica and taxodione were assessed using alamarBlue(®) assay. Intracellular ROS production was measured by fluorimetry using 2',7'-dichlorofluorescin diacetate (DCFH-DA). The levels of PARP, Bcl-2, and Bax proteins were detected after western blot analysis. It was shown that taxodione (0.2-1.5 μM) significantly increased cell viability in a dose-dependent manner after ischemic insult. Taxodione has antioxidant activity and protects PC12 cells against oxidative stress-induced apoptotic cell death. Meanwhile, pretreatment with taxodione significantly induced an increase in Bcl-2 and a decrease in Bax protein level. The results of this study confirmed the protective effect of taxodione in serum/glucose deprivation-induced ischemic injury and the putative role of apoptosis as a underling mechanisms. Thus, it would be fair to consider taxodione as a promising ingredient of S. chorassanica for the expansion on novel class of anti-ischemic agents.

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Section: Discussionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Anti-apoptotic Effect of Taxodione on Serum/Glucose Deprivation-Induced PC12 Cells Death

et al. 2014

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“…They posses antioxidant, antibacterial, antitumor, cardioactive and antidiabetic activities (Ulubelen, 2003;Kabouche et al, 2007). Antioxidant activity of Lamiaceae (Labiatae) plants which are widely grown in Turkey were also investigated by our group (Kolak et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and anticholinesterase activities of lupane triterpenoids and other constituents of Salvia trichoclada

et al. 2015

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The methanol extract of the aerial parts of Salvia trichoclada Bentham (Lamiaceae) was studied for bioactive non-volatile secondary metabolites, and nine compounds were isolated. Structures of the isolated compounds were elucidated as lupeol (1), lupenone (2), glochidone (3), monogynol A (4), oleanolic acid (5), ursolic acid (6), b-sitosterol (7), apigenin-7-O-rhamnoside (8), and rosmarinic acid (9) by using 1D and 2D-NMR spectroscopic techniques. A lupane triterpene glochidone was isolated from a Salvia species and Lamiaceae family for the first time in this study. The antioxidant potential of the extract and the isolated compounds were carried out by using lipid peroxidation inhibitory activity (b-carotene bleaching method) and DPPH free radical scavenging activity test assays. Their anticholinesterase activity was investigated by the Ellman method against both acetylcholinesterase (AChE) and butyrylcholinesterase enzymes.Compounds 1, 3, 5, 6, 8 and 9 showed fairly high anticholinesterase activity almost at all concentrations. Among them, a flavone glycoside apigenin-7-O-rhamnoside exhibited the highest and selective AChE inhibitory activity. Glochidone (3) was found to be the most active one among the isolated lupanes, which exhibited a close activity to that of standard compound galanthamine. Among all the tested compounds, rosmarinic acid (9) exhibited highest antioxidant and good anticholinesterase activity.

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“…On pokazuje antitumorsku, 34 antibakterijsku, 35 antioksidativnu, 36 antifugalnu, 37 i insekticidnu aktivnost.…”

Section: Kinon-metidi Prisutni U Prirodiunclassified

Kinon-metidi (I. dio): Reaktivni međuprodukti u kemiji fenola i njihova primjena u organskoj sintezi

2017

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Ovo djelo je dano na korištenje pod Creative Commons Attribution 4.0International LicenseInstitut Ruđer Bošković, Bijenička cesta 54, 10 000 Zagreb Sažetak Kinon-metidi (QM, naziv po IUPAC-u: kinometani) su reaktivni međuprodukti koji zauzimaju vrlo značajno mjesto u organskoj kemiji. Njihova primjena u organskoj sintezi je veoma velika, što je dovelo do razvoja velikog broja metoda za njihovo generiranje. Korisni su i u stereoselektivnim reakcijama, čime im je otvoren put za primjenu u totalnoj sintezi, nerijetko struktura koje su već pokazale značajnu biološku aktivnost. Ovim pregledom dan je uvid u metode sintetskog (termičkog) generiranja QM-a te njihovu primjenu u organskoj sintezi, s osvrtom na biološka svojstva samih QM-a ili produkata koji se iz njih dobivaju u sintezi. Ključne riječi Kinon-metidi, derivati fenola, termičko generiranje kinon-metida, kinon-metidi u organskoj sintezi, antiproliferativna aktivnost* Autor za dopisivanje: dr. sc. Đani Škalamera e-pošta: Djani.Skalamera@irb.hr ** Iako IUPAC više ne preporučuje upotrebu naziva kinon-metid, već preporučuje kinometan, autori ovog pregleda odlučili su zadržati stari naziv kinon-metid. Razlog tome je ponajprije usklađenost ovog članka sa svom ostalom relevantnom i recentnom literaturom o kinon-metidima, koja se koristi upravo tim nazivom. 354Đ. ŠKALAMERA et al.: Kinon-metidi (I. dio): Reaktivni međuprodukti u kemiji fenola…, (2017) 353−372 Osim osnovnih (roditeljskih) QM-a 1-3, u literaturi je uobičajeno kinon-metidima nazivati i sve ostale spojeve koji u svojoj strukturi sadrže metilensku i karbonilnu skupinu u vinilognom položaju. Tako se kinon-metidima nazivaju i derivati srodni m-QM-u 2, uobičajeni kod spojeva kod kojih zbog nemogućnosti konjugacije između metilenske skupine i kisika odgovarajući QM ima zwitterionski ili biradikalski karakter. Primjeri za navedene slučajeve prikazani su slikom 3.Slika 3 -Primjer neutralnog 6 2a i zwitterionskog 7 21 QM-a Fig. 3 -Example of neutral 6 2a and zwitterionic 7 21 QM Svojstva i kemijska reaktivnost kinon-metidaQM su reaktivne kratkoživuće vrste, vremena života tipično od <1 ns pa do nekoliko minuta, te je stoga za njihovo proučavanje potrebno primjenjivati tehnike tranzijentne spektroskopije, primjerice lasersku pulsnu fotolizu (LFP, od engl. laser flash photolysis). QM reagiraju s elektrofilima preko kisikova atoma, na način koji je tipičan za fenolate, a s nukleofilima reagiraju na metilenskom položaju pri čemu nastaju produkti Michaelove adicije 10 (shema 1). Kako su QM znatno reaktivniji od običnih enona kakvi su npr. α,β-nezasi eni ketoni, oni mogu reagirati i u [4+2] cikloadicijskim reakcijama (Diels-Alder) s dienofilima bogatim elektronima daju i kao produkte derivate kromana 9 (shema 1).Rearomatizacija koja se događa u reakciji adicije ujedno je i pokretačka sila navedenih reakcija. Supstituenti na QM znatno utječu na brzinu reakcija, te tako mogu utjecati na duljinu vremena života QM-a. 22 Obično su QM sami po sebi elektronski siromašni, pa će zbog toga elektron-odvlačeće skupine djelo...

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Antioxidant diterpenoids from the roots of Salvia barrelieri

Abstract: Taxodione exhibited the highest antioxidant activity among the tested compounds.

Cited by 63 publications

References 24 publications

Anti-apoptotic Effect of Taxodione on Serum/Glucose Deprivation-Induced PC12 Cells Death

Anti-apoptotic Effect of Taxodione on Serum/Glucose Deprivation-Induced PC12 Cells Death

Antioxidant and anticholinesterase activities of lupane triterpenoids and other constituents of Salvia trichoclada

Kinon-metidi (I. dio): Reaktivni međuprodukti u kemiji fenola i njihova primjena u organskoj sintezi

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