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Keywords = bisabolane-type sesquiterpene

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12 pages, 1473 KB  
Article
Fusarium foetens AQF6 Isolated from Amentotaxus ynnanensis H.L.Li as a Prolific Source of Antioxidant Compounds
by Thi Hanh Nguyen Vu, Ngoc Son Pham, Ngoc Tung Quach, Phuong Chi Le, Quynh Anh Pham, Cao Cuong Ngo, Van The Nguyen, Do Hoang Anh, Tran Hong Quang, Hoang Ha Chu and Quyet-Tien Phi
Appl. Sci. 2024, 14(5), 2048; https://doi.org/10.3390/app14052048 - 29 Feb 2024
Cited by 4 | Viewed by 2071
Abstract
Amentotaxus yunnanensis H.L.Li is a threatened conifer distributed only in China, Laos, and Vietnam, whose fungal endophytes have not been exploited yet. The aims of this study were to screen and characterize antioxidant metabolites from endophytic fungi obtained from A. yunnanensis. Using [...] Read more.
Amentotaxus yunnanensis H.L.Li is a threatened conifer distributed only in China, Laos, and Vietnam, whose fungal endophytes have not been exploited yet. The aims of this study were to screen and characterize antioxidant metabolites from endophytic fungi obtained from A. yunnanensis. Using the surface sterilization method, sixteen endophytic fungi were isolated from A. yunnanensis and classified into seven genera including Fusarium, Penicillium, Aspergillus, Diaporthe, Neopestalotiopsis, Purpureocillium, and Simplicillium through the analysis of Internal Transcribed Spacer (ITS) gene sequences. Among the ethyl acetate crude extracts, Fusarium foetens AQF6 contained the highest amount of polyphenol (117.76 ± 0.94 mg gallic acid equivalent/g) and flavonoid (169.01 ± 2.09 mg quercetin equivalent/g). Importantly, 400 µg/mL AQF6 extract exhibited 95.75 ± 1.1% and 85.66 ± 1.91% of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical-scavenging activities, respectively. Chemical investigation led to the isolation and identification of a new bisabolane-type sesquiterpene fusafoetriol (FUS) and 14 known compounds, among which six pure compounds showed free-radical scavenging activity against DPPH and hydroxyl radicals. Under H2O2 stress, the yeast model Saccharomyces cerevisiae treated with 4 mM FUS showed 43.31% increase in viability. FUS has the potential to be applied in nutraceutical, pharmaceutical and food technological applications. Thus, this is the first report demonstrating the presence of endophytic fungi inhabiting A. yunnanensis and their potential as a prolific source of antioxidant metabolites. Full article
(This article belongs to the Section Applied Microbiology)
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14 pages, 2812 KB  
Article
The First Phytochemical Investigation of Artemisia divaricate: Sesquiterpenes and Their Anti-Inflammatory Activity
by Siqi Yan, Changqiang Ke, Zheling Feng, Chunping Tang and Yang Ye
Molecules 2023, 28(10), 4254; https://doi.org/10.3390/molecules28104254 - 22 May 2023
Cited by 7 | Viewed by 2179
Abstract
Artemisia divaricate belongs to the Artemisia genus of the family of Compositae, a sort of perennial herb endemic in most regions of China. For the first time, a phytochemical investigation was carried out on the whole plant of Artemisia divaricate, resulting in [...] Read more.
Artemisia divaricate belongs to the Artemisia genus of the family of Compositae, a sort of perennial herb endemic in most regions of China. For the first time, a phytochemical investigation was carried out on the whole plant of Artemisia divaricate, resulting in the identification of 39 sesquiterpenes, with 9 of them being new (19). The structures of the new compounds were fully established using extensive analysis of MS and 1D and 2D NMR spectroscopic data and density functional theory (DFT) NMR calculations. Their structures involve germacrane, eudesmane, and bisabolane types. All the new isolates were evaluated for their anti-inflammatory activities in lipopolysaccharide (LPS)-stimulated murine macrophages of RAW 264.7 cells. Compounds 2 and 8 showed a significant inhibition effect on NO production, with IC50 values of 5.35 ± 0.75 and 7.68 ± 0.54 µM, respectively. Full article
(This article belongs to the Special Issue Chemicals of Natural Origin and Their Biological Activities)
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12 pages, 1400 KB  
Article
Comparative Analysis of Volatile Constituents in Root Tuber and Rhizome of Curcuma longa L. Using Fingerprints and Chemometrics Approaches on Gas Chromatography–Mass Spectrometry
by Guang-Mei Tang, Yi-Ting Shi, Wen Gao, Meng-Ning Li, Ping Li and Hua Yang
Molecules 2022, 27(10), 3196; https://doi.org/10.3390/molecules27103196 - 17 May 2022
Cited by 15 | Viewed by 3636
Abstract
The root tuber and rhizome of Curcuma longa L., abbreviated, respectively, as RCL and RHCL, are used as different medicines in China. In this work, volatile oils were extracted from RCL and RHCL. Then, gas chromatography–mass spectrometry (GC–MS) was used for RCL and [...] Read more.
The root tuber and rhizome of Curcuma longa L., abbreviated, respectively, as RCL and RHCL, are used as different medicines in China. In this work, volatile oils were extracted from RCL and RHCL. Then, gas chromatography–mass spectrometry (GC–MS) was used for RCL and RHCL volatile oils analysis, and 45 compounds were identified. The dominant constituents both in volatile oils of RCL and RHCL were turmerone, (−)-zingiberene, and β-turmerone, which covered more than 60% of the total area. The chromatographic fingerprint similarities between RCL and RHCL were not less than 0.943, indicating that their main chemical compositions were similar. However, there were also some compounds that were varied in RCL and RHCL. Based on the peak area ratio of 45 compounds, the RCL and RHCL samples were separated into principal component analysis (PCA) and partial least squares discriminant analysis (PLS-DA). Then, 20 compounds with a variable importance for the projection (VIP) value of more than 1 were the high potential contributors for RCL and RHCL differences. Furthermore, ferric ion-reducing antioxidant power (FRAP) assay results demonstrated that the volatile oils of RCL and RHCL had antioxidant activities. This study provided the material basis for the research of volatile components in RCL and RHCL and contributed to their further pharmacological research and quality control. Full article
(This article belongs to the Special Issue State-of-the-Art Analytical Technologies for Natural Products)
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19 pages, 5922 KB  
Article
Structure-Based Molecular Networking for the Discovery of Anti-HBV Compounds from Saussurea lappa (Decne.) C.B Clarke
by Tao Wu, Xin-Jian Yan, Tian-Rong Yang, Yun-Fen Wang, Jing-Yi He, Yang Feng, Li-Hua Su, Hao Chen and Min Xu
Molecules 2022, 27(6), 2023; https://doi.org/10.3390/molecules27062023 - 21 Mar 2022
Cited by 6 | Viewed by 3458
Abstract
It is a crucial to find target compounds in natural product research. This study presents a concept of structure-guided isolation to find candidate active molecules from herbs. We establish a process of anti-viral sesquiterpene networking. An analysis of the networking suggested that new [...] Read more.
It is a crucial to find target compounds in natural product research. This study presents a concept of structure-guided isolation to find candidate active molecules from herbs. We establish a process of anti-viral sesquiterpene networking. An analysis of the networking suggested that new anti-HBV sesquiterpene may be attributable to eudesmane-, guaiane-, cadinane-, germacane- and bisabolane-type sesquiterpenes. In order to evaluate the efficiency of the structure-based molecular networking, ethanol extract of Saussurea lappa (Decne.) C.B Clarke was investigated, which led to the isolation of two guaiane-type (1 and 14), ten eudesmane-type (25 and 813), two chain (6 and 7) and one germacrane-type (15) sesquiterpenes, including seven new ones, lappaterpenes A–G (17), which are reported on herein. The absolute configurations of the new compounds were established by coupling constants, calculated ECD and ROESY correlations, as well as comparisons of optical rotation values with those of known compounds. The absolute configuration of compound 2 was further confirmed by X-ray diffraction. Compounds 115 were evaluated for their potency against hepatitis B virus. Compounds 4, 6, 7 and 9 showed effect on HBsAg with inhibition ratios of more than 40% at 30 μM concentrations. Compounds 14 and 15 inhibited HBsAg secretion with the values of IC50 0.73 ± 0.18 and 1.43 ± 0.54 μM, respectively. Structure-based molecular networking inspired the discovery of target compounds. Full article
(This article belongs to the Special Issue Discovery of Bioactive Ingredients from Natural Products, 2nd Edition)
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43 pages, 9507 KB  
Review
Monoterpenes and Sesquiterpenes of Essential Oils from Psidium Species and Their Biological Properties
by Renan Campos e Silva, Jamile S. da Costa, Raphael O. de Figueiredo, William N. Setzer, Joyce Kelly R. da Silva, José Guilherme S. Maia and Pablo Luis B. Figueiredo
Molecules 2021, 26(4), 965; https://doi.org/10.3390/molecules26040965 - 12 Feb 2021
Cited by 61 | Viewed by 7122
Abstract
Psidium (Myrtaceae) comprises approximately 266 species, distributed in tropical and subtropical regions of the world. Psidium taxa have great ecological, economic, and medicinal relevance due to their essential oils’ chemical diversity and biological potential. This review reports 18 Psidium species growing around the [...] Read more.
Psidium (Myrtaceae) comprises approximately 266 species, distributed in tropical and subtropical regions of the world. Psidium taxa have great ecological, economic, and medicinal relevance due to their essential oils’ chemical diversity and biological potential. This review reports 18 Psidium species growing around the world and the chemical and biological properties of their essential oils. Chemically, 110 oil records are reported with significant variability of volatile constituents, according to their seasonality and collection sites. Monoterpenes and sesquiterpenes with acyclic (C10 and C15), p-menthane, pinane, bisabolane, germacrane, caryophyllane, cadinane, and aromadendrane skeleton-types, were the primary constituents. The essential oils showed various biological activities, including antioxidant, antifungal, antibacterial, phytotoxic, larvicidal, anti-inflammatory, and cytotoxic properties. This review contributes to the Psidium species rational and economic exploration as natural sources to produce new drugs. Full article
(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)
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10 pages, 1077 KB  
Article
Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor
by Zhi-Yong Guo, Ming-Hui Tan, Cheng-Xiong Liu, Meng-Meng Lv, Zhang-Shuang Deng, Fei Cao, Kun Zou and Peter Proksch
Molecules 2018, 23(6), 1291; https://doi.org/10.3390/molecules23061291 - 28 May 2018
Cited by 35 | Viewed by 5916
Abstract
Aspergoterpenins A–D (14), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (512), and their structures were elucidated by a comprehensive analysis of their [...] Read more.
Aspergoterpenins A–D (14), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (512), and their structures were elucidated by a comprehensive analysis of their NMR (Nuclear Magnetic Resonance), MS (Mass Spectrum) and CD (Circular Dichroism) spectra. Aspergoterpenin A (1) was the first example with a characteristic ketal bridged-ring part in the degraded natural bisabolane-type sesquiterpene structures. The compounds 112 displayed no significant activities against four cancer cell lines (A549, Caski, HepG2 and MCF-7). Further, the antimicrobial activities to Erwinia carotovora sub sp. Carotovora were evaluated, and the results showed that compounds 112 displayed antimicrobial activities with MIC values ranging from 15.2 to 85.2 μg/mL. Full article
(This article belongs to the Collection Bioactive Compounds)
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