5928-25-6

Basic information

• Product Name: DECURSIN
• Synonyms: DECURSIN;DECURSINOL ANGELATE;(7S)-7,8-Dihydro-8,8-dimethyl-7-[(3-methyl-2-butenoyl)oxy]-2H,6H-benzo[1,2-b:5,4-b']dipyran-2-one;3-Methyl-2-butenoic acid (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-7-yl ester;3-Methyl-2-butenoic acid (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-pyrano[3,2-g]-1-benzopyran-7-yl ester;(7S)-7,8-Dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo[1,2-b:5,4-b′]dipyran-7-yl 3-methyl-2-butenoate;(S)-(+)-decursin;Decursin, 98%, from Angelica decursiva (Miq.) Franch. & Sav.
• CAS NO: 5928-25-6
• Molecular Formula: C19H20O5
• Molecular Weight: 328.36
• Product Categories: Miscellaneous Natural Products
• Mol File: 5928-25-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 93-94℃
• Boiling Point: 469.4 °C at 760 mmHg
• Flash Point: 206.6 °C
• Appearance: white to beige/
• Density: 1.24
• Vapor Pressure: 5.54E-09mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble5mg/mL, clear
• CAS DataBase Reference: DECURSIN(CAS DataBase Reference)
• NIST Chemistry Reference: DECURSIN(5928-25-6)
• EPA Substance Registry System: DECURSIN(5928-25-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 5928-25-6(Hazardous Substances Data)

Usage

Description

Decursin is a phytochemical originally isolated from A. gigas with diverse biological activities. It reduces the growth of B16/F10 murine melanoma cells, but not NIH-3T3 fibroblasts, via induction of apoptosis and increased caspase-3 activity when used at concentrations ranging from 40 to 100 μM. In vivo, decursin (10 mg/kg, i.p.) reduces tumor growth in a B16/F10 mouse xenograft model. Decursin inhibits RANKL-induced osteoclast differentiation and decreases fusion and migrations of pre-osteoclasts in vitro and prevents LPS-induced bone erosion in mice. In a mouse model of seizures induced by kainic acid , decursin (20 mg/kg) increases latency to the first electroencephalographic (EEG) discharge and attenuates the intensity and reduces the frequency of seizure discharges in the parietal cortex. Decursin inhibits tube formation and expression of VEGF receptor 2 (VEGFR2) in human retinal microvascular endothelial cells (HRMECs) and human umbilical vein endothelial cells (HUVECs) in vitro and reduces retinal expression of VEGFR2 and neovascularization in rats with diabetes induced by streptozotocin . It also reduces hepatic collagen expression, serum levels of ALT, AST, and ALP, and production of reactive oxygen species (ROS) in a mouse model of CCL4-induced liver fibrosis.

Uses

Decursin is a bioactive metabolites from the root of Angelica gigas Nakai which exhibits neuro-protective and cognitive enhancement effects. Human monoamine oxidase (MAO) inhibitor. Also, it could be useful for the treatment of bone associated with excessive bone resorption.

Biochem/physiol Actions

Decursin is a cumarin isolated from Radix peucedani that exhibits a number of physiological actions including anticancer, antibacterial, antinematodal and antioxidant. Decursin is potent anti-angiogenic agent targeting the VEGFR-2 signaling pathway. Decursin exhibits potent neuroprotective activity against glutamate and Ab- induced neurotoxicity. Apparently, decursin stimulates activation of Nerf2. Also, decursin inhibits androgen stimulated AR translocation to the nucleus in LNCaP prostate cancer cells.

InChI:InChI=1/C19H20O5/c1-11(2)7-18(21)23-16-9-13-8-12-5-6-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/t16-/m0/s1

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 5993-18-0 decursinol 
• 325138-04-3 7-(methoxymethoxy)-6-[(Z)-3-oxo-1-butenyl]chromen-2-one 
• 325137-92-6 7-(methoxymethoxy)-6-[(E)-3-oxo-1-butenyl]chromen-2-one 
• 325137-90-4 6-[(1R,2S)-1,2-epoxy-3-oxobutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-94-8 7-(methoxymethoxy)-6-(trifluoromethanesulfonyl)chromen-2-one 
• 325137-96-0 6-[(1R,2S)-1,2-epoxy-3-hydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 616241-73-7 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 616241-75-9 (S)-7,8-dihydro-8,8-dimethyl-7-triethylsilyloxy-6H-pyrano[3,2-g]chromen-2-one 
• 325137-98-2 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(trifluoromethanesulfonyl)chromen-2-one 
• 325138-00-9 6-[(2S)-3-hydroxy-3-methyl-2-(triethylsilyloxy)butyl]-7-(trifluoromethanesulfonyl)chromen-2-one 
• 108-46-3 recorcinol 
• 354576-62-8 acetic acid 2,2-dimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalen-5-yl ester 
• 94527-05-6 4,7-dihydroxy-2,2-dimethylchroman 

Downstream Products

• 5993-18-0 decursinol 
• 51019-80-8 (-)-cis-decursidinol 
• 5993-18-0 decursinol 

Relevant articles and documents

Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor

The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC50 value of 9.9 μM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5- methoxypsoralen (35), 8-geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC50 values 25.0 μM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.

NOVEL DECURSIN DERIVATIVES AND THE USE THEREOF

The present invention relates to novel (+)-decursin derivatives having anti-cancer activity, the preparation thereof and a composition containing the same for treating cancer disease. The (+)-decursin derivatives of the present invention showed potent inh

Decursin suppresses human androgen-independent PC3 prostate cancer cell proliferation by promoting the degradation of β-catenin

Alterations in the Wnt/β-catenin pathway are associated with the development and progression of human prostate cancer. Decursin, a pyranocoumarin isolated from the Korean Angelica gigas root, inhibits the growth of androgen-independent human prostate cancer cells, but little is known about its mechanism of action. Using a cell-based screen, we found that decursin attenuates the Wnt/β-catenin pathway. Decursin antagonized β-catenin response transcription (CRT), which was induced with Wnt3a-conditioned medium and LiCl, by promoting the degradation of β-catenin. Furthermore, decursin suppressed the expression of cyclin D1 and c-myc, which are downstream target genes of β-catenin and thus inhibited the growth of PC3 prostate cancer cells. In contrast, decursinol, in which the (CH3) 2-C=CH-COO- side chain of decursin is replaced with -OH, had no effect on CRT, the level of intracellular β-catenin, or PC3 cell proliferation. Our findings suggest that decursin exerts its anticancer activity in prostate cancer cells via inhibition of the Wnt/β-catenin pathway. Copyright