A new class of anti-MRSA and anti-VRE agents: Preparation and antibacterial activities of indole-containing compounds

Yamamoto, Yasuo; Kurazono, Mizuyo

doi:10.1016/j.bmcl.2006.12.081

Cited by 83 publications

(24 citation statements)

References 8 publications

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“…Compound 2 was first isolated from a natural source, although it has been mentioned by Yamamoto as a reactant for synthesizing a new class of anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) and anti-vancomycin-resistant enterococci (anti-VRE) agents. 19) Compound 3 was also isolated as colorless oil. The HR-ESI-MS spectrum gave a molecule ion [MϩNa] ϩ at m/z 224.3139, consistent with a molecular formula of C 13 H 15 NONa.…”

Section: Secondary Metabolites From the Mycelia Of The Fungus Monascumentioning

confidence: 99%

Secondary Metabolites from the Mycelia of the Fungus Monascus pilosus BCRC 38072

Cheng

Chen

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Monascus has been used in oriental fermented foods for thousands of years.1) Red mold rice fermented with Monascus spp. produces bioactive metabolites such as gaminobutyric acid (GABA), polyketides monacolin K, and some pigments, which, respectively, function as an anti-hypertension agent,2) a cholesterol-lowering drug, [3][4][5] and possess antibacterial activity.6) Monascus pigments, secondary metabolites possessing mainly azaphilone skeletons, have traditionally been used as natural food colorants.1) Many other metabolites have also been reported in previous research, 7-15) most of them isolated from red mold rice obtained from solid fermentation. In contrast, the metabolites contained in the mycelia pellets from submerged cultures have rarely been investigated. The antioxidant effects exhibited in the methanol extract fraction of the mycelia pellets of M. pilosus BCRC 38072 were monitored using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. 16,17) Subsequent chemical examination of the methanol extract of mycelia from M. pilosus led to the isolation of two new phenylacetic acid derivatives, monaspilosin (1) and monaspiloindole (2), and one new pyranoindole alkaloid, monaspyranoindole (3), along with twelve known compounds. This paper reports on the isolation, structural elucidation and the DPPH free radical scavenging activity of these fungal metabolites. Results and DiscussionExtensive chromatographic purification of the EtOAc-soluble fraction of the MeOH extract of the pellets of M. pilosus afforded fifteen compounds. The new compound 1, isolated as colorless oil, was assigned the molecular formula C 16 fragments, 1a, 1b, and 1c, for compound 1. The entire skeleton of 1 was constructed from the HMBC spectrum (Fig. 2). The 2 J and 3 J correlations of the signal at d H 3.60 (H-7) and d H 4.26 (H-10), with the carbon signal at d C 171.6 (C-8), helped to establish the connections of fragments 1a and 1b with the carbonyl group at C-8. That is, fragments 1a and 1b can be connected to produce 1d. In addition, the cross peak between d H 2.84 (H-11) and d C 130.0 (C-13, 17), as well as d H 4.26 (H-10) and d C 129.6 (C-12), suggest that fragments 1c and 1d were linked together at C-11. The structure was further confirmed by 13 C-NMR, DEPT, COSY, NOESY (Fig. 1), HSQC, and HMBC (Fig. 2) experiments. Thus, the structure of 1 was determined to be a phenylacetic acid 2-(4-hydroxyphenyl)ethyl ester, and was given the name monaspilosin.Compound 2, also a colorless oil, was assigned the molecular formula C 18 H 17 NO 2 , as deduced by ESI-MS and HR-ESI-MS. The presence of an ester group was revealed by an Three new compounds, including two phenylacetic acid derivatives, monaspilosin (1) and monaspiloindole (2), and one pyranoindole alkaloid, monaspyranoindole (3), were isolated from the EtOAc-soluble fraction of the MeOH extract of the mycelia of Monascus pilosus BCRC 38072. Twelve known compounds were also obtained in this study. The structures were elucidated by 1D and 2D NMR spectroscopy and m...

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Section: Secondary Metabolites From the Mycelia Of The Fungus Monascumentioning

confidence: 99%

Secondary Metabolites from the Mycelia of the Fungus Monascus pilosus BCRC 38072

Cheng

Chen

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Benzopyrrole, a privileged structure, represents a key motif in heterocyclic chemistry and have shown excellent performances in antibacterial , antiviral , antifungal , inflammatory , antianxiety , and antitubercular activities. Meanwhile, alcohol derivatives are also known to exhibit a wide spectrum biological activities because the group is an important core found in many biologically active compounds with a wide range of biological activity including antibacterial , antifungal , insecticidal , antiviral , herbicidal , anticancer , anti‐HIV‐1 , antihepatitis , antitumor , and anti‐inflammatory properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Novel 1H‐indol‐2‐ol Derivatives

Hong

et al. 2017

Journal of Heterocyclic Chem

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A series of novel 1H-indol-2-ol derivatives were synthesized and evaluated their antibacterial activities against rice bacterial leaf blight, tobacco bacterial wilt, and citrus canker caused by Xanthomonas oryzae pv. oryzae (Xoo), Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri via the turbidimeter test in vitro. Antibacterial bioassay indicated that most compounds demonstrated good inhibitory effect against Xoo and Ralstonia solanacearum. Especially, compound 4k demonstrated the best inhibitory effect against Xoo with half-maximal effective concentration (EC 50 ) value of 8.27 μg/mL, which was even better than those of commercial agents Bismerthiazol and Thiodiazole copper.

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“…The synthesis of compounds belonging to quinolones constitutes an important area of research because of their interesting pharmacological activities, particularly anti‐HIV , antibiotics , antibacterial , anticancer , antimalarial , antimicrobial , antioxidant , and antileishmanial activities . In addition, 4‐hydroxyquinolones were found to serve as key intermediates for the synthesis of nonpeptide gonadotropin releasing hormone receptor antagonists .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, PM3‐Semiempirical, and Biological Evaluation of Pyrazolo[4,3‐c]quinolinones

Hamama

Hassanien

El-Fedawy

et al. 2016

Journal of Heterocyclic Chem

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A series of α,β‐unsaturated ketones containing quinolone moieties 2, 3, 4, 5, 6 were synthesized by condensation of 7‐methoxyquinoline‐2,4(1H,3H)‐dione (1) with different aryl aldehydes. Pyrazole derivatives 8, 9, 10, 11 were also synthesized via refluxing of α,β‐unsaturated ketones 2, 3, 4, 5, 6 with hydrazine derivatives. Newly synthesized compounds were characterized by elemental analyses, spectral data, and screened for their antioxidant and antitumor activities. Geometrical optimizations of the molecular structures for different synthesized compounds were studied.

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A new class of anti-MRSA and anti-VRE agents: Preparation and antibacterial activities of indole-containing compounds

Cited by 83 publications

References 8 publications

Secondary Metabolites from the Mycelia of the Fungus Monascus pilosus BCRC 38072

Secondary Metabolites from the Mycelia of the Fungus Monascus pilosus BCRC 38072

Synthesis and Antibacterial Activity of Novel 1H‐indol‐2‐ol Derivatives

Synthesis, PM3‐Semiempirical, and Biological Evaluation of Pyrazolo[4,3‐c]quinolinones

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