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FOOD RESEARCH INTERNATIONAL · 2020 · IF 4.972

Screening of key flavonoids and monoterpenoids for xanthine oxidase inhibitory activity-oriented quality control of Chrysanthemum morifolium Ramat. ‘Boju’ based on spectrum-effect relationship coupled with UPLC-TOF-MS and HS-SPME-GC/MS

An Peng,Lianzhu Lin,Mouming Zhao

This study aimed at obtaining precise quality control standards to efficiently screen Chrysanthemum morifolium Ramat. ‘ Boju ’ with strong xanthine oxidase (XO) inhibitory activity for developing C. morifolium ‘ Boju ’ extract based-hypouricemic functional food. The results indicated significant differences in volatile and phenolic profiles and XO inhibitory (XOI) activities of 31 batches of C. morifolium ‘ Boju ’ collected in herb/tea market. The minority of C. morifolium ‘ Boju ’ having abundant characteristic monoterpenoids and flavonoid aglycones showed strong XOI activities, while the majority of C. morifolium ‘ Boju ’ possessing few corresponding monoterpenoids and flavonoid aglycones exhibited moderate XOI activities. Seven XOI activity-directly related phenolics and ten XOI activity-indirectly related volatiles were identified by UPLC-ESI-QTOF/MS-based and HS-SPME-GC/MS-based spectrum-effect relationships, respectively. Three flavonoids (luteolin, apigenin and acacetin) identified as key XO inhibitors and four monoterpenoids (filifolone, α-terpineol, thymol and piperitenone) closely related to key XO inhibitors were screened for XOI activity-oriented quality control of C. morifolium ‘ Boju ’.

CAS / MDL: 64-18-6
研究领域: 药理学 · 分析化学 · 植物科学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Affinity ultrafiltration based metabolomic profiling directed discovery novel butyrylcholinesterase inhibitors from Uncaria sessilifructus

Chang Xu,Xiao Yu,Guiyang Wang,Shiqing You,Linlin Zhu,Ying Liu,Nuan Zhang,Zhengdong Wang,Bin Liu,Wei Zhang

The butyrylcholinesterase (BChE) is an attractive target for treating Alzheimer's disease. In this study, we report the discovery of five new monoterpene indole alkaloids (MIAs) along with three known analogues from Uncaria sessilifructus Roxb. as BChE inhibitors using affinity ultrafiltration based metabolomic profiling directed isolation strategy. Their structures were well identified through comprehensive spectroscopic and chiroptical analyses. Compounds 1 – 2 featured unique glycosidic linkages with 1, 3-dioxane structure. All the compounds exhibited BChE inhibitory bioactivity without any cytotoxic effects. Enzymatic kinetic and molecular docking analyses of compounds 1 and 6 demonstrated their inhibiting mechanisms and binding patterns to BChE. These findings provide a valuable workflow for efficiently screening ligands that bind to proteins, and scientific recognition in the discovery of BChE inhibitors for treating neurodegenerative disorders.

CAS / MDL: 1953-04-4
研究领域: 药理学 · 神经科学 · 药物化学 · 植物化学
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INDUSTRIAL CROPS AND PRODUCTS · 2022 · IF 6.449

Identification of TPS-d subfamily genes and functional characterization of three monoterpene synthases in slash pine

Shu Diao,Yini Zhang,Qifu Luan,Xianyin Ding,Jiaming Sun,Jingmin Jiang

Oleoresin terpenoids have been widely used in the food , pharmaceutical, and chemical industries. A thorough understanding of oleoresin terpenoid biosynthesis is important for the metabolic engineering of high-valued terpenoid products in plants and microbes and the improvement of oleoresin traits using molecular breeding strategies. TPS-d subfamily members, specific to conifers, determine the oleoresin terpenoid compound diversity. Here, we aimed to identify the TPS-d genes in slash pine ( Pinus elliottii ) and characterize their function and expression patterns in population. Our study reveals two main results: (1) A total of 52 terpene synthase (TPS) candidate genes were identified based on long-read transcripts of slash pine, 12 of which were successfully cloned from the secondary developing xylem RNA. Two levopimaradiene/abietadiene synthases (LAS), one monofunctional isopimaradiene synthase (mISO1)-like, and two α-pinene synthases were identified by comparing with previously known TPS. Next, the two α-pinene synthases and one β-pinene synthase producing multiple products were validated through heterologous expression and in vitro enzyme activity assays, which showed different product profiles from previously identified TPS. (2) The expression status of the cloned TPS genes in 240 slash pine individuals were analyzed. Four exhibited very low expression levels, including those identical to copalyl diphosphate synthases, hemiterpene synthases, diterpene synthases without activity, and one obtained without soluble protein in the heterologous expression. The expression levels of eight TPS genes participating in slash pine oleoresin biosynthesis varied in different individuals and were highly correlated with multiple transcriptional regulators, namely, MYB and MYC. The expression of two α-pinene synthase genes was significantly higher than that of the other TPS genes. Some TPS gene expression levels were positively correlated with the corresponding oleoresin component content. Our results provide an essential reference for exploring the mechanisms of terpene biosynthesis and regulation.

CAS / MDL: 138-86-3 7705-14-8
研究领域: 植物生物化学 · 分子生物学 · 遗传学 · 代谢工程
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ANALYTICAL LETTERS · 2022 · IF 2.267

Photoinduced Associative Ionization Time-of-Flight Mass Spectrometry for the Sensitive Determination of Monoterpenes

Zuojian Zhang,Haijie Wang,Bo Yang,Jinian Shu,Zhangqi Yu,Zhiyang Wei,Jingyun Huang,Kui Jiang,Yedong Guo,Zhen Li

Recently, photoinduced associative ionization (PAI) has been demonstrated to be extremely efficient for the determination of oxygenated volatile organic compounds. However, its application for the determination hydrocarbons has not yet been reported. In this study, associative ionization of nine typical monoterpenes induced by dichloromethane (CH2Cl2) under vacuum ultraviolet (VUV) light was investigated using a laboratory-constructed PAI time-of-flight mass spectrometer (PAI-TOFMS). Without doping CH2Cl2, VUV light generated ordinary photoionization mass spectra of monoterpenes that were dominated by fragment ions, while the molecular ions were inconspicuous. In contrast, doping with CH2Cl2 resulted in the appearance of mass peaks of the characteristic protonated molecular ions of the monoterpenes. The PAI method significantly enhanced the signals for the monoterpenes. The intensities of protonated molecular ions derived from PAI were amplified by 52 to 108 fold compared with those of molecular ions produced by VUV photoionization (VUV PI). With the high ionization efficiency of PAI toward monoterpenes, the sensitivities of PAI-TOFMS toward limonene, β-ocimene, β-myrcene, β-pinene, and α-pinene were from 291 ± 6 to 1338 ± 20 counts pptv−1 using an acquisition time of 30 s. The limits of detection were from 0.32 to 1.45 pptv, equivalent to between 1.92 and 8.83 ng m−3. The applicability of this ionization mode was further characterized by the determination of monoterpenes from potted Sabina chinensis. This study provides a new and highly efficient ionization method for the determination of plant monoterpenes using mass spectrometry.

CAS / MDL: 123-35-3
研究领域: 分析化学 · 环境科学 · 质谱学 · 植物科学
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2024 · IF 4.2

Salicylic acid functionalized chitosan nanocomposite increases bioactive components and insect resistance of Agastache rugosa

Huimin Liao,Jinghong Wang,Feiran Chen,Le Ya,Ningke Fan,Yinghua Shu,Zhenggao Xiao,Zhenyu Wang

The abundance of monoterpenoids and phenolic compounds determines the medicinal quality and anti-insect properties of Agastache rugosa , which can be compromised by biotic stress such as herbivore attacks. The traditional use of chemical pesticides to mitigate herbivore interference is increasingly incompatible with sustainable agriculture. In response, nanotechnology-based biostimulants, which can activate metabolic processes to enhance plant growth and stress resistance, offer a more cost-effective and environmentally-friendly alternative. However, to date, it remains unknown how nano-biostimulants improve the therapeutic value and insect resistance of medicinal plants simultaneously. This study investigates the effect of 0–1000 mg/L of a nano-biostimulant salicylic acid functionalized chitosan nanocomposite (SCN) on the pharmacological and anti-herbivore properties of medicinal plant A. rugosa . Results showed that 100 mg/L SCN significantly inhibited Spodoptera litura growth by 62.9 %, and increased plant shoot and root biomass by 107.2 % and 77.6 %, respectively. Moreover, 100 mg/L SCN significantly upregulated the expression of the key genes ( e.g. , LS , L3OH , and CHS ) involved in monoterpene and phenolic compounds biosynthesis by 1.4–10.1 folds, thus boosting the production of active compounds such as pulegone, β-myrcene, and chlorogenic acid by 1.5–24.4 folds. These enhancements were superior to salicylic acid or chitosan alone. Altogether, our findings promote the sustainable and eco-friendly application of nano-biostimulant in improving the quality of medicinal plants and green pest control in agroecosystems.

CAS / MDL: 3391-90-0 89-82-7
研究领域: 植物科学 · 农业生物技术 · 植物化学 · 昆虫学
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COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY · 2016 · IF 1.651

Dendroctonus armandi (Curculionidae: Scolytinae) cytochrome P450s display tissue specificity and responses to host terpenoids

Lulu Dai,Mingyuan Ma,Guanqun Gao,Hui Chen

Bark beetles oxidize the defensive allelochemicals of their host trees both to detoxify them and convert them into components of their pheromone systems which were catalyzed by cytochrome P450 enzymes (CYPs) and occur in different tissues of the insect. We study P450 genes in the Chinese white pine beetle ( Dendroctonus armandi ), and some bio-information analysis was done for the full-length deduced amino acid sequences. The tissue specificity of these P450 genes was determined in three tissues (antenna, gut and reproductive organs). Differential expression of the P450 genes was observed between sexes, and within these significant differences exposed to stimuli (α-pinene (1:1 racemic mix), (S)-(−)-α-pinene, (S)-(−)-β-pinene, (+)-3-carene, (±)-limonene and turpentine oil) at 24   h. Increased expression of P450 genes suggested that they play a role in the detoxification of monoterpenes released by the host trees. The different transcript accumulation patterns of these bark beetle P450 genes provided insight into ecological interactions of D . armandi with its host pine.

研究领域: 昆虫学 · 分子生物学 · 生态学 · 生物信息学
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PROTEOMICS · 2022 · IF 5.393

Proteomic analysis suggests that monoterpenes in lemongrass disrupt Ca2+ homeostasis in Haemaphysalis longicornis leading to mitochondrial depolarization and cytotoxicity

Desmond O. Agwunobi,Mengxue Li,Ningmei Wang,Guomin Chang,Xiaojing Zhang,Xiaomin Xue,Zhijun Yu,Hui Wang,Jingze Liu

Complex mixtures of bioactive ingredients in plant essential oils present complex chemistries which involve different modes of action. An increasing body of scientific reports has recently focused on the acaricidal activities of plant essential oils attributed to their monoterpene components, but information about their underlying molecular mechanism of action is scarce. Here, after the chemical analysis of lemongrass oil, a proteomic analysis of the ovary, salivary gland, and midgut of Haemaphysalis longicornis exposed to Cymbopogon citratus (lemongrass) essential oil was performed via data-independent acquisition mass spectrometry (DIA-MS) technology to further elucidate the molecular mechanisms involved. Pathway analysis reveals the activation of metabolic pathways mediated by oxidoreductases and transferases. Furthermore, the upregulation of various calcium-associated proteins and the upregulation of cytochrome c1, cytochrome c oxidase polypeptide IV, and programmed cell death protein 6-like isoform X1 suggest a cytotoxic mode of action via the formation of reactive oxygen species (ROS), mitochondrial Ca 2+ overload, mitochondrial uncoupling, and depolarization, and ATP depletion leading to either apoptotic or necrotic death. Morphological alterations observed after the RNAi of a major detoxification enzyme (glutathione S-transferase) merit further investigation. Hence, the cytotoxic mode of action exhibited by C. citratus oil could be vital for the development of eco-friendly acaricide.

研究领域: 蛋白质组学 · 昆虫学 · 药理学 · 分子生物学
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BIOORGANIC CHEMISTRY · 2021 · IF 5.275

Monoterpenoid indole alkaloids from the fruits of Gelsemium elegans and their anti-inflammatory activities

Ni-Ping Li,Jun-Shan Liu,Jiao-Wen Liu,Hai-Yan Tian,Hong-Ling Zhou,Yuan-Ru Zheng,Xiao-Jun Huang,Jia-Qing Cao,Wen-Cai Ye,Lei Wang

Two novel monoterpenoid indole alkaloids (MIAs), gelsechizines A-B ( 1 – 2 ), along with four known ones ( 3 – 6 ) were isolated from the fruits of Gelsemium elegans . Compound 1 features a new carbon skeleton with two additional carbon atoms forming a 4-methylpyridine unit. Their structures with absolute configurations were elucidated by NMR, MS, X-ray diffraction and electronic circular dichroism (ECD) calculations. Compounds 1 – 3 showed significant anti-inflammatory effects in vivo and in vitro , which may be related to the inhibition of the trecruitment of neutrophils and macrophages as well as the secretion of TNF- α and IL-6. Preliminary structure–activity relationship analysis revealed that the β - N -acrylate moiety plays an important role in the anti-inflammatory effect.

CAS / MDL: 7758-98-7 103-85-5
研究领域: 药理学 · 有机化学 · 炎症研究
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FITOTERAPIA · 2023 · IF 3.4

Yueju volatile oil plays an integral role in the antidepressant effect by up-regulating ERK/AKT-mediated GLT-1 expression to clear glutamate

Bike Zhang,Dan Su,Yonggui Song,Huizhen Li,Changlian Chen,Liangliang Liao,Hongjie Zhang,Jian Luo,Ming Yang,Genhua Zhu,Zhifu Ai

Phytochemical investigation of the volatile oil of Yueju (YJVO) and its constituent herbs induced the detection of 52 compounds in YJVO, mainly monoterpenes and sesquiterpenes as well as a small amount of aromatic and aliphatic compounds. 5 of these compounds were found only in the YJVO instead of the volatile oil of its constituent herbs. The anti-depressant effect of YJVO was proved by behavioral tests in chronic unpredictable mild stress (CUMS) mice. An acute oral toxicity evaluation determined the LD 50 of YJVO was 5.780 mL/kg. Doppler ultrasound and laser speckle imaging have detected that the YJVO could improve depression-related cerebral blood flow. In addition, related neurotransmitters and proteins were analyzed through targeted metabolomics and immunofluorescence. The potential antidepressant mechanisms of YJVO related to significantly decreasing Glu in CUMS mice by up-regulating the ERK/AKT-mediated expression of GLT-1.

CAS / MDL: 9005-65-6
研究领域: 药理学 · 神经科学 · 植物化学 · 行为科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Methyl Eugenol Binds Recombinant Gamma-Aminobutyric Acid Receptor-Associated Protein from the Western Flower Thrips Frankliniella occidentalis

Li Wang,Maoxi Huang,Zilin Wu,Min Huang,Yunlong Yan,Baoan Song,Xiangyang Li,Qing X. Li

The western flower thrips (Frankliniella occidentalis) is a major pest insect in agriculture. However, few insecticides are effective for their control. The recombinant gamma-aminobutyric acid receptor-associated protein (rGABARAP) was examined as a potential target of the monoterpenoids responsible for their insecticidal activities. The insecticidal activity of anethole, linalool, and methyl eugenol (ME) was evaluated in the laboratory. The half-maximum lethal concentration (LC50) of ME against second-instar nymphs of F. occidentalis was 5.5 mg/L using membrane and leaf immersion methods, while that of spinosyn A was 1.0 mg/L. The dissociation constants of ME binding to rGABARAP were 1.30 and 4.22 μmol/L, respectively, according to microscale thermophoresis (MST) and isothermal titration calorimetry (ITC) measurements. A molecular docking study showed interactions between ME and Tyr174 via π–π stacking. The MST and ITC experiments showed loss of specific binding between ME and the rGABARAPY174A mutant. Therefore, Tyr174 is a key amino acid residue of rGABARAP involving ME binding. The results revealed GABARAP as a potential target for the development of monoterpenoid insecticides.

研究领域: 昆虫学 · 害虫管理 · 生物化学 · 分子生物学
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PHYTOCHEMISTRY · 2023 · IF 3.8

Monoterpenoids from the root bark of Acanthopanax gracilistylus and their inhibitory effects on neutrophil elastase, 5-lipoxygenase, andcyclooxygenase-2 in vitro

Hao-Dong Yang,Zhi-Shu Tang,Tao-Tao Xue,Huai-Li Xu,Bao-Long Hou,Ya-Ya Zhu,Zeng-Hu Su,Hong-Bo Xu

Twenty-four monoterpenoids , including three previously undescribed compounds ( 1 – 3 ), were isolated from the root bark of Acanthopanax gracilistylus W. W. Smith ( Acanthopanacis Cortex ). Their structures were unambiguously established based on spectroscopic analysis (HR-ESIMS, IR, 1D, and 2D NMR), and the absolute configurations of 1 – 3 were elucidated by comparing their experimental and calculated electronic circular dichroism spectra. In addition, the structure of 8 was confirmed by single-crystal X-ray diffraction. The inhibitory activities of 1 – 24 against neutrophil elastase , 5-lipoxygenase, and cyclooxygenase-2 (COX-2) were studied in vitro for the first time, and the results showed that compound 24 possessed a significant inhibitory effect on COX-2 with an IC 50 value of 1.53 ± 0.10 μ Μ. This research first reported the presence of monoterpenoids in Acanthopanacis Cortex , including one monoterpenoid 2 with an unusual 4/5 bicyclic lactone system, and compounds 4 and 5 have never been reported in nature.

CAS / MDL: 150374-95-1
研究领域: 药用植物学 · 药理学 · 化学 · 植物科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Food Chemistry-X · 2024 · IF 6.5

Sensory omics combined with mathematical modeling for integrated analysis of retronasal Muscat flavor in table grapes

Xiaomiao Zhou,Bingqi Shan,Songyu Liu,Wenping Gao,Xiaoyue Wang,Huiling Wang,Haiying Xu,Lei Sun,Baoqing Zhu

This study focused on analyzing the aroma formation mechanism of retronasal muscat flavor in table grapes. The sensory characteristics and fragrance components of table grape juice with different intensities of Muscat were investigated using GC-Quadrupole-MS, quantitative descriptive analysis and three-alternate forced choice. Free monoterpenoids were the main contributors to the retronasal Muscat flavor. The contribution of Muscat compounds to this flavor was quantified by Stevens coefficient, the most and the least sensitive compounds to concentration changes were citronellol and linalool, respectively. To predict the Muscat flavor intensity by mathematical modeling, established a model between Muscat flavor intensity and monoterpenoids concentration, and an optimal partial least squares regression model with a linear relationship between natural logarithms was obtained. These findings provide reference for understanding the formation mechanism of specific aromas in fruits and provide a basis for the development and quality control of processed products such as Muscat flavor grape juice.

CAS / MDL: 106-24-1 5989-27-5
研究领域: 食品科学 · 分析化学 · 感官科学
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