Quantitative structure–activity relationship of sesquiterpene lactones with cytotoxic activity

Scotti, Luciana; Fernandes, Mariane B.; Ferreira, Marcelo J. P.; Emerenciano, Vicente P.

doi:10.1016/j.bmc.2007.02.005

Cited by 100 publications

(53 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The structure of 3 derived from the 1 H and 13 C NMR data shown in tables 1 and 2 was similar to that of 1 except for the C-8 methine signal that was shown slightly more up field, and the C-7 methine and C-9 methylene signals that were shifted slightly downfield in 3. 13 C and 1 H NMR data were almost identical to the literature values [32].…”

Section: Resultssupporting

confidence: 71%

“…Moreover, they are characterized by the presence of sesquiterpene lactones as secondary metabolites [5][6][7][8][9][10], that have provided several biological activities including anti-fungal, anti-bacterial, anti-inflammatory and cytotoxic effects [5][6][7][8][9][11][12][13]. Centaurea aegyptiaca L. (Family Asteraceae) grows wild in Sinai, Egypt.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Isolation of Bioactive Compounds From Centaurea Aegyptiaca

Sary

Ayoub

Singab

et al. 2018

Int J Pharm Pharm Sci

View full text Add to dashboard Cite

Objective: In a previous study, Centaurea aegyptiaca ethanol and ethyl acetate extracts showed potent cytotoxic effects against laryngeal (HEP2) and hepatic (HEPG2) carcinoma cell lines. Additionally, two novel compounds were isolated and identified. The aim of this study is to continue isolating and identifying another compound (s) that may, also, be responsible for this potent biological activity. Methods:C. aegyptiaca dried aerial parts were extracted with ethanol and ethyl acetate. Both extracts were chromatographed separately to afford seven guaianolides that were identified using different spectroscopic methods. Moreover, compounds 1-7 were evaluated for their cytotoxicity (IC50, µM) against HEP2 and HEPG2 cells in comparison to the normal fibroblasts (BHK) using sulforhodamine B assay. Doxorubicin was used as a positive control.Results: Seven sesquiterpene lactones, centaurepensin, also known as chlorohyssopifolin A (1), 8α-hydroxy-11α, 13-dihydrozaluzanin C (2), chlorohyssopifolin B (3), desacylcynaropicrin (4), chlorohyssopifolin C, acroptilin (5), subluteolide (6), and solstitiolide (7) were isolated from C. aegyptiaca extracts and identified. This is the first report on the occurrence of 2, 4, 5 and 6 in C. aegyptiaca. Compounds 1-4 and 6 exhibited selective cytotoxic effects against HEP2 and HEPG2 cells. However, compounds 1 and 7 showed the highest activities against HEP2 with IC50 values of 10.6±0.02 and 10.9±0.03 µM, respectively. Moreover, compound 3 was the most potent one against HEPG2 cells with IC50 value of 13.8±0.05 µM. Conclusions:Chemical investigation of C. aegyptiaca ethanol and ethyl acetate extracts led to the isolation and identification of seven guaianolides. These compounds exhibited good cytotoxic activities against HEP2 and HEPG2 cell lines.

show abstract

Section: Resultssupporting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Isolation of Bioactive Compounds From Centaurea Aegyptiaca

Sary

Ayoub

Singab

et al. 2018

Int J Pharm Pharm Sci

View full text Add to dashboard Cite

show abstract

“…Although qualitative and quantitative TLC and HPLC studies of several guaianolides have been described (Merfort, 2002;Glasl et al, 2003;Poli et al, 2002;Mares et al, 2005), a literature search on QSRR concerning this class of compounds revealed that no articles have been published. Nevertheless, some QSAR studies on this class of compounds exist (Scotti et al, 2007;Cortés-Selva et al, 2004;Macías et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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

Atrrog

Natić

Tosti

et al. 2008

Biomedical Chromatography

View full text Add to dashboard Cite

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.

show abstract

“…The semiempirical AM1 method is suitable to give a satisfactory conformation of small organic compounds but as a semiempirical molecular orbital method it has limited accuracy. The major drawback of semi-empirical methods is in the parametrization process, as conformation flexibility [8,[23][24][25].…”

Section: Datasetmentioning

confidence: 99%

“…There are few studies involving the influence of the molecular structure of SLs related to their anti-HCV activity [7][8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpene Lactones with Anti-Hepatitis C Virus Activity Using Molecular Descriptors

Rossini

Scotti²,

Correia³

et al. 2012

LDDD

View full text Add to dashboard Cite

Hepatitis C is a worldwide public health problem. The available therapies are limited by their partial effectiveness and with meaningful side-effects. Sesquiterpene lactones (SLs) are a group of natural products with a wide variety of chemical structures and biological activities associated. There are few studies about the influence of the molecular structure of SLs for the anti-hepatitis C virus activity. In the present work, SLs are investigated in a subgenomic RNA replicon assay system and were analyzed using multiple linear regression along with self-organizing maps with DRAGON descriptors in order to identify the structural requirements for their biological activity and to predict the inhibitory potency of SLs. Characteristics such as stereochemistry and electronic effects demonstrated to be important for their anti-HCV activity, and the SOM produced a clear separation betwenn active and inactive compounds. Therefore, it is possible to use this map as a filter for virtual screening to predict the anti-HCV activity of SLs.

show abstract

Quantitative structure–activity relationship of sesquiterpene lactones with cytotoxic activity

Cited by 100 publications

References 29 publications

Isolation of Bioactive Compounds From Centaurea Aegyptiaca

Isolation of Bioactive Compounds From Centaurea Aegyptiaca

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

Sesquiterpene Lactones with Anti-Hepatitis C Virus Activity Using Molecular Descriptors

Contact Info

Product

Resources

About