Three new isoflavanones from<i>Erythrina costaricensis</i>

Tanaka, Hitoshi; Hattori, Hisanori; Oh-Uchi, Tomoko; Satô, Masaru; Sako, M.; Tateishi, Yohei; Rizwani, Ghazala H.

doi:10.1080/14786410802292286

Cited by 20 publications

(14 citation statements)

References 8 publications

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“…This highlights the conservative biosynthesis of most class A compounds in Erythrina. The best to exemplify this is diprenyl costarone [41], which had an MIC value in the class A range but was keyed out in the decision tree to a class D. This is due to the presence of the 3'-prenyl, 4'-methoxy, 5'-hydroxy configuration of ring B, also seen on prenyl costarone and lysisteisoflavone. Due to the poor representation of these structures in the published literature, it is difficult to predict the effects of this character; however studies on methoxylation in chalcones and isoflavones depict both attenuation and enhancement of antimicrobial activity [22].…”

Section: Figure 6 Sar Predicted Class D Structuresmentioning

confidence: 99%

“…On a few occasions, studies were not included due to unrealistically low MIC values. Data included in the current study were taken as either true or averaged from a set of values out of the following studies: [3,4,18,24,[28][29][30]41,[56][57][58][59][60][61][62]. For convenience, the new isoflavanones from Erythrina costaricensis Micheli, in the study by Tanaka et al [41], were named (1) diprenyl costarone, (2) prenyl costarone and (3) costarone, in the same numerical order as used in that study.…”

Section: Sar and Qsar Analysismentioning

confidence: 99%

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Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus aureus

et al. 2020

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Prenylated (iso)flavonoids, -flavans and pterocarpans from taxa in Erythrina are repeatedly flagged as potent antimicrobial compounds. In the current study, bark from E. lysistemon was extracted and seven isoflavone derivatives were purified: erybraedin A (1), phaseollidin (2), abyssinone V-4′ methyl ether (3), eryzerin C (4), alpumisoflavone (5), cristacarpin (6) and lysisteisoflavone (7). Minimum inhibition concentration (MIC) values were determined against a range of species of bacteria (skin pathogens), then values for another 67 derivatives from Erythrina, only against Staphylococcus aureus, were mined from the literature. Of the seven isolates, MIC values widely ranged from 1–600 μg/mL, with no obvious pattern of selectivity for Gram-types. Nevertheless, using the mined and experimentally determined values against S. aureus, Klekota-Roth fragments (Structure Activity Relationship: SAR) were determined then used as molecular descriptors to make a ‘decision tree’ based on structural characters inspired by the classes of antimicrobial potency (classes A-D). Furthermore, to make quantitative predictions of MIC values (Quantitative SAR: QSAR) ‘pace regression’ was utilized and validated (R² = 0.778, Q² = 0.727 and P² = 0.555). Evidently, the position and degree of prenylation is important; however, the presence of hydroxyl groups at positions 5 and 7 in ring A and 4′ in ring B is associated with lower MIC values. While antimicrobial results continue to validate the traditional use of E. lysistemon extracts (or Erythrina generally) in therapeutic applications consistent with anti-infection, it is surprising that this class of compound is not being utilized more often in general industry applications, such as food or cosmetic preservation, or in topical antimicrobial creams. Prenylated (iso)flavonoids are derived from several other Genera, such as Dorstenia (Moraceae), Ficus (Moraceae), Glycyrrhiza (Fabaceae), Paulownia (Lamiales) or Pomifera (Moraceae).

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Section: Figure 6 Sar Predicted Class D Structuresmentioning

confidence: 99%

Section: Sar and Qsar Analysismentioning

confidence: 99%

Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus aureus

et al. 2020

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“…Isoflavanones are a member of the flavonoid class of secondary plant metabolites whose natural occurrence is limited chiefly to the Leguminosae family of flowering plants 11. Isoflavanones display a range of biological activity and have been shown to act as immunosuppressive agents,12 possess anti‐bacterial13 and anti‐cancer14 activity and act as α‐glucosidase inhibitors 15. To the best of our knowledge, the synthesis of any naturally occurring isoflavanones in high enantioselectivity has yet to be reported.…”

Section: Methodsmentioning

confidence: 99%

Copper(I) Bromide: An Alternative Emitter for Blue‐Colored Flame Pyrotechnics

Juknelevicius

Karvinen

Klapötke

et al. 2015

Chemistry A European J

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Copper(I) bromide was evaluated as an alternative emitter for blue flame pyrotechnic compositions. CuBr and CuCl emission spectra were recorded from a butane torch flame and compared. Cu(BrO3 )2 was synthesized and used in pyrotechnic compositions as an oxidizer and the source for the generation of CuBr species. Pyrotechnic compositions, which contained copper and potassium bromates as oxidizers, were optimized for the generation of blue flames. The experimental data, including emission spectra of the flames, chromaticity coordinates, burning rates, luminous intensities, and sensitivity tests, were analyzed and compared.

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“…Notably, cristacarpin can also be found in Erythrina burana Chiov. [37][38][39]. More recently, E. suberosa leaf aqueous extract was incorporated into silver nanoparticles and then used in an osteosarcoma cancer cell line (A-431) [40].…”

Section: Pharmacological Propertiesmentioning

confidence: 99%

Erythrina suberosa: Ethnopharmacology, Phytochemistry and Biological Activities

et al. 2019

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Plants are a great and irreplaceable source of medicines, fuel, food, energy and even cosmetics. Since prehistory, humans have learned to use plants for survival, growth and proliferation and still today it relies on natural and cultivated vegetables for food and the source of novel compounds with pharmacological activity. Not only herbs and flowers, but also trees are used. Indeed, Erythrina suberosa Roxb. is a deciduous tree of the family Fabaceae, common in Southeast Asia. In India, E. suberosa is called the “corky coral tree” or simply the “Indian coral tree”, given its peculiar red-orange flowers that can flower throughout the year and its corky irregular bark covered by prickles. It is a plant commonly used as an ornamental tree, but it also holds ethnopharmacological and socioeconomic uses. This article explored phytobiological features of E. suberosa, analysing its taxonomy, examining its traditional and common uses and investigating its bioactive components and pharmacological properties.

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Three new isoflavanones fromErythrina costaricensis

Cited by 20 publications

References 8 publications

Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus aureus

Antimicrobial Isoflavones and Derivatives from Erythrina (Fabaceae): Structure Activity Perspective (Sar & Qsar) on Experimental and Mined Values Against Staphylococcus aureus

Copper(I) Bromide: An Alternative Emitter for Blue‐Colored Flame Pyrotechnics

Erythrina suberosa: Ethnopharmacology, Phytochemistry and Biological Activities

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