Enhanced antimicrobial activities of polymerized arbutin and its derivatives prepared by oxidative polymerization of arbutin

Kajiwara, Rika; Seto, Ayaka; Kofujita, Hisayoshi; Shiba, Yoko; Oishi, Yoshiyuki; Shibasaki, Yuji

doi:10.1016/j.reactfunctpolym.2019.02.008

Cited by 11 publications

(4 citation statements)

References 35 publications

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“…Several studies have performed rutin polymerization using different laccases ( 49 – 52 ) and conversions of arbutin with peroxidases ( 53 – 56 ). Arbutin polymerization has also been performed using chemical catalysts ( 57 , 58 ), resulting in enhanced anti-microbial properties. This study showed that arbutin can also be polymerized using dye-decolorizing peroxidases, which may have the advantage of controlling the degree of polymerization by modulating the concentration of H 2 O 2 , as well as milder operating conditions.…”

Section: Discussionmentioning

confidence: 99%

Characterization of Amycolatopsis 75iv2 dye-decolorizing peroxidase on O -glycosides

Välimets,

Sun,

Virginia

et al. 2024

Appl Environ Microbiol

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Dye-decolorizing peroxidases are heme peroxidases with a broad range of substrate specificity. Their physiological function is still largely unknown, but a role in the depolymerization of plant cell wall polymers has been widely proposed. Here, a new expression system for bacterial dye-decolorizing peroxidases as well as the activity with previously unexplored plant molecules are reported. The dye-decolorizing peroxidase from Amycolatopsis 75iv2 (DyP2) was heterologously produced in the Gram-positive bacterium Streptomyces lividans TK24 in both intracellular and extracellular forms without external heme supplementation. The enzyme was tested on a series of O -glycosides, which are plant secondary metabolites with a phenyl glycosidic linkage. O -glycosides are of great interest, both for studying the compounds themselves and as potential models for studying specific lignin-carbohydrate complexes. The primary DyP reaction products of salicin, arbutin, fraxin, naringin, rutin, and gossypin were oxidatively coupled oligomers. A cleavage of the glycone moiety upon radical polymerization was observed when using arbutin, fraxin, rutin, and gossypin as substrates. The amount of released glucose from arbutin and fraxin reached 23% and 3% of the total substrate, respectively. The proposed mechanism suggests a destabilization of the ether linkage due to the localization of the radical in the para position. In addition, DyP2 was tested on complex lignocellulosic materials such as wheat straw, spruce, willow, and purified water-soluble lignin fractions, but no remarkable changes in the carbohydrate profile were observed, despite obvious oxidative activity. The exact action of DyP2 on such lignin-carbohydrate complexes therefore remains elusive. IMPORTANCE Peroxidases require correct incorporation of the heme cofactor for activity. Heterologous overproduction of peroxidases often results in an inactive enzyme due to insufficient heme synthesis by the host organism. Therefore, peroxidases are incubated with excess heme during or after purification to reconstitute activity. S. lividans as a production host can produce fully active peroxidases both intracellularly and extracellularly without the need for heme supplementation. This reduces the number of downstream processing steps and is beneficial for more sustainable production of industrially relevant enzymes. Moreover, this research has extended the scope of dye-decolorizing peroxidase applications by studying naturally relevant plant secondary metabolites and analyzing the formed products. A previously overlooked artifact of radical polymerization leading to the release of the glycosyl moiety was revealed, shedding light on the mechanism of DyP peroxidases. The key aspect is the continuous addition, rather than the more common approach of a single addition, of the cosubstrate, hydrogen peroxide. This continuous addition allows the peroxidase to complete a high number of turnovers without self-oxidation.

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Section: Discussionmentioning

confidence: 99%

Characterization of Amycolatopsis 75iv2 dye-decolorizing peroxidase on O -glycosides

Välimets,

Sun,

Virginia

et al. 2024

Appl Environ Microbiol

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“…In vitro Kajiwara et al (2019) Parkinson's disease (PD) These results suggested that arbutin can act as a neuroprotective agent and can considerably decrease behavioral deficits, oxidative and nitrosative stress in PD animal models both in vitro and in vivo.…”

Section: Diureticmentioning

confidence: 99%

A comprehensive review of the therapeutic potential of α‐arbutin

Saeedi

Khezri

Zakaryaei

et al. 2021

Phytotherapy Research

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Cosmetic dermatology preparations such as bleaching agents are ingredients with skin‐related biological activities for increasing and improving skin beauty. The possibility of controlling skin hyperpigmentation disorders is one of the most important research goals in cosmetic preparations. Recently, cosmetics containing herbal and botanical ingredients have attracted many interests for consumers of cosmetic products because these preparations are found safer than other preparations with synthetic components. However, high‐quality trial studies in larger samples are needed to confirm safety and clinical efficacy of phytotherapeutic agents with high therapeutic index. Arbutin (p‐hydroxyphenyl‐β‐d‐glucopyranoside) is a bioactive hydrophilic polyphenol with two isomers including alpha‐arbutin (4‐hydroxyphenyl‐α‐glucopyranoside) and β‐arbutin (4‐hydroxyphenyl‐β‐glucopyranoside). It is used as a medicinal plant in phytopharmacy. Studies have shown that alpha‐arbutin is 10 times more effective than natural arbutin. A comparison of IC50 values showed that α‐arbutin (with concentration 2.0 mM) has a more potent inhibitory activity on human tyrosinase against natural arbutin (with higher concentration than 30 mM). A review of recent studies showed that arbutin could be beneficial in treatment of various diseases such as hyperpigmentation disorders, types of cancers, central nervous system disorders, osteoporosis, diabetes, etc. This study was designed to describe the therapeutic efficiencies of arbutin.

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“…Polymeric materials with antimicrobial activity are used in many fields, particularly in medical devices technology, drug delivery systems, health care products and hygienic applications 1‐9 . One particular approach for therapeutic applications is the use of polymeric carriers or polymer active substance conjugate systems.…”

Section: Introductionmentioning

confidence: 99%

Preparation and antimicrobial properties of LL‐37 peptide immobilized lignin/caprolactone polymer film

Ogan

Yüce‐Dursun

Abdullah

et al. 2020

Polymers for Advanced Techs

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The use of biopolymers has gained priority in tissue engineering and biotechnology, both as dressing material and for enhancing treatment efficiency. There is a demand for new biopolymers designed with protease inhibitors and antimicrobials. LL‐37 is an important antimicrobial peptide in human skin and exhibits a broad spectrum of antimicrobial activity against bacteria, fungi, and viral pathogens. Using lignin which is an abundant carbohydrate polymer in nature and a polyacrylic acid, we prepared a lignin/caprolactone biodegradable film by plastifying caprolactone and polyacyrlic acid. Lignin/caprolactone biodegradable film was activated with CDI and then immobilized LL‐37 peptide. The structure was elucidated in terms of its functional groups by attenuated total reflectance‐fourier transform infrared spectroscopy (ATR‐FTIR), and the morphology of the lignin/caprolactone biodegradable film was characterized by scanning electron microscopy (SEM) before and after the immobilization process. The amount of LL‐37 immobilized was determined by ELISA method. It was found that 97% of LL‐37 peptide was successfully immobilized onto the lignin/caprolactone biodegradable film. Antimicrobial activity was determined in the lignin/caprolactone biodegradable film samples by quantitative antimicrobial activity method. According to the results, LL‐37 immobilized lignin/caprolactone biodegradable film samples were effective on test organisms; Gram‐positive Staphylococcus aureus and Gram‐negative Escherichia coli. In bio‐compatibility assays, the ability to support tissue cell integration was detected by using 3 T3 mouse fibroblasts. Samples were examined under transverse microscope, non‐immobilized sample showed a huge cellular death, whereas LL‐37 immobilized lignin/caprolactone biodegradable film had identical cellular growth with the control group. This dual functional lignin/caprolactone biodegradable film with enhanced antibacterial properties and increased tissue cell compatibility may be used to design new materials for various types of biological applications.

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Enhanced antimicrobial activities of polymerized arbutin and its derivatives prepared by oxidative polymerization of arbutin

Cited by 11 publications

References 35 publications

Characterization of Amycolatopsis 75iv2 dye-decolorizing peroxidase on O -glycosides

Characterization of Amycolatopsis 75iv2 dye-decolorizing peroxidase on O -glycosides

A comprehensive review of the therapeutic potential of α‐arbutin

Preparation and antimicrobial properties of LL‐37 peptide immobilized lignin/caprolactone polymer film

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