Acetophenone Monomers from <i>Acronychia trifoliolata</i>

Miyake, Katsunori; Suzuki, Airi; Morita, Chihiro; Goto, Masuo; Newman, David J.; O’Keefe, Barry R.; Morris‐Natschke, Susan L.; Lee, Kuo Hsiung̀; Nakagawa‐Goto, Kyoko

doi:10.1021/acs.jnatprod.6b00645

Cited by 17 publications

(36 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The physical data ( 1 H NMR, 13 C NMR, HRMS) were essentially identical to the reported data for the natural product. 9 …”

Section: Methodsmentioning

confidence: 99%

“…7 In the course of the discovery of unknown bioactive natural products from rainforest plants, six new acetophenone monomers, named acronyculatins I ( 1 ), J ( 2 ), K ( 3 ), L ( 4 ), M, N ( 5 ), and O ( 6 ), were isolated from a 1:1 CH 3 OH/CH 2 Cl 2 extract of this plant. 9 In addition, the structure of acronyculatin B ( 7 ), originally identified by Su et al, 10 was revised to be 1-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-methylbut-2-en-1-yl)-2,3-dihydrobenzofuran-5-yl]ethan-1-one based on extensive NMR studies. Because the isolation was performed on a limited amount (4.9 g) of extract provided by the U.S. National Cancer Institute (NCI), and no more material was available, small quantities of each compound were obtained.…”

mentioning

confidence: 99%

“…Compounds 1 – 7 showed weak or no antiproliferative activity. 9 However, prior studies have indicated that acetophenone derivatives display potent inhibition of tumor-promoting activities. 11,12 In addition, the importance of a prenyl-like functional group was discussed in our previous reports.…”

mentioning

confidence: 99%

See 2 more Smart Citations

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

et al. 2016

Self Cite

View full text Add to dashboard Cite

Six acetophenone derivatives, acronyculatins I (1), J (2), K (3), L (4), N (5), and O (6), were recently isolated from Acronychia trifoliolata, and the structure of the known acronyculatin B (7) was revised. Because of the limited quantities of isolated products as well as their structure similarity, racemic acronyculatins I–L, N, O, and B (1–7) were synthesized to confirm their structures and to obtain sufficient material for biological evaluation. Trihydroxyacetophenone was converted to the target compounds by various sequences of hydroxy group protection, allylation or prenylation, and epoxidation followed by cyclization. C-Prenylations were carried out by direct addition of a prenyl group or through 1,3- or 3,3-sigmatropic rearrangement. The synthesized racemic compounds were evaluated in an anti-tumor-promoting assay using the Epstein–Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. All tested compounds significantly inhibited EBV-EA activation. Especially, racemic acronyculatin I (1) displayed the most potent inhibitory effects, with an IC50 value of 7.3 μM.

show abstract

“…The physical data ( 1 H NMR, 13 C NMR, HRMS) were essentially identical to the reported data for the natural product. 9 …”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 2016

Self Cite

View full text Add to dashboard Cite

show abstract

“…In a continuing investigation on bioactive compounds from rainforest plants, 10 L. corymbulosa was selected for exploration of its cytotoxic components. A CH 3 OH–CH 2 Cl 2 (1:1) extract of the bark of this species (N005829), as provided by the U.S. National Cancer Institute (NCI, Frederick, MD, USA), was found to exhibit broad cytotoxicity in the NCI-60 human tumor cell assay (IC 50 < 10 µg/mL against all 60 cell lines, as performed by NCI in 1989).…”

mentioning

confidence: 99%

Corymbulosins D–H, 2-Hydroxy- and 2-Oxo-clerodane Diterpenes from the Bark of Laetia corymbulosa

et al. 2017

Self Cite

View full text Add to dashboard Cite

A bioactive CH3OH–CH2Cl2 (1:1) extract of the bark of Laetia corymbulosa provided five new clerodane diterpenes with an isozuelanin skeleton, designated as corymbulosins D–H (1–5), as well as the known corymbulosins B (6) and C (7), for which the relative configurations were not previously determined. The structures of 1–5 were characterized on the basis of 1D and 2D NMR spectroscopic and HRMS analysis. The absolute configurations of all isolated compounds 1–7 were verified through chemical methods, including modified Mosher esterifications or oxidation of the hydroxy group at C-2, ECD experiments, and spectroscopic data comparison. The isolated compounds were evaluated for antiproliferative activity against a small panel of human cancer cell lines.

show abstract

“…[13,14] We previously reported the new acetophenones acrophenone A, B and C and several known acetophenone dimer compounds, [15] such as acrovestenol and acrovestone. Previous reports [9,11,[16][17][18] have indicated that the biological activities of acetophenone monomers are low. Our experiments have also shown that the acetophenone monomers prenylacronylin and acronylin, which are predicted to be components in acetophenone dimers, have cytotoxic effects.…”

Section: Introductionmentioning

confidence: 99%

Acrofolione A and B, acetophenone dimers from Acronychia pendunculata, induce an apoptotic effect on human NALM-6 pre-B cell leukaemia cells

Matsui

Ito

Kato

et al. 2019

Journal of Pharmacy and Pharmacology

View full text Add to dashboard Cite

Objectives We investigated the apoptotic activities of acrofolione A (1) and B (2) isolated from Acronychia pedunculata against a human pre‐B cell leukaemia cell line (NALM‐6) to explore the apoptosis‐related signalling molecules targeted by 1 and 2. Methods The apoptosis effects of 1 and 2 in NALM‐6 cells were investigated by TUNEL staining, annexin V, mitochondria membrane potential and caspase 3/7 activity. We carried out a protein array to explore the signalling molecules involved in apoptosis comprehensively. Key findings Acrofolione A (1) suppressed the growth of NALM‐6, K562 and HPB‐ALL cells (IC50 16.7 ± 1.9, 17.9 ± 0.3 and 10.1 ± 0.2 μm, respectively) more effectively than acrofolione B (2). Both compounds time‐dependently increased the number of NALM‐6 cells with abnormal nuclei, and increased the number of annexin V‐positive cells and decreased the mitochondrial membrane potential of NALM‐6 cells. Acrofolione A (1) markedly elevated caspase 3/7 activity and increased the number of TUNEL‐positive cells. Cells treated with either compound showed enhanced expression of cleaved PARP and cleaved caspase 3 and 7, and reduced survivin protein levels. Conclusions Acrofolione A (1) and B (2) may be useful in the treatment of various types of leukaemia.

show abstract

Acetophenone Monomers from Acronychia trifoliolata

Cited by 17 publications

References 15 publications

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

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

Corymbulosins D–H, 2-Hydroxy- and 2-Oxo-clerodane Diterpenes from the Bark of Laetia corymbulosa

Acrofolione A and B, acetophenone dimers from Acronychia pendunculata, induce an apoptotic effect on human NALM-6 pre-B cell leukaemia cells

Contact Info

Product

Resources

About