Anti-inflammatory 2-(2-phenylethyl)chromone derivatives from Chinese agarwood

Huo, Hui-Xia; Gu, Yufan; Sun, Hui; Zhang, Yunfeng; Liu, Wenjing; Zhu, Zhixiang; Shi, She‐Po; Song, Yuelin; Jin, Hongwei; Zhao, Yunfang; Tu, Pengfei; Li, Jun

doi:10.1016/j.fitote.2017.02.009

Cited by 70 publications

(42 citation statements)

References 25 publications

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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%

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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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Section: Total Chromone Analysismentioning

confidence: 99%

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 a well-known as incense in the oriental region such as in Taiwan, Thailand and China used as a sedative, analgesic, and digestive agent in traditional medicine. Flavonoid glycoside, volatile oil, benzenoid, sesquiterpenes and chromone derivatives were isolated and identified from the seed, leaves or stem of these plants [2][3][4][5][6][7][8][9][10]. Phytochemical constituents obtained from the agarwood including apigenin-7, 4'-dimethylether, genkwanin, quercetin, kaemperfol and 5, 6, 7, 8-tetrahydro-2-(2-phenylethtl) chromes with different pharmacological activities [8,11,12].…”

Section: Introductionmentioning

confidence: 99%

“…Phytochemical constituents obtained from the agarwood including apigenin-7, 4'-dimethylether, genkwanin, quercetin, kaemperfol and 5, 6, 7, 8-tetrahydro-2-(2-phenylethtl) chromes with different pharmacological activities [8,11,12]. The plant Aquilaria sinensis and Aquilaria agallocha have several pharmacological activities and shows antioxidant, anti-diabetic, antiinflammatory, and antibacterial activities [2][3][4][5][6][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

The antioxidation and antiproliferation activity of flavonoids from Aquilaria agallocha and Aquilaria sinensis

Liu¹,

Perng²,

Chen³

2018

biomedicalresearch

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Studies have shown that herbal extractions may be effective against various diseases like cancer and cardiovascular disease. In this study, we intended to evaluate the cytotoxicity and antioxidation activity of phytochemical constituents from the leaves of Aquilaria agallocha and the stems of Aquilaria sinensis.The chemical structures were identified by UV, IR, ESI-MS, 1H NMR and 13C NMR analyses. 5-hydroxy-7, 4'-dimethoxyflavone (1), 5, 3'-dihydroxy-7, 4'-dimethoxyflavone (2), 5-hydroxy-7, 3', 4'-trimethoxyflavone (3), 5, 7, 4′-trihydroxyflavone (4), and 3', 4', 5, 7-tetrahydroxyflavone (5) were isolated and further examined antioxidation and antiproliferation activity by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and MTT assay. According these results, 5-hydroxy-7, 3', 4'-trimethoxyflavone (3) had DPPH radical scavenging activity. Further, 5-hydroxy-7, 3', 4'-trimethoxyflavone (3) also showed significant positive anticancer activities (10-100 μM) against human skin cancer cell line A375 cells.

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“…Due to their abundance in plants and their low mammalian toxicity, chromone derivatives are existing in large amounts in the diet of humans . Chromone derivatives revealed a wide range of pharmacological activities including anti‐HIV , anti‐inflammatory , antibacterial , anticancer , antimalarial agents , as well as α‐glucosidase and acetylcholinesterase inhibitors , and treatment of Alzheimer's disease . Also, coumarins (2 H ‐chromen‐2‐ones) displayed various biological applications such as antifungal, antibacterial, antioxidant, anticoagulant, antiinflammatory, antiviral, anticancer, antitumor, anti‐diabetic, antitubercular, antiplasmodial, and antimalarial activities, as well as fluorescent sensors .…”

Section: Introductionmentioning

confidence: 99%

Heteroannulated Coumarins and Chromones from Chemical Transformations of 6,8‐Dimethylchromone‐3‐carbonitrile

Ibrahim

Badran

Hashiem

2018

Journal of Heterocyclic Chem

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A novel series of heterocyclic systems fused coumarins and chromones were efficiently synthesized from chemical transformations of 6,8-dimethylchromone-3-carbonitrile (1) with a variety of carbon nucleophilic reagents. Ring opening ring closure reactions of carbonitrile 1 with cyanoacetohydrazide, malononitrile dimer (2-aminoprop-1-ene-1,1,3-tricarbonitrile), and isomeric cyclohexanediones led to a diversity of coumarins and chromones fused nitrogen heterocyclic systems. Also, 1-ethyl-4-hydroxyquinolin-2(1H)-one (13) and 6-ethyl-4-hydroxypyrano[3,2-c]quinoline-2,5(6H)-dione (14) are chemical equivalent towards carbonitrile 1 leading to benzo [h]chromeno[2,3-b][1, 6] naphthyridine derivative 15. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.Scheme 3. Reaction of compound 5 with malononitrile dimer. Scheme 2. Reaction of carbonitrile 1 with malononitrile dimer. Scheme 4. Condensation of carbonitrile 1 and compound 5 with cyclohexane-1,2-dione. Scheme 5. Condensation of carbonitrile 1 with 1,3-cyclohexanedione. Scheme 6. The suggested mechanism for the formation of compound 11. Scheme 7. Condensation of carbonitrile 1 and compound 5 with cyclohexane-1,4-dione. Scheme 8. Formation of benzo[h]chromeno[2,3-b][1,6]naphthyridine derivative 15. DMF, dimethylformamide.

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Anti-inflammatory 2-(2-phenylethyl)chromone derivatives from Chinese agarwood

Cited by 70 publications

References 25 publications

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

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

The antioxidation and antiproliferation activity of flavonoids from Aquilaria agallocha and Aquilaria sinensis

Heteroannulated Coumarins and Chromones from Chemical Transformations of 6,8‐Dimethylchromone‐3‐carbonitrile

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