69768-95-2Relevant academic research and scientific papers
Metabolite Profiling of Javanese Ginger Zingiber purpureum and Identification of Antiseizure Metabolites via a Low-Cost Open-Source Zebrafish Bioassay-Guided Isolation
Allard, Pierre-Marie,Brillatz, Théo,Crawford, Alexander D.,Fish, Richard,Fukuyama, Yoshiyasu,Harada, Kenichi,Ishizawa, Keisuke,Jozukuri, Natsumi,Kubo, Miwa,Marcourt, Laurence,Queiroz, Emerson Ferreira,Takahashi, Shimon,Takechi, Kenshi,Wolfender, Jean-Luc
, p. 7904 - 7915 (2020/09/01)
The rhizomes of Zingiber purpureum, Bangle , were investigated for its antiseizure properties using a streamlined and cost-effective zebrafish screening strategy and a mouse epilepsy assay. Its hexane extract demonstrated strong antiseizure activity in zebrafish epilepsy assay and was, therefore, selected for bioactivity-guided fractionation. Twelve compounds (1-12) were isolated, and two bioactive phenylbutenoids, trans- (11) and cis-banglene (12), reduced up to 70percent of pentylenetetrazole (PTZ)-induced seizures. These compounds showed moderate activity against PTZ-induced seizures in a mouse epilepsy assay. To understand the specificity of Z. purpureum active compounds, its chemical profile was compared to that of Z. officinale. Their composition was assessed by differential metabolite profiling visualized by a molecular network, which revealed only vanillin derivatives and terpenoids as common metabolites and gave a comprehensive view of Z. purpureum composition. This study demonstrates the efficacy of a streamlined zebrafish epilepsy assay, which is therefore suitable for routine screening in phytochemistry laboratories.
Synthesis and anti-inflammatory activity of phenylbutenoid dimer analogs
Kim, Sung-Soo,Fang, Yuanying,Park, Haeil
, p. 1676 - 1680 (2015/07/15)
Several phenylbutenoid dimer (PBD) analogs were synthesized and evaluated for their inhibitory activities against nitric oxide (NO) production and TNF-α release. The PBD analogs were synthesized via Diels - Alder and subsequent Schlosser reactions as key steps. Among the tested compounds, two analogs (8c, 8f) exhibited much stronger inhibitory activity against LPS-stimulated NO production and TNF-α release in RAW 264.7 cells than that of wogonin.
PHENYLBUTENOID DIMERS FROM THE RHIZOMES OF ZINGIBER CASSUMUNAR
Jitoe, Akiko,Masuda, Toshiya,Nakatani, Nobuji
, p. 357 - 364 (2007/10/02)
Two new phenylbutenoid dimers, (+/-)-trans-3-(2,4,5-trimethoxyphenyl)-4-cyclohexene and cis-1,2-biscyclobutane, have been isolated from the fresh rhizomes of Zingiber cassumunar along with the two known phenylbutenoid dimers.Their structures were elucidated by spectroscopic and chemical methods.The stereochemistry of these cyclohexene compounds was clarified on the basis of 1H NMR data of their derivatives.The substituted positions for the 3,4-dimethoxystyryl groups of the cyclobutane compound were confirmed from a Cope rearrangement product in the pyrolysis of the cyclobutane, and the stereochemistry of the cyclobutane was confirmed by 1H NMR evidence.Key Word Index - Zingiber cassumunar; Zingiberaceae; rhizomes; phenylbutenoid; dimer.
Syntheses of Some Constituents of Zingiber cassumunar
Tuntiwachwuttikul, Pittaya,Limchawfar, Burin,Reutrakul, Vichai,Pancharoen, Orasa,Kusamran, Kosan,Byrne, Lindsay T.
, p. 913 - 916 (2007/10/02)
Syntheses of the aromatic compounds cis-3-(2',4',5'-trimetoxyphenyl)-4-cyclohex-1-ene (1), cis-3-(3',4'-dimethoxyphenyl-4-cyclohex-1-ene (2), cis-3-(3',4'-dimethoxyphenyl)-4-cyclohex-1-ene (3), (E)-4-(3',4'-dimethoxyphenyl)but-3-en-1-ol (5), and (E)-4-(3',4'-dimethoxyphenyl)but-3-enyl acetate (6) have been carried out.
