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Maackiain

$1,232

  • Brand : BIOFRON

  • Catalogue Number : BD-P0958

  • Specification : 98.0%(HPLC)

  • CAS number : 2035-15-6

  • Formula : C16H12O5

  • Molecular Weight : 284.267

  • PUBCHEM ID : 91510

  • Volume : 10mg

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Catalogue Number

BD-P0958

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

284.267

Appearance

Powder

Botanical Source

Sophora japonica and Dalbergia spruceana

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C2C(C3=C(O1)C=C(C=C3)O)OC4=CC5=C(C=C24)OCO5

Synonyms

6a,12a-Dihydro-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-ol/6a,12a-Dihydro-6H-[1,3]dioxolo[4',5':5,6][1]benzofuro[3,2-c]chromen-3-ol/maackiain/(6aR,12aR)-6a,12a-dihydro-6H-[1,3]dioxolo[4',5':5,6]benzofuro[3,2-c]chromen-3-ol/6a,12a-Dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol/(−)-maackiain/6a,12a-Dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)chromen-3-ol/6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-

IUPAC Name

(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-ol

Applications

(-)-Maackiain is a pterocarpan phytoalexin produced from Red clover (Trifolium pretense L.). (-)-Maackiain is toxic to several genera of fungal pathogens of legume and non legume hosts[1].

Density

1.5±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

217.6±28.7 °C

Boiling Point

436.2±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16-/m0/s1

InChl Key

HUKSJTUUSUGIDC-ZBEGNZNMSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:2035-15-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

26516579

Abstract

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 Tyr(311) 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.

KEYWORDS

Allergic disease sensitive gene; IL-4 gene; Kujin; PKC δ; histamine H1 receptor gene; maackiain

Title

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

Author

Mizuguchi H1, Nariai Y1, Kato S1, Nakano T1, Kanayama T1, Kashiwada Y2, Nemoto H3, Kawazoe K4, Takaishi Y2, Kitamura Y5, Takeda N5, Fukui H6.

Publish date

2015 Oct

PMID

27575476

Abstract

Monoamine oxidase (MAO) catalyzes the oxidation of monoamines and its two isoforms, MAO-A and MAO-B, break down neurotransmitter amines. Of the compounds isolated from the roots of Sophora flavescens, (-)-maackiain (4), a pterocarpan, was found to potently and selectively inhibit human MAO-B, with an IC50 of 0.68μM, and to have a selectivity index of 126.2 for MAO-B. As compared with other herbal natural products, the IC50 value of 4 for MAO-B is one of the lowest reported to date. Genistein (1) highly, effectively and non-selectively inhibited MAO-A and MAO-B with IC50 values of 3.9μM and 4.1μM, respectively. (-)-4-Hydroxy-3-methoxy-8,9-methylenedioxypterocarpan (2) effectively and non-selectively inhibited MAO-A and MAO-B with IC50 values of 20.3μM and 10.3μM, respectively. In addition, compound 4 reversibly and competitively inhibited MAO-B with a Ki value of 0.054μM. Molecular docking simulation revealed that the binding affinity of 4 for MAO-B (-26.6kcal/mol) was greater than its affinity for MAO-A (-8.3kcal/mol), which was in-line with our inhibitory activity findings. Furthermore, Cys172 of MAO-B was found to be a key residue for hydrogen bonding with compound 4. The findings of this study suggest compound 4 be viewed as a new potent, selective, and reversible MAO-B inhibitor, and that compounds 1 and 2 be considered useful lead compounds for the developments of nonselective and reversible MAO inhibitors for the treatment of disorders like Parkinson’s disease, Alzheimer disease, and depression.

Copyright © 2016 Elsevier Ltd. All rights reserved.

KEYWORDS

4-Hydroxy-3-methoxy-8,9-methylenedioxypterocarpan; Human monoamine oxidase; Maackiain; Molecular docking; Selective competitive inhibitor; Sophora flavescens

Title

Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens.

Author

Lee HW1, Ryu HW2, Kang MG3, Park D3, Oh SR2, Kim H4.

Publish date

2016 Oct 1

PMID

25819294

Abstract

The larvicidal activities of extracts of three hardwood species (Hymenaea stigonorcapa, Anadenanthera colubrina and Bowdichia virgilioides) against 4th instar larvae of Aedes aegypti were evaluated using WHO guidelines. Extracts of H. stignocarpa and A. colubrina showed weak activity. The highest larvicidal effect was obtained with the cyclohexane extract of the heartwood of B. virgilioides, which caused 100% mortality at concentrations at 50 and 100 µg/mL. Fraction toluene/EtOAc (8:2) from this extract showed larvicidal activity (LC₅₀ = 34.90 ± 1.27 µg/mL). A mixture of two compounds identified as medicarpin and maackiain exhibited a very good larvicidal activity (sub-fraction 2, LC₅₀ = 17.5 ± 1.87 µg/mL) and maackiain showed to be a strong larvicidal compound (LC₅₀ = 21.95 ± 1.34 µg/mL). This result can be of value in the search for new natural larvicidal compounds from other hardwood plant extracts and presents the first report of B. virgilioides being used to control a mosquito vector.

Copyright © 2015 Elsevier Inc. All rights reserved.

KEYWORDS

Aedes aegypti; Bowdichia virgilioides; Hardwood; Maackiain; Medicarpin

Title

Extract of Bowdichia virgilioides and maackiain as larvicidal agent against Aedes aegypti mosquito.

Author

Bezerra-Silva PC1, Santos JC1, Santos GK1, Dutra KA1, Santana AL2, Maranhão CA3, Nascimento MS4, Navarro DM5, Bieber LW1.

Publish date

2015 Jun