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Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica

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Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica. / Zhang, Rong-Rong; Tian, Hai-Yan; Tan, Ya-Fang et al.
In: Organic and Biomolecular Chemistry , Vol. 12, No. 44, 2014, p. 8919-8929.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Zhang, R-R, Tian, H-Y, Tan, Y-F, Chung, T-Y, Sun, X-H, Xia, X, Ye, W-C, Middleton, DA, Fedosova, N, Esmann, M, Tzen, JTC & Jiang, R-W 2014, 'Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica', Organic and Biomolecular Chemistry , vol. 12, no. 44, pp. 8919-8929. https://doi.org/10.1039/c4ob01545b

APA

Zhang, R-R., Tian, H-Y., Tan, Y-F., Chung, T-Y., Sun, X-H., Xia, X., Ye, W-C., Middleton, D. A., Fedosova, N., Esmann, M., Tzen, J. T. C., & Jiang, R-W. (2014). Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica. Organic and Biomolecular Chemistry , 12(44), 8919-8929. https://doi.org/10.1039/c4ob01545b

Vancouver

Zhang R-R, Tian H-Y, Tan Y-F, Chung T-Y, Sun X-H, Xia X et al. Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica. Organic and Biomolecular Chemistry . 2014;12(44):8919-8929. Epub 2014 Sept 17. doi: 10.1039/c4ob01545b

Author

Zhang, Rong-Rong ; Tian, Hai-Yan ; Tan, Ya-Fang et al. / Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica. In: Organic and Biomolecular Chemistry . 2014 ; Vol. 12, No. 44. pp. 8919-8929.

Bibtex

@article{f96f4fa6c08a485c89f4eb39cd1ca106,
title = "Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica",
abstract = "Five new cardenolide lactates (1-5) and one new dioxane double linked cardenolide glycoside (17) along with 15 known compounds (6-16 and 18-21) were isolated from the ornamental milkweed Asclepias curassavica. Their structures were elucidated by extensive spectroscopic methods (IR, UV, MS, 1D- and 2D-NMR). The molecular structures and absolute configurations of 1-3 and 17 were further confirmed by single-crystal X-ray diffraction analysis. Simultaneous isolation of dioxane double linked cardenolide glycosides (17-21) and cardenolide lactates (1-5) provided unique chemotaxonomic markers for this genus. Compounds 1-21 were evaluated for the inhibitory activities against DU145 prostate cancer cells. The dioxane double linked cardenolide glycosides showed the most potent cytotoxic effect followed by normal cardenolides and cardenolide lactates, while the C21 steroids were non-cytotoxic. Enzymatic assay established a correlation between the cytotoxic effects in DU145 cancer cells and the K-i for the inhibition of Na+, K+-ATPase. Molecular docking analysis revealed relatively strong H-bond interactions between the bottom of the binding cavity and compounds 18 or 20, and explained why the dioxane double linked cardenolide glycosides possessed higher inhibitory potency on Na+, K+-ATPase than the cardenolide lactate.",
keywords = "CARDIAC-GLYCOSIDES, CARDIOTONIC STEROIDS, CRYSTAL-STRUCTURE, BINDING, STEREOCHEMISTRY, NA+,K+-ATPASE, PRINCIPLES, POTASSIUM, INSIGHTS, AGENTS",
author = "Rong-Rong Zhang and Hai-Yan Tian and Ya-Fang Tan and Tse-Yu Chung and Xiao-Hui Sun and Xue Xia and Wen-Cai Ye and Middleton, {David A.} and Natalya Fedosova and Mikael Esmann and Tzen, {Jason T. C.} and Ren-Wang Jiang",
year = "2014",
doi = "10.1039/c4ob01545b",
language = "English",
volume = "12",
pages = "8919--8929",
journal = "Organic and Biomolecular Chemistry ",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "44",

}

RIS

TY - JOUR

T1 - Structures, chemotaxonomic significance, cytotoxic and Na+, K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica

AU - Zhang, Rong-Rong

AU - Tian, Hai-Yan

AU - Tan, Ya-Fang

AU - Chung, Tse-Yu

AU - Sun, Xiao-Hui

AU - Xia, Xue

AU - Ye, Wen-Cai

AU - Middleton, David A.

AU - Fedosova, Natalya

AU - Esmann, Mikael

AU - Tzen, Jason T. C.

AU - Jiang, Ren-Wang

PY - 2014

Y1 - 2014

N2 - Five new cardenolide lactates (1-5) and one new dioxane double linked cardenolide glycoside (17) along with 15 known compounds (6-16 and 18-21) were isolated from the ornamental milkweed Asclepias curassavica. Their structures were elucidated by extensive spectroscopic methods (IR, UV, MS, 1D- and 2D-NMR). The molecular structures and absolute configurations of 1-3 and 17 were further confirmed by single-crystal X-ray diffraction analysis. Simultaneous isolation of dioxane double linked cardenolide glycosides (17-21) and cardenolide lactates (1-5) provided unique chemotaxonomic markers for this genus. Compounds 1-21 were evaluated for the inhibitory activities against DU145 prostate cancer cells. The dioxane double linked cardenolide glycosides showed the most potent cytotoxic effect followed by normal cardenolides and cardenolide lactates, while the C21 steroids were non-cytotoxic. Enzymatic assay established a correlation between the cytotoxic effects in DU145 cancer cells and the K-i for the inhibition of Na+, K+-ATPase. Molecular docking analysis revealed relatively strong H-bond interactions between the bottom of the binding cavity and compounds 18 or 20, and explained why the dioxane double linked cardenolide glycosides possessed higher inhibitory potency on Na+, K+-ATPase than the cardenolide lactate.

AB - Five new cardenolide lactates (1-5) and one new dioxane double linked cardenolide glycoside (17) along with 15 known compounds (6-16 and 18-21) were isolated from the ornamental milkweed Asclepias curassavica. Their structures were elucidated by extensive spectroscopic methods (IR, UV, MS, 1D- and 2D-NMR). The molecular structures and absolute configurations of 1-3 and 17 were further confirmed by single-crystal X-ray diffraction analysis. Simultaneous isolation of dioxane double linked cardenolide glycosides (17-21) and cardenolide lactates (1-5) provided unique chemotaxonomic markers for this genus. Compounds 1-21 were evaluated for the inhibitory activities against DU145 prostate cancer cells. The dioxane double linked cardenolide glycosides showed the most potent cytotoxic effect followed by normal cardenolides and cardenolide lactates, while the C21 steroids were non-cytotoxic. Enzymatic assay established a correlation between the cytotoxic effects in DU145 cancer cells and the K-i for the inhibition of Na+, K+-ATPase. Molecular docking analysis revealed relatively strong H-bond interactions between the bottom of the binding cavity and compounds 18 or 20, and explained why the dioxane double linked cardenolide glycosides possessed higher inhibitory potency on Na+, K+-ATPase than the cardenolide lactate.

KW - CARDIAC-GLYCOSIDES

KW - CARDIOTONIC STEROIDS

KW - CRYSTAL-STRUCTURE

KW - BINDING

KW - STEREOCHEMISTRY

KW - NA+,K+-ATPASE

KW - PRINCIPLES

KW - POTASSIUM

KW - INSIGHTS

KW - AGENTS

U2 - 10.1039/c4ob01545b

DO - 10.1039/c4ob01545b

M3 - Journal article

VL - 12

SP - 8919

EP - 8929

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 44

ER -