Two New Aromatic Compounds from Hericium erinaceum (BULL.: FR.) PERS.

Yaoita, Yasunori; Danbara, Kuniko; Kikuchi, Masao

doi:10.1248/cpb.53.1202

Cited by 61 publications

(58 citation statements)

References 11 publications

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“…These derivatives are structurally related to the ganomycins, a new chemical class of antibacterial compounds 18) and to other antibacterial active isolates 19,20) therefore interesting as coupling partner for b-lactams using laccase as initiator of the reaction to produce novel hybridantibiotics by biotransformation.…”

Section: -13)mentioning

confidence: 99%

“…[14][15][16][17] Now we have employed laccase to achieve derivatisation of b-lactam antibiotics and to couple them with derivatives of 2,5-dihydroxybenzoic acid. These derivatives are structurally related to the ganomycins, a new chemical class of antibacterial compounds 18) and to other antibacterial active isolates 19,20) therefore interesting as coupling partner for b-lactams using laccase as initiator of the reaction to produce novel hybridantibiotics by biotransformation.…”

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Novel Penicillins Synthesized by Biotransformation Using Laccase from Trametes spec.

et al. 2006

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There is an urgent need to develop new antimicrobial agents due to increasing bacterial resistance to therapeutically used drugs. Most methicillin-resistent Staphylococcus aureus (MRSA) strains are resistent not only to b-lactams, but also to most other antimicrobial agents.1) Penicillin resistance among Streptococcus pneumoniae strains is widely accepted as a global problem. [2][3][4][5] Bacteria have developed several strategies for escaping the lethal action of b-lactams. It may be expected that specific circumstance will make one the more effective stragegy than the other. 6) Much effort has been devoted to the discovery of drugs which would not be cleaved by b-lactamases of pathogenic strains and which have suitable physicochemical and pharmacodynamic profiles. 7,8) The modifications of b-lactam antibiotics could not keep pace with the development of resistance in the pathogenic microorganisms, so that numerous bacteria, among them multidrug resistant Staphylococcus strains, can no longer be treated with the currently available b-lactam antibiotics. 1,9,10) Besides the modification of existing antibiotics by chemical or biochemical methods the coupling of presently used antibiotics with other bioactive compounds or components from them which are not in use till now is a promising way to generate novel molecules with improved therapeutic properties.Laccase (benzenediol:oxygen oxidoreductase, EC 1.10.3.2), classically considered a hydroquinone oxidizing enzyme, is able to oligomerize molecules. Up to now main application fields of this enzyme are waste detoxification, textile dye transformation, biosensors and diagnostic application, where the capability to catalyze polymerization reactions is used. 11-13)Recently we reported about our synthetic results on coupling reactions with laccase.14-17) Now we have employed laccase to achieve derivatisation of b-lactam antibiotics and to couple them with derivatives of 2,5-dihydroxybenzoic acid. These derivatives are structurally related to the ganomycins, a new chemical class of antibacterial compounds 18) and to other antibacterial active isolates 19,20) therefore interesting as coupling partner for b-lactams using laccase as initiator of the reaction to produce novel hybridantibiotics by biotransformation.The use of laccase for the derivatisation of antibiotics is limited to a few examples including the phenolic oxidation of 7-(4-hydroxyphenylacetamido)cephalosporinic acid, 21) the dimerization of penicillin X 22) and the oxidative coupling of hydroquinone and mithramicine. 23) In the examples realized to date, the sought object of enhancement of the bioactive effect has not been achieved. 21-23)The aim of this study was (i) to investigate whether laccase can be used for the synthesis of novel penicillins by heteromolecular coupling of two different compounds, (ii) to characterize the products of the reaction, and (iii) to analyze the biological activity of the novel penicillins. Results and DiscussionBiotransformation of Amoxicillin and Ampicillin by Laccase of Tr...

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Novel Penicillins Synthesized by Biotransformation Using Laccase from Trametes spec.

et al. 2006

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“…Chemical components of this mushroom have been reported to have hericenones A and B as cytotoxic constituents, 7 hericenones C, D and E as stimulators of nerve growth factor synthesis, 8 hericenone J as an endoplasmic reticulum stress-suppressive substance, 9 hericerin as a pollen growth inhibitor 10 and antitumor-active polysaccharides 11 as the bioactive components. A bioassay-guided fractionation and chemical investigation of its MeOH extract resulted in the isolation of a new isoindolinone alkaloid named isohericenone (1), together with nine known compounds, namely isohericerin (2), 6 erinacerin B (3), 12 hericenone A (4), 7 hericenone J (5), 9 3,4-dihydro-5-methoxy-2-methyl-2-(4 0 -methyl-2 0 -oxo-3 0 -pentenyl)-9(7H)-oxo-2H-furo [3,4-h] benzopyran (6), 13 erinacerin A (7), 12 hericenone F (8), 14 hericenone D (9) 8 and hericenone E (10) 8 (Figure 1). Here, we describe the isolation and structural elucidation of (1) as well as the cytotoxic activities of compounds 1-10.…”

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“…It seems that the reported data of C-3a and C-7a should be changed with each other, similar with the case of isohericenone (1) and erinacerin A (7). 12 Here, the corrected 13 C-NMR data of isohericerin (2) are reported (Table 1).…”

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Isohericenone, a new cytotoxic isoindolinone alkaloid from Hericium erinaceum

et al. 2012

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“…to derivatize N-analogous corollosporines and to couple them both with 4-methylcatechol and with derivatives of 2,5-dihydroxybenzoic acid. The 2,5-dihydroxybenzoic acid derivatives are structurally related to the ganomycins, a new chemical class of antibacterial compounds 16) and to other antibacterial active substances, 17,18) and therefore they are interesting as coupling partner for N-analogous corollosporines. To our delight the resulting products inhibit the growth of several Gram positive bacterial strains in the agar diffusion assay, among them methicillin-resistant Staphylococcus aureus (MRSA).…”

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Synthesis of New N-Analogous Corollosporine Derivatives with Antibacterial Activity by Laccase-Catalyzed Amination

Mikolasch

Hessel

Salazar

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward laccase-catalyzed amination of dihydroxylated arenes with N-analogous corollosporines. In biological assays the obtained amination products are more active than the parent compounds.

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Two New Aromatic Compounds from Hericium erinaceum (BULL.: FR.) PERS.

Cited by 61 publications

References 11 publications

Novel Penicillins Synthesized by Biotransformation Using Laccase from Trametes spec.

Novel Penicillins Synthesized by Biotransformation Using Laccase from Trametes spec.

Isohericenone, a new cytotoxic isoindolinone alkaloid from Hericium erinaceum

Synthesis of New N-Analogous Corollosporine Derivatives with Antibacterial Activity by Laccase-Catalyzed Amination

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