Structure-Activity Relationships of Protoberberines Having Antimicrobial Activity

Iwasa, Kinuko; Nanba, Hiroaki; Lee, Dong‐Ung; Kang, S.H.

doi:10.1055/s-2006-957572

Cited by 73 publications

(51 citation statements)

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“…Some of them are used as medicines, such as anticancer drugs, and play an important role in plants as an endogenous biological barrier to protect against pathogens or herbivores because of their strong antimicrobial activities and cytotoxicity. For instance, berberine, a yellow benzylisoquinoline alkaloid, which is used as a bitter stomachic and an antidiarrhetic, shows strong antimicrobial activity toward both Gram-positive and -negative bacteria as well as other microorganisms (1).…”

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confidence: 99%

Involvement of CjMDR1, a plant multidrug-resistance-type ATP-binding cassette protein, in alkaloid transport in Coptis japonica

Shitan

Bazin²,

Dan³

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

245

181

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Alkaloids comprise one of the largest groups of plant secondary metabolites. Berberine, a benzylisoquinoline alkaloid, is preferentially accumulated in the rhizome of Coptis japonica, a ranunculaceous plant, whereas gene expression for berberine biosynthetic enzymes has been observed specifically in root tissues, which suggests that berberine synthesized in the root is transported to the rhizome, where there is high accumulation. We recently isolated a cDNA encoding a multidrug-resistance protein (MDR)-type ATP-binding cassette (ABC) transporter (Cjmdr1) from berberineproducing cultured C. japonica cells, which is highly expressed in the rhizome. Functional analysis of Cjmdr1 by using a Xenopus oocyte expression system showed that CjMDR1 transported berberine in an inward direction, resulting in a higher accumulation of berberine in Cjmdr1-injected oocytes than in the control. Typical inhibitors of ABC proteins, such as vanadate, nifedipine, and glibenclamide, as well as ATP depletion, clearly inhibited this CjMDR1-dependent berberine uptake, suggesting that CjMDR1 functioned as an ABC transporter. Conventional membrane separation methods showed that CjMDR1 was localized in the plasma membrane of C. japonica cells. In situ hybridization indicated that Cjmdr1 mRNA was expressed preferentially in xylem tissues of the rhizome. These findings strongly suggest that CjMDR1 is involved in the translocation of berberine from the root to the rhizome.

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confidence: 99%

Involvement of CjMDR1, a plant multidrug-resistance-type ATP-binding cassette protein, in alkaloid transport in Coptis japonica

Shitan

Bazin²,

Dan³

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

245

181

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“…The antimicrobial activity of the BCCM can be explained by the following reasons: first, plentiful studies have validated the broad antibacterial spectrum of berberine, not only inhibiting Gram-positive bacteria C. Yan et al [21], but Gram-negative bacteria as well [22]. Second, berberine retards the growth of some fungi [23].…”

Section: Discussionmentioning

confidence: 99%

Disease control during peach preservation with a berberine-chitosan composite membrane

Yan¹,

Tian³

2012

Fruits

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Disease control during peach preservation with a berberine-chitosan composite membrane.Abstract -Introduction. Peach brown rot caused by the fungus Monilinia fructicola is a major disease leading to considerable economic loss during storage. Our previous study uncovered the striking inhibition of the natural alkaloid berberine against M. fructicola. Materials and methods. A berberine-chitosan composite membrane (BCCM) able to slowly release berberine was prepared and used for peach preservation. The examined fruits were stored at 4°C and treated as follows: (I) control fruits without packaging; (ii) fruits that were transiently immersed in pre-solidified BCCM liquid and taken out; (iii) fruit coating either with a BCCM, or with a membrane containing chitosan only (without berberine), and (iv) fruit coating with a PVC membrane. Results and discussion. The group immersed in BCCM showed a high infection rate due to the cytotoxicity of acetic acid, but the coating group showed only a 10% infection rate after 40 days of storage. Moreover, the BCCM-coating group showed a significantly lower infection rate than that coated with chitosan membrane (without berberine), clearly indicating the antimicrobial activity of berberine therein. Consequently, packed in BCCM and stored at 4°C, peach fruits could be well preserved over 40 days with very low infection. Conclusion. Considering its safety and low cost, the berberine-containing chitosan composite membrane could be applicable in controlling diseases during peach storage.China / Prunus persica / peaches / storage / disease control / Monilinia fructicola / postharvest technology / coating / membranes Protection sanitaire de la pêche en cours de stockage à l'aide d'une membrane composite de berbérine-chitosane.Résumé -Introduction. La pourriture brune de la pêche causée par le champignon Monilinia fructicola est une maladie grave entraînant une perte économique considérable pendant le stockage. L'une de nos études précédentes avait mis en évidence l'inhibition surprenante de la berbérine, alcaloïde naturel, contre M. fructicola. Matériel et méthodes. Une membrane composite de berbérine-chitosane (BCCM) capable de libérer lentement de la berbérine a été préparée et utilisée pour la protection de pêches. Les fruits étudiés ont été stockés à 4°C et ont subi les traitements suivant : (i) fruits témoins sans emballage; (ii) fruits transitoirement immergés dans une solution de BCCM pré-solidifiée, puis sortis; (iii) fruits revêtus soit avec une membrane BCCM, soit avec une membrane à base de chitosane seule (sans berbérine), et (iv) fruits revêtus avec un film de PVC. Résultats et discussion. Les fruits immergés dans une solution de BCCM ont montré un taux d'infection élevé du fait de la cytotoxicité de l'acide acétique présent dans le liquide, mais les fruits avec revêtement n'ont présenté que 10 % de fruits infectés après 40 jours de stockage. De plus, les fruits revêtus d'une membrane BCCM ont présenté un taux d'infection significativement plus faible que celui des fruits revêt...

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“…The rhizome of the perennial medicinal plant Coptis japonica (Ranunculaceae) contains high amounts of the benzylisoquinoline alkaloid berberine, which has antibacterial activity (Iwasa et al 1998), and the C. japonica rhizome has long been used to treat gastrointestinal infections in Asian countries. Plants may accumulate anti-microbial berberine in the rhizome for defense purposes, as the rhizome has rich stores of starch and therefore is vulnerable to soil-borne pathogens (Shitan and Yazaki 2007).…”

Section: Berberine Transport In Coptis Japonicamentioning

confidence: 99%

“…Alkaloids contain nitrogen and are usually alkaline secondary metabolites with diverse chemical structures and biological activities (Iwasa et al 1998;Steppuhn et al 2004). Their bioactive properties make alkaloids important players in plant defense responses against microbes, insects, and other herbivores.…”

Section: Introductionmentioning

confidence: 99%

Alkaloid transporters in plants

Shitan

Kato

Shoji

2014

Plant Biotechnology

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Plants produce a multitude of secondary metabolites, including alkaloids with biological activities, and many alkaloids have been used for medicinal purposes. The biosynthetic enzymes and genes involved in alkaloid metabolic pathways exhibit divergent localizations, implying that alkaloid metabolites, including pathway products and intermediates, travel from organelle to organelle, cell to cell, and organ to organ. Biochemical studies have indicated that specific transporters move these metabolites. Indeed, molecular and cellular approaches have identified alkaloid transporters of the ATP-binding cassette (ABC) protein, multidrug and toxic compound extrusion (MATE), and purine permease (PUP) families. Interestingly, some of these transporters were found to be required for the efficient biosynthesis of alkaloids in plants. Here, we provide an updated inventory of alkaloid transporters and discuss the possibility of genetically manipulating the expression of these transporters to increase the accumulation of valuable alkaloid compounds.

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Structure-Activity Relationships of Protoberberines Having Antimicrobial Activity

Cited by 73 publications

References 3 publications

Involvement of CjMDR1, a plant multidrug-resistance-type ATP-binding cassette protein, in alkaloid transport in Coptis japonica

Involvement of CjMDR1, a plant multidrug-resistance-type ATP-binding cassette protein, in alkaloid transport in Coptis japonica

Disease control during peach preservation with a berberine-chitosan composite membrane

Alkaloid transporters in plants

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