Antiproliferative Trihydroxyalkylcyclohexenones from Pleiogynium timoriense

Abstract

Investigation of a DCM extract of the bark of Pleiogynium timoriense from the former Merck collection of natural product extracts for antiproliferative activity indicated that it was active with an IC50 value of 1.3 μg/mL against the A2780 ovarian cancer cell line. Bioassay-directed fractionation of this extract yielded the three new bioactive trihydroxyalkylcyclohexenones 1–3. Their structures were determined by a combination of spectroscopic and chemical methods. Compounds 1–3 exhibited submicromolar antiproliferative activity against the A2780 human ovarian cancer cell line, with IC50 values of 0.8, 0.7, and 0.8 μM, respectively.

Antihyperglycaemic and Antihyperlipidemic Activities of <i>Pleiogynium timorense</i> Seeds and Identification of Bioactive Compounds

“…Shimadzu UV-visible recording spectrophotometer model-UV 240 (NRC, Egypt). 1 H-NMR and 13 C-NMR (Varian Unity Inova). MS (Finnigan MAT SSQ 7000, 70 ev).…”

“…1 H-NMR spectral data of compound 3in CDCl 3 : 3.7 (s, 3H, Me), 6.9 (d, 2H, 3&5), 7.9 (d, 2H, 2&6) and 9.7 (s, 1H, CHO). 13 13 C NMR in CDCl3 spectral data of compound 5: δ 22.7 (C 3 and C4) &δ 51.09 (C2, C5).…”

“…From the seeds, α-amyrin and 5,24 (28)-cholestadien-24-methylen-3b-ol were isolated and identified [12]. The bark showed antiproliferative activity, in addition, three new bioactive trihydroxyalkylcyclohexenones were isolated and identified [13]. In our recent research, the constituents of the seeds and pericarp of the plant were identified by using HPLC-ESI-MS/MS [14].…”

Chemoenzymatic Synthesis of Pleiogenone A: An Antiproliferative Trihydroxyalkylcyclohexenone Isolated from Pleiogynium timorense

“…Several hydroxylated cyclohexenones recently reported have been shown to have potent biological activities . Alkylcyclohexenones 1 – 3 , named pleiogenones A–C (Scheme ), were isolated from the extract of the bark of Pleiogynium timorense and displayed IC 50 values of 0.8, 0.7, and 0.8 μ m , respectively, against the A2780 ovarian cancer cell line .…”

ChemInform Abstract: Chemoenzymatic Synthesis of Pleiogenone A: An Antiproliferative Trihydroxyalkylcyclohexenone Isolated from Pleiogynium timorense.

“…[1a] Alkylcyclohexenones 1-3,n amed pleiogenones A-C [1b] (Scheme 1), were isolated from the extract of the bark of Pleiogynium timorense and displayed IC 50 values of 0.8, 0.7, and 0.8 mm,r espectively, against the A2780 ovarian cancerc ell line. [1] (+)-3-O-Debenzoylzeylenone 4 is ac ongener of zeylenols that occurs in both enantiomeric series in various Uvaria species. [2] Structurally similar compounds, such as (À)-zeylenone, have shown antitumor and antifeedant activities.…”