19908-48-6Relevant articles and documents
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.
(±)-3,4-Dihydroxy-8,9-methylenedioxypterocarpan and derivatives: Cytotoxic effect on human leukemia cell lines
Netto, Chaquip D.,Santos, Eduardo S.J.,Castro, Carolina Pereira,da Silva, Alcides J.M.,Rumjanek, Vivian M.,Costa, Paulo R.R.
body text, p. 920 - 925 (2009/09/08)
Naturally occurring pterocarpans 1a,b, pterocarpan 1c, isoflavane 2 and ortho-quinone 3 were synthesized in the racemic form and their cytotoxic effect was evaluated on the human leukemia cell lines K562 (resistant to oxidative stress), Lucena-1 (MDR phenotype) and HL-60. Ortho-quinone 3 (IC50 = 1.5 μM, 1.8 μM and 0.2 μM, respectively) and catechol pterocarpan 1a (IC50 = 3.0 μM, 3.7 μM and 2.1 μM, respectively) were the most active compounds on these cells and were also evaluated on other human leukemia cell lines (Jurkat and Daudi). Ortho-quinone 3 was 2 to 10 times more potent than pterocarpan 1a, depending on the cell line considered, however, showed a greater toxicity for lymphocytes activated by PHA.
Absolute configuration and total synthesis of (-)-cabenegrin A-I
Tokes, Adrienne L.,Litkei, Gyoergy,Gulacsi, Katalin,Antus, Sandor,Baitz-Gacs, Eszter,Szantay, Csaba,Darko, Laszlo L.
, p. 9283 - 9296 (2007/10/03)
The total synthesis of (-)-cabenegrin A-I [(-)-1] in five steps was achieved from (-)-6aR, 11aR-maackiain [(-)-5], which in turn was prepared by the optical resolution of racemic (±)-5 using S-(-)α-methylbenzyl isocyanate as the the chiral auxiliary. The homochirality of(-)-maackiain [(- )-5] and (-)cabenegrin A-I [(-)-1] was proved by CD measurements. Synthesis of (±)maackiain [(±)-5] is also presented, starting from the readily available phenol derivatives resorcinol and sesamol, which demonstrates the synthetic utility of the Heck-type oxyarylation process for obtaining pterocarpane derivatives on a multigram scale. A new ring-opening reaction of pterocarpanes (7 → 28) is described.
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).
