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Decursinol

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-D1006

  • Specification : 98%

  • CAS number : 23458-02-8

  • Formula : C14H14O4

  • Molecular Weight : 246.262

  • PUBCHEM ID : 442127

  • Volume : 10mg

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Catalogue Number

BF-D1006

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

246.262

Appearance

Powder

Botanical Source

roots of Angelica gigas

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C(CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O)C

Synonyms

Smyrinol/(S)-(+)-decursinol/(3S)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one/Smirino/(+)-Decursinol/Decursinol [INCI]

IUPAC Name

(3S)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one

Applications

Decursinol, isolated from the roots of Angelica gigas, possesses antinociceptive effect with orally bioavailability. Decursinol possesses anti-tumor and anti-metastasis activity[1].

Density

1.293g/cm3

Solubility

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

Flash Point

167.9ºC

Boiling Point

433.6ºC at 760mmHg

Melting Point

InChl

InChI=1S/C14H14O4/c1-14(2)12(15)6-9-5-8-3-4-13(16)17-10(8)7-11(9)18-14/h3-5,7,12,15H,6H2,1-2H3/t12-/m0/s1

InChl Key

BGXFQDFSVDZUIW-LBPRGKRZSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:23458-02-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29121805

Abstract

We have previously shown that the ethanol extract of dried Angelica gigas Nakai (AGN) root exerts anticancer activity against androgen receptor (AR)-negative human DU145 and PC-3 prostate cancer xenografts and primary carcinogenesis in the transgenic adenocarcinoma of mouse prostate (TRAMP) model. The major pyranocoumarin isomers decursin (D) and decursinol angelate (DA), when provided at equi-molar intake to that provided by AGN extract, accounted for the inhibitory efficacy against precancerous epithelial lesions in TRAMP mice. Since we and others have shown in rodents and humans that D and DA rapidly and extensively convert to decursinol, here we tested whether decursinol might be an in vivo active compound for suppressing xenograft growth of human prostate cancer cells expressing AR. In SCID-NSG mice carrying subcutaneously inoculated human LNCaP/AR-Luc cells overexpressing the wild type AR, we compared the efficacy of 4.5[Formula: see text]mg decursinol per mouse with equi-molar dose of 6[Formula: see text]mg D/DA per mouse. The result showed that decursinol decreased xenograft tumor growth by 75% and the lung metastasis, whereas D/DA exerted a much less effect. Measurement of plasma decursinol concentration, at 3[Formula: see text]h after the last dose of respective dosing regimen, showed higher circulating level in the decursinol-treated NSG mice than in the D/DA-treated mice. In a subsequent single-dose pharmacokinetic experiment, decursinol dosing led to 3.7-fold area under curve (AUC) of plasma decursinol over that achieved by equi-molar D/DA dosing. PK advantage notwithstanding, decursinol represents an active compound to exert in vivo prostate cancer growth and metastasis inhibitory activity in the preclinical model.

KEYWORDS

Angelica gigas Nakai; Decursin; Decursinol; Decursinol Angelate; In Vivo Anticancer Efficacy; Pharmacokinetics

Title

Prostate Cancer Xenograft Inhibitory Activity and Pharmacokinetics of Decursinol, a Metabolite of Angelica Gigas Pyranocoumarins, in Mouse Models

Author

Wei Wu 1 2 , Su-Ni Tang 2 , Yong Zhang 2 , Manohar Puppala 3 , Timothy K Cooper 4 , Chengguo Xing 3 5 , Cheng Jiang 1 2 , Junxuan Lu 1 2 6

Publish date

2017

PMID

29701699

Abstract

Coumarins in Cham-dang-gwi, the dried root of Angelica gigas Nakai (AGN), possess pharmacological effects on anemia, pain, infection, and articular rheumatism. The AGN root containes decursin (D), decursinol angelate (DA), nodakenin, and decursinol (DOH), a major metabolite of D and DA. The aim of this study was to develop a simultaneous determination method for these four coumarins in human plasma using ultra high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). Chromatographic separation was performed on dual columns (Kinetex® C18 column and Capcell core C18 column) with mobile phase consisting of water and acetonitrile at a flow rate of 0.3 mL/min using gradient elution. Multiple reaction monitoring was operated in positive ion mode with precursors to product ion transition values of m/z 328.9→228.8, 328.9→228.9, 409.4→248.8, and 246.8→212.9 to measure D, DA, nodakenin, and DOH, respectively. Linear calibration curves were fitted over concentration range of 0.05⁻50 ng/mL for these four components, with correlation coefficient greater than 0.995. Inter- and intra-day accuracies were between 90.60% and 108.24%. These precisions were within 11.19% for all components. The established method was then applied to a pharmacokinetic study for the four coumarins after usual dosing in Korean subjects.

KEYWORDS

UHPLC-MS/MS; decursin; decursinol; decursinol angelate; nodakenin.

Title

Simultaneous Determination of Decursin, Decursinol Angelate, Nodakenin, and Decursinol of Angelica gigas Nakai in Human Plasma by UHPLC-MS/MS: Application to Pharmacokinetic Study

Author

Sook-Jin Kim 1 , Se-Mi Ko 2 , Eun-Jeong Choi 3 , Seong-Ho Ham 4 , Young-Dal Kwon 5 , Yong-Bok Lee 6 , Hea-Young Cho 7

Publish date

2018 Apr 26

PMID

30060484

Abstract

Inflammation is considered the root cause of various inflammatory diseases, including cancers. Decursinol angelate (DA), a pyranocoumarin compound obtained from the roots of Angelica gigas, has been reported to exhibit potent anti-inflammatory effects. In this study, the anti-inflammatory effects of DA on the MAP kinase and NFκB signaling pathways and the expression of pro-inflammatory cytokines were investigated in phorbol 12-myristate 13-acetate (PMA)-activated human promyelocytic leukemia (HL-60) and lipopolysaccharide (LPS)-stimulated macrophage (Raw 264.7) cell lines. PMA induced the activation of the MAP kinase-NFκB pathway and the production of pro-inflammatory cytokines in differentiated monocytes. Treatment with DA inhibited the activation of MAP kinases and the translocation of NFκB, and decreased the expression and exogenous secretion of IL-1β and IL-6. Furthermore, LPS-stimulated Raw 264.7 cells were found to have increased expression of M1 macrophage-associated markers, such as NADPH oxidase (NOX) and inducible nitric oxide synthase (iNOS), and the M2 macrophage-associated marker CD11b. LPS also activated pro-inflammatory cytokines and Erk-NFκB. Treatment with DA suppressed LPS-induced macrophage polarization and the inflammatory response by blocking Raf-ERK and the translocation of NFκB in Raw 264.7 cells. Treatment with DA also inhibited the expression of pro-inflammatory cytokines, such as IL-1β and IL-6, NOX, and iNOS in Raw 264.7 cells. These results suggest that DA has the potential to inhibit macrophage polarization and inflammation by blocking the activation of pro-inflammatory signals. These anti-inflammatory effects of DA may contribute to its potential use as a therapeutic strategy against various inflammation-induced cancers.

KEYWORDS

MAP kinase; NFκB; cytokines; decursinol angelate; inflammation.

Title

Decursinol Angelate Inhibits LPS-Induced Macrophage Polarization Through Modulation of the NFκB and MAPK Signaling Pathways

Author

Salman Ul Islam 1 , Jung Ho Lee 2 , Adeeb Shehzad 3 , Eun-Mi Ahn 4 , You Mie Lee 5 , Young Sup Lee 6

Publish date

2018 Jul 27