Xanthomicrol (I) Is the Main Cytotoxic Component of Dracocephalum kotschyii and a Potential Anticancer Agent.

Jahaniani, Fereshteh; Ebrahimi, Soltan Ahmad; Rahbar‐Roshandel, Nahid; Mahmoudian, Massoud

doi:10.1002/chin.200549191

Cited by 7 publications

(10 citation statements)

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“…Dracocephalum kotschyi has been widely used in modern medicine for the treatment of numerous diseases and as a prophylactic for tumor proliferation across the world . Xanthomicrol, the most common phytochemical composition in D. kotschyi leaves, possesses an anticancer effect . Moreover methoxylated flavonoids in this plant have various biological and pharmacological qualities including antibacterial, antifungal, anti‐inflammatory, antispasmodic, analgesic, antihyperlipidemic, and immunomodulatory properties .…”

Section: Introductionmentioning

confidence: 99%

“…6 Xanthomicrol, the most common phytochemical composition in D. kotschyi leaves, possesses an anticancer effect. 7 Moreover methoxylated flavonoids in this plant have various biological and pharmacological qualities including antibacterial, antifungal, anti-inflammatory, antispasmodic, analgesic, antihyperlipidemic, and immunomodulatory properties. [8][9][10] The anticancer property of D. kotschi has been attributed to methoxylated flavones such as apigenin, luteolin, isokaempferid, crisimaritin, penduletin, and xanthomicrol, and the antioxidant activity might be due to the phenolic compounds (like caffeic acid, chlorogenic acid, phenylpropanoids, and flavonoids) present in this plant.…”

Section: Introductionmentioning

confidence: 99%

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Iron oxide nanoparticles: a novel elicitor to enhance anticancer flavonoid production and gene expression in Dracocephalum kotschyi hairy‐root cultures

et al. 2019

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BACKGROUND Dracocephalum kotschyi Boiss. is a valuable source of rosmarinic acid (RA) and methoxylated hydroxyflavones (such as xanthomicrol and cirsimaritin) with antioxidative and antiplatelet effects and with antiproliferative potential against various cancer cells. The extensive application of nanotechnology in hairy root cultures is a new sustainable production platform for producing these active constituents. In the present study, hairy roots derived from 4‐week‐old leaves and Agrobacterium rhizogenes strain ATCC15834 were used to investigate the impact of various concentrations of iron oxide nanoparticles (Fe NPs) in two elicitation time exposures (24 and 48 h) on growth, antioxidant enzyme activity, total phenolic and flavonoid content (TPC and TFC), and some polyphenols. Gene expression levels of phenylalanine ammonia‐lyase (pal) and rosmarinic acid synthase (ras) were also analyzed. RESULTS Iron nanoparticles enhanced biomass accumulation in hairy roots. The treatment time and Fe NP dosage largely improved the activity of antioxidant enzymes, TPC and TFC. The highest RA (1194 μg g−1 FW) content (9.7‐fold), compared to controls, was detected with 24 h of exposure to 75 mg L−1 Fe NP, which was consistent with the expression of pal and ras genes under the influence of elicitation. The xanthomicrol, cirsimaritin, and isokaempferide content was increased 11.87, 3.85, and 2.27‐fold, respectively. CONCLUSION Stimulation of D. kotschyi hairy roots by Fe NPs led to a significant increase in the induction and production of important pharmaceutical compounds such as rosmarinic acid and xanthomicrol. © 2019 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Iron oxide nanoparticles: a novel elicitor to enhance anticancer flavonoid production and gene expression in Dracocephalum kotschyi hairy‐root cultures

et al. 2019

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“…For the analysis correlating the 13 C NMR data (table in supplementary material) and the flavonoid inhibitory activities, the former were obtained from the literature (Al-Yahya et al, 1988;Flamini et al, 2001;Agrawal, 1989;Maldonado & Ortega, 1997;Greenham et al, 2001;Jahaniani et al, 2005;Youssef & Frahm, 1995;Horie et al, 1998;Nagao, 2002) and, for some structures, they were extracted using ACDlabs software (ACD/HNMR, 2003), since flavonoids are plane aromatic compounds, and so, the aditivity model can be applied satisfactorily to predict 13 C NMR data. To validate the method employed in the 13 C NMR data prediction, the chemical shifts of some flavonoids were predicted and compared to the literature data (table in supplementary material), showing errors smaller than 3ppm.…”

Section: Self-organizing Maps Approachmentioning

confidence: 99%

Self-organizing maps and VolSurf approach to predict aldose reductase inhibition by flavonoid compounds

Scotti

Fernandes

Muramatsu

et al. 2011

Rev. bras. farmacogn.

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Aldose Reductase (AR) is the polyol pathway key enzyme which converts glucose to sorbitol. High glucose availability in insulin resistant tissues in diabetes leads into an accumulation of sorbitol, which has been associated with typical chronic complications of this disease, such as neuropathy, nephropathy and retinopathy. In this study, 71 flavonoids AR inhibitors were subjected to two methods of SAR to verify crucial substituents. The first method used the PCA (Principal Component Analysis) to elucidate physical and chemical characteristics in the molecules that would be essential for the activity, employing VolSurf descriptors. The rate obtained explained 53% of the system total variance and revealed that a hydrophobic-hydrophilic balance in the molecules is required, since very polar or nonpolar substituents decrease the activity. Artificial Neural Networks (ANNs) was also employed to determine key substituents by evaluating substitution patterns, using NMR data. This study had a high success rate (85% accuracy in the training set and 88% accuracy in the test set) and showed polihydroxilations are essential for high activity and methoxylations and glicosilations primarily at positions C7, C3' and C4' decrease the activity.

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“…[3] It is one of the constituents of Spinal-Z, a traditional Iranian anticancer remedy, which was used by traditional healers as a plant concoction for the treatment of many forms of cancer in humans. [4] Pharmacological studies have confirmed some medicinal properties of the plant, including antihyperlipidemic, [5] immunomodulatory, [6] antinociceptive, [7] and cytotoxic [8] effects. In recent years, it has been reported that neuroprotective and immunoinhibitory effects of the plant are due to its methxylated flavonoid, calycopterin.…”

Section: Introductionmentioning

confidence: 99%

Chemical composition and antibacterial activity of Dracocephalum kotschyi essential oil obtained by microwave extraction and hydrodistillation

Farimani

Mirzania

Sonboli

et al. 2017

International Journal of Food Properties

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Dracocephalum kotschyi essential oils obtained by hydrodistillation (HD), microwave-assisted hydrodistillation (MAHD), and solvent-free microwave extraction (SFME) were investigated by GC-FID (Gas Chromatography-Flame Ionization Detector) and GC-MS (Gas Chromatography-Mass Spectrometry). The percentage of oxygenated compounds was significantly increased from 62.52% in HD to 76.47% in MAHD, and 84.52% in SFME. Conversely, the monoterpene hydrocarbons were decreased from 30.84% in HD to 13.71% in MAHD, and 5.85% in SFME. The main compound in the essential oil obtained by HD is limonene, which accounted for more than 30% of the oil, while the percentage of this compound was reduced to 9.52% in MAHD, and 5.60% in SFME. The percents of other oxygenated compounds such as neral, geranial, geraniol, geranyl acetate, α-terpineol, trans-verbenol, carvon, and transcarveol were noticeably higher in microwave methods than those present in HD method. In aqueous medium, linear oxygenated monoterpenes may be converted to a monocyclic terpinyl cation, which it could lose a proton to give limonene. The main biosynthetic pathway of these compounds, as well as a possible route of their conversion into limonene, due to prolonged heating in the HD method, was proposed. The antimicrobial activity of D. kotschyi essential oils against Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria was evaluated by broth microdilution susceptibility manner. The most sensitive bacteria to these oils was found to be S. aureus with the lowest minimum inhibitory concentration value of 2 mg mL −1 for MAHD and SFME specimens. The results indicated that oils obtained by microwave methods were more active against S. aureus. ARTICLE HISTORY

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Xanthomicrol (I) Is the Main Cytotoxic Component of Dracocephalum kotschyii and a Potential Anticancer Agent.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 7 publications

References 1 publication

Iron oxide nanoparticles: a novel elicitor to enhance anticancer flavonoid production and gene expression in Dracocephalum kotschyi hairy‐root cultures

Iron oxide nanoparticles: a novel elicitor to enhance anticancer flavonoid production and gene expression in Dracocephalum kotschyi hairy‐root cultures

Self-organizing maps and VolSurf approach to predict aldose reductase inhibition by flavonoid compounds

Chemical composition and antibacterial activity of Dracocephalum kotschyi essential oil obtained by microwave extraction and hydrodistillation

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