19380-05-3

Upstream product

• 2221-67-2 3'-keto,3',4'-dihydroseselin 
• 518-76-3 (±)-cis-khellactone 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 374768-02-2 7-[(4-methoxybenzyl)oxy]-2H-chromen-2-one 
• 1356928-60-3 4-p-methoxybenzyloxy-o-hydroxycinnamic acid methyl ester 
• 1356928-61-4 4-p-methoxybenzyloxy-o-prenyloxycinnamic acid methyl ester 
• 1356928-62-5 7-p-methoxybenzyloxy-6-prenylcoumarin 
• 21422-04-8 7-demethylsuberosin 
• 27421-18-7 7-((2-methylbut-3-yn-2-yl)oxy)-2H-chromen-2-one 
• 27421-19-8 7-(2-methylbut-3-en-2-yloxy)-2H-chromen-2-one 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 484-14-0 osthenol 
• 141243-21-2 (+)-lomatin-3'-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabinohexopyranoside) 
• 1165-60-2 (-)-O-angeloyllomatin 

Downstream Products

• 15885-51-5 selinidin 
• 1165-60-2 (-)-O-angeloyllomatin 

Relevant academic research and scientific papers

Phytotoxic compounds from Prionosciadium watsoni

Bioassay-guided fractionation of a phytotoxic extract of Prionosciadium watsoni led to the isolation of three new pyranocoumarins and two pyranochromones. The new compounds were characterized as propionic acid (9R,10R)-9-acetoxy-8,8-dimethyl-9-10-dihydro-2H,8H-benzo[1,2-b:3,4-b ′]dipyran-2-one-10-yl ester (1), isobutyric acid (9R,10R)-9-hydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4. b′]-dipyran-2-one-10-yl ester (2), isobutyric acid (9R)-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b′]dipyran-2 -one-9-yl ester (10), 2-methylbut-(2Z)-enoic acid (3R)-5-methoxy-3,4-dihydro-2,2,8-trimethyl-6-oxo-2H, 6H-benzo[1,2.b:5,4-b′]dipyran-3-yl ester (11), and isobutyric acid (3R)-5-methoxy-3,4-dihydro-2,2,8-trimethyl-6-oxo-2H,6H-benzo[1,2-b:5, 4-b′]dipyran-3-yl ester (12) by spectroscopic and chemical methods. The stereochemistry at the stereogenic centers was established by applying the Mosher ester methodology. The structures of 1 and 2 were corroborated by single-crystal X-ray diffraction studies. The phytotoxic activity of the isolated compounds was assessed on Amaranthus hypochondriacus, Echinochloa crus-galli, and Lemna pausicostata. The phytotoxins also modified the electrophoretic mobility of calmodulin from both bovine-brain and spinach.

Synthesis of coumarin derivatives and their cytoprotective effects on t-BHP-induced oxidative damage in HepG2 cells

Coumarins are ubiquitous in higher plants and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of coumarin derivatives on tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in human hepatoma HepG2 cells. A series of coumarin derivatives were prepared and assessed for their cytoprotective effects. Among these, a caffeoyl acid-conjugated dihydropyranocoumarin derivative, caffeoyllomatin, efficiently protected against cell damage elicited by t-BHP. Our findings suggest that caffeoyllomatin appears to be a potent cytoprotective agent.

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.

Asymmetric synthesis of 2-Substituted dihydrobenzofurans and 3-hydroxydihydrobenzopyrans through the enantioselective epoxidation of O-silyl-protected ortho-allylphenols

The Shi-type epoxidation of O-tert-butyldiphenylsilyl (TBDPS) protected o-allylphenols serves as an efficient strategy to construct the dihydrobenzofurans and dihydrobenzopyrans in up to 97% ee. This methodology led to the enantioselective synthesis of (+)-marmesin, (-)-(3′R)-decursinol, and (+)-lomatin.

Coumarins from the fruits of Seseli devenyense

Eight new coumarins were isolated from the fruits of Seseli devenyense Simonkai. Their structures were established from NMR and mass data and their absolute configurations from chemical degradation correlation reactions. The new structures are the decanoic and dodecanoic esters of (+)-lomatin (3, 4), the decanoates of (+)-cis-khellactone at positions 4′ (5) and 3′ (6) as well as the 2′S epimer of 8-(2,3-dihydroxy-3-methylbutyl)-7- hydroxychromen-2-one (7) named devenyol, its two O-monoglucosides at positions 3′ and 7 named devenyosides A (8) and B (9), and the corresponding 3′- and 7-O-diglucoside named devenyoside C (10). This plant is an interesting example of stereochemical diversity based on biodiversity given that other members of the Apiaceae family produce exclusively the 2′R epimers of compounds 7-9.

Medicinal foodstuffs. XX. Vasorelaxant active constituents from the roots of Angelica furcijuga Kitagawa: Structures of hyuganins A, B, C, and D

From the methanolic extract with vasorelaxant activity obtained from Angelica furcijuga Kitagawa, four new khellactone-type coumarins, hyuganins A, B, C, and D, were isolated together with twelve known coumarins, two known acetylenic compounds, and a known lignan. The structures of hyuganins A, B, C, and D were determined on the basis of chemical and physicochemical evidence. Nine principal coumarins (hyuganin A, anomalin, pteryxin, isopteryxin, isoepoxypteryxin, praerosides II and IV, apiosylskimmin, (R)-peucedanol 7-O-β-D-glucopy-ranoside), two acetylenic compounds [(-)-falcarinol and falcarindiol], and related compounds were examined for inhibitory activities on high concentration of K+ (High K+)- and dl-norepinephrine (NE)-indueed contractions. The results indicate that the 3'- and 4'-acyl groups of khellactone-type coumarins are essential for the inhibitory activity on the contractions by High K+. Hyuganin A and anomalin showed inhibitory effects on High K+-induced contraction, but not on NE-induced contraction. Other active coumarins (pteryxin, isopteryxin, isoepoxypteryxin) and an acetylenic compound (falcarindiol) non-selectively inhibited both contractions by High K+ and NE.

SYNTHESIS, GLYCOSIDATION AND RESOLUTION OF (+/-)-LOMATIN

The first resolution of a racemic hydroxydihydropyranocoumarin, (+/-)-lomatin (1) was achieved by means of glycosidation, followed by separation of the diastereoisomeric glycosides and subsequent acid hydrolysis.

COUMARIN SULPHATES OF SESELI LIBANOTIS

Three new sulphate ester salts derived from known coumarin alcohols - one of them tertiary - have been obtained from roots of Seseli libanotis subsp. eu-libanotis.Their structures were established as (2'S)-rutaretin-1''-sulphate, (3'R)-lomatin-3'-sulphate and (3'R,4'R)-khellactone-3'-sulphate.They were together with their parent alcohols characterized by 13C NMR spectroscopy.It is the first report on coumarin sulphates in plants.Key Word Index - Seseli libanotis subsp. eu-libanotis; Umbelliferae; dihydrofurocoumarins; dihydropyranocoumarins; coumarin sulphates; sulphate ester salts; FDMS; 13C NMR.