2-(2-Phenylethyl)chromone derivatives from Chinese agarwood induced by artificial holing

Wei, Li; Cai, Cai-Hong; Dong, Wei; Guo, Zhi‐Kai; Wang, Hao; Mei, Wen‐Li; Dai, Hao‐Fu

doi:10.1016/j.fitote.2014.07.011

Cited by 86 publications

(63 citation statements)

References 20 publications

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“…DMSO solutions of 1 and dimolybdenum tetraacetate [Mo 2 (AcO) 4 ] were homogeneously mixed, and the induced circular dichroism (ICD) spectrum was recorded. In the ICD spectrum of 1 (Figure 2), the positive Cotton effect at 310 nm suggested a positive dihedral angle of the O´C´C´O moiety, which allowed to the assignment of the absolute configuration of C-6 and C-7 as R and S, respectively.…”

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%

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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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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“…Research on the chemical components of the eaglewood began half a century ago. So far, a large number of compounds have been reported from this resin wood, including aromatics [2,3], sesquiterpenes [4], chromone derivatives [5][6][7][8], triterpenes, and diterpenes [9]. Some of them showed certain anti-microbial, anti-inflammation, neuroprotective, and anti-depressant activities.…”

Section: Introductionmentioning

confidence: 99%

Three New Sesquiterpenoids and One New Sesquiterpenoid Derivative from Chinese Eaglewood

et al. 2016

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Abstract:Three new sesquiterpenoids (1-3) and one new sesquiterpenoid derivative (4), along with three known sesquiterpenoids (5-7), were isolated from the 95% ethanolic extract of Chinese eaglewood [Aquilaria sinensis (Lour.) Gilg]. The structures of these compounds were elucidated through extensive analysis of spectroscopic data including IR, NMR, HRESIMS, and X-ray diffraction experiments. In addition, the above new compounds were detected for their bioactivities against LPS-induced NO production in RAW 264.7 cells. Among them, compound 2 exhibited obvious anti-inflammatory activity with an IC 50 value of 8.1 µM.

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Chemical and Bioactivity Diversity of 2‐(2‐Phenylethyl)chromones in Agarwood: A Review

Meng

Chen

et al. 2022

Chemistry & Biodiversity

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2‐(2‐Phenylethyl)chromone derivatives are regarded as key components in agarwood. An oxygen‐containing heterocycle with a benzoannelated γ‐pyrone moiety form the bioactive core of 2‐(2‐phenylethyl)chromones. With different substituents and positions, 2‐(2‐phenylethyl)chromone derivatives exhibit diverse biological properties, such as antioxidant, antimicrobial, neuroprotective, anti‐inflammatory, and acetylcholinesterase inhibitory activities. In this review, we summarized the studies (from January 1976 to September 2021) on phytochemistry, bioactivity and quality control of 2‐(2‐phenylethyl)chromones. These studies aimed to clarify the chemical specificity, diversity and structure‐activity relationship of 2‐(2‐phenylethyl)chromones. In addition, we assumed that diverse factors such as tree species, induction methods and formation time contribute to the chemical diversity of 2‐(2‐phenylethyl)chromones. Furthermore, this review contends that different types of 2‐(2‐phenylethyl)chromones should be utilized in the quality control methods of agarwood.

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2-(2-Phenylethyl)chromone derivatives from Chinese agarwood induced by artificial holing

Cited by 86 publications

References 20 publications

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

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

Three New Sesquiterpenoids and One New Sesquiterpenoid Derivative from Chinese Eaglewood

Chemical and Bioactivity Diversity of 2‐(2‐Phenylethyl)chromones in Agarwood: A Review

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