Isoimperatorin

Names

[ CAS No. ]:
482-45-1

[ Name ]:
Isoimperatorin

[Synonym ]:
7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(3-methyl-2-buten-1-yl)oxy]-
IisoiMperatorin
buten-1-yl)oxy]
7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(3-methyl-2-butenyl)oxy]-
Iso Imperatorin
Isoimperatoin
MFCD00272155
4-[(3-Methyl-2-buten-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
7H-Furo[3,2-g][1]benzopyran-7-one, 4-((3-methyl-2-butenyl)oxy)-
Isoimperatorin
4-PRENYLOXYPSORALEN
Isomperatorin
Auraptin
isoimperatonin
4-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3-methyl-2-butenyl)oxy)-
Cnidin

Biological Activity

[Description]:

Isoimperatorin is a methanolic extract of the roots of Angelica dahurica shows significant inhibitory effects on acetylcholinesterase (AChE) with the IC50 of 74.6 μM.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> AChE

Natural Products >> Phenylpropanoids

Research Areas >> Neurological Disease

[Target]

IC50: 74.6 μM (AChE)[1]

[In Vitro]

During a screening program for new agrochemicals from Chinese medicinal herbs, the ethanol extract of Notopterygium incisum rhizomes is found to possess strong nematicidal activity against the two species of nematodes, Bursaphelenchus xylophilus and Meloidogyne incognita. Based on bioactivity-guided fractionation, the four constituents are isolated from the ethanol extract and identified as Columbianetin, Falcarindiol, Falcarinol, and Isoimperatorin. Isoimperatorin also has LC50 values of 21.83 μg/mL against B. xylophilus. When using 15 min UV light treatment, falcarindiol, falcarinol, and isoimperatorin demonstrated almost five times more toxic to the southern root-knot nematodes than in dark treatment while columbianetin showed only two times more toxic. isoimperatorin has been demonstrated to possess insecticidal activity against several insects, such as the cabbage aphid (Brevicoryne brassicae)[2]. Isoimperatorin is identified in the active fraction of Angelica dahurica (AD) extract[3]. Isoimperatorin is usually used as the internal standard (IS)[4].

[References]

[1]. Kim DK, et al. Acetylcholinesterase inhibitors from the roots of Angelica dahurica. Arch Pharm Res. 2002 Dec;25(6):856-9.

[2]. Liu G, et al. Identification of Nematicidal Constituents of Notopterygium incisum Rhizomes against Bursaphelenchus xylophilus and Meloidogyne incognita. Molecules. 2016 Sep 23;21(10). pii: E1276.

[3]. Park EY, et al. Angelica dahurica Extracts Improve Glucose Tolerance through the Activation of GPR119. PLoS One. 2016 Jul 8;11(7):e0158796.

[4]. Yu XA, et al. The pharmacokinetics, bioavailability and excretion of bergapten after oral and intravenous administration in rats using high performance liquid chromatography with fluorescence detection. Chem Cent J. 2016 Oct 14;10:62.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
448.3±45.0 °C at 760 mmHg

[ Melting Point ]:
109ºC

[ Molecular Formula ]:
C₁₆H₁₄O₄

[ Molecular Weight ]:
270.280

[ Flash Point ]:
224.9±28.7 °C

[ Exact Mass ]:
270.089203

[ PSA ]:
52.58000

[ LogP ]:
3.88

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.606

[ Storage condition ]:
-20°C Freezer

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
LV1513000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

In vitro activity of isoimperatorin, alone and in combination, against Mycobacterium tuberculosis.

Lett. Appl. Microbiol. 58(4) , 344-9, (2014)

Previous studies have shown that isoimperatorin (IO), a furanocoumarin isolated from several medicinal plants, has antimycobacterial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 2729...

Study on pharmacokinetics and tissue distribution of pteryxin in mice by ultra-pressure liquid chromatography with tandem mass spectrometry.

Biomed. Chromatogr. 26(7) , 802-7, (2012)

Pteryxin is a coumarin compound naturally occurring in the roots of Radix Peucedani, a commonly used as traditional Chinese medicine for the treatment of certain respiratory diseases and hypertension....

Ethyl acetate extract from Angelica Dahuricae Radix inhibits lipopolysaccharide-induced production of nitric oxide, prostaglandin E2 and tumor necrosis factor-alphavia mitogen-activated protein kinases and nuclear factor-kappaB in macrophages.

Pharmacol. Res. 55(4) , 263-70, (2007)

Angelica dahurica (Umbelliferae) has been used to treat headache of common cold, supraorbital neuralgia, painful swelling on the body, nasal stuffiness, leukorrhea and arthralgia due to wind-dampness ...