Natural Coumarins VII: Isolation and Structure of a New Coumarin, Peuruthenicin, from Peucedanum ruthenicum M.B.

Soine, Taito O.; Zheleva, A.; Mahandru, M. M.; Erhardt, Paul; Bubeva-Ivanova, L.

doi:10.1002/jps.2600621133

Cited by 10 publications

(4 citation statements)

References 2 publications

(1 reference statement)

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“…The umbelliferon carboxylic acid 3 , the starting compound for the synthesis of triazolyl substituted coumarins 4a – c (Scheme 1), was conveniently obtained by treatment of peuruthenicin ( 2 ) with NaOH in dioxane [19]. The peptide coupling reaction of 3 with propargyl amine 5 using DCC as a coupling reagent gave the corresponding 6-(prop-2-ynylcarbamoyl)umbelliferone ( 6 ) in 67% yield.…”

Section: Resultsmentioning

confidence: 99%

“…Peucedanin ( 1 ) was isolated from Peucedanum morisonii according to [31]. Peuruthenicin ( 2 ) [32], umbelliferone carboxylic acid 3 [19], azidobenzoic acids 7а – с [33], methyl ether of 9-aminopelargonic acid hydrochloride [34], D,L-2-aminobutyric acid and L-phenylalanine hydrochlorides [35], methyl 2-(prop-2-ynylamino)butanoate ( 14 ), and ( S )-methyl 3-phenyl-2-(prop-2-ynylamino)propanoate ( 15 ) [36], methyl ethynylantranilate ( 23 ) [37] and 2-azidooreoselone ( 35 ) [14] were synthesized according to published procedures. Solvents (CH 2 Cl 2 , CHCl 3 , MeCN, DMF, THF, benzene, dioxane) and Et 3 N were purified by standard methods and distilled under a stream of argon just before use.…”

Section: Methodsmentioning

confidence: 99%

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Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

et al. 2019

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Synthesis of 1,2,3-triazole-substituted coumarins and also 1,2,3-triazolyl or 1,2,3-triazolylalk-1-inyl-linked coumarin-2,3-furocoumarin hybrids was performed by employing the cross-coupling and copper catalyzed azide-alkyne cycloaddition reaction approaches. The synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Bacillius subtilis, Actinomyces viscosus and Escherichia coli bacterial strains. Coumarin-benzoic acid hybrids 4с, 42с and 3-((4-acetylamino-3-(methoxycarbonyl)phenyl)ethynyl)coumarin (29) showed promising activity against S. aureus strains, and the 1,2,3-triazolyloct-1-inyl linked coumarin-2,3-furocoumarin hybrid 37c was endowed with high selectivity against B. subtilis and E. coli species. The in vitro antibacterial activity of 4с, 29, 37c and 42с can potentially be compared with that of a number of modern antibiotic drugs used in the clinic, suggesting promising prospects for further research. A detailed study of the molecular interactions with the targeted protein MurB was performed using docking simulations and the obtained results are quite promising.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

et al. 2019

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“…Nonglycosidic simple coumarins 4, 5, 6, and 7 were identified as umbelliferone, scopoletin, 30) isofraxidin, 31) and 8-carboxy-7-hydroxy coumarin 32) based on analysis of their physical and spectral data (MS, This is the first reported identification of simple coumarin (7) as a constituent of plant materials.…”

Section: Studies Of Coumarins From the Chinese Drug Qianhu XXVII 1) mentioning

confidence: 99%

Studies of Coumarins from the Chinese Drug Qianhu, XXVII: Structure of a New Simple Coumarin Glycoside from Bai-Hua Qianhu, Peucedanum praeruptorum

Ishii

Okada

Baba

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new simple coumarin glycoside, named praeroside VI (1), along with six known coumarins, were isolated from an aqueous extract of Bai-Hua Qianhu, the root of Peucedanum praeruptorum DUNN. (Umbelliferae). Spectroscopic analysis and chemical studies were carried out to investigate the structure of the new coumarin, which was concluded to be 1. Additionally, two simple glycosidic coumarins and four simple nonglycosidic coumarins were identified as apiosylskimmin (2), hymexelsin (3), umbelliferone (4), scopoletin (5), isofraxidin (6) and 8-carboxy-7-hydroxy coumarin (7), respectively. This is the first reported identification of compound 7 as a constituent of plant materials.

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“…Previous phytochemical studies on this species showed the presence of furanocoumarins and their glycoside derivatives, linear-type furanocoumarin glycosides, and simple coumarin glycosides (Ahn et al, 1996;Lu et al, 2001). From P. ruthenicum, a native Bulgarian Umbelliferae, peucedanin (furanocoumarin) and a coumarin (peuruthenicin) in the roots and rutin (flavonol glycoside) in the flowers (Soine et al, 1973) have been isolated. Several new coumarins from P. praeruptorum Dunn.…”

Section: Introductionmentioning

confidence: 98%

A New Furanocoumarin fromPeucedanum ruthenicum.

Alavi

Yassa

Shafiee

et al. 2008

Pharmaceutical Biology

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Natural Coumarins VII: Isolation and Structure of a New Coumarin, Peuruthenicin, from Peucedanum ruthenicum M.B.

Cited by 10 publications

References 2 publications

Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

Studies of Coumarins from the Chinese Drug Qianhu, XXVII: Structure of a New Simple Coumarin Glycoside from Bai-Hua Qianhu, Peucedanum praeruptorum

A New Furanocoumarin fromPeucedanum ruthenicum.

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