A new 2-(2-phenylethyl)chromone derivative in Chinese agarwood ‘Qi-Nan’ from <i>Aquilaria sinensis</i>

Yang, De-Lan; Wang, Hao; Guo, Zhi‐Kai; Dong, Wei; Mei, Wen‐Li; Dai, Hao‐Fu

doi:10.1080/10286020.2014.896342

Cited by 44 publications

(21 citation statements)

References 21 publications

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“…It has been reported that 54 2-(2-phenylethyl)chromones have been isolated from various Aquilaria species [ 4 , 5 ]. In recent years, 35 new 2-(2-phenylethyl)chromones, including 13 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones, have been identified in differing qualities of agarwood products [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. Among 89 2-(2-phenylethyl)chromones, 33 highly oxidized chromones appear to be unique to agarwood and are not found in healthy Aquilaria specimens [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Analysis of 2-(2-Phenylethyl)chromones by UPLC-ESI-QTOF-MS and Multivariate Statistical Methods in Wild and Cultivated Agarwood

Sheng

Wang

et al. 2016

IJMS

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Agarwood is the fragrant resinous material mainly formed from species of Aquilaria. 2-(2-phenylethyl)chromones, especially the highly oxidized 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones, are the main representative compounds from agarwood. It is important to determine whether agarwood in trade is from cultivated trees or natural trees in the Convention on the International Trade in Endangered Species (CITES). We characterized the 2-(2-phenylethyl)chromones in agarwood by ultra-performance liquid chromatography coupled with electrospray ionization mass spectrometry (UPLC–ESI-QTOF-MS) and differentiated wild from cultivated agarwood by metabolomic analysis. A total of 141 chromones including 50 potentially new compounds were evaluated as belonging to four structural classes (unoxidized 2-(2-phenylethyl)chromones, 5,6,7,8-tetrahydro-2-(2-phenylethyl)-chromones, bi-2-(2-phenylethyl)chromones, and tri-2-(2-phenylethyl)chromones). The metabolic difference between wild and cultivated agarwood was analyzed by component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA). Fourteen markers of metabolisms in wild and cultivated agarwood were constructed (e.g., 6,7-dimethoxy-2-(2-phenylethyl)chromone, 6,8-dihydroxy-2-(2-phenylethyl)chromone, 6-methoxy-2-(2-phenylethyl)chromone, etc.). These results indicated that UPLC–ESI-QTOF-MS-based metabonomics analysis in agarwood may be useful for distinguishing wild agarwood from cultivated agarwood.

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Section: Introductionmentioning

confidence: 99%

Analysis of 2-(2-Phenylethyl)chromones by UPLC-ESI-QTOF-MS and Multivariate Statistical Methods in Wild and Cultivated Agarwood

Sheng

Wang

et al. 2016

IJMS

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Section: Resultsmentioning

confidence: 99%

“…Additionally, feruloyl amides, nucleosides, and lignins have been extensively reported as being involved in plant defenses [25][26][27][28]. The identification of 2-(2-phenylethyl)chromones (1)(2)(3)(4)(5), feruloyl amides (6)(7)(8), nucleosides (9)(10)(11)(12)(13)(14), and (+)-syringaresinol (15) would be useful for further exploring the mechanism of agarwood formation. [13], N-trans-feruloyltyramine (6) [14], N-trans-feruloyloctopamine (7) [14], N-cis-feruloyltyramine (8) [14], N 6 -methyladenosine (9) [15], adenosine (10) [16], 2'-deoxy-D-adenosine (11) [16], thymidine (12) [17], 2'-deoxyuridine (13) [17], uridine (14) It is well known that biotic and abiotic stresses could adversely affect plant growth and subsequently cause the production of specific secondary metabolites for plant defense.…”

Section: Resultsmentioning

confidence: 99%

“…Hitherto, more than 100 congeners of 2-(2-phenylethyl)chromones have been reported, and many of them have potentially anti-inflammatory [1], neuroprotective [2], antitumor activities, etc. [3][4][5]. Under stress conditions, such as wounding or fungal infections, some resin-impregnated heartwood containing a variety of 2-(2-phenylethyl)chromones are slowly forming in the trunk and branches of some species of Thymelaeaceae.…”

Section: Introductionmentioning

confidence: 99%

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Five 2-(2-Phenylethyl)chromones from Sodium Chloride-Elicited Aquilaria sinensis Cell Suspension Cultures

et al. 2016

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Five 2-(2-phenylethyl)chromones including a new one, (5S,6R,7S,8R)-5, 8-dichloro-6,7 -dihydroxy-2-phenylethyl-5,6,7,8-tetrahydro-4H-chromen-4-one (1), and four known ones (2-5), were isolated from 150 mM NaCl-elicited Aquilaria sinensis cell suspension cultures. In addition, three feruloyl amides (6-8), six nucleosides (9-14), (+)-syringaresinol (15), indole-3-carboxaldehyde (16), and two glycosides (17-18) were also obtained. The structures were unambiguously identified by analysis of their UV, IR, NMR, and HRESIMS data. The absolute configuration of the new 2-(2-phenylethyl)chromone (1) was established by a dimolybdenum tetraacetate-induced circular dichroism experiment. Compared to un-elicited cell lines, the appearance of 2-(2-phenylethyl)chromones in NaCl-treated cells occurred on the 3rd and 5th days of their treatment. 2-(2-Phenylethyl)chromones, feruloyl amides, nucleosides, and lignins have been reported to be closely related to plant defense; therefore, the identification of these compounds from NaCl-elicited A. sinensis cell suspension cultures would be useful for further exploring the mechanism of agarwood formation.

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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%

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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A new 2-(2-phenylethyl)chromone derivative in Chinese agarwood ‘Qi-Nan’ from Aquilaria sinensis

Cited by 44 publications

References 21 publications

Analysis of 2-(2-Phenylethyl)chromones by UPLC-ESI-QTOF-MS and Multivariate Statistical Methods in Wild and Cultivated Agarwood

Analysis of 2-(2-Phenylethyl)chromones by UPLC-ESI-QTOF-MS and Multivariate Statistical Methods in Wild and Cultivated Agarwood

Five 2-(2-Phenylethyl)chromones from Sodium Chloride-Elicited Aquilaria sinensis Cell Suspension Cultures

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

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