Antitubercular potential of some semisynthetic analogues of phytol

Saikia, Dharmendra; Parihar, Swati; Chanda, Debabrata; Ojha, Shweta; Kumar, Jonnala Kotesh; Chanotiya, Chandan Singh; Shanker, Karuna; Negi, Arvind S.

doi:10.1016/j.bmcl.2009.11.107

Cited by 61 publications

(41 citation statements)

References 9 publications

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“…In addition to that, phytol derivatives have been found to act as immunostimulants by providing long-term memory induction and activating both innate and acquired immunity (Chowdhury & Ghosh 2012). The diterpene phytol has also been reported to possess antimicrobial potentials against Staphylococcus aureus and tuberculosis (Inoue et al 2005;Saikia et al 2010). Chang et al (2007) demonstrated that phytol exhibit neuroprotective effects on human neuroblastoma SH-SY5Y cells when evaluated in vitro by using a simulated ischemia model.…”

Section: Discussionmentioning

confidence: 99%

Neuroprotective effect of the marine macroalgaGelidiella acerosa: identification of active compounds through bioactivity-guided fractionation

Syad

Shafreen

Shunmugaiah

et al. 2016

Pharmaceutical Biology

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Context Gelidiella acerosa (Forsskål) Feldmann & G. Hamel (Rhodophyta-Gelidiales) is a marine red macroalga. Our previous work found that a benzene extract of G. acerosa possesses noticeable neuroprotective activity, when evaluated through in vitro and in vivo systems. Objective Bioactive-guided fractionation and identification of active compounds by column chromatography using solvents of varying polarity. Materials and methods Fractionation was done by column chromatography, antioxidant and anticholinesterase activity was assessed by DPPH and cholinesterase inhibition assays (50-200 mg/ml), compound identification was done by LC-MS analysis, the mode of interaction of active compound was analyzed through docking studies and quantification was done by highperformance thin-layer chromatography (HPTLC) analysis.Results The results suggest that fractions F9-F13 exhibited significant (p50.05) antioxidant and anticholinesterase activities. Hence, these fractions were pooled together and verified for neuroprotective activity. The pooled fraction was subjected to LC-MS analysis and among all the compounds, phytol was previously reported to possess excellent neuroprotective potential. Hence, the neuroprotective potential of phytol was assessed. The results suggest that phytol showed significant (p50.05) antioxidant activities (25-125 mg/ml) with an IC 50 value of 95.27 ± 1.65 mg/ml and cholinesterase inhibitory potential (5-25 mg/ml) with IC 50 values of 2.704 ± 0.07 and 5.798 ± 0.72 mg/ml for AChE and BuChE, respectively. Molecular docking studies suggest that phytol interacts with cholinesterase through the arginine residue of the enzyme. HPTLC quantification showed that about 6.266 mg of phytol was present per mg of pooled fraction. Conclusion The study suggests that phytol might act as the key compound in contributing to the neuroprotective potential of G. acerosa. ARTICLE HISTORY

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Section: Discussionmentioning

confidence: 99%

Neuroprotective effect of the marine macroalgaGelidiella acerosa: identification of active compounds through bioactivity-guided fractionation

Syad

Shafreen

Shunmugaiah

et al. 2016

Pharmaceutical Biology

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“…In addition, an increased number of OH groups may increase the polarity of diterpenes. Recently, aldehyde, oxime, and ethyl bromocrotonyl derivatives of PYT have been shown to have 2, 4, and 6.5 folds more potent antitubercular activities, respectively [47], thus featuring a better pharmacological profile with synthetic products of PYT.…”

Section: Study-based Conclusive Talksmentioning

confidence: 99%

Preparation of phytol-loaded nanoemulsion and screening for antioxidant capacity

Islam

Streck²,

Paz³

et al. 2016

Int Arch Med

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The study prepared a nanoemulsion with a diterpenoid isoprenoid alcohol called phytol (PYT) and subsequently tested it for antioxidant capacity. For this, PYT-loaded nanoemulsion was prepared by phase inversion method and both PYT-containing nanoemulsion (PNE) and PYT-free nanoemulsion (PFNE) (2-16 µM) were tested for antiradical activity (DPPH•: 1,1-dipheny-picrylhydrazyl radical; ABTS•+: azino-bisethylbenzthiazoline-sulfonic acid; •OH: hydroxyl radical scavenging; NO•: nitrite oxide radical), lipid peroxidation (LP), reduction potential (RP), and inhibition of hemolysis (HL) in rat erythrocytes in comparison with an α-tocopherol analogue (Trolox -TRO -positive control). In addition, an in vivo test was performed with wildtype and deficient Saccharomyces cerevisiae strains using hydrogen peroxide (H 2 O 2 ) as a stressor. Results suggest that PNE exhibited higher antioxidant than the PFNE. Increasing doses reveled antioxidant capacity in a dose-dependent manner. In the S. cerevisiae study, both PFNEand PNE-treated groups exhibited decreased rates of survival with the highest doses, whichever in the presence of stressor increased the survival rates, which indicates antioxidative defense capacity of PYT. In this occasion, PNE exhibited prominent antioxidative defense in the presence of stressor rather than PFNE. In conclusion, PYT exhibited potential antioxidant activity but at high concentration it was toxic to the yeast cells. The production of PYT-nanoemulsions may be relevant to the pharmaceutical sciences.

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“…Deng et al, in 2000, reported that 103 and its derivatives inhibit DNA polymerase β, which is an entirely different mechanism than that of INH, RMP, and EMB, which explains the synergism [63]. A diterpene alcohol such as phytol (104) and its modified derivatives (105-107) showed very good antimycobacterial activity [64].…”

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confidence: 99%

“…prop-2-en-1-one (30 µg/mL) [45] cordiachrome C (1.5 µg/mL) [52] aromatic alkene, and pyrrolidine amide (25 µg/mL) [69] 5,4′-dihydroxy-3,7,8,3′-tetramethoxy flavones (> 50 µg/mL) (25 µg/mL) [28] palmarumycin JC2 (6.25 µg/mL) [39] Isobavachalcone (18 µg/mL) [45] globiferin (6.2 µg/mL) [52] tetrahydroxy squalene (10 µg/mL) [70] 5,4′-dihydroxy-3,7,8-trimethoxyflavone (> 50 µg/mL) (25-50 µg/mL) [28] α-tocopheryl quinone (25 µg/mL) [40] scopoletin (42 µg/mL) [45] diol derivative of labdane (250 µg/mL) [53] trans,trans-1,7,diphenylhepta-4,6-dien-3-one (> 128 µg/mL) [71] nevadensin and isothymusin (200 µg/mL) [29] 2′,5′′-dimethoxysesamin (63 µg/mL) [47] dioxime derivative of labdane and labdane (500 µg/mL) [53] xanthones (10 µg/mL) [72] pisonivanone (12.5 µg/mL) [32] ethoxycubebin (62.4 µM) [49] caniojane (25 µg/mL) [54] continued phytol derivatives (15.6-50 µg/mL) [64] phytol (100 µg/mL) [64] zylamine (2) inhibited both the sensitive and MDR strains of M. tuberculosis at minimum inhibitory concentrations (MIC) of 50 and 200 µg/mL, respectively [8]. Justicia adhatoda L., Acanthaceae, is known as vasaka in the Indian system of medicine.…”

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confidence: 99%