Studies on Di- and Triterpenoids from<i>Salvia staminea</i>with Cytotoxic Activity

Topcu, Gülaçtı; Altiner, Esra N.; Gozcu, Seyda; Halfon, Belkıs; Aydoğmuş, Zeynep; Pezzuto, J. M.; Bin, Zhou; Kingston, David G. I.

doi:10.1055/s-2003-39705

Cited by 40 publications

(12 citation statements)

References 11 publications

(18 reference statements)

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“…The trans conformation of compound 7 formed in the cyclization step was confirmed at this stage by correlated spectroscopy (COSY) and nuclear overhauser and exchange spectroscopy (NOESY) NMR analysis. The 1 H NMR chemical shifts were also consistent with those of similar trans derivatives reported ( − ). Epoxidation of styrene 7 with m -chloroperoxybenzoic acid was followed by an acid-catalyzed rearrangement to ketone 8 in 45% yield.…”

Section: Resultssupporting

confidence: 87%

“…Synthesis of Diterpenone Catechol 1. The homoconjugated diterpenone catechol 1 was designed as a simplified model of the triterpene QMs that show antitumor activity possibly through DNA intercalation and alkylation ( , ). Diterpenone catechol was synthesized based on published procedures with modifications (Scheme , 12 , 28 ).…”

Section: Resultsmentioning

confidence: 99%

“…Terpene quinone methides (QMs) have been isolated from a variety of plants and show broad activities against bacteria, fungi, and cancerous cell lines ( − ). The biological activity has been attributed to a reactive QM moiety in the structure (Scheme , 1−7 ).…”

Section: Introductionmentioning

confidence: 99%

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Quinone Methide Formations in the Cu²⁺-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA

Zhou

Zúñiga

2005

Chem. Res. Toxicol.

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Terpene quinone methides have been isolated from natural resources and exhibit broad biological activities against bacteria, fungi, and tumor cells through the reactive quinone methide (QM) moiety. The biological potential of the oxidation of terpene QM precursors, however, has not been assessed even though Cu(2+)-induced oxidation of catechol shows detrimental effects on cells. In this study, a diterpenone catechol was investigated as a precursor of terpene QM under aqueous conditions in the presence of Cu2+. Direct QM formation was implied in the Cu(2+)-induced oxidation through the study of thiol addition using HPLC and ESI-MS analysis. In addition, oxidation of the initial QM adduct to a second-QM intermediate was observed. The direct QM oxidation pathway may be unique for diterpenone catechol in the Cu(2+)-induced oxidation and is an addition to the reported isomerization pathway of o-quinones to QMs. The DNA damage by the Cu(2+)-induced oxidation of diterpenone catechol was assessed on a short duplex DNA target. Both direct DNA cleavage and nucleobase oxidation were observed extensively by in situ-generated hydroxyl radicals.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 99%

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Quinone Methide Formations in the Cu²⁺-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA

Zhou

Zúñiga

2005

Chem. Res. Toxicol.

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“…Natural terpene quinone methides (QM) are a category of closely related compounds, and their biological activity attracts numerous research efforts to develop them as effective therapeutics against fungi, bacteria, and tumor growth ( − ). While many focus on derivatives and analogues of terpene QM ( − ), we are interested in the biological potential of catechol precursors and their conversion to terpene QMs through an oxidation process.…”

Section: Introductionmentioning

confidence: 99%

DNA Oxidative Damage by Terpene Catechols as Analogues of Natural Terpene Quinone Methide Precursors in the Presence of Cu(II) and/or NADH

Zúñiga

Dai

Wehunt

et al. 2006

Chem. Res. Toxicol.

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Natural terpene quinone methides (QM) and their derivatives have been investigated as therapeutics due to their broad antifungal, antibacterial, and antitumor activities. Recently, we reported that a terpene QM was formed from the catechol precursor through the disproportionation of Cu(II)/(I) redox cycle, and extensive DNA damage was observed throughout the oxidation process. In this paper, we investigate DNA damage with a series of terpene catechols as analogues of natural QM precursors and suggest that reactive oxygen species (ROS) are responsible for the observed DNA damage in the Cu(2+)-induced oxidation despite the stereo- and structural difference of these catechol or subsequent oxidation products. In addition, the presence of NADH significantly enhanced the extent of DNA damage by oxidation of these catechols. Especially with alkene catechols 6-7, the extent of DNA damage was independent of the concentration of catechols, implying that NADH enables the continuous production of ROS through the redox cycle of catechols/quinones.

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“…: [ 30 ] 264–265 °C); [α] D = +69.4° ( c 0.30, CHCl 3 ) [(lit. : [ 31 ] [α] D = +74.0° ( c 1.0, CHCl 3 )]; MS (ESI, MeOH): m / z 499.4 ([100%, M + H] + ), 516.3 (36%, [M + NH 4 ] + , 521.5 [35%, [M + Na] + .…”

Section: Methodsmentioning

confidence: 99%

Rhodamine 101 Conjugates of Triterpenoic Amides Are of Comparable Cytotoxicity as Their Rhodamine B Analogs

et al. 2022

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Pentacyclic triterpenoic acids (betulinic, oleanolic, ursolic, and platanic acid) were selected and subjected to acetylation followed by the formation of amides derived from either piperazine or homopiperazine. These amides were coupled with either rhodamine B or rhodamine 101. All of these compounds were screened for their cytotoxic activity in SRB assays. As a result, the cytotoxicity of the parent acids was low but increased slightly upon their acetylation while a significant increase in cytotoxicity was observed for piperazinyl and homopiperazinyl amides. A tremendous improvement in cytotoxicity was observed; however, for the rhodamine B and rhodamine 101 conjugates, and compound 27, an ursolic acid derived homopiperazinyl amide holding a rhodamine 101 residue showed an EC50 = 0.05 µM for A2780 ovarian cancer cells while being less cytotoxic for non-malignant fibroblasts. To date, the rhodamine 101 derivatives presented here are the first examples of triterpene derivatives holding a rhodamine residue different from rhodamine B.

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Studies on Di- and Triterpenoids fromSalvia stamineawith Cytotoxic Activity

Cited by 40 publications

References 11 publications

Quinone Methide Formations in the Cu²⁺-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA

Quinone Methide Formations in the Cu²⁺-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA

DNA Oxidative Damage by Terpene Catechols as Analogues of Natural Terpene Quinone Methide Precursors in the Presence of Cu(II) and/or NADH

Rhodamine 101 Conjugates of Triterpenoic Amides Are of Comparable Cytotoxicity as Their Rhodamine B Analogs

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Studies on Di- and Triterpenoids fromSalvia stamineawith Cytotoxic Activity

Cited by 40 publications

References 11 publications

Quinone Methide Formations in the Cu2+-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA

Quinone Methide Formations in the Cu2+-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA

DNA Oxidative Damage by Terpene Catechols as Analogues of Natural Terpene Quinone Methide Precursors in the Presence of Cu(II) and/or NADH

Rhodamine 101 Conjugates of Triterpenoic Amides Are of Comparable Cytotoxicity as Their Rhodamine B Analogs

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Quinone Methide Formations in the Cu²⁺-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA

Quinone Methide Formations in the Cu²⁺-Induced Oxidation of a Diterpenone Catechol and Concurrent Damage on DNA