Inhibitory Effects of Phenylpropanoids Isolated from the Bark of Ailanthus altissima on COX-2 Activity

Hwang, Seon Woo; Lee, Jun; Shin, Ji‐Sun; Lee, Jae Yeol; Lee, Kyung Tae; Jang, Dae Sik

doi:10.5012/bkcs.2012.33.8.2759

Cited by 7 publications

(3 citation statements)

References 26 publications

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“…For instance, C -veratroylglycol ( 10t ) is a naturally occurring 2,3-dihydroxy-1-phenylpropanone that has been isolated from a variety of plants, fruits, and tree saps (Scheme ). It has been shown to demonstrate modest antioxidant, antiproliferative (against human colon cancer cells), and COX-2 inhibitory activity in various studies. The key issues in studying the activity of 10t are its low abundance in natural sources which gives rise to poor isolated yields.…”

Section: Resultsmentioning

confidence: 99%

Base-Mediated Cascade Aldol Addition and Fragmentation Reactions of Dihydroxyfumaric Acid and Aromatic Aldehydes: Controlling Chemodivergence via Choice of Base, Solvent, and Substituents

2018

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The diester derivative of dihydroxyfumaric acid (DHF) has been used exclusively as an electrophile in organic synthesis. However, the synthetic utility of DHF's nucleophilic reactivity, contained in the ene-diol moiety, has been underexplored. Inspired by recently observed pH-dependent chemodivergent nucleophilic aldol reactions of dihydroxyfumarate (DHF) with glyoxylate and formaldehyde, we report herein the control and synthetic application of base-controlled chemodivergent reactions between dihydroxyfumarate and aromatic and heteroaromatic aldehydes. With hydroxide as the base in a predominantly aqueous medium, aldol addition followed by deoxalation occurs to provide various 3-aryl-2,3-dihydroxypropanoic acids. With triethylamine as the base in THF, 1-aryl-2,3-dihydroxypropanones are the products of the reaction. In order to understand the difference in reactivity between DHF, its dicarboxylate, and its dimethyl ester, we undertook computational and experimental studies that provide a rationale as to why the dihydroxyfumarate (DHF) is a nucleophile while the corresponding diester reacts as an electrophile.

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Section: Resultsmentioning

confidence: 99%

Base-Mediated Cascade Aldol Addition and Fragmentation Reactions of Dihydroxyfumaric Acid and Aromatic Aldehydes: Controlling Chemodivergence via Choice of Base, Solvent, and Substituents

2018

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“…Scopoletin ( 1 ) is a widely distributed coumarin found in a number of plant families such as Rutaceae and Apiaceae (Jain & Joshi, 2012), Clusiaceae (Marcondes et al, 2015), Convolvulaceae (Sood, Pradhan & Biswasroy, 2014; Khan & Hossain, 2015; Ojha, Mishra & Mishra, 2016), Solanaceae (Valizadeh et al, 2014), Asteraceae (Adams, Efferth & Bauer, 2006), Burseraceae (Mogana, Teng-Jin & Wiart, 2013), Asclepiadaceae (El-Demerdash et al, 2009), and Rubiaceae (Swe, 2008; Mohammed et al, 2013; Chen, Zhang & Chen, 2016). Isofraxidin ( 2 ) is found in species of Araliaceae (Maruyama et al, 2008; Yamazaki & Tokiwa, 2010; Bai et al, 2011; Lee et al, 2013), Asteraceae (Kwak, Lee & Schmitz, 2001; Gliszczyńska & Brodelius, 2012; Yim et al, 2017), Apiaceae (Yim et al, 2017), Simaroubaceae (Hwang et al, 2012), Rutaceae (Brown et al, 1988), Chloranthaceae (Niu et al, 2012; Li et al, 2016), and Rubiaceae (De Araújo et al, 2012).…”

Section: Discussionmentioning

confidence: 99%

Chemovariation and antibacterial activity of extracts and isolated compounds from species of Ixora and Greenea (Ixoroideae, Rubiaceae)

Buathong

Chamchumroon²,

Schinnerl

et al. 2019

PeerJ

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Background A large number of secondary metabolites can be obtained from plants used for traditional medicine in two related genera (Ixora and Greenea) in the subfamily Ixoroideae (Rubiaceae), but there are only a few detailed studies on their bioactivities. Therefore, the main goals of this study were to determine the antibacterial activities of lipophilic extracts from plants of some Ixora and Greenea species native to Thailand, and to isolate some pure compounds from those extracts. Moreover, we compared the occurrence of compounds in different plant parts of samples from different habitats to better understand their variation. Methods A total of 56 lipophilic extracts were obtained from the leaves, stem bark, and root bark of eight Ixora and two Greenea species collected at various locations in Thailand. Isolated compounds were identified using nuclear magnetic resonance. Antimicrobial activities were evaluated against four Gram-positive and nine Gram-negative human pathogenic bacterial strains. Results Extracts from I. javanica, I. nigricans, I. brunonis, and G. montana, along with isolated scopoletin, exhibited antibacterial activities against Gram-positive methicillin-resistant Staphylococcus aureus ATCC 43300, with minimum inhibitory concentration values ranging from 64 to 256 µg/mL. The occurrence of scopoletin, isofraxidin, and geniposidic acid in lipophilic extracts showed some variation among different plant parts and species. Conclusions Lipophilic extracts of Ixora and Greenea species have the potential to be developed as anti-Gram-positive agents, in particular to counter infections of methicillin-resistant S. aureus strains. The chemical profiles showed differences between floristic regions but similarity within the same plant parts.

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“…In addition, it can be used to know mechanism of drug-receptor interactions. In this study the researcher docked insulin tyrosine kinase with main content of ethanol extract of P. peruviana as ligand by Molegro Virtual Docker (MVD) (Hwang et al, 2012;Molegro Virtual Docker, 2010;Naeem et al, 2013;Nogrady and Weaver, 2005).…”

Section: Introductionmentioning

confidence: 99%

Docking studies of Physalis peruviana ethanol extract using molegro virtual docker on insulin tyrosine kinase receptor as antidiabetic agent

Puspaningtyas¹

2014

Int Curr Pharm J

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Physalis peruviana Linn in Indonesia was better known as ciplukan, based on information from urban people in Indonesia is as antidiabetic. In the previeous studies, the levels of blood glucose in animals experimental of Physalis peruviana quantified with glucometer and compared with oral antidiabetic drugs gliclazide, showed that Gliclazide was decrease more levels of glucose significantly than ethanol extract of Physalis peruviana. We have done molecular docking using Molegro Virtual Docker (MVD) on ethanol extract of Physalis peruviana and gliclazide to compare between in silico and in vivo studies. Based on studies before the main content of the ethanol extract of Physalis peruviana were withanolide, 4-OH-withanolide, and perulactone. In this study the results showed that gliclazide had been better bond in insulin tyrosine kinase receptor than main content of Physalis peruviana which can be seen from Moldock score 105.217 and Rerank score -68,2931 means that the energy was lower and more stable binding. Moldock Score of main content Physalis peruviana (withanolide, 4-OH-withanolide, and perulactone) were -93.5472; 70.5843; 88.7881, respectively. Rerank score of main content Physalis peruviana (withanolide, 4-OH-withanolide, and perulactone) were -61.5149; -67.5345; -65.7979, respectively. The hydrogen bonds of withanolide, 4-OH-withanolide, perulactone and gliclazide with amino acid of insulin tyrosine kinase receptor were Phe 1186 and Thr 1186. Finally, in the 3D MVD visualization between main content of ethanol extract of Physalis peruviana and gliclazide can be concluded that interaction of gliclazide was more harmonious than main content of ethanol extract Physalis peruviana.DOI: http://dx.doi.org/10.3329/icpj.v3i5.18534 International Current Pharmaceutical Journal, April 2014, 3(5): 265-269

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Inhibitory Effects of Phenylpropanoids Isolated from the Bark of Ailanthus altissima on COX-2 Activity

Cited by 7 publications

References 26 publications

Base-Mediated Cascade Aldol Addition and Fragmentation Reactions of Dihydroxyfumaric Acid and Aromatic Aldehydes: Controlling Chemodivergence via Choice of Base, Solvent, and Substituents

Base-Mediated Cascade Aldol Addition and Fragmentation Reactions of Dihydroxyfumaric Acid and Aromatic Aldehydes: Controlling Chemodivergence via Choice of Base, Solvent, and Substituents

Chemovariation and antibacterial activity of extracts and isolated compounds from species of Ixora and Greenea (Ixoroideae, Rubiaceae)

Docking studies of Physalis peruviana ethanol extract using molegro virtual docker on insulin tyrosine kinase receptor as antidiabetic agent

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