Prenylflavonoids isolated from Artocarpus champeden with TRAIL-resistance overcoming activity

Minakawa, Tomohiro; Toume, Kazufumi; Arai, Midori A.; Koyano, Takashi; Kowithayakorn, Thaworn; Ishibashi, Masami

doi:10.1016/j.phytochem.2013.08.015

Cited by 11 publications

(17 citation statements)

References 26 publications

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“…9 A previous study reported that ROS modulated TRAIL signals by enhancing DR5 expression 20 Collectively, artonin E (5) and heterophyllin (8) may be presumed to be responsible for most of the effects on the TRAIL signaling pathway by the A. communis root extract investigated.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Prenylated Flavonoids and Resveratrol Derivatives Isolated from Artocarpus communis with the Ability to Overcome TRAIL Resistance

et al. 2014

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In a screening program on natural products that can abrogate tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) resistance, four new prenylated flavonoid and resveratrol derivatives (1-4) were isolated from Artocarpus communis, together with eight known prenylflavonoids (5-12). The structures of 1-4 were elucidated spectroscopically. Pannokin D [corrected] (1) (2 μM) and artonin E (5) (3 μM) potently exhibited the ability to overcome TRAIL resistance. Artonin E (5) induced caspase-dependent apoptosis in combination with TRAIL, increased caspase 3/7 activity, and enhanced the protein levels of p53 and DR5. Moreover, this substance decreased cell viability in combination with TRAIL and enhanced the protein levels of DR5, and these effects were mediated by increases in the production of ROS (reactive oxygen species). Thus, artonin E (5) was found to induce extrinsic apoptotic cell death by the ROS- and p53-mediated up-regulation of DR5 expression in AGS cells.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Prenylated Flavonoids and Resveratrol Derivatives Isolated from Artocarpus communis with the Ability to Overcome TRAIL Resistance

et al. 2014

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“…Therefore, identifying compounds that can overcome TRAIL-resistance has become an important strategy in the development of new anticancer drugs. The ability of chromomycin A 3 ( 2 ) to overcome TRAIL resistance was evaluated using the previously described method [14,15]. As shown in Figure 3, the treatment of AGS cells with 100 ng/mL TRAIL for 24 h resulted in only a slight decrease in cell viability (20%), while luteolin [16] at 17.5 μM, which was used as a positive control, was 35% more potent when administered in combination with TRAIL than when the compound was administrated alone.…”

Section: Resultsmentioning

confidence: 99%

Chromomycins A2 and A3 from Marine Actinomycetes with TRAIL Resistance-Overcoming and Wnt Signal Inhibitory Activities

et al. 2014

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A biological screening study of an actinomycetes strain assembly was conducted using a cell-based cytotoxicity assay. The CKK1019 strain was isolated from a sea sand sample. Cytotoxicity-guided fractionation of the CKK1019 strain culture broth, which exhibited cytotoxicity, led to the isolation of chromomycins A2 (1) and A3 (2). 1 and 2 showed potent cytotoxicity against the human gastric adenocarcinoma (AGS) cell line (IC50 1; 1.7 and 2; 22.1 nM), as well as strong inhibitory effects against TCF/β-catenin transcription (IC50 1; 1.8 and 2; 15.9 nM). 2 showed the ability to overcome tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) resistance. To the best of our knowledge, the effects of chromomycins A2 (1) and A3 (2) on TRAIL resistance-overcoming activity, and on the Wnt signaling pathway, have not been reported previously. Thus, 1 and 2 warrant potential drug lead studies in relation to TRAIL-resistant and Wnt signal-related diseases and offer potentially useful chemical probes for investigating TRAIL resistance and the Wnt signaling pathway.

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“…The isolation of a number of prenylated flavonoids was previously described from its heartwood. 39) Bioassay activity-guided separation of A. champeden roots resulted in the isolation of six com- pounds, pannokins A-C (29-31), 40) artonin B (32), 41,42) artoheterophyllin D (33), 43) and heterophyllin (34) 44) (Fig. 12).…”

Section: Prenylflavonoids From Artocarpus Champedenmentioning

confidence: 99%

“…Experimental evidence showed that the apoptotic cell death induced by the combined treatment of AGS cells with 34 and TRAIL was due to C/ EBP-homologous protein (CHOP)-dependent upregulation of DR5 expression to induce apoptosis. 40) …”

Section: Prenylflavonoids From Artocarpus Champedenmentioning

confidence: 99%

“…Its sprouts and fruit are traditionally used for the treatment of cancer. 45) Bioassay-guided separation of P. pinnata fruit collected from Bangladesh led to the isolation of a new compound (35) 46) together with six known compounds (36)(37)(38)(39)(40)(41), which were identified as 5-methoxy-(3″,4″-dihydro-3″,4″-diacetoxy)-2″,2″-dimethylpyrano- ( [2″,3″:7,8] furanoflavone 50) (40), and isopongaflavone 51) (41), respectively (Fig. 14).…”

Section: Flavonoids From the Fruit Of Pongamia Pinnatamentioning

confidence: 99%

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Bio-active Natural Products with TRAIL-Resistance Overcoming Activity

Ahmed

Ishibashi

2016

Chem. Pharm. Bull.

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Tumor necrosis factor related apoptosis-inducing ligand (TRAIL) has emerged as a promising anticancer agent as it selectively kills cancer cells. However, TRAIL resistance limits its use as a therapeutic agent. An understanding the mechanisms responsible for TRAIL resistance and strategies to overcome it are important for its effective use as an anticancer agent. During our studies to screen natural products from medicinal plants, we identified a number of compounds with synergistic effects on TRAIL-induced apoptosis in tumor cells. This review describes our recent studies on the isolation of bioactive compounds with TRAILresistance overcoming activity.

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Prenylflavonoids isolated from Artocarpus champeden with TRAIL-resistance overcoming activity

Cited by 11 publications

References 26 publications

Prenylated Flavonoids and Resveratrol Derivatives Isolated from Artocarpus communis with the Ability to Overcome TRAIL Resistance

Prenylated Flavonoids and Resveratrol Derivatives Isolated from Artocarpus communis with the Ability to Overcome TRAIL Resistance

Chromomycins A2 and A3 from Marine Actinomycetes with TRAIL Resistance-Overcoming and Wnt Signal Inhibitory Activities

Bio-active Natural Products with TRAIL-Resistance Overcoming Activity

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