25245-91-4

Upstream product

• 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 
• 19012-98-7 7-acetoxy-2,2-dimethyl-2H-chromene 
• 19012-97-6 2,2-dimethyl-7-hydroxy-2H-1-benzopyran 
• 541-47-9 3-Methylbutenoic acid 
• 17771-33-4 7-hydroxy-2,2-dimethyl-chroman-4-one 
• 325138-00-9 6-[(2S)-3-hydroxy-3-methyl-2-(triethylsilyloxy)butyl]-7-(trifluoromethanesulfonyl)chromen-2-one 
• 325137-98-2 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(trifluoromethanesulfonyl)chromen-2-one 
• 616241-75-9 (S)-7,8-dihydro-8,8-dimethyl-7-triethylsilyloxy-6H-pyrano[3,2-g]chromen-2-one 
• 616241-73-7 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-96-0 6-[(1R,2S)-1,2-epoxy-3-hydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-94-8 7-(methoxymethoxy)-6-(trifluoromethanesulfonyl)chromen-2-one 
• 325137-90-4 6-[(1R,2S)-1,2-epoxy-3-oxobutyl]-7-(methoxymethoxy)chromen-2-one 

Downstream Products

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

Relevant academic research and scientific papers

Enantioselective total syntheses of novel PKC activator (+)-decursin and its derivatives using catalytic asymmetric epoxidation of an enone

The catalytic asymmetric total syntheses of (+)-decursin and three related natural products, (+)-decursinol, (-)-prantschimgin and (+)-marmesin, were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. The catalytic asymmetric epoxidation of enone was found to be promoted effectively by novel multifunctional asymmetric catalyst generated from La(O-i-Pr)3, BINOL and O=AsPh3 in a 1:1:1 ratio to afford epoxide in 94% yield and 96% ee, which was recrystallized to give the optically pure epoxide. (C) 2000 Elsevier Science Ltd.

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

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.

Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells

We report the synthesis of a novel series of highly potent melanin inhibitors which were obtained through structural modification of an anticancer compound S-(+)-decursinol. The in vitro inhibitory potencies of the newly synthesized compounds were evaluated against α-MSH induced melanin production in B16 murine melanoma cells. Among the compounds evaluated, compounds 2, 3, 6b, 7a, 7b, 8a and 8b emerged as highly potent inhibitors of melanin production. Besides, these compounds demonstrated significantly low cytotoxicity.

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

COMPOSITION COMPRISING DECURSIN DERIVATIVE FOR TREATING AND PREVENTING ATOPIC DERMATITIS

The present invention relates to the novel decursin derivatives, the preparation thereof and the composition comprising the same. The novel decursin derivatives of the present invention showedpotent inhibiting activity of the release of MCP-1, IL-6 and IL-8 induced by dermite in THP-1 or EoL-1 cell, therefore the compounds can be useful in treating or preventing atopic dermatitis.

Enantioselective total syntheses of (+)-decursin and related natural compounds using catalytic asymmetric epoxidation of an enone

The enantioselective total syntheses of (+)-decursin (1) and related natural dihydropyranocoumarins (-)-prantschimgin (3), (+)-decursinol (4), and (+)-marmesin (5) were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. Catalytic asymmetric epoxidation of the enone was effectively promoted by the novel multifunctional asymmetric catalyst generated from La(O-i-Pr)3, BINOL, and Ph3As=O in a 1:1:1 ratio to afford epoxide in 94% yield and 96% ee, which was recrystallized to give optically pure epoxide. After conversion to the common key intermediate (-)-peucedanol (7), all natural dihydropyranocoumarins were synthesized through palladium-catalyzed intramolecular C-O coupling reactions. A possible reaction mechanism of the catalytic asymmetric epoxidation of enones is also described based on X-ray analysis, laser desorption/ionization time-of-flight mass spectrometry, kinetic studies, and asymmetric amplification studies.

Enantioselective syntheses of decursinol angelate and decursin

The practical enantioselective syntheses of decursinol angelate and decursin were achieved in eight steps from resorcinol. The stereochemistry was addressed using the catalytic asymmetric epoxidation of 7-acetoxy-2,2-dimethylchromene by chiral (salen)Mn complexes as the key step.