Amide-esters from Aglaia tenuicaulis – First representatives of a class of compounds structurally related to bisamides and flavaglines

Greger, Harald; Hofer, Margit; Teichmann, Klaus D.; Schinnerl, Johann; Pannell, Caroline M.; Vajrodaya, Srunya; Hofer, Otmar

doi:10.1016/j.phytochem.2007.10.015

Cited by 19 publications

(16 citation statements)

References 35 publications

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“…Cytotoxic activities were also observed in other isolated compounds from A. tenuicaulis and A. forbesii such as amide esters [14,17], which also demonstrated bioactivity, e.g. anti-inflammatory and antimicrobial [35], antiviral [17], and anticancer activities [36].…”

Section: Discussionmentioning

confidence: 99%

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A phenolic ester from Aglaia loheri leaves reveals cytotoxicity towards sensitive and multidrug-resistant cancer cells

Dapat

Jacinto

Efferth

2013

BMC Complement Altern Med

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BackgroundBioactivity-guided fractionation of extracts of Aglaia loheri Blanco (Meliaceae) yielded a cytotoxic isolate, termed Maldi 531.2[M + H]+. This phenolic ester was further investigated for its in vitro cytotoxicity toward human CCRF-CEM leukemia cells and their multi-drug resistant (MDR) subline, CEM/ADR5000. The intrinsic mitochondrial membrane potential (ΔΨm) and induction of apoptosis by this isolate were evaluated.MethodsChromatography techniques, mass spectrometry and proton NMR were employed to isolate Maldi 531.2[M + H]+. XTT cell proliferation and viability assay was used for cytotoxic test, and JC-1[5’,5’,6,6’,-tetrachloro-1,1’,3,3’-tetraethylbenzimidazoyl carbocyanine iodide was used to assess ΔΨm and initiation of apoptosis; Annexin V/FITC-PI staining was employed to analyse apoptosis.ResultsMaldi 531.2[M + H]+ was cytotoxic towards both CCRF-CEM and CEM/ADR5000 cells with IC50 values of 0.02 and 0.03 μM, respectively. The mitochondrial membrane potential (ΔΨm) of MDR cells was significantly reduced in a dose-dependent manner leading to apoptosis as detected by flow cytometric Annexin V-FITC/ PI staining.ConclusionMaldi 531.2[M + H]+ may be a potential anti-cancer drug candidate whose mode of action include reduction of the mitochondrial membrane potential and induction of apoptosis.

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Section: Discussionmentioning

confidence: 99%

“…Amide esters are structurally related to bisamides and flavaglines from Aglaia sp. [14] and exhibited anti-fungal [15], insecticidal [16], anti-tuberculosis and anti-viral activities [17]. Remarkably, this class of compounds also induces apoptosis in resistant human cancer cells [18-20].…”

Section: Introductionmentioning

confidence: 99%

A phenolic ester from Aglaia loheri leaves reveals cytotoxicity towards sensitive and multidrug-resistant cancer cells

Dapat

Jacinto

Efferth

2013

BMC Complement Altern Med

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“…110), are mainly present in Achillea even though pyrrolidides have also been identified in the Convolvulaceae as well as in the Meliaceae family (Greger et al, 1981(Greger et al, , 1983(Greger et al, , 2008Tofern et al, 1999). In the latter case, it concerns a bisamide structure (259) (Greger et al, 2008). The piperidide amides are typically found in Anthemideae tribe and Piperaceae family.…”

Section: Q10mentioning

confidence: 99%

“…265) and an amide alcohol (e.g. 260), which all can be defined as cinnamamides (Greger et al, 2008).…”

Section: Q10mentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

137

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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“…Whereas odorine derivatives are dominating in Australian collections, samples in the Western Group are characterized by piriferine derivatives. Both types of bisamides were also found as characteristic building blocks in the flavaglines (Greger et al 2008). Different patterns of lignans and flavonoids may also contribute to a taxonomic segregation of the Eastern Group of A. elaeagnoidea (Hofer 2002, Greger unpubl.…”

Section: Additional Evidence Derived From Biogenetic Trendspatterns Omentioning

confidence: 99%

Genetic diversity and geographic structure in Aglaia elaeagnoidea (Meliaceae, Sapindales), a morphologically complex tree species, near the two extremes of its distribution

Muellner¹,

Greger²,

Pannell³

2009

blum - j plant tax and plant geog

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Aglaia elaeagnoidea is the most widespread and one of the more morphologically diverse complex species in the largest genus of the mahogany family (Meliaceae, Sapindales). We performed maximum parsimony, maximum likelihood and Bayesian analyses (nuclear ITS rDNA) to estimate genetic relations among samples of Aglaia elaeagnoidea, and their phylogenetic position within Aglaia (more than 120 species in Indomalesia, Australasia, and the Pacific islands). Based on 90 accessions of Melioideae (ingroup) and four taxa of Cedreloideae (outgroup), this study 1) provides a first assessment of the genetic diversity of Aglaia elaeagnoidea; 2) investigates the geographic structure of the data in selected eastern and western regions of its distribution; and 3) suggests that Australia has been colonized only recently by A. elaeagnoidea and other species within the genus (Miocene/Pliocene boundary to Pliocene). Based on DNA data, morphology and additional evidence derived from biogenetic trends (secondary metabolites), the name Aglaia roxburghiana could be reinstated for specimens from the western end (India, Sri Lanka), but we have no data yet to indicate definitely where A. roxburghiana ends and A. elaeagnoidea begins either morphologically or geographically. Viewed in a more general context, Aglaieae are an ideal model group for obtaining more insights into the origin and evolution of Indomalesian and Australian biotas.

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Amide-esters from Aglaia tenuicaulis – First representatives of a class of compounds structurally related to bisamides and flavaglines

Cited by 19 publications

References 35 publications

A phenolic ester from Aglaia loheri leaves reveals cytotoxicity towards sensitive and multidrug-resistant cancer cells

A phenolic ester from Aglaia loheri leaves reveals cytotoxicity towards sensitive and multidrug-resistant cancer cells

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Genetic diversity and geographic structure in Aglaia elaeagnoidea (Meliaceae, Sapindales), a morphologically complex tree species, near the two extremes of its distribution

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