Synthetic secofriedelane and friedelane derivatives as inhibitors of human lymphocyte proliferation and growth of human cancer cell lines in vitro.

Abstract

Controlled silylation of friedelin (1) from cork smoker wash solids, a byproduct generated during processing of corkboard by steam baking, gave 3-trimethylsiloxyfriedel-2-ene (3) in high yields. Oxidation of 3 with OsO(4)/NMMO produced 2alpha-hydroxyfriedelan-3-one (cerin) (5), from which the new 2,3-secofriedelan-2-al-3-oic acid (6) was obtained quantitatively by periodic acid oxidation. Oxidation of 3 with DDQ afforded friedel-1-en-3-one (8). Reductive ozonolysis of 3 gave 2alpha,3beta-dihydroxyfriedelane, pachysandiol A (7). Compound 6 proved to be a potent inhibitor of human lymphocyte proliferation (IC(50) = 10.7 microM) and of the growth of a human cancer cell line (GI(50) = 5.4-17.2 microM). (13)C NMR data for compounds (3, 4, 5, 6a,7, and 8) are described for the first time.

• Authors: C Moiteiro, F Justino, R Tavares, M J Marcelo-Curto, M H Florêncio, M S Nascimento, M Pedro, F Cerqueira, M M Pinto
• Journal: Journal of natural products (J Nat Prod) Vol. 64 Issue 10 Pg. 1273-7 (Oct 2001) ISSN: 0163-3864 [Print] United States
• PMID: 11678649 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 2,3-secofriedelan-2-al-3-oic acid
• 2-hydroxyfriedelan-3-one
• 3-trimethylsiloxyfriedel-2-ene
• Antineoplastic Agents, Phytogenic
• Triterpenes
• friedel-1-en-3-one
• friedelane

Topics

• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Brain Neoplasms
• Breast Neoplasms
• Chromatography, Thin Layer
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor
• Humans
• Inhibitory Concentration 50
• Kidney Neoplasms
• Lung Neoplasms
• Lymphocytes (drug effects)
• Magnetic Resonance Spectroscopy
• Melanoma
• Molecular Structure
• Oxidation-Reduction
• Portugal
• Quercus (chemistry)
• Structure-Activity Relationship
• Triterpenes (chemistry, isolation & purification, pharmacology)
• Tumor Cells, Cultured (drug effects)