23513-53-3

Basic information

• Product Name: (+)-MAACKIAIN
• Synonyms: (+)-MAACKIAIN
• CAS NO: 23513-53-3
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• Mol File: 23513-53-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-MAACKIAIN(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-MAACKIAIN(23513-53-3)
• EPA Substance Registry System: (+)-MAACKIAIN(23513-53-3)

Safety Data

• Hazardous Substances Data: 23513-53-3(Hazardous Substances Data)

Usage

General Description

(+)-Maackiain is a natural bioactive compound belonging to the flavonoid group, commonly found in the fruits and leaves of the Maackia amurensis tree. It has been identified as an estrogenic and antioxidant agent, exhibiting potential therapeutic properties. Studies have suggested that (+)-maackiain has the ability to bind to estrogen receptors and may therefore have potential applications in hormone-related conditions. Additionally, its antioxidant properties make it a promising candidate for use in the prevention and treatment of various diseases associated with oxidative stress. Overall, (+)-maackiain shows great promise as a natural compound with potential pharmaceutical and nutraceutical applications.

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Relevant articles and documents

Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes

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.

Absolute configuration and total synthesis of (-)-cabenegrin A-I

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.