Obtusastyrene and obtustyrene, cinnamylphenols from Dalbergia retusa

Gregson, Michael; Ollis, W. D.; Redman, B. T.; Sutherland, I. O.; Dietrichs, H. H.; Gottlieb, Otto R.

doi:10.1016/s0031-9422(00)94596-5

Cited by 51 publications

(22 citation statements)

References 35 publications

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“…An examination of the previously mentioned docking results for compounds 1-58 (Table 2) was performed to select the best-docked compounds as putative COX-2 binders. Hence, from the global mean Vina scores (GMVS < −10.5 kj/mol)), best-pose convergence (RMSD < 0.5) and scoring reproducibility (%RSD <6%) along nine COX-2 structures, the compounds 9 -nor-7, 8-dehydro-isolicarin-B (11), moracin H (29) psoralidin (42), and maximol (49) were established as the best-docked compounds among the test set. These selected compounds were, therefore, clustered in the green group of the PCA-derived score plot (Figure 4b), which exhibits the lowest-scoring behavior.…”

Section: Selection Of the Best-docked Compoundsmentioning

confidence: 99%

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Discrimination of Naturally-Occurring 2-Arylbenzofurans as Cyclooxygenase-2 Inhibitors: Insights into the Binding Mode and Enzymatic Inhibitory Activity

Coy-Barrera

2020

Biomolecules

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2-arylbenzofuran-containing compounds are chemical entities that can be naturally produced by several organisms. A wide-range of activities is described for several compounds of this kind and they are, therefore, valuable moieties for a lead finding from nature. Although there are in-vitro data about the activity of 2-arylbenzofuran-related compounds against cyclooxygenase (COX) enzymes, the molecular level of these COX-inhibiting constituents had not been deeply explored. Thus, 58 2-arylbenzofurans were initially screened through molecular docking within the active site of nine COX-2 crystal structures. The resulting docking scores were statistically analyzed and good reproducibility and convergence were found to discriminate the best-docked compounds. Discriminated compounds exhibited the best performance in molecular dynamics simulations as well as the most-favorable binding energies and the lowest in-vitro IC50 values for COX-2 inhibition. A three-dimensional quantitative activity-structure relationship (3D-QSAR) was also demonstrated, which showed some crucial structural requirements for enhanced enzyme inhibition. Therefore, four hits are proposed as lead structures for the development of COX-2 inhibitors based on 2-arylbenzofurans in further studies.

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Section: Selection Of the Best-docked Compoundsmentioning

confidence: 99%

“…HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energies (in eV), HOMO-LUMO gaps (∆E), and corresponding orbitals obtained by density functional theory (DFT) level for the best docked compounds(11,29,42,49, and celecoxib (cel)).…”

mentioning

confidence: 99%

Discrimination of Naturally-Occurring 2-Arylbenzofurans as Cyclooxygenase-2 Inhibitors: Insights into the Binding Mode and Enzymatic Inhibitory Activity

Coy-Barrera

2020

Biomolecules

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“…Often valued for their use in wooden crafts, the heartwoods are also used in traditional medicine and have antibiotic and cytotoxic activities (Yahara et al, 1989;Zhao et al, 2000;Goda et al, 1992;Hamburger et al, 1987;Ansari et al, 2002). Chemical investigations of Dalbergia heartwoods have shown the typical occurrence of monomeric isoflavonoids, neoflavonoids and cinnamylphenols (Goda et al, 1992;Dewick, 1994;Donnelly and Roland, 1994;Geiger, 1988;Gregson et al, 1978). A limited number of oligomers with mixed monomers of the isoflavonoid-neoflavonoid and isoflavonoid-cinnamylphenol type have also been reported (Bekker et al, 2002;Czako´and Ma´rton, 2001;Hamburger et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

“…Neocandenatone 1 (vestitol[6!9 00 ;7O!7 00 ]obtusaquinone) is an isomer of candenatone, isolated from Dalbergia candenatensis (Hamburger et al, 1988), a dimer of the isoflavan vestitol and the cinnamylphenol obtusaquinone. Both vestitol and obtusaquinone have been commonly found in Dalbergia heartwoods (Bekker et al, 2002;Gregson et al, 1978). A related isomer, retusapurpurine, extracted from Dalbergia retusa cell cultures has recently been reported (Czako´and Ma´rton, 2001).…”

Section: Introductionmentioning

confidence: 99%

Neocandenatone, an isoflavan-cinnamylphenol quinone methide pigment from Dalbergia congestiflora

Barragán-Huerta¹,

Peralta-Cruz²,

González‐Laredo³

et al. 2004

Phytochemistry

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“…ϩ50.0°, cϭ0.58, MeOH), 14) dalbergin (16), 17) isoparvifuran (17), 18) and (2R,3R)-obtusafuran (18) 19) Flavonoids and related plant-derived phenolic compounds are well-known to have a wide range of biological activities. Accordingly, in this study we investigated whether isolated compounds affect cytoprotection of HT22 cells by antioxidative effect.…”

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confidence: 99%

Flavonoids from the Heartwood of Dalbergia odorifera and Their Protective Effect on Glutamate-Induced Oxidative Injury in HT22 Cells

Jeong

Kim

2008

Chem. Pharm. Bull.

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Dalbergia odorifera T. CHEN (Leguminosae) is a perennial tree that mainly grows in China. The heartwood of the plant is used to treat blood stagnation syndrome, ischemia, swelling, necrosis, and rheumatic pain in China and Korea. 1)Previous phytochemical studies on this plant have isolated flavonoids, quinones, and phenolic constituents.2-4) We have isolated two new flavonoids, 4,2Ј,5Ј-trihydroxy-4Ј-methoxychalcone (1) and (2S)-6,7,4Ј-trihydroxyflavan (2) together with sixteen known compounds, including flavonoids and arylbenzofurans. In this paper, we report the structure elucidation of new compounds and the cytoprotective effects of isolated compounds on glutamate-induced oxidative injury in immortalized mouse hippocampal cells. Results and DiscussionRepeated chromatography purification of the ethanol extracts of the heartwood of the D. odorifera gave two new compounds, 1 and 2, along with the known compounds 3-18 (Fig. 1).Compound 1 was obtained as a yellow amorphous solid. HR-FAB-MS showed an [MϩH] ϩ ion peak in accordance with the empirical molecular formula, C 16 H 14 O 5 , which was supported by the 13 C-NMR spectrum and distortionless enhancement by polarization transfer (DEPT) data. The UV spectrum displayed bands assignable to a chalcone system at 355 and 207 nm. 6) The 13 C-NMR and DEPT experiments were consistent with these data, indicating the presence of eight methines, five non-protonated, and one methoxy carbon. The signals for each proton and carbon of this molecule were assigned unambiguously by the assistance of 2D-NMR (HMQC and HMBC). The two olefinic protons at d 7.77 (H-b) and 7.50 (H-a) showed long-range correlations with the carbons at d 192.2 (CϭO), 130.5 (C-2, C-6), and 126.5 (C-1) (Fig. 2). The two aromatic protons at d 7.40 (H-6Ј) and 6.48 (H-3Ј), showed long-range correlations with the carbons at d 192.2 (CϭO), 159.8 (C-2Ј), 155.6 (C-4Ј), 138.8 (C-5Ј), and 112.4 (C-1Ј). One methoxyl proton at d 3.90 (4Ј-OCH 3 ) showed a long-range correlation with the carbon at d 155.6 (C-4Ј). From the above data, the structure of the new natural product 1 was elucidated as 4,2Ј,5Ј-trihydroxy-4Ј-methoxychalcone.Compound 2 was isolated as a yellow amorphous solid. HR-FAB-MS showed a molecular ion at m/z 258.0894 (M ϩ , Calcd 258.0892), indicating the molecular formula C 15 H 14 O 4 . The 1 H-and 13 C-NMR spectral data of 2 were very similar to those of 6,4Ј-dihydroxy-7-methoxyflavan, 7) except for the ab- Two flavonoids, 4,2,5-trihydroxy-4-methoxychalcone (1) and (2S)-6,7,4-trihydroxyflavan (2), along with fourteen known flavonoids and two other known arylbenzofurans were isolated from the heartwood of Dalbergia odorifera. The structure of compounds 1 and 2 were established by spectroscopic (NMR and MS) analyses. Of the isolates, eight compounds (1, 4, 7, 10, 12, 14, 15, 17) were found to have potent protective effect on glutamateinduced oxidative injury in HT22 cells.

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Obtusastyrene and obtustyrene, cinnamylphenols from Dalbergia retusa

Cited by 51 publications

References 35 publications

Discrimination of Naturally-Occurring 2-Arylbenzofurans as Cyclooxygenase-2 Inhibitors: Insights into the Binding Mode and Enzymatic Inhibitory Activity

Discrimination of Naturally-Occurring 2-Arylbenzofurans as Cyclooxygenase-2 Inhibitors: Insights into the Binding Mode and Enzymatic Inhibitory Activity

Neocandenatone, an isoflavan-cinnamylphenol quinone methide pigment from Dalbergia congestiflora

Flavonoids from the Heartwood of Dalbergia odorifera and Their Protective Effect on Glutamate-Induced Oxidative Injury in HT22 Cells

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