13710-70-8

Usage

Uses

Used in Pharmaceutical Industry:
Marmesin is used as an anti-inflammatory and antibacterial agent for its potential medicinal properties. It has been studied for its ability to reduce inflammation and inhibit bacterial growth, making it a candidate for the development of new drugs to treat various conditions.
Used in Dermatology:
Marmesin is used as a potential treatment for certain skin conditions such as psoriasis and vitiligo. Its ability to increase the sensitivity of the skin to UV radiation has been investigated for its potential to improve the effectiveness of phototherapy in treating these conditions. However, the potential harmful effects of Marmesin on the skin and its toxicity have raised concerns about its safety for human use in this application.
Used in Research:
Marmesin is used as a subject of research to better understand its properties, potential applications, and safety concerns. Studies are being conducted to explore its potential as a therapeutic agent, as well as to investigate methods to mitigate its harmful effects on the skin when exposed to sunlight.

Upstream product

• 495-30-7 (S)-marmesinin 
• 13209-79-5 (-)-prantschimgin 
• 1269598-90-4 C₃₀H₃₂O₃Si 
• 1269599-02-1 C₂₀H₂₈O₃Si 
• 1269599-03-2 C₃₀H₃₂O₄Si 
• 21422-04-8 7-demethylsuberosin 
• 1334509-43-1 candinoside C 
• 1384983-00-9 marmesin-11-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside 
• 495-30-7 1'-O-β-D-glucopyranosyl-(2R)-marmesin 
• 5980-10-9 prangeferol angelate 
• 35178-20-2 prantschimgin 
• 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 

Downstream Products

• 66-97-7 psoralen 
• 64-19-7 acetic acid 
• 108-46-3 recorcinol 
• 53106-45-9 secorin 

Relevant academic research and scientific papers

Four novel furanocoumarin glucosides, candinosides A, B, C and D, from Heracleum candicans Wall

Four novel furanocoumarin glucosides, candinosides A, B, C and D (1-4), were isolated from the roots of Heracleum candicans Wall. Their structures were established using chemical and spectral methods.

Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant evaluation of the constituents from Angelica dahurica roots

Two undescribed phenolic compounds, angelicols A (1) and B (2) and one undescribed coumarin rhamnoside, angelicoside A (3), together with 17 known compounds (4–20) were isolated from the roots of Angelica dahurica. Their structures were characterized by physical data analyses such as NMR, HRESIMS, and X-ray diffraction. Compounds 2, 3, 5, 6 and L-ascorbic acid (positive control) exhibited obvious DPPH radical scavenging activities with IC50 values of 0.36?mM, 0.43?mM, 0.39?mM, 0.44?mM, 0.25?mM, respectively. At a concentration of 25?μM, all compounds showed weaker tyrosinase inhibition activities (%inhibition 50 = 44.29 ± 0.06?μM).

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.

Coumarins from Ferulago capillaris and F. brachyloba

Four new coumarins, (+)-senecioylprangol, (-)-3'-senecioyloxymarmesin, (+)-3'-hydroxyprantschimgin and (+)-2''-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3'-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively. (C) 2000 Elsevier Science Ltd.

A simple and efficient approach for the preparation of dihydroxanthyletin, xanthyletin, decursinol and marmesin

A simple and efficient approach has been developed for the preparation of coumarin natural products such as dihydroxanthyletin, xanthyletin, decursinol and marmesin starting from commercially available 2,4-dihydroxybenzaldehyde with very good yields. Wittig homologation and Claisen rearrangement are the protocols used to achieve these molecules.

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.

Glycosides from the methanol extract of Notopterygium incisum

Five new (15) and twelve known (617) different types of glycosides together with a known sesquiterpene triol (18) were isolated from the methanol extract of the rhizomes of Notopterygium incisum. The new structures were elucidated by means of spectroscopic and chemical methods to be pregn-5-en-3,20(S)-diol-3-O- bis - D-glucopyranosyl-(l2,16) - D-glucopyranoside (1), oleuropeic aldehyde 8-O - D-glucopyranoside (2), 2(R)-(3,4-dimethoxyphenyl)-propane-1,3-diol-1-O - D-glucopyranoside (3), eudesman-3,4,11-triol-11-O - D-glucopyranoside (4), and marmesin-11-O - D-glucopyranosyl-(16) - D-glucopyranoside (5). The absolute configuration of the aglycone in compound 3 was assigned by application of Klyne's rule. Georg Thieme Verlag KG Stuttgart - New York.

Pharmaceutical Composition Useful as Acetylcholinesterase Inhibitors

A pharmaceutical composition useful as acetylcholinesterase inhibitors. The present invention relates to pharmaceutical composition comprising the naturally occurring compounds selected from (±) Marmesin, Columbianetin, Dihydroxanthyletin and substituted coumarin derivatives of 7-allyloxy coumarin, 7-benzyloxy coumarin, 7-methoxy coumarin, 7-acetyloxy coumarin, 4-methyl-7-hydroxy coumarin and 4-methyl-7-acetyloxy coumarin. The said compositions posses a high degree of acetylcholinesterase inhibitory (AChE) property.