Stereoselective Reduction of Carbonyl Compounds Using the Cell-Free Extract of the Earthworm,<i>Lumbricus rubellus</i>, as a Novel Source of Biocatalyst

Ishihara, Kohji; Nakajima, Nobuyoshi

doi:10.1271/bbb.60408

Cited by 9 publications

(2 citation statements)

References 18 publications

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“…Earthworm (Lumbrucis terrestris) belongs to the annelida phylum (in the animalia kingdom) and is a decomposer in the world-wide ecosystem [ 6 ]. The segmented earthworm’s body cavity is filled with coelomic fluid, containing 18 amino acids, fatty acids, microelements, lumbritin, lumbrofebrin, terrestrolum brolysin, purine, choline, cholesterin, and vitamins [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

The effect of earthworm extract on promoting skin wound healing

et al. 2018

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Chronic nonhealing wounds pose a significant challenge to healthcare system because of its tremendous utilization of resources and time to heal. It has a well-deserved reputation for reducing the quality of life for those affected and represent a substantial economic burden to the healthcare system overall. Earthworms are used as a traditional Chinese medicine, and have been applied pharmacologically and clinically since a long time in China. However, there is paucity in data regarding its wound healing effects. Therefore, we investigated the effect of earthworm extract (EE) on skin wound healing process. The obtained data showed that EE has healing effects on local wound of mice. It decreased the wound healing time and reduced the ill-effects of inflammation as determined by macroscopic, histopathologic, hematologic, and immunohistochemistry parameters. The potential mechanism could be accelerated hydroxyproline and transforming growth factor-β secretion—thus increasing the synthesis of collagen, promoting blood capillary, and fibroblast proliferation. It could accelerate the removal of necrotic tissue and foreign bodies by speeding up the generation of interleukin-6, white blood cells, and platelets. It thus enhances immunity, reduces the risk of infection, and promotes wound healing. All in all, the obtained data demonstrated that EE improves quality of healing and could be used as a propitious wound healing agent.

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Section: Introductionmentioning

confidence: 99%

The effect of earthworm extract on promoting skin wound healing

et al. 2018

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“…Nakajima et al reported that one of the earthworm serine protease acts on the hydrolysis of triacylglycerols [15]. They also reported the stereoselective reduction of carbonyl compounds using the cell-free extract from earthworms ( Lumbricus rubellus ) in the presence of NADH or NADPH as a coenzyme [16]. Recently, Santos et al describe β-carboline imine reductions in high yields and enantiomeric excesses employing the cell-free extract from earthworms ( Eisenia foetida ) in the presence of NADPH [17].…”

Section: Introductionmentioning

confidence: 99%

Earthworm Is a Versatile and Sustainable Biocatalyst for Organic Synthesis

Guan

Chen

et al. 2014

PLoS ONE

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A crude extract of earthworms was used as an eco-friendly, environmentally benign, and easily accessible biocatalyst for various organic synthesis including the asymmetric direct aldol and Mannich reactions, Henry and Biginelli reactions, direct three-component aza-Diels-Alder reactions for the synthesis of isoquinuclidines, and domino reactions for the synthesis of coumarins. Most of these reactions have never before seen in nature, and moderate to good enantioselectivities in aldol and Mannich reactions were obtained with this earthworm catalyst. The products can be obtained in preparatively useful yields, and the procedure does not require any additional cofactors or special equipment. This work provides an example of a practical way to use sustainable catalysts from nature.

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Efficient Stereoselective Synthesis of Structurally Diverse γ‐ and δ‐Lactones Using an Engineered Carbonyl Reductase

et al. 2019

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Structurally diverse γ‐ and δ‐lactones were efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500‐fold) and thermostability toward 14 γ‐/δ‐keto acids and esters, compared with the wild‐type enzyme, with 110‐fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4‐oxodecanoate. The preparative synthesis of alkyl and aromatic γ‐ and δ‐lactones with 95 %–>99 % ee and 78 %–90 % yields was demonstrated. The highest space‐time yield, 1175 g L−1 d−1, was achieved for (R)‐γ‐decalactone.

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Stereoselective Reduction of Carbonyl Compounds Using the Cell-Free Extract of the Earthworm,Lumbricus rubellus, as a Novel Source of Biocatalyst

Cited by 9 publications

References 18 publications

The effect of earthworm extract on promoting skin wound healing

The effect of earthworm extract on promoting skin wound healing

Earthworm Is a Versatile and Sustainable Biocatalyst for Organic Synthesis

Efficient Stereoselective Synthesis of Structurally Diverse γ‐ and δ‐Lactones Using an Engineered Carbonyl Reductase

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