Potent Antibacterial Prenylated Acetophenones from the Australian Endemic Plant Acronychia crassipetala

Tran, Trong D.; Olsson, Malin A; McMillan, David; Cullen, Jason K.; Parsons, Peter G.; Reddell, Paul; Ogbourne, Steven M.

doi:10.3390/antibiotics9080487

Cited by 14 publications

(9 citation statements)

References 29 publications

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“…Cell growth/survival assays. Cell growth/ survival of non-adherent K562 cells (3 × 10 3 cells per well) was determined using the CellTiter 96 AQueous One Solution cell proliferation assay kit as previously described 57 . Cell growth/survival of adherent cell lines (3 × 10 3 cells per well) was determined using a sulforhodamine B (SRB) assay as previously detailed 16 .…”

Section: Methodsmentioning

confidence: 99%

Activation of PKC supports the anticancer activity of tigilanol tiglate and related epoxytiglianes

Cullen

Boyle

Yap

et al. 2021

Sci Rep

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The long-standing perception of Protein Kinase C (PKC) as a family of oncoproteins has increasingly been challenged by evidence that some PKC isoforms may act as tumor suppressors. To explore the hypothesis that activation, rather than inhibition, of these isoforms is critical for anticancer activity, we isolated and characterized a family of 16 novel phorboids closely-related to tigilanol tiglate (EBC-46), a PKC-activating epoxytigliane showing promising clinical safety and efficacy for intratumoral treatment of cancers. While alkyl branching features of the C12-ester influenced potency, the 6,7-epoxide structural motif and position was critical to PKC activation in vitro. A subset of the 6,7-epoxytiglianes were efficacious against established tumors in mice; which generally correlated with in vitro activation of PKC. Importantly, epoxytiglianes without evidence of PKC activation showed limited antitumor efficacy. Taken together, these findings provide a strong rationale to reassess the role of PKC isoforms in cancer, and suggest in some situations their activation can be a promising strategy for anticancer drug discovery.

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Section: Methodsmentioning

confidence: 99%

Activation of PKC supports the anticancer activity of tigilanol tiglate and related epoxytiglianes

Cullen

Boyle

Yap

et al. 2021

Sci Rep

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“…Moreover, enhanced research is needed to conserve the species and to obtain new sources for further natural product discovery. Acetophenones and chromenes have been discovered in 14 species of Melicope [ 11 , 14 , 15 , 16 , 17 , 27 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 ] as well as in some species of its close relatives Acronychia and Medicosma [ 33 , 46 , 59 , 60 , 61 , 62 , 63 , 64 ]. Due to the great variability of the acetophenones and chromenes in these genera, they may be of interest as biomarkers for chemotaxonomy.…”

Section: Resultsmentioning

confidence: 99%

New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray

Bandolik

Kassack

et al. 2021

Molecules

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The dichloromethane extract from leaves of Melicope barbigera (Rutaceae), endemic to the Hawaiian island of Kaua’i, yielded four new and three previously known acetophenones and 2H-chromenes, all found for the first time in M. barbigera. The structures of the new compounds obtained from the dichloromethane extract after purification by chromatographic methods were unambiguously elucidated by spectroscopic analyses including 1D/2D NMR spectroscopy and HRESIMS. The absolute configuration was determined by modified Mosher’s method. Compounds 2, 4 and the mixture of 6 and 7 exhibited moderate cytotoxic activities against the human ovarian cancer cell line A2780 with IC50 values of 30.0 and 75.7 µM for 2 and 4, respectively, in a nuclear shrinkage cytotoxicity assay.

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“…Careful separation by reverse-phase chromatography provided pure samples of the two prenylation products 7a and 7b for biological assays. As O -prenylation is a modification found in antimicrobial natural flavonoids and acetophloroglucinols [ 37 ], the O -prenylated DHC 7b was also subjected to biological assays.…”

Section: Resultsmentioning

confidence: 99%

Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor

et al. 2021

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Several families of naturally occurring C-alkylated dihydrochalcones display a broad range of biological activities, including antimicrobial and cytotoxic properties, depending on their alkylation sidechain. The catalytic Friedel–Crafts alkylation of the readily available aglycon moiety of neohesperidin dihydrochalcone was performed using cinnamyl, benzyl, and isoprenyl alcohols. This procedure provided a straightforward access to a series of derivatives that were structurally related to natural balsacones, uvaretin, and erioschalcones, respectively. The antibacterial and cytotoxic potential of these novel analogs was evaluated in vitro and highlighted some relations between the structure and the pharmacological properties of alkylated dihydrochalcones.

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Potent Antibacterial Prenylated Acetophenones from the Australian Endemic Plant Acronychia crassipetala

Cited by 14 publications

References 29 publications

Activation of PKC supports the anticancer activity of tigilanol tiglate and related epoxytiglianes

Activation of PKC supports the anticancer activity of tigilanol tiglate and related epoxytiglianes

New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray

Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor

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