Cytotoxic Prenylated Acetophenone Dimers from Acronychia pedunculata

Abstract

Three new acetophenone dimers or Acronychia-type acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC(50) values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively.

Ion tree-based structure elucidation of acetophenone dimers (AtA) fromAcronychia pedunculataand their identification in extracts by liquid chromatography electrospray ionization LTQ-Orbitrap mass spectrometry

“…The reference AtA investigated in this study (Fig. ) have been previously isolated from the trunk bark of Acronychia pedunculata and unambiguously identified by spectroscopic methods . The purity of all compounds was determined by Reversed Phase High Performance Liquid Chromatography equipped with photodiode array detector (RP‐HPLC‐PDA) and found >89%.…”

“…A standard mixture of the reference compounds (10 µg/ml) was also prepared. For the preparation of the Acronychia extracts, a previous method was applied . Briefly, an aliquot of 2 g of plant material was extracted using a two steps procedure.…”

“…Their biological interest is focused mainly on their significant cytotoxicity against several human tumor cell lines and anti‐inflammatory activities . Up to date, a small number of derivatives have been reported exhibiting high potential as anticancer agents against human melanoma and prostate tumor cell lines . The cytotoxicity of these compounds seems to be strongly associated to the different structural elements of the core structure of AtA modulating their biological properties.…”

“…This particular nature of AtA renders their identification challenging, and until now, limited data have been reported for the structure elucidation thereof. A previous study presenting the X‐ray crystallography of acrovestone ( 1 ), a model AtA compound, is available, but mainly, the structure elucidation of these compounds has been performed using nuclear magnetic resonance techniques . However, high temperature nuclear magnetic resonance (47 °C) acquisitions and nuclear Overhauser effect experiments are highly required for the elucidation of isomers .…”

Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata

“…Interesting dimeric acetophenones, such as acrove-stone, acropyrone, and acropyraonols, are found only in Acronychia . 4–8 …”