Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp. E. plantagineum and E. gaditanum

Alexandra G. Durán, M. Teresa Gutiérrez, Carlos Rial, Ascensión Torres, Rosa M. Varela, Manuel M. Valdivia, José M.G. Molinillo, Dominik Skoneczny, Leslie A. Weston, Francisco A. Macías

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Isohexenylnaphthazarins are commonly found in the root periderm of several Boraginaceous plants and are known for their broad range of biological activities. The work described herein concerns the biological activity of compounds from the roots of Echium plantagineum L. and Echium gaditanum Boiss (Boraginaceae) collected from field sites in southern Spain and Australia. Bioactivity was assessed using etiolated wheat coleoptile bioassay and in vitro growth inhibitory activity in HeLa and IGROV-1 cells. The quantification of four isohexenylnaphthazarins (shikonin/alkannin, deoxyshikonin/deoxyalkannin, acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin) was performed by LC-MS/MS using juglone as internal standard. Correlation coefficient values for the activities and concentrations of these four analytes were in the linear range and were greater than 0.99. Acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin were present in the highest concentrations in extracts of both species. The results reveal that greatest overall inhibition was observed in both bioassays with E. gaditanum extracts. Strong correlations between time of collection, sampling location and bioactivity were identified.

Original languageEnglish
Pages (from-to)162-170
Number of pages9
JournalPhytochemistry
Volume141
Early online dateJun 2017
DOIs
Publication statusPublished - Sep 2017

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Echium
periderm
Bioactivity
Biological Assay
quantitative analysis
bioactive properties
Echium plantagineum
bioassays
Boraginaceae
juglone
Cotyledon
Bioassay
extracts
coleoptiles
Chemical analysis
Spain
Triticum
wheat
Growth
cells

Grant Number

  • ARCDP130104346

Cite this

Durán, A. G., Gutiérrez, M. T., Rial, C., Torres, A., Varela, R. M., Valdivia, M. M., ... Macías, F. A. (2017). Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp. E. plantagineum and E. gaditanum. Phytochemistry, 141, 162-170. https://doi.org/10.1016/j.phytochem.2017.06.004
Durán, Alexandra G. ; Gutiérrez, M. Teresa ; Rial, Carlos ; Torres, Ascensión ; Varela, Rosa M. ; Valdivia, Manuel M. ; Molinillo, José M.G. ; Skoneczny, Dominik ; Weston, Leslie A. ; Macías, Francisco A. / Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp. E. plantagineum and E. gaditanum. In: Phytochemistry. 2017 ; Vol. 141. pp. 162-170.
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abstract = "Isohexenylnaphthazarins are commonly found in the root periderm of several Boraginaceous plants and are known for their broad range of biological activities. The work described herein concerns the biological activity of compounds from the roots of Echium plantagineum L. and Echium gaditanum Boiss (Boraginaceae) collected from field sites in southern Spain and Australia. Bioactivity was assessed using etiolated wheat coleoptile bioassay and in vitro growth inhibitory activity in HeLa and IGROV-1 cells. The quantification of four isohexenylnaphthazarins (shikonin/alkannin, deoxyshikonin/deoxyalkannin, acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin) was performed by LC-MS/MS using juglone as internal standard. Correlation coefficient values for the activities and concentrations of these four analytes were in the linear range and were greater than 0.99. Acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin were present in the highest concentrations in extracts of both species. The results reveal that greatest overall inhibition was observed in both bioassays with E. gaditanum extracts. Strong correlations between time of collection, sampling location and bioactivity were identified.",
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Durán, AG, Gutiérrez, MT, Rial, C, Torres, A, Varela, RM, Valdivia, MM, Molinillo, JMG, Skoneczny, D, Weston, LA & Macías, FA 2017, 'Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp. E. plantagineum and E. gaditanum', Phytochemistry, vol. 141, pp. 162-170. https://doi.org/10.1016/j.phytochem.2017.06.004

Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp. E. plantagineum and E. gaditanum. / Durán, Alexandra G.; Gutiérrez, M. Teresa; Rial, Carlos; Torres, Ascensión; Varela, Rosa M.; Valdivia, Manuel M.; Molinillo, José M.G.; Skoneczny, Dominik; Weston, Leslie A.; Macías, Francisco A.

In: Phytochemistry, Vol. 141, 09.2017, p. 162-170.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp.

T2 - E. plantagineum and E. gaditanum

AU - Durán, Alexandra G.

AU - Gutiérrez, M. Teresa

AU - Rial, Carlos

AU - Torres, Ascensión

AU - Varela, Rosa M.

AU - Valdivia, Manuel M.

AU - Molinillo, José M.G.

AU - Skoneczny, Dominik

AU - Weston, Leslie A.

AU - Macías, Francisco A.

N1 - Includes bibliographical references.

PY - 2017/9

Y1 - 2017/9

N2 - Isohexenylnaphthazarins are commonly found in the root periderm of several Boraginaceous plants and are known for their broad range of biological activities. The work described herein concerns the biological activity of compounds from the roots of Echium plantagineum L. and Echium gaditanum Boiss (Boraginaceae) collected from field sites in southern Spain and Australia. Bioactivity was assessed using etiolated wheat coleoptile bioassay and in vitro growth inhibitory activity in HeLa and IGROV-1 cells. The quantification of four isohexenylnaphthazarins (shikonin/alkannin, deoxyshikonin/deoxyalkannin, acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin) was performed by LC-MS/MS using juglone as internal standard. Correlation coefficient values for the activities and concentrations of these four analytes were in the linear range and were greater than 0.99. Acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin were present in the highest concentrations in extracts of both species. The results reveal that greatest overall inhibition was observed in both bioassays with E. gaditanum extracts. Strong correlations between time of collection, sampling location and bioactivity were identified.

AB - Isohexenylnaphthazarins are commonly found in the root periderm of several Boraginaceous plants and are known for their broad range of biological activities. The work described herein concerns the biological activity of compounds from the roots of Echium plantagineum L. and Echium gaditanum Boiss (Boraginaceae) collected from field sites in southern Spain and Australia. Bioactivity was assessed using etiolated wheat coleoptile bioassay and in vitro growth inhibitory activity in HeLa and IGROV-1 cells. The quantification of four isohexenylnaphthazarins (shikonin/alkannin, deoxyshikonin/deoxyalkannin, acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin) was performed by LC-MS/MS using juglone as internal standard. Correlation coefficient values for the activities and concentrations of these four analytes were in the linear range and were greater than 0.99. Acetylshikonin/acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin were present in the highest concentrations in extracts of both species. The results reveal that greatest overall inhibition was observed in both bioassays with E. gaditanum extracts. Strong correlations between time of collection, sampling location and bioactivity were identified.

KW - Bioactivity

KW - Boraginaceae

KW - Echium gaditanum

KW - Echium plantagineum

KW - LC-MS-MS

KW - Naphthoquinones

KW - Quantification

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