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

doi: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

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

Faculty Office, Science and Health

Universidad de Cádiz

Research output: Contribution to journal › Article › peer-review

14 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 language	English
Pages (from-to)	162-170
Number of pages	9
Journal	Phytochemistry
Volume	141
Early online date	Jun 2017
DOIs	https://doi.org/10.1016/j.phytochem.2017.06.004
Publication status	Published - Sept 2017

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10.1016/j.phytochem.2017.06.004

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Durán, A. G., Gutiérrez, M. T., Rial, C., Torres, A., Varela, R. M., Valdivia, M. M., Molinillo, J. M. G., Skoneczny, D., Weston, L. A., & 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

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title = "Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp.: E. plantagineum and E. gaditanum",

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.",

keywords = "Bioactivity, Boraginaceae, Echium gaditanum, Echium plantagineum, LC-MS-MS, Naphthoquinones, Quantification",

author = "Dur{\'a}n, {Alexandra G.} and Guti{\'e}rrez, {M. Teresa} and Carlos Rial and Ascensi{\'o}n Torres and Varela, {Rosa M.} and Valdivia, {Manuel M.} and Molinillo, {Jos{\'e} M.G.} and Dominik Skoneczny and Weston, {Leslie A.} and Mac{\'i}as, {Francisco A.}",

note = "Includes bibliographical references.",

year = "2017",

month = sep,

doi = "10.1016/j.phytochem.2017.06.004",

language = "English",

volume = "141",

pages = "162--170",

journal = "Phytochemistry",

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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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U2 - 10.1016/j.phytochem.2017.06.004

DO - 10.1016/j.phytochem.2017.06.004

M3 - Article

C2 - 28633108

AN - SCOPUS:85020842557

SN - 0031-9422

VL - 141

SP - 162

EP - 170

JO - Phytochemistry

JF - Phytochemistry

ER -

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

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