Phenylethylchromones with In Vitro Antitumor Promoting Activity from Aquilaria filaria

Suzuki, Airi; Miyake, Katsunori; Saito, Yohei; Rasyid, Faradiba Abdul; Tokuda, Harukuni; Takeuchi, Misa; Suzuki, Nobutaka; Ichiishi, Eiichiro; Fujie, Tetsuo; Goto, Masuo; Sasaki, Yohei; Nakagawa‐Goto, Kyoko

doi:10.1055/s-0042-110858

Cited by 13 publications

(12 citation statements)

References 29 publications

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“…26,27 The average EBV-EA induction of the test compound was determined as a ratio relative to the control. The viability of treated Raji cells was evaluated by trypan blue staining.…”

Section: Methodsmentioning

confidence: 99%

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

et al. 2016

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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.

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“…26,27 The average EBV-EA induction of the test compound was determined as a ratio relative to the control. The viability of treated Raji cells was evaluated by trypan blue staining.…”

Section: Methodsmentioning

confidence: 99%

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

et al. 2016

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“…Chromones in agarwood have recently received considerable attention for their importance in identification of quality (Espinoza et al 2014), pharmacological effects (Zhu et al 2016;Huo et al 2017;Suzuki et al 2017), chemical isolation (Liao et al 2016(Liao et al , 2017Xiang et al 2017;Yang et al 2017), and their biosynthesis pathways . The determination of chromones in agarwood is a reasonable option for quality control (Lancaster and Espinoza 2012).…”

Section: Total Chromone Analysismentioning

confidence: 99%

“…Analysis of 2-(2-phenylethyl) chromones is promising to distinguish cultivated from wild harvested agarwood, especially the highly oxidized 5,6,7,8-tetrahydro-2-(2phenylethyl) chromones (Espinoza et al 2014). Some new chromones in agarwood show antitumor immunity (Suzuki et al 2017), inhibition of innate and adaptive immunity (Guo et al 2017) and anti-inflammatory properties (Zhu et al 2016;Huo et al 2017). More chromones have been isolated from agarwood in recent years (Liao et al 2016(Liao et al , 2017Xiang et al 2017;Yang et al 2017).…”

Section: Introductionmentioning

confidence: 99%

Dynamic analysis of gene expression and determination of chemicals in agarwood in Aquilaria sinensis

Liu

et al. 2019

J. For. Res.

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Agarwood is the resinous heartwood of Aquilaria species. However, low yields and high costs of existing stimulation methods have led to the need for new techniques to produce agarwood rapidly and effectively. We developed a biological agarwood-inducing technique (Agar-Bit) that produces high yields and quality within 6 months. To better understand agarwood formation by Agar-Bit, dynamic gene expressions of key synthetases pathways of sesquiterpenes and chalcone-related enzymes at different times were determined after both Agar-Bit and the traditional burning chisel drilling (BCD) stimulation on Aquilaria sinensis trees. The qRT-PCR results show that some characteristic synthase genes were expressed at greatly different levels and times compared with the controls. For the Agar-Bit technology, main changes were after the 3rd or 5th month, while BCD expression clearly changed at the 5th month. Essential oils and total chromone contents were simultaneously determined. In the Agar-Bit group, both were higher and similar to natural levels. The Agar-Bit methodology is a new option for producing agarwood as demonstrated by genetic and chemical aspects. The differences in gene expression within 6 months for both groups indicates that the mechanisms of the two methods are different. These findings provide information on genetic variation during the process of agarwood formation.

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“…A total of three studies obtained from PRISMA analysis from Scopus database used methanol as a solvent in extracting agarwood parts Study 1 (Suzuki et al, 2017), Study 2 (Huo et al, 2018) and Study 3 (Jayaraman and Mohamed, 2015)). Methanol is often being used as an extraction solvent since aqueous methanol was more effective in extracting total phenolics and antioxidative components compared to water (Zhou and Yu, 2004).…”

Section: Methanolmentioning

confidence: 99%

“…Jayaraman and Mohamed (2015) were developed plant tissue culture from agarwood leaves cell for rapid mass production to regenerate agarwood plant and produce secondary metabolites from the plant such as aromatic compounds. Suzuki et al (2017) extracted powdered Aquilaria filaria heartwood with 95% methanol (room temperature, 72 hr). From the crude methanolic extract, 11 compounds have been isolated namely, 2-(2-hydroxy -2-phenylethyl)chromone, 6-hydroxy-7-methoxy-2-[2-(4 -methoxyphenyl)ethyl]chromone, 8-chloro-6-hydroxy-2-(2-phenylethyl)chromone, 6-hydroxy-7-methoxy-2-(2- phenylethyl)chromone, 6,7-dimethoxy-2-(2-phenylethyl) chromone, 6-hydroxy-2-[2-(4-methoxyphenyl)ethyl] chromone, 6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl] chromone, 6-hydroxy-2-(2-phenylethyl)chromone, 8hydroxy-2-(2-phenylethyl)chromone, 6,8-dihydroxy-2-(2 -phenylethyl)chromone, and 2-(2-phenylethyl)chromone.…”

Section: Methanolmentioning

confidence: 99%

Solvent used in extraction process of agarwood: a systematic review

Zakaria¹,

Talip²,

Kahar³

et al. 2020

Food Res.

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The method of extraction of Agarwood is usually dependent on the purpose of the extract. This systematic review aims to look at the number of studies that use different types of solvents in the process of extraction. There are 3 types of solvents commonly used in the extraction of agarwood essential oils namely methanol, ethanol and water. Each solvent produces different extracts in terms of quantity and quality of the final product. However, there is controversy over the use of solvents as it may cause a cytotoxic effect on the user. Another common type of solvent is water. Although water is a cheap solvent and relatively safe, aqueous extracts have more impurities that make isolating the desired compound difficult. After the extraction process, the crude extract was fractionated into the desired compounds and this technique is widely applied, especially in the whole process of extraction of the agarwood. In conclusion, extraction solvents have certain advantages and disadvantages, and this is one of the reasons why this extraction method depends on the purpose of using the final product such as agarwood essential oil.

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Phenylethylchromones with In Vitro Antitumor Promoting Activity from Aquilaria filaria

Cited by 13 publications

References 29 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

Dynamic analysis of gene expression and determination of chemicals in agarwood in Aquilaria sinensis

Solvent used in extraction process of agarwood: a systematic review

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