Euphosantianane A⁻D: Antiproliferative Premyrsinane Diterpenoids from the Endemic Egyptian Plant Euphorbia Sanctae-Catharinae

Mohamed-Elamir F Hegazy; Ahmed R Hamed; Mahmoud A A Ibrahim; Zienab Talat; Eman H Reda; Nahla S Abdel-Azim; Faiza M Hammouda; Seikou Nakamura; Hisashi Matsuda; Eman G Haggag; Paul W Paré; Thomas Efferth

doi:10.3390/molecules23092221

Euphosantianane A⁻D: Antiproliferative Premyrsinane Diterpenoids from the Endemic Egyptian Plant Euphorbia Sanctae-Catharinae

Molecules. 2018 Sep 1;23(9):2221. doi: 10.3390/molecules23092221.

Authors

Mohamed-Elamir F Hegazy^{1

2}, Ahmed R Hamed^{3

4}, Mahmoud A A Ibrahim⁵, Zienab Talat⁶, Eman H Reda⁷, Nahla S Abdel-Azim⁸, Faiza M Hammouda⁹, Seikou Nakamura¹⁰, Hisashi Matsuda¹¹, Eman G Haggag¹², Paul W Paré¹³, Thomas Efferth¹⁴

Affiliations

¹ Chemistry of Medicinal Plants Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza 12622, Egypt. Elamir77@live.com.
² Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, University of Mainz, Staudinger Weg 5, 55128 Mainz, Germany. Elamir77@live.com.
³ Chemistry of Medicinal Plants Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza 12622, Egypt. n1ragab2004@yahoo.com.
⁴ Biology Unit, Central Laboratory for Pharmaceutical and Drug Industries Research Division, National Research Centre, 33 El-Bohouth St., Dokki, Giza 12622, Egypt. n1ragab2004@yahoo.com.
⁵ Computational Chemistry Laboratory, Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt. m.ibrahim@compchem.net.
⁶ Phytochemistry Lab., National Organization for Drug Control and Research, Giza 12622, Egypt. zizishakour@yahoo.com.
⁷ Phytochemistry Lab., National Organization for Drug Control and Research, Giza 12622, Egypt. dremanhusseinreda@gmail.com.
⁸ Chemistry of Medicinal Plants Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza 12622, Egypt. nahlaabdelazim@yahoo.com.
⁹ Chemistry of Medicinal Plants Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza 12622, Egypt. fmhammouda@yahoo.com.
¹⁰ Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
¹¹ Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan. matsuda@mb.kyoto-phu.ac.jp.
¹² Department of Pharmacognosy, Helwan University, Cairo 12622, Egypt. wemisr@hotmail.com.
¹³ Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA. paul.pare@ttu.edu.
¹⁴ Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, University of Mainz, Staudinger Weg 5, 55128 Mainz, Germany. efferth@uni-mainz.de.

Abstract

Euphorbia species are rich in diterpenes. A solvent extraction of Euphorbia sanctae-catharinae, a species indigenous to the Southern Sinai of Egypt, afforded several premyrsinane diterpenoids (1⁻4) as well as previously reported metabolites (5⁻13) that included three flavonoids. Isolated compounds were chemically characterized by spectroscopic analysis. Identified compounds were bioassayed for anti-proliferative activity in vitro against colon (Caco-2) and lung (A549) tumor cell lines. Compound 9 exhibited robust anti-proliferative activity against A549 cells (IC₅₀ = 3.3 µM). Absolute configurations for 8 versus 9 were determined by experimental and TDDFT-calculated electronic circular dichorism (ECD) spectra.

Keywords: Euphorbia sanctae-catharinae; Euphorbiaceae; TDDTF-ECD; diterpenes; flavonoids; tumor anti-proliferative activity.

MeSH terms

A549 Cells
Caco-2 Cells
Carbon-13 Magnetic Resonance Spectroscopy
Cell Proliferation / drug effects
Circular Dichroism
Diterpenes / chemistry
Diterpenes / pharmacology*
Euphorbia / chemistry*
Humans
Inhibitory Concentration 50
Proton Magnetic Resonance Spectroscopy

Substances

Diterpenes
euphosantianane A
euphosantianane D

Abstract

MeSH terms

Substances

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