New immunosuppressive cyclomyrsinol diterpenes from Euphorbia kopetdaghi Prokh

• Published in: Natural product research Vol. 27; no. 3; pp. 246 - 254
• Main Authors: Ghanadian, Syed Mustafa, Ayatollahi, Abdul Majid, Mesaik, M. Ahmed, Abdalla, Omer Mohamed
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis Group 01-02-2013
• Subjects: 3T3-L1 Cells; Animals; Cell Line; Cell Proliferation - drug effects; cytotoxicity; Diterpenes - chemistry; Diterpenes - pharmacology; Euphorbia; Euphorbia - chemistry; Euphorbiaceae; immunomodulation; Immunosuppressive Agents - chemistry; Immunosuppressive Agents - pharmacology; Lymphocytes - drug effects; Magnetic Resonance Spectroscopy; Mice; Molecular Structure; NMR spectra; Phagocytes - drug effects; Rats; terpenoids
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2012.671318

Aceton : chloroform (1 : 2) extracts of the aerial parts of Euphorbia kopetdaghi Prokh. (Euphorbiaceae) were investigated for its diterpenoids and afforded three new five-membered ring, pentacyclic myrisinane polyester comprised of 3,5,10-O-triacetyl-8-O-isobutanoyl-14-O-benzoylcyclomyrsinol (1), 3,5,10,14-O-tetraacetyl-8-O-(2′-methyl butanoyl)-cyclomyrsinol (2) and 3,5,10,14-O-tetracetyl-8-O-isobutanoylcyclomyrsinol (3). The structures were elucidated based on
13
C- and
1
H-NMR as well as 2D-NMR, IR and different MS spectra and the immunomodulation activity for compound 1 was evaluated through lymphocyte proliferation assay, IL-2 assay, oxidative burst of phagocytic leukocytes and through their cytotoxicity on two cell lines. Compound 1 showed significant suppressive activity against phytohemagglutinin-activated T-cell proliferation with an IC
50
of 1.83 µg mL
−1
, IL-2 suppressive activity with an IC
50
of 19.0 µg mL
−1
and oxidative burst suppressive activity with an IC
50
of 1.6 µg mL
−1
and ignorable cytotoxic effect on the CC-1 rat hepatocyte and 3T3-L1 mouse fibroblast cell-lines.