FLAVOUR AND FRAGRANCE JOURNAL
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2022
·Vol. 37
·期 4
·254-261
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IF 2.5
Zongquan Li,Yunjian Ma,Frank Hollmann,Yonghua Wang
Carvol and carvone are oxidation products from the natural product limonene. They are important raw materials for the flavours and fragrances industry and also act as pharmaceutical active ingredients. Orange waste peels possibly represent an attractive source for limonene, but studies on valorizing orange peel wastes are rare. In this study, we report a new enzymatic cascade system for the in-situ conversion of limonene from orange peel into valued-added carvol and carvone. The use of deep eutectic solvents (DES) allows for efficient in-situ extraction of limonene from waste orange peels. We propose a dual function use of DES as solvent for the extraction and the biocatalytic oxidation of limonene as well as cosubstrate to promote the oxidation reaction. Using ChCl-Pro-H 2 O DES for the extraction of limonene from waste orange peels, approximately 17 milligrams of limonene per gram of orange peel was achieved at 40°C for 24 h. Then, with ChCl-Pro-H 2 O DES as the extractant and reaction medium, a cascade reaction system of choline oxidase (ChOx) and unspecific peroxygenase (UPO) was established to catalyse the conversion of limonene into carvol and carvone. The concentration of the final products was up to about 1.6 mmol L −1 . This study showed a biocatalytic transformation pathway and provides technical support for the high-value utilization of waste in orange peel.
研究领域:
生物化学
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环境科学
·
香料工业
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DOI
高影响因子
BIOORGANIC CHEMISTRY
·
2020
·
IF 4.831
Yong Guo,Enhua Hou,Nannan Ma,Zhiyan Liu,Jiangping Fan,Ruige Yang
Nowadays, the discovery and development of α -glucosidase inhibitors from natural products or their derivatives represents an attractive approach. Here we reported studies on a series of novel N -acyl-2-aminothiazoles fused (+)-nootkatone and evaluation for their α -glucosidase inhibitory activities. Most of (+)-nootkatone derivatives exhibited more potent α -glucosidase inhibitory ability than the positive drug acarbose. In particular, compounds II7 and II14 showed the most promising α -glucosidase inhibitory ability with IC 50 values of 13.2 and 13.8 µM. II7 and II14 also exhibited relatively low cytotoxicities towards normal LO2 cells. Kinetic study indicated that compounds II7 and II14 inhibited the α -glucosidase in a noncompetitive manner, and molecular docking results were in line with the noncompetitive characteristics that II7 and II14 did not bind to the known active sites (Asp214, Glu276 and Asp349). Based on our findings, these (+)-nootkatone derivatives could be used as antidiabetic candidates.
研究领域:
药理学
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药物化学
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天然产物
·
糖尿病研究
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产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2014
·Vol. 19
·期 4
·4510-4523
·
IF 2.095
Feng Chen,Hai-Long Li,Yin-Feng Tan,Wei-Wei Guan,Jun-Qing Zhang,Yong-Hui Li,Yuan-Sheng Zhao,Zhen-Miao Qin
Plant secondary metabolites are known to not only play a key role in the adaptation of plants to their environment, but also represent an important source of active pharmaceuticals.Alpinia oxyphyllacapsular fruits, made up of seeds and pericarps, are commonly used in traditional East Asian medicines. In clinical utilization of these capsular fruits, inconsistent processing approaches (i.e., hulling pericarps or not) are employed, with the potential of leading to differential pharmacological effects. Therefore, an important question arises whether the content levels of pharmacologically active chemicals between the seeds and pericarps ofA. oxyphyllaare comparable. Nine secondary metabolites present inA. oxyphyllacapsular fruits, including flavonoids (e.g., tectochrysin, izalpinin, chrysin, apigenin-4',7-dimethylether and kaempferide), diarylheptanoids (e.g., yakuchinone A and B and oxyphyllacinol) and sesquiterpenes (e.g., nootkatone), were regarded as representative constituents with putative pharmacological activities. This work aimed to investigate the abundance of the nine constituents in the seeds and pericarps ofA. oxyphylla. Thirteen batches ofA. oxyphyllacapsular fruits were gathered from different production regions. Accordingly, an ultra-fast high performance liquid chromatography/quadrupole tandem mass spectrometry (UFLC-MS/MS) method was developed and validated. We found that: (1) the nine secondary metabolites were differentially concentrated in seeds and fruit capsules; (2) nootkatone is predominantly distributed in the seeds; in contrast, the flavonoids and diarylheptanoids are mainly deposited in the capsules; and (3) the content levels of the nine secondary metabolites occurring in the capsules varied greatly among different production regions, although the nootkatone levels in the seeds were comparable among production regions. These results are helpful to evaluating and elucidating pharmacological activities ofA. oxyphyllacapsular fruits. Additionally, it may be of interest to elucidate the mechanisms involved in the distinct accumulation profiles of these secondary metabolites between seeds and pericarps.Keywords:secondary metabolites;A. oxyphyllacapsular fruits;diarylheptanoids;flavonoids;nootkatone;production region;UFLC-MS/MS
研究领域:
药用植物学
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分析化学
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传统医学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
·
2014
·
IF 2.829
Feng Chen,Hai-Long Li,Yin-Feng Tan,Yong-Hui Li,Wei-Yong Lai,Wei-Wei Guan,Jun-Qing Zhang,Yuan-Sheng Zhao,Zhen-Miao Qin
Alpinia oxyphylla (Yizhi) capsularfruits are commonly used in traditional medicine. Pharmacological studies have demonstrated that A. oxyphylla capsularfruits have some beneficial roles. Besides volatile oil, sesquiterpenes, diarylheptanoids and flavonoids are main bioactive constituents occurring in the Yizhi capsularfruits. The representative constituents include tectochrysin, izalpinin, chrysin, apigenin-4′,7-dimethylether, kaempferide, yakuchinone A, yakuchinone B, oxyphyllacinol and nootkatone. Their content levels in the fruit and its pharmaceutical preparations have been reported by our group. The nine phytochemicals are also the major components present in the Yizhi alcoholic extracts, which have anti-diarrheal activities. However, the fates of these constituents in the body after oral or intravenous administration remain largely unknown. In the present study, we focus on these phytochemicals albeit other concomitant compounds. The chemicals and their metabolites in rat plasma were identified using liquid chromatography/tandem mass spectrometry with selected reaction monitoring mode after orally administered Yizhi extract to rats. Rat plasma samples were treated by methanol precipitation, acidic or enzymatic hydrolysis. This target analysis study revealed that: (1) low or trace plasma levels of parent chemicals were measured after p.o. administration of Yizhi extract, Suoquan capsules and pills to rats; (2) flavonoids and diarylheptanoids formed mainly monoglucuronide metabolites; however, diglucuronide metabolites for chrysin, izalpinin and kaempferide were also detected; (3) metabolic reduction of Yizhi diarylheptanoids occurred in rats. Yakuchinone B was reduced to yakuchinone A and then to oxyphyllacinol in a stepwise manner and subsequently glucuronidated by UDP-glucuronosyl transferase. Further research is needed to characterize the UDP-glucuronosyl transferase and reductase involved in the biotransformation of Yizhi chemicals.
研究领域:
药理学
·
分析化学
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DOI
高影响因子
FOOD CONTROL
·
2020
·
IF 4.258
Arakkaveettil Kabeer Farha,Qiong-Qiong Yang,Gowoon Kim,Dan Zhang,Vuyo Mavumengwana,Olivier Habimana,Hua-Bin Li,Harold Corke,Ren-You Gan
Staphylococcus aureus , a foodborne pathogen , poses serious problems to the food industries owing to biofilm formation, and over 25% of the foodborne illnesses in China have been attributed to S. aureus only. Phytochemicals are widely used as anti-biofilm agents with promising efficacy, and most of them are widely available and safe. This study reported the anti-biofilm efficacy of (+)-nootkatone, a sesquiterpene ketone found in a common fruit grapefruit, against multidrug-resistant S. aureus and its potential molecular mechanism. (+)-Nootkatone exhibited bacteriostatic and bactericidal effects at 200 and 400 μg/mL, respectively, against S. aureus SJTUF 20758 and S. aureus ATCC 25923. Crystal violet staining indicated that (+)-nootkatone inhibited S. aureus biofilm formation (p < 0.05) at a sub-MIC of 50 μg/mL and reduced exopolysaccharide production. The thickness of biofilms was significantly reduced by (+)-nootkatone, which was supported by the light microscopy and confocal laser scanning microscopy. Growth curve of bacteria showed that the antibacerial activity of (+)- nootkatone was dose-dependent, and the sub-MIC concentrations did not affect the bacterial growth of planktonic cells. Besides, (+)-nootkatone affected the sliding motility of S. aureus . At 200 μg/mL, (+)-nootkatone led to the reduction of preformed biofilm mass by 50% and bacterial cell death of 79%, accompanied with a reduction of exopolysaccharide. The expression of biofilm-related genes, including sarA, icaA , agrA , RNAIII, and spa , was suppressed by (+)-nootkatone, as revealed by the transcriptional analysis. Additionally, MTT assay revealed that there was no toxicity of (+)-nootkatone to the human foreskin fibroblasts (HFF) cells. Therefore, (+)-nootkatone is a promising phytochemical against S. aureus biofilms, and has the potential to be used in food industry to fight against S. aureus -induced safety issues.
研究领域:
食品科学
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微生物学
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药理学
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分子生物学
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产品关联
DOI
高影响因子
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
·
2024
·
IF 3.1
Yufang Huang,Xikang Ren,Yonghui Li,Junqing Zhang,Na Wei,Hailong Li,Yinfeng Tan
The Liangfu formula, as described in 'Liangfang Jiye', is well-known for its efficacy in treating stomach pain, abdominal pain, and dysmenorrhea. This research aimed to investigate the pharmacokinetics and tissue distribution of 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-3-heptanone (DPHA), Galangin, Kaempferide, 5-Hydroxy-1,7-diphenyl-3-heptanone (DPHC), α-Cyperone, and Nootkatone in vivo using an LC-MS/MS method. The method successfully separated the six active components and internal standards (Chrysin and Yakuchinone-A) on an XB-C18 column with a mobile phase of 0.2 ‰ formic acid water-acetonitrile. It demonstrated good linearity with a correlation coefficient (r 2 ) ≥ 0.9911 and a lower limit of quantification (LLOQ) of 5–80 ng/mL for the different components. Precision, accuracy, matrix effects, and recovery rates were within acceptable ranges. Pharmacokinetic analysis revealed significant differences in parameters between primary dysmenorrhea (PD) and normal rats (especially AUC, T max, and CL z /F). Tissue distribution showed that the six active components of the herbal pair Alpinia officinarum Hance- Cyperus rotundus L. (HPAC) extract was primarily distributed in the liver, lung, and kidney. This study offers valuable insights into the potential mechanisms of action and drug development for treating PD.
研究领域:
药理学
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中医
·
分析化学
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药物动力学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）