76240-25-0Relevant academic research and scientific papers
Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes
Mizuguchi, Hiroyuki,Nariai, Yuki,Kato, Shuhei,Nakano, Tomohiro,Kanayama, Tomoyo,Kashiwada, Yoshiki,Nemoto, Hisao,Kawazoe, Kazuyoshi,Takaishi, Yoshihisa,Kitamura, Yoshiaki,Takeda, Noriaki,Fukui, Hiroyuki
, (2017/11/09)
Kujin contains antiallergic compounds that inhibit upregulation of histamine H1 receptor (H1R) and interleukin (IL)-4 gene expression. However, the underlying mechanism remains unknown. We sought to identify a Kujin-derived antiallergic compound and investigate its mechanism of action. The H1R and IL-4 mRNA levels were determined by real-time quantitative RT-PCR. To investigate the effects of maackiain in?vivo, toluene-2,4-diisocyanate (TDI)-sensitized rats were used as a nasal hypersensitivity animal model. We identified (?)-maackiain as the responsible component. Synthetic maackiain showed stereoselectivity for the suppression of IL-4 gene expression but not for H1R gene expression, suggesting distinct target proteins for transcriptional signaling. (?)-Maackiain inhibited of PKCδ translocation to the Golgi and phosphorylation of Tyr311 on PKCδ, which led to the suppression of H1R gene transcription. However, (?)-maackiain did not show any antioxidant activity or inhibition of PKCδ enzymatic activity per se. Pretreatment with maackiain alleviated nasal symptoms and suppressed TDI-induced upregulations of H1R and IL-4 gene expressions in TDI-sensitized rats. These data suggest that (?)-maackiain is a novel antiallergic compound that alleviates nasal symptoms in TDI-sensitized allergy model rats through the inhibition of H1R and IL-4 gene expression. The molecular mechanism underlying its suppressive effect for H1R gene expression is mediated by the inhibition of PKCδ activation.
Structure-activity relationship of wedelolactone analogues: Structural requirements for inhibition of Na+,K+-ATPase and binding to the central benzodiazepine receptor
Pocas, Elisa S.C.,Lopes, Daniele V.S.,da Silva, Alcides J.M.,Pimenta, Paulo H.C.,Leitao, Fernanda B.,Netto, Chaquip D.,Buarque, Camilla D.,Brito, Flavia V.,Costa, Paulo R.R.,Noel, Francois
, p. 7962 - 7966 (2007/10/03)
Coumestans 2a-i, bearing different patterns of substitution in A- and D-rings, were synthesized and evaluated as inhibitors of kidney Na+,K+-ATPase and ligands for the central benzodiazepine (BZP) receptor. The presence of a hydroxyl group in position 2 favours the effect on Na+,K+-ATPase but decreases the affinity for the BZP receptor, allowing the design of more selective molecules than the natural wedelolactone. On the other hand, the presence of a catechol in ring D is important for the effect on both molecular targets.
4-Chromenesulphones: Synthesis and transformation to isoflavonoid models
Simas, Alessandro Bolis C.,Furtado, Luis F.O.,Costa, Paulo R.R.
, p. 6893 - 6895 (2007/10/03)
Novel sulphones derived from chromenes through substitution at C-4 were prepared. It has been shown that, after conjugate addition of phenyl lithium and sulphone function manipulation on the adducts, these molecules lead to isoflavan, isoflavene and isoflavanone models.
Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation
Da Silva, Alcides J.M.,Melo, Paulo A.,Silva, Noelson M.V.,Brito, Flavia V.,Buarque, Camilla D.,De Souza, Daniele V.,Rodrigues, Veronica P.,Pocas, Elisa S.C.,Noel, Francois,Albuquerque, Edson X.,Costa, Paulo R.R.
, p. 283 - 286 (2007/10/03)
Five coumestans with different patterns of oxygenation in rings A and D were synthesized from resorcinol and aromatic aldehydes, and screened for their antimyotoxic activity. The most potent compound (2b, IC50 = 1 μM) was selected for study of
A convenient synthesis of (±)-4-prenylpterocarpin
Coelho,Vasconcellos,Simas,Rabi,Costa
, p. 914 - 916 (2007/10/02)
Coupling of 7-methoxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran (4a) with 2-chloromercurio-4,5-methylenedioxyphenol (5) yields (±)-6a,12a-cis-dihydro-3-methoxy-4-(3-methyl-2-butenyl)-6H-[1,3]diox olo[5,6]benzofuro[3,2-c][1]benzopyran (6; ±-4-prenylpterocarpi
A Short Synthesis of 2H-1-Benzopyrans
Schuda, Paul Francis,Phillips, Jennifer L.
, p. 669 - 672 (2007/10/02)
A two-step process for synthesizing 2H-1-benzopyrans from phenols and β-halopropionaldehyde acetals is detailed.
CLAISEN REARRANGEMENT OF META-SUBSTITUTED ARYL PROPARGYL ETHERS IN POLY(ETHYLENE GLYCOL)
Rao, Usha,Balasubramanian, Kalpattu Kuppuswa.
, p. 1351 - 1357 (2007/10/02)
The thermal rearrangement of meta-substituted aryl propargyl ethers was studied in poly(ethylene glycol)-200.The rearrangement was not regiospecific.
SYNTHESIS OF (+/-)-CABENEGRINS A-I AND A-II
Ishiguro, Masaji,Tatsuoka, Toshio,Nakatsuka, Nobuo
, p. 3859 - 3862 (2007/10/02)
(+/-)-Cabenegrins A-I and A-II, the potent antidotes against snake venoms, have been synthesized from maakiain (9) and 2-carbomethoxy-3-benzyl maakiain (20).
Structure and Synthesis of Isoflavonoid Analogues from Neorautanenia amboensis Schinz
Breytenbach, Jaco C.,Rall, Gerhardus J.H.
, p. 1804 - 1809 (2007/10/02)
The isolation and structural elucidation of six pterocarpans: neorautenane, neorautanol, edulenane, edulenanol, ambonane, and neorautenanol, as well as two new isoflavanones: ambonone and neoraunone, are reported.The structures of neorautenane and neoraut
