Ethylidene-4,6-dimethoxycoumaran-3-one: the C2C8 double bond configuration

Klika, Karel D.; Cheriyamundath, Sanith; Raghavan, Rahul; Megha, K. B.; Banerji, Asoke; Owen, Robert W.; Madassery, Joseph

doi:10.1016/j.tetlet.2014.10.008

Cited by 5 publications

(6 citation statements)

References 25 publications

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“…NMR analysis was performed in additional to confirm the compound. The results obtained were completely consistent with the data we reported earlier (Klika et al, 2014).…”

Section: Results and Discussion Isolation And Identification Of (Z)-esupporting

confidence: 93%

(Z)-Ethylidene-4, 6-Dimethoxycoumaran-3-One Induces Apoptosis in Chronic Myelogenous Leukemia Cell Line

Cheriyamun¹,

Raghavan²,

Megha³

et al. 2015

International J. of Biological Chemistry

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The present study was performed to evaluate the antiproliferative property of (Z)-ethylidene-4, 6-dimethoxycoumaran-3-one (EDC), isolated from Pogostemon quadrifolius (Benth.) leaf against chronic myelogenous leukemia cell line (K-562). The purity and identity of the compound were confirmed by HPLC and ESI-MS analysis. Cell viability assay (MTT) was performed to evaluate the antiproliferative effect of EDC on K-562 cell line. The result showed that EDC inhibited the proliferation of K-562 cell line with an IC 50 of 7.77±0.21 µg mLG 1 (35.3 µM). Further DNA fragmentation assay was performed to identify the mode of action of EDC against K-562 cell line. The clear laddering pattern obtained after treating the cell line for 24 h with 50 µM EDC indicated that EDC induces cell death in K-562 cells by inducing apoptosis. Thus, the present study evidenced the potential antiproliferative property of EDC against chronic myelogenous leukemia cancer in vitro.

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“…NMR analysis was performed in additional to confirm the compound. The results obtained were completely consistent with the data we reported earlier (Klika et al, 2014).…”

Section: Results and Discussion Isolation And Identification Of (Z)-esupporting

confidence: 93%

(Z)-Ethylidene-4, 6-Dimethoxycoumaran-3-One Induces Apoptosis in Chronic Myelogenous Leukemia Cell Line

Cheriyamun¹,

Raghavan²,

Megha³

et al. 2015

International J. of Biological Chemistry

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“…1 H NMR (500MHz, CDCl 3 , 25°C, TMS) δ 1.16 (d, 3J=7.2Hz, 3H, H9), 1.53 (3H, s, H15), 1.57, 1.73 (2H, m, H10), 1.64 (3H, s, H14), 1.8 (2H, m, H11), 2.0 (3H, d, 3 J=1.5Hz, H7), 3.09 (1H, m, H8), 3.94 (3H, s, OMe), 5.06 (1H, m, H12), 6.5 (1H, q, H5). 13 (6). n-butyllithium (3.75 ml of 1.6M solution in hexane) was added to a cold (0°C) solution of 5-methyl -3,4-(methylenedioxy) anisole (0.35g, 2.14mmol) in dry THF (10ml) [21].…”

Section: Synthesis Of 2-(15-dimethyl-4-hexenyl)-3-methoxy-5-methyl-1mentioning

confidence: 99%

“…Under normal conditions for nOe mixing time employed varies between 500-800ms and for ROE between 300-500ms, and long-range nOe, beyond 5 Å are not observable. Nevertheless, some cases have been described and some of these weak nOes were observed and used for structural purposes [6]. Since these signals can be quite relevant from the structural and conformational standpoint, it is important to rigorously establish their nature.…”

Section: Introductionmentioning

confidence: 99%

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The Folded Conformation of Perezone Revisited. Long Range nOe Interaction in Small Molecules: Interpretable Small Signals or Useless Large Artifacts?

et al. 2017

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The nuclear Overhauser effect (nOe) is a consequence of the cross-relaxation and it involves the transfer of nuclear spin polarization from one population to another intra or inter-molecularly. It is generally accepted that a proton-proton distance between 4 and 5 Å is the upper limit for the occurrence of measurable nOe´s in small molecules. However, we herein show how detectable nOe´s may, in fact, take place between alkyl groups of quinones with substitutions at 1-4 relative positions, showing distances longer than 6 Å. Although the signals of interest are very small, of the order of 1% of a normal nOe, so a priori are considered artifacts originated by decoupling modulation, they maintain, properties that make them interesting and give them coherence as interpretable signals. If the signals of interest are not artifacts these observations represent an important breakthrough with impact on the standard protocols that are commonly used for determination of molecular structure and conformation.

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“…J. Med. Plant, 9 (7): 361-367, 2015 and it induces apoptosis in cancer cell line (Cheriyamundath et al, 2015;Klika et al, 2014). Even though the plant possesses all these medicinal properties, till now there are no reports available on the antioxidant property of this plant.…”

Section: Introductionmentioning

confidence: 99%

DPPH Radical Scavenging Property of Methanol Leaf Extract from Pogostemon quadrifolius (Benth.)

Cheriyamun¹,

Raghavan²,

Madassery³

2015

Research J. of Medicinal Plant

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The study was conducted to evaluate the DPPH scavenging property of leaf extracts of plant P. quadrifolius (Benth.). In this study, plant leaves were solvent extracted by soxhlet method using petroleum ether, chloroform and methanol sequentially. The extracts were then analyzed for DPPH scavenging properties. Among the three extracts used, only methanol extract has exhibited the DPPH scavenging property. The results showed that the methanol extract of P. quadrifolius (Benth.) leaf exhibit DPPH scavenging property with IC 50 14.5±1.05 µg mLG 1 . The phytochemical analysis indicated that the methanol extract is a rich source of phenolic compounds and this may be the reason for DPPH radical scavenging property of this extract.

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Ethylidene-4,6-dimethoxycoumaran-3-one: the C2C8 double bond configuration

Cited by 5 publications

References 25 publications

(Z)-Ethylidene-4, 6-Dimethoxycoumaran-3-One Induces Apoptosis in Chronic Myelogenous Leukemia Cell Line

(Z)-Ethylidene-4, 6-Dimethoxycoumaran-3-One Induces Apoptosis in Chronic Myelogenous Leukemia Cell Line

The Folded Conformation of Perezone Revisited. Long Range nOe Interaction in Small Molecules: Interpretable Small Signals or Useless Large Artifacts?

DPPH Radical Scavenging Property of Methanol Leaf Extract from Pogostemon quadrifolius (Benth.)

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