Guaianolides from Centaurea babylonica

Bruno, Maurizio; Rosselli, Sergio; Maggio, Antonella; Raccuglia, Rosa Angela; Arnold, Nelly Apostolides

doi:10.1016/j.bse.2004.12.028

Cited by 22 publications

(18 citation statements)

References 16 publications

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“…The most active compound on both cell lines is compound 6. A lack of biological activity for compound 9 is in accordance with literature reports and can be explained by the absence of a O&dbond;C&sbond;CH&dbond;CH 2 structural fragment which is believed to be the main determining factor responsible for cytotoxic activity (Lee et al, 1977;Bruno et al, 2005).…”

Section: Relationship Between Cytotoxic Activity and Lipophilicity Pasupporting

confidence: 88%

Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

Atrrog

Natić

Tosti

et al. 2008

Biomedical Chromatography

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In this study 10 guaianolide-type sesquiterpene gamma-lactones named amphoricarpolides, isolated from the aerial parts of two endemic subspecies of Amphoricarpos neumayeri (ssp. neumayeri and ssp. murbeckii Bosnjak), were investigated by means of reversed-phase thin-layer chromatography. Methanol-water and tetrahydrofuran-water binary mixtures were used as mobile phase in order to determine lipophilicity parameters R (0) (M) and C(0). Some of the investigated compounds were screened for their cytotoxic activity against HeLa and B16 cells. Chromatographically obtained lipophilicity parameters were correlated with calculated logP values and IC(50) values. Principal component analysis identified the dominant pattern in the chromatographically obtained data.

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Section: Relationship Between Cytotoxic Activity and Lipophilicity Pasupporting

confidence: 88%

Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

Atrrog

Natić

Tosti

et al. 2008

Biomedical Chromatography

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“…The physical and spectroscopic data were in perfect agreement with those reported in the literature [11,16,24,[26][27][28][29][31][32][33].…”

Section: Methodssupporting

confidence: 89%

Guaianolides from the Aerial Parts of Centaurea Hololeuca

Bruno¹,

Raccuglia

Maggio³

et al. 2006

Natural Product Communications

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Seven guaianolides were isolated from the acetone extract of the aerial parts of Centaurea hololeuca Boiss. The antifeedant activity of the natural compounds (1–7) and of four chloro derivatives (8–11), synthesized from repin (1) and janerin (3) were tested against larvae of Spodoptera littoralis. Cebellin J (6) and chlorojanerin (11) showed significant antifeedant activity at 100 ppm, whereas at this concentration cebellin G (4) and 15-deschloro-15-hydroxychlorojanerin (7) stimulated feeding. Cebellin G (4) stimulated larvae of S. littoralis to feed at low concentration, but deterred feeding at high concentrations. The addition of chlorine to repin (1) resulted in an increase in antifeedant activity.

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“…The rationale behind this descriptor is that different plant species from specific tribes have special trends of accumula- 43 ANT ANT. es2 7 Centaurea babylonica 44 CAR CAR.es1 6 Centaurea acaulis 45 CAR CAR.es2 6 SteVia alpina var. glutinosa 46 EUP EUP.es1 9 Viguiera eriophora 47 HLT HLT.es1 11 Carpesium abrotanoides 48 INU INU.es1 8 Leontodon palisae 49 LAC LAC.es1 5 Vernonanthura lipeoensis 50 VER VER.es1 17 total 72 tion of compounds which show certain features at specific positions of their skeletons, e.g.…”

Section: Atom Countsmentioning

confidence: 99%

Sesquiterpene Lactones-Based Classification of the Family Asteraceae Using Neural Networks and k-Nearest Neighbors

Hristozov

Costa

Gasteiger

2006

J. Chem. Inf. Model.

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In a recent publication we described the application of an unsupervised learning method using self-organizing maps to the separation of three tribes and seven subtribes of the plant family Asteraceae based on a set of sesquiterpene lactones (STLs) isolated from individual species. In the present work, two different structure representations--atom counts (2D) and radial distribution function (RDF) (3D)--and two supervised classification methods--counterpropagation neural networks and k-nearest neighbors (k-NN)--were used to predict the tribe in which a given STL occurs. The data set was extended from 144 to 921 STLs, and the Asteraceae tribes were augmented from three to seven. The k-NN classifier with k = 1 showed the best performance, while the RDF code outperformed the atom counts. The quality of the obtained model was assessed with two test sets, which exemplified two possible applications: (1) finding a plant source for a desired compound and (2) based on a plant species chemical profile (STLs): (a) study the relationship between the current taxonomic classification and plant's chemistry and (b) assign a species to a tribe by majority vote. In addition, the problem of defining the applicability domain of the models was assessed by means of two different approaches-principal component analysis combined with Hotelling T2 statistic and an a posteriori probability-based rule.

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Guaianolides from Centaurea babylonica

Cited by 22 publications

References 16 publications

Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

Guaianolides from the Aerial Parts of Centaurea Hololeuca

Sesquiterpene Lactones-Based Classification of the Family Asteraceae Using Neural Networks and k-Nearest Neighbors

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