MOLECULES
·
2022
·Vol. 27
·期 16
·5350
·
IF 4.927
Lili Chen,Yunyun Liu,Yifei Li,Wu Yin,Yongxian Cheng
Two new guaiane sesquiterpenes, aquisinenoids A and B (1and2), two new eudesmane-type sesquiterpenoids, aquisinenoids C and D (3and4), one new cucurbitacin, aquisinenoid E (5), and five known cucurbitacins (6–10) were isolated from agarwood ofAquilaria sinensis. The structures of these new compounds, including their absolute configurations, were characterized by spectroscopic and computational methods. The biological evaluation showed that compounds3and9had an anti-cancer effect on most of the cancer cells at 5 μM, especially in human breast cancer cells. Interestingly, the new compound3exhibited more sensitivity on cancer cells than normal cells, highlighting its potential as a novel anti-cancer agent. Mechanically, compound3treatment increased the ROS generation and triggered apoptosis of human breast cancer cells.Keywords:Aquilaria sinensis;agarwood;sesquiterpenes;cucurbitacins;anti-cancer
研究领域:
药理学
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化学
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肿瘤学
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产品关联
DOI
PubMed
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2024
·
IF 5.6
Guoqiong Li,Yi Chen,Xin Wen,Xin Geng,Sai Zhang,Yimian Ma,Chengmin Yang,Liping Zhang,Yuan Li,Zheng Zhang
Aquilaria sinensis (Lour.) Gilg is one of the most important plant resources that produce agarwood, a fragrant resinous wood of high commercial value. Sesquiterpenes, the predominant constituents and important criterion for the quality of agarwood, play an essential role in stress and defence responses. However, the biosynthesis mechanisms of volatile sesquiterpenes and genes involved in these processes have not been comprehensively studied in Aquilaria . In this study, four sesquiterpene synthase genes were cloned from 3-year-old A. sinensis and identified using a yeast expression system as novel genes critical for sesquiterpene biosynthesis. AsTPS14, which catalyses the production of equal amounts of 4,11-selinadiene and α-selinene, is the first selinene synthase identified in Aquilaria . AsTPS13 can catalyse the production of three oxygenated sesquiterpenes, namely, β-eudesmol, γ-eudesmol and hinesol. AsTPS3 and AsTPS10 are two α-humulene synthases that can catalyse the production of α-humulene, and AsTPS3 is the most efficient α-humulene synthase in A. sinensis . Findings in this study reveal the diversity of sesquiterpene synthases and their multi-faceted functions, and offer further insights into the molecular mechanism of agarwood sesquiterpene biosynthesis. This work provides a solid theoretical and experimental foundation for molecularly assisted breeding of A. sinensis and efficient synthesis of sesquiterpenes.
研究领域:
植物生化
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分子生物学
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植物化学
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生物技术
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产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2025
·
IF 5.2
Xuehui Zhang,Qing Sun,Yuan Chen,Yanju Lu,Lu Li
The characteristics of natural aromatic compounds have promoted the research of efficient extraction methods. In this study, quantum chemical (QC) calculation, molecular dynamics (MD) simulation and experimental verification were combined to solve the problems of low extraction rate and solvent pollution of agarwood essential oil, and the screening and extraction mechanism of green extractants were systematically analyzed. Based on the mechanism of ethanol extraction of the main components of agarwood essential oil, through QC calculation, extraction experiments and Fourier transform infrared spectroscopy (FT-IR), it was found that choline chloride:ethylene glycol (ChCl:EG) at 1: 4, T = 40 °C , under the condition of 8 h, the extraction rate reached 24.2 %, which was 226 % higher than that of traditional ethanol solvent, and maintained good stability in five reuse cycles. In addition, the extraction mechanism of the process was clarified. The hydroxyl group in ChCl:EG forms additional interaction sites with the oxygen atoms on the ring structure of the target compound, which enhances the hydrogen bond and van der Waals force, and significantly improves the selective dissolution of the target compound. The effects of different ChCl:EG ratios and temperatures on the extraction efficiency were evaluated by MD simulation. The results show that the effect of temperature on the interaction of the system is greater than that of the proportion, and ethylene glycol in Deep Eutectic Solvents (DES) plays a major role. This research provides new insights into the use of DES for green extraction of natural products and establishes a theoretical and experimental basis for future industrial applications.
研究领域:
植物化学
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天然产物开发
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分子生物学
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产品关联
DOI
高影响因子
Pharmaceuticals
·
2025
·Vol. 18
·期 4
·510
·
IF 4.8
Mengyuan Yang,Yanan Yuan,Jingfan Wei,Yifei Pei,Yuanfei Niu,Yifan Zhao,Xiangying Kong,Zhijie Zhang
Background/Objectives: Agarwood has a good neuroprotective effect and is often used to relieve anxiety and treat insomnia. This study compared the similarities and differences in the chromone components of two types of agarwood. It further investigated the absorption and brain distribution characteristics of these components in rats and their neuroprotective effects mediated through anti-neuroinflammatory pathways.Methods: This study confirmed, through ITS2 barcoding and chloroplast genome analysis, that both the ordinary and Qi-Nan agarwood are derived fromAquilaria sinensis. A comparative analysis of chromones in ethanol extracts derived from ordinary and Qi-Nan agarwood, as well as those capable of penetrating the blood-brain barrier in vivo, was conducted using UPLC-Q-TOF-MS. Subsequently, an in vitro neuroinflammatory model was established via lipopolysaccharide (LPS)-stimulated BV-2 cells to evaluate the anti-neuroinflammatory activity of differential chromones.Results: UPLC-Q-TOF-MS characterization revealed the chromone components in the two types of agarwood: A total of 81 chromone compounds were identified in the ethanol extracts of ordinary agarwood (OAE) (20 THPECs, 42 FTPECs, and 19 BI), while 41 were identified in the ethanol extracts of Qi-Nan agarwood (QNE) (11 THPECs and 30 FTPECs). Pharmacokinetic analysis in rats showed that 14 components from OAE (eight THPECs and six FTPECs) penetrated the rat serum, and 10 of these 14 components penetrated the blood–brain barrier (BBB). Twelve FTPECs from QNE penetrated the rat serum, all of which penetrated the BBB. The total peak area of the total ion current (TIC) was calculated for the samples, and the TIC of the serum was compared to that of the brain tissue from the same rat to roughly estimate the ratio. The results demonstrated that the capability of FTPECs to traverse the blood–brain barrier is substantially superior to that of THPECs. Correspondingly, only FTPECs were detected using DESI-MS imaging; no THPECs were detected in rat brain tissue, and DESI-MS imaging localized FTPECs to neuroanatomic regions (cerebral cortex, thalamus, and hippocampus). In vitro neuroinflammatory assays revealed the superior anti-inflammatory efficacy of QNE over OAE (IL-6/TNF-α suppression,p< 0.05), correlating with its FTPEC-rich composition.Conclusions: Structure–activity relationships identified FTPECs as potent inhibitors of pro-inflammatory cytokines, exhibiting enhanced BBB penetration (blood–brain relative abundance > 1). These findings establish FTPECs as prioritized candidates for CNS-targeted therapeutics, with QNE’s pharmacological superiority attributed to its FTPEC dominance and optimized BBB transit capacity.
研究领域:
药理学
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神经科学
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植物化学
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产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2016
·Vol. 21
·期 5
·555
·
IF 2.465
Zhongxiu Zhang,Xiaohui Wang,Wanqing Yang,Juan Wang,Cong Su,Xiao Liu,Jun Li,Yunfang Zhao,Shepo Shi,Pengfei Tu
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-elicitedAquilaria sinensiscell 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-elicitedA. sinensiscell suspension cultures would be useful for further exploring the mechanism of agarwood formation.Keywords:2-(2-phenylethyl)chromone;induced circular dichroism;Aquilaria sinensis;agarwood;cell suspension cultures;sodium chloride elicitation
研究领域:
植物学
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天然产物化学
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药用植物研究
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产品关联
DOI
PubMed
高影响因子
FITOTERAPIA
·
2024
·
IF 2.5
Yuan Wei,Wen-Hua Dong,Wei Li,Jun Zeng,Hui-Qin Chen,Sheng-Zhuo Huang,Li Yang,Wen-Li Mei,Ya-Li Wang,Zhi-Yong Guo,Hao-Fu Dai,Hao Wang
Six new dimeric 2-(2-phenylethyl)chromones ( 1 – 6 ) were successfully isolated from the ethanol extract of agarwood of Aquilaria filaria from Philippines under HPLC-MS guidance. Compounds 1 – 6 are all dimers formed by linking 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and flindersia 2-(2-phenylethyl)chromone via a single ether bond, and the linkage site (C5-O-C8′′) of compound 2 is extremely rare. A variety of spectroscopic methods were used to ascertain their structures, including extensive 1D and 2D NMR spectroscopic analysis, HRESIMS, and comparison with literature. The in vitro tyrosinase inhibitory and anti-inflammatory activities of each isolate were assessed. Among these compounds, compound 2 had a tyrosinase inhibition effect with an IC 50 value of 27.71 ± 2.60 μM, and compound 4 exhibited moderate inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with an IC 50 value of 35.40 ± 1.04 μM.
研究领域:
植物化学
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药理学
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产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2023
·Vol. 28
·期 2
·635
·
IF 4.6
Yinfang Lai,Liping Hua,Jiali Yang,Juewen Xu,Junduo Chen,Shuangshuang Zhang,Shunyao Zhu,Jingjing Li,Senlin Shi
Objective: To study the extraction process of agarwood active ingredients (AA) and investigate the safety and effectiveness of AA in the treatment of insomnia rats by nasal administration. Method: A β-cyclodextrin (β-CD) inclusion compound (a-β-CD) was prepared from agarwood essential oil (AEO), and the preparation process was optimized and characterized. The safety of AA in nasal mucosa was evaluated throughBufo gargarizansmaxillary mucosa and rat nasal mucosa models. Insomnia animal models were replicated by injectingp-chlorophenylalanine (PCPA), conducting behavioral tests, and detecting the expression levels of monoamine neurotransmitters (NE and 5-HT) and amino acids (GABA/Glu) in the rat hypothalamus. Results: The optimum inclusion process conditions of β-CD were as follows: the feeding ratio was 0.35:1.40 (g:g), the inclusion temperature was 45 °C, the inclusion time was 2 h, and the ICY% and IEO% were 53.78 ± 2.33% and 62.51 ± 3.21%, respectively. The inclusion ratio, temperature, and time are the three factors that have significant effects on the ICY% and IEO% of a-β-CD. AA presented little damage to the nasal mucosa. AA increased the sleep rate, shortened the sleep latency, and prolonged the sleep time of the rats. The behavioral test results showed that AA could ameliorate depression in insomnia rats to a certain extent. The effect on the expression of monoamine neurotransmitters and amino acids in the hypothalamus of rats showed that AA could significantly reduce NE levels and increase the 5-HT level and GABA/Glu ratio in the hypothalamus of insomnia rats. Conclusion: The preparation of a-β-CD from AEO can reduce its irritation, improve its stability, increase its curative effect, and facilitate its storage and transport. AA have certain therapeutic effects on insomnia. The mechanism of their effect on rat sleep may involve regulating the expression levels of monoamine neurotransmitters and amino acids in the hypothalamus.Keywords:agarwood;supercritical fluid extraction;β-cyclodextrin;nose-to-brain delivery;insomnia
研究领域:
药理学
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神经科学
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药剂学
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中医中药
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产品关联
DOI
PubMed
高影响因子
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