Antibacterial activity and structure-activity relationships of berberine analogs

Iwasa, Kinuko; Kamigauchi, Miyoko; Ueki, Masaaki; Taniguchi, Makoto

doi:10.1016/0223-5234(96)85167-1

Cited by 155 publications

(80 citation statements)

References 9 publications

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“…isomer (4-19)>o-nitro isomer (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). An exception was trifluoromethyl-substituted isomers (4-15-4-17).…”

Section: Resultsmentioning

confidence: 99%

“…11,12,17) The similar cases were also found for antitumor activity of 7-demethyl chelerythrine (NK109) 21) and antibacterial activity of berberine. 9) In addition, the molecular planarity was also proven to be an important factor for the activity. 21) Based on understanding of the structure-activity relationship above and the aim of developing more potent QBAs-like drugs, we intended to design a class of structurally simple C= N + -containing isoquinoliniums by imitating structural characteristics of sanguinarine or chelerythrine, and know their bioactivities.…”

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confidence: 99%

“…1). In the past decades, these compounds have aroused interests of both chemists and pharmacologists for their chemical reactivity and extensive bioactivities including antitumor, [3][4][5] antimicrobial, [6][7][8][9][10][11][12] anti-inflammation, 13) antiplatelet aggregation, 14) anti-angiogenesis, 15) anti-acetylcholinesterase, 16) and antiparasite activities. [17][18][19][20] Our previous studies demonstrated that sanguinarine and chelerythrine ( Fig.…”

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Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Yang

Yao

Qin

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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2-Aryl-3,4-dihydroisoquinolin-2-iums might be considered as a class of simple analogues of natural quaternary benzo[c]phenanthridine alkaloids. In this paper, 26 new 2-aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium bromides with various substituents in N-aromatic ring were synthesized from commercially available 1,3-benzodioxole in good to excellent yields. All the compounds were elucidated by MS, high resolution (HR)-MS, IR, 1 H-and 13 C-NMR analysis, and evaluated for antifungal activities in vitro against Alternaria alternate, Curvularia lunata and Fusarium oxysporum sp. niveum at 50 µg/mL. Most of the compounds showed higher activities against all the test fungi than their natural model compounds sanguinarine and chelerythrine. For A. alternate and Curvularia lunata, most of them were also more active than thiabendazole, a commercial fungicide standard. The structure-activity relationship indicated that the substituent in N-aromatic ring and its position had significant effect on the activity. The general trend was that halogen atoms and CF 3 remarkably enhanced the activity while CH 3 and OCH 3 decreased the activity. Generally, osubstituted isomers were more active than m-and p-substituted isomer. The present results suggest that the title compounds are potential for the development of new isoquinoline antimicrobial agents.Key words 3,4-dihydroisoquinolinium; 1,2,3,4-tetrahydroisoquinoline; N-heterocyclization; antifungal activity; CuCl 2 -catalyzed oxidative coupling reaction; 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation Alkaloids represent a very extensive group of secondary metabolites with diverse structures, distribution in nature, and biological effects. Natural isoquinolines are one of the largest groups of alkaloids. Among them, there is a relatively small but important class of iminium moiety-containing isoquinoline alkaloids, such as quaternary benzo[c] phenanthridine alkaloids (QBAs), quaternary N-naphthyl isoquinolines, berberines and so on 1,2) (Fig. 1). In the past decades, these compounds have aroused interests of both chemists and pharmacologists for their chemical reactivity and extensive bioactivities including antitumor, [3][4][5] antimicrobial, [6][7][8][9][10][11][12] anti-inflammation, 13) antiplatelet aggregation, 14) anti-angiogenesis, 15) anti-acetylcholinesterase, 16) and antiparasite activities. [17][18][19][20] Our previous studies demonstrated that sanguinarine and chelerythrine ( Fig. 1) might serve as ideal lead compounds to develop new isoquinoline antimicrobial and acaricidal agents. Meanwhile, the iminium moiety (C= N + ) was their determinant for their bioactivities. 11,12,17) The similar cases were also found for antitumor activity of 7-demethyl chelerythrine (NK109) 21) and antibacterial activity of berberine.9) In addition, the molecular planarity was also proven to be an important factor for the activity.21) Based on understanding of the structure-activity relationship above and the aim of developing more potent QBAs-like drugs, we intended to design a cl...

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“…isomer (4-19)>o-nitro isomer (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). An exception was trifluoromethyl-substituted isomers (4-15-4-17).…”

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Yang

Yao

Qin

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Berberrubine (Fig. 1B) is isolated from the medicinal plant Berberis vulgaris (13), but is also readily derived from berberine by pyrolysis (14). Kim et al (15) studied the antimicrobial activity of berberine, berberrubine, 9-O-acylberberrubines and 9-O-alkylberberrubines.…”

Section: Introductionmentioning

confidence: 99%

Sensitization of Candida albicans to terbinafine by berberine and berberrubine

et al. 2016

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Abstract. Candida albicans (C. albicans) is an opportunistic fungal pathogen, particularly observed in immunocompromised patients. C. albicans accounts for 50-70% of cases of invasive candidiasis in the majority of clinical settings. Terbinafine, an allylamine antifungal drug, has been used to treat fungal infections previously. It has fungistatic activity against C. albicans. Traditional Chinese medicines can be used as complementary medicines to conventional drugs to treat a variety of ailments and diseases. Berberine is a quaternary alkaloid isolated from the traditional Chinese herb, Coptidis Rhizoma, while berberrubine is isolated from the medicinal plant Berberis vulgaris, but is also readily derived from berberine by pyrolysis. The present study demonstrates the possible complementary use of berberine and berberrubine with terbinafine against C. albicans. The experimental findings assume that the potential application of these alkaloids together with reduced dosage of the standard drug would enhance the resulting antifungal potency.

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“…Berberine and its structural relatives, the major alkaloids in these plants, have been reported to have various biological activities, 10,11) including antimicrobial, antimalarial and antifungicidal activities. Furthermore, these alkaloids exhibit a wide variety of pharmacological eŠects via their inhibition of enzymes and W or their interaction with proteins.…”

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confidence: 99%

Potentiation of Nerve Growth Factor-Induced Neurite Outgrowth in PC12 Cells by a Coptidis Rhizoma Extract and Protoberberine Alkaloids

Shigeta

Ootaki

Tatemoto

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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Antibacterial activity and structure-activity relationships of berberine analogs

Cited by 155 publications

References 9 publications

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Sensitization of Candida albicans to terbinafine by berberine and berberrubine

Potentiation of Nerve Growth Factor-Induced Neurite Outgrowth in PC12 Cells by a Coptidis Rhizoma Extract and Protoberberine Alkaloids

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