Antimicrobial activity of juncusol, a novel 9-10-dihydrophenanthrene from the marsh plant

Chapatwala, Kirit D.; Cruz, Armando A. de la; Miles, D. Howard

doi:10.1016/0024-3205(81)90609-3

Cited by 24 publications

(17 citation statements)

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“…Dehydrojuncusol and the uncommon simple phenanthrene derivative have been isolated from roots of Juncus roemerianus [3]. Concerning the biological activity of Juncaceae, phenolic compounds of dihydrophenanthrine derivatives showed very good activity as an antimicrobial against gram positive and gram negative bacteria and some fungi [4]. The chemistry and pharmacological use of Juncaceae have been little studied.…”

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confidence: 99%

Phenolic glycosides of Juncus acutus and its anti-eczematic activity

Awaad

2006

Chem Nat Compd

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OR 1 OR OR 2 HO 1: R = H, R 1 = β-D-Glcp, R 2 = H 2: R = β-D-Glcp, R 1 = H, R 2 = β-D-Glcp 1, 2 O H HO H O H HO OR 2 OR 1 R OH OCH 3 3, 4 3: R = H, R 1 = H, R 2 = Apiose 4: R = OCH 3 , R 1 = Apiose, R 2 = H HO HO C O OR 5 5: R = Glucose-Rhamnose H H effect of the alcohol extract of the plant was studied on mice to determine their LD 50 , which proved to be nontoxic up to 3000 mg/kg body weight. The anti-eczematic activity of the isolated compounds was tested in mice and showed variable effect. Compounds 3 and 4 were found to have the highest activity; they cured eczema by 90 and 100% respectively.Juncaceae is a very large family distributed all over the world; it holds a rather unique position among angiosperms. However, very little is known about its chemical constituents. Red pigments in juncaceae were studied in 1975 by some worker and they reported the presence of glycosides of luteolinidin and 3-deoxyanthocyanidine but no ordinary anthocyanidines [1]. Seed fats of the family juncaceae were shown to be somewhat similar to one another in fatty acid composition [2]. Dehydrojuncusol and the uncommon simple phenanthrene derivative have been isolated from roots of Juncus roemerianus [3]. Concerning the biological activity of Juncaceae, phenolic compounds of dihydrophenanthrine derivatives showed very good activity as an antimicrobial against gram positive and gram negative bacteria and some fungi [4]. The chemistry and pharmacological use of Juncaceae have been little studied. Our plant under study is Juncus acutus L. This plant has been mentioned by bedewing in the treatment of infection and inflammation, but there is no scientific background on this, so our study was carried out to investigate the chemical content and biological activity of this plant. From Juncus acutus L. we identified five substances (1-5).The 13 C NMR spectrum of compound 1 indicated the presence of one β-D-glucopyranosyl unit together with 14 carbon signals for the aglycone moiety. Acid hydrolysis gave glucose, and the 1 H NMR showed the signals of an ABX aromatic ring system in addition to two oleofinic proton at 7.21(1H, d, J = 16.4 Hz) and 6.83 (1H, d, J = 16.4 Hz). The spectral data of the aglycone part was similar to those published for oxyresveratrol [5] except for the additional signal for sugar. From this data and by comparing with published [5] data this compound was identified as oxyresveratrol 2-O-β-D-glucopyranoside.

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confidence: 99%

Phenolic glycosides of Juncus acutus and its anti-eczematic activity

Awaad

2006

Chem Nat Compd

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“…32 These findings suggested that juncusol may inhibit a specific system, or a specific reaction found only in gram-positive microorganisms, although the mechanism of action of juncusol was not established. In another study, the antibacterial activity of dehydroeffusol and juncusol isolated from J. effusus was tested against methicillin resistant and -sensitive S. aureus.…”

Section: Enterobacter Aerogenes Escherichia Coli and Pseudomonas Aermentioning

confidence: 97%

“…Phenanthrenes isolated from different Juncaceae species exert many different activities, including antitumor, [28][29][30][31][32] anti-inflammatory, 23,27,29,31 antioxidant, 23 anxiolytic, 7,9 cell-protective, 11 sedative, 8,9 and spasmolytic 32 effects.…”

Section: Pharmacology Of Juncaceae Phenanthrenesmentioning

confidence: 99%

“…The compound inhibited the growth of highly metastatic cancer cell lines [SGC-7901 (human gastric carcinoma) and AGS (human caucasian gastric adenocarcinoma)] in a dose-dependent manner. 32 The effective inhibition of gastric cell adhesion, migration, invasion and gastric cancer cell mediated vasculogenic mimicry with very low toxicity makes dehydroeffusol a very promising candidate for anti-gastric cancer drug development.…”

Section: Cytotoxic and Antiproliferative Activitymentioning

confidence: 99%

“…antitumor, antibacterial, anti-inflammatory, antioxidant, anxiolytic, cell-protective, sedative, and spasmolytic activities) and their broad structural diversity. [7][8][9]11,23,[27][28][29][30][31][32][33][34][35] Probably, the most investigated naturally occurring phenanthrene derivate is denbinobin, which displays remarkable antitumour activity against several cancer cell lines. Moreover, its anti-HIV property is also very promising.…”

Section: Introductionmentioning

confidence: 99%

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Bioactive secondary metabolites from Juncaceae species

Tóth

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An Innovative Protocol for the Synthesis of 3‐(Pyridin‐2‐yl)‐5‐sec‐aminobiphenyl‐4‐carbonitriles and 9,10‐Dihydro‐3‐(pyridine‐2‐yl)‐1‐sec‐aminophenanthrene‐2‐carbonitriles

Patil

Mahulikar

2013

Journal of Heterocyclic Chem

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Herein, we present an innovative, novel, and highly convenient protocol for the synthesis of 3‐(pyridin‐2‐yl)‐5‐sec‐aminobiphenyl‐4‐carbonitriles (6a, 6b, 6c, 6d, 6e, 6f, 6g) and 9,10‐dihydro‐3‐(pyridine‐2‐yl)‐1‐sec‐aminophenanthrene‐2‐carbonitriles (10a, 10b, 10c, 10d, 10e), which have been delineated from the reaction of 4‐sec‐amino‐2‐oxo‐6‐aryl‐2H‐pyran‐3‐carbonitrile (4a, 4b, 4c, 4d, 4e, 4f, 4g) and 4‐sec‐amino‐2‐oxo‐5,6‐dihydro‐2H‐benzo[h]chromene‐3‐carbonitriles (9a, 9b, 9c, 9d, 9e) with 2‐acetylpyridine (5) through the ring transformation reaction by using KOH/DMF system at RT. The salient feature of this procedure is to provide a transition metal‐free route for the synthesis of asymmetrical 1,3‐teraryls like 3‐(pyridin‐2‐yl)‐5‐sec‐aminobiphenyl‐4‐carbonitriles (6a, 6b, 6c, 6d, 6e, 6f, 6g) and 9,10‐dihydro‐3‐(pyridine‐2‐yl)‐1‐sec‐aminophenanthrene‐2‐carbonitriles (10a, 10b, 10c, 10d, 10e). The novelty of the reaction lies in the creation of an aromatic ring from 2H‐pyran‐2‐ones and 2H‐benzo[h]chromene‐3‐carbonitriles via two‐carbon insertion from 2‐acetylpyridine (5) used as a source of carbanion.

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Antimicrobial activity of juncusol, a novel 9-10-dihydrophenanthrene from the marsh plant

Cited by 24 publications

References 3 publications

Phenolic glycosides of Juncus acutus and its anti-eczematic activity

Phenolic glycosides of Juncus acutus and its anti-eczematic activity

Bioactive secondary metabolites from Juncaceae species

An Innovative Protocol for the Synthesis of 3‐(Pyridin‐2‐yl)‐5‐sec‐aminobiphenyl‐4‐carbonitriles and 9,10‐Dihydro‐3‐(pyridine‐2‐yl)‐1‐sec‐aminophenanthrene‐2‐carbonitriles

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