4194-71-2Relevant articles and documents
Comparison of the Key Aroma Compounds in Fresh, Raw Ginger (Zingiber officinale Roscoe) from China and Roasted Ginger by Application of Aroma Extract Dilution Analysis
Schaller, Tanja,Schieberle, Peter
, p. 15292 - 15300 (2021/01/09)
By application of a comparative aroma extract dilution analysis on the volatile fractions isolated by solvent extraction and solvent-assisted flavor evaporation (SAFE) from fresh raw Chinese ginger (Zingiber officinale Roscoe) and roasted ginger, 21 or 33 odorants, respectively, with flavor dilution (FD) factors in the range of 32-4096 were identified. In raw ginger, the highest FD factors were found for (E)-isoeugenol, 1,8-cineol, vanillin, geranial, and linalool. After roasting, in particular, the FD factors of 3-(methylthio)propanal (cooked potato-like), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), 3-hydroxy-4,5-dimethyl-2(5H)-furanone (seasoning-like), and geraniol were substantially increased. The application of static headspace/olfactometry (SHO) on ground raw ginger revealed a high FD factor for highly volatile acetaldehyde which clearly decreased after roasting. By contrast, the SHO application revealed high FD factors for malty smelling methylpropanal and 3-methylbutanal, which both were exclusively detected in roasted ginger. Thirteen odorants, namely, decanoic acid, (Z)-2-decenal, (Z)-4-decenal, (E)-4,5-epoxy-(E)-2-decenal, (E)-4,5-epoxy-(E)-2-undecenal, fenchol, (Z)-3-hexenal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-methyl-2-buten-1-thiol, 2-methylpropanal, (E)-2-nonenal, and 1-nonen-3-one, were identified in ginger for the first time. Chiral analysis showed a much higher percent by weight portion for the (R)-enantiomer in citronellal, citronellol, and linalool, which was not much changed during pan-frying.
Stereoselective Synthesis of the Isomers of Notoincisol A: Assigment of the Absolute Configuration of this Natural Product and Biological Evaluation
Rycek, Lukas,Ticli, Vincenzo,Pyszkowski, Jakob,Latkolik, Simone,Liu, Xin,Atanasov, Atanas G.,Steinacher, Theresa,Bauer, Rudolf,Schuster, Daniela,Dirsch, Verena M.,Schnürch, Michael,Ernst, Margot,Mihovilovic, Marko D.
supporting information, p. 2419 - 2428 (2018/12/11)
The total syntheses of all stereoisomers of notoincisol A, a recently isolated natural product with potential anti-inflammatory activity, are reported. The asymmetric synthesis was conducted employing a lipase-mediated kinetic resolution, which enables easy access to all required chiral building blocks with the aim of establishing the absolute configuration of the naturally occurring isomer. This was achieved by comparison of optical properties of the isolated compound with the synthetic derivatives obtained. Moreover, an assessment of the biological activity on PPARγ (peroxisome proliferator-activated receptor gamma) as a prominent receptor related to inflammation is reported. Only the natural isomer was found to activate the PPARγ receptor, and this phenomenon could be explained based on molecular docking studies. In addition, the pharmacological profiles of the isomers were determined using the GABAA (gamma-aminobutyric acid A) ion channel receptor as a representative target for allosteric modulation related to diverse CNS activities. These compounds were found to be weak allosteric modulators of the α1β3 and α1β2γ2 receptor subtypes.
Total syntheses of 9-epoxyfalcarindiol and its diastereomer
Zhou, Yun,Huang, Yanli,Li, Shuoning,Yang, Pengfei,Zhong, Jiangchun,Yin, Jingwei,Ji, Kaijie,Yang, Yanqing,Ye, Ning,Wang, Lifeng,Wang, Mingan,Wang, Min,Bian, Qinghua
, p. 288 - 295 (2017/02/18)
The first total syntheses of 9-epoxyfalcarindiol 1a and its diastereomer 1b have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)4.
