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Search Results (4)

Search Parameters:
Keywords = selinane

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10 pages, 892 KiB  
Article
Chemical Investigation on the Volatile Part of the CO2 Supercritical Fluid Extract of Infected Aquilaria sinensis (Chinese Agarwood)
by Marko Z. Mladenović, Ou Huang, Bo Wang, Alexandre Ginestet, Didier Desbiaux and Nicolas Baldovini
Molecules 2024, 29(10), 2297; https://doi.org/10.3390/molecules29102297 - 14 May 2024
Cited by 1 | Viewed by 1581
Abstract
This work is focused on the characterization of the composition of a CO2 supercritical fluid extract of Aquilaria sinensis (Chinese agarwood) collected in the Dongguan area (China) and infected by mechanical methods. The constituents of this extract were analyzed by gas chromatography–mass [...] Read more.
This work is focused on the characterization of the composition of a CO2 supercritical fluid extract of Aquilaria sinensis (Chinese agarwood) collected in the Dongguan area (China) and infected by mechanical methods. The constituents of this extract were analyzed by gas chromatography–mass spectrometry (GC-MS) and quantified accurately by gas chromatography with a flame ionization detector (GC-FID), using an internal reference and predicted response factors. Since a significant number of components of this extract remained non-identified after the initial GC-MS analysis of the whole extract, its fractionation by chromatography on silica gel helped to characterize several additional constituents by isolation and structural analysis by NMR spectroscopy. The main components are the classical agarwood chromones (Flindersia chromone and its mono-, di-, and trimethoxylated analogues (respectively, 11.01% and 0.11–4.02%) along with sesquiterpenic constituents typically found in agarwood essential oils, like baimuxinal (1.90%) and kusunol (1.24%), as well as less common selinane dialdehydes (1.58–2.27%) recently described in the literature. Moreover, the structure and stereochemistry of a new sesquiterpenic alcohol, 14β,15β-dimethyl-7αH-eremophila-9,11-dien-8β-ol (0.67%), was determined unambiguously by the combination of structural analysis (NMR, MS), hemisynthesis, and total synthesis, leading to dihydrokaranone and a neopetasane epimer. Full article
(This article belongs to the Section Flavours and Fragrances)
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9 pages, 672 KiB  
Communication
New Sesquiterpenoids from the Fermented Broth of Termitomyces albuminosus and Their Anti-Acetylcholinesterase Activity
by Wei Li, Qian Liu, Shimian Cheng, Shanren Li and Yongbiao Zheng
Molecules 2019, 24(16), 2980; https://doi.org/10.3390/molecules24162980 - 16 Aug 2019
Cited by 15 | Viewed by 3730
Abstract
Termitomyces albuminosus is the symbiotic edible mushroom of termites and cannot be artificially cultivated at present. In the project of exploring its pharmaceutical metabolites by microbial fermentation, four new selinane type sesquiterpenoids—teucdiol C (1), D (2), E (3 [...] Read more.
Termitomyces albuminosus is the symbiotic edible mushroom of termites and cannot be artificially cultivated at present. In the project of exploring its pharmaceutical metabolites by microbial fermentation, four new selinane type sesquiterpenoids—teucdiol C (1), D (2), E (3), and F (4), together with two known sesquiterpenoids teucdiol B (5) and epi-guaidiol A (6)—were obtained from its fermented broth of T. albuminosus. Their structures were elucidated by the analysis of NMR data, HR Q-TOF MS spectral data, CD, IR, UV, and single crystal X-ray diffraction. Epi-guaidiol A showed obvious anti-acetylcholinesterase activity in a dose-dependent manner. The experimental results displayed that T. albuminosus possess the pharmaceutical potential for Alzheimer’s disease, and it was an effective way to dig new pharmaceutical agent of T. albuminosus with the microbial fermentation technique. Full article
(This article belongs to the Collection Bioactive Compounds)
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6 pages, 95 KiB  
Article
Brominated Selinane Sesquiterpenes from the Marine Brown Alga Dictyopteris divaricata
by Nai-Yun Ji, Wei Wen, Xiao-Ming Li, Qin-Zhao Xue, Hua-Ling Xiao and Bin-Gui Wang
Mar. Drugs 2009, 7(3), 355-360; https://doi.org/10.3390/md7030355 - 22 Jul 2009
Cited by 28 | Viewed by 11412
Abstract
Two new brominated selinane sesquiterpenes, 1-bromoselin-4(14),11-diene (1) and 9-bromoselin-4(14),11-diene (2), one known cadinane sesquiterpene, cadalene (3), and four known selinane sesquiterpenes, α-selinene (4), β-selinene (5), β-dictyopterol (6), and cyperusol C (7), were isolated from a sample of marine brown alga [...] Read more.
Two new brominated selinane sesquiterpenes, 1-bromoselin-4(14),11-diene (1) and 9-bromoselin-4(14),11-diene (2), one known cadinane sesquiterpene, cadalene (3), and four known selinane sesquiterpenes, α-selinene (4), β-selinene (5), β-dictyopterol (6), and cyperusol C (7), were isolated from a sample of marine brown alga Dictyopteris divaricata collected off the coast of Yantai (China). Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with literature data. Full article
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9 pages, 287 KiB  
Article
Germacrene D Cyclization: An Ab Initio Investigation
by William N. Setzer
Int. J. Mol. Sci. 2008, 9(1), 89-97; https://doi.org/10.3390/ijms9010089 - 25 Jan 2008
Cited by 17 | Viewed by 12627
Abstract
Essential oils that contain large concentrations of germacrene D are typically accompanied by cadinane sesquiterpenoids. The acid-catalyzed cyclization of germacrene D to give cadinane and selinane sesquiterpenes has been computationally investigated using both density functional (B3LYP/6-31G*) and post Hartree-Fock (MP2/6-31G**) ab initio methods. [...] Read more.
Essential oils that contain large concentrations of germacrene D are typically accompanied by cadinane sesquiterpenoids. The acid-catalyzed cyclization of germacrene D to give cadinane and selinane sesquiterpenes has been computationally investigated using both density functional (B3LYP/6-31G*) and post Hartree-Fock (MP2/6-31G**) ab initio methods. The calculated energies are in general agreement with experimentally observed product distributions, both from acid-catalyzed cyclizations as well as distribution of the compounds in essential oils. Full article
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
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