Isolation and Identification of Picronolide, Methynolide and Neomethynolide Produced by Streptomyces Venezuelae

Maezawa, Isao; Kinumaki, Akio; Suzuki, Makoto

doi:10.7164/antibiotics.27.84

Cited by 22 publications

(9 citation statements)

References 4 publications

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“…In the nutrient SCM medium, S. venezuelae produces both the 12- and the 14-membered-ring macrolide antibiotics . Only the 14-membered-ring macrolide antibiotic 2 was isolated when S. venezuelae was cultured in Suzuki glucose-peptone medium . In our current study, antibiotic production was conducted in a vegetative medium that results in accumulation of the 12-membered-ring metabolites .…”

mentioning

confidence: 88%

“…16 Only the 14-membered-ring macrolide antibiotic 2 was isolated when S. venezuelae was cultured in Suzuki glucose-peptone medium. 17 In our current study, antibiotic production was conducted in a vegetative medium that results in accumulation of the 12-memberedring metabolites. 16 The new metabolite and other related compounds were extracted following similar procedures as previously described.…”

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confidence: 99%

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Isolation and Structure Determination of Novamethymycin, a New Bioactive Metabolite of the Methymycin Biosynthetic Pathway in Streptomyces venezuelae

Zhang

Sherman

2001

J. Nat. Prod.

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Novamethymycin (9), a novel macrolide antibiotic, was isolated from Streptomyces venezuelae, the producer of methymycin (4) and neomethymycin (5). Spectroscopic analysis of 9 indicated that it is highly related to 4 and 5 but contains hydroxy groups at both C-10 and C-12 on the macrolactone ring. Bioconversion studies using the PikC cytochrome P450 hydroxylase demonstrated that 4 is converted to 9, further broadening the remarkable substrate flexibility of this enzyme.

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confidence: 88%

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confidence: 99%

Isolation and Structure Determination of Novamethymycin, a New Bioactive Metabolite of the Methymycin Biosynthetic Pathway in Streptomyces venezuelae

Zhang

Sherman

2001

J. Nat. Prod.

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“…The keto form [ 3 ] is the only species to have significant antibacterial activity, whereas enol ether [ 3d ] is a potent agonist of the motilin receptor and is the main cause of the gastrointestinal distress associated with erythromycin therapy. The 12-membered macrolide methymycin and the 14-membered macrolide pikromycin are made in the same host, Streptomyces venezuelae . With the exception of the additional two carbons in the aglycone component of pikromycin, the two compounds are identical in structure.…”

Section: 2 Fourteen-membered Macrolidesmentioning

confidence: 99%

“…Five compound families have been identified in this class: erythromycin A [3] and its B, C, and D congeners [4][5][6], pikromycin [7] and its 12-deoxy congener narbomycin [8], megalomicin A [9] and its congeners, oleandomycin [10], and lankamycin [11]. Erythromycin A is commonly referred to simply as erythromycin.…”

Section: Fourteen-membered Macrolidesmentioning

confidence: 99%

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Translation and Protein Synthesis: Macrolides

Katz¹,

Ashley²

2005

Chem. Rev.

163

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Macrolides

Kirst¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Macrolide antibiotics are well‐established antimicrobial agents in both clinical and veterinary medicine. These agents can be administered orally and are generally used to treat infections in the respiratory tract, skin and soft tissues, and genital tract caused by gram‐positive organisms, Mycoplasma species, and certain susceptible gram‐negative and anaerobic bacteria. The macrolide class is large and structurally diverse. Macrolides are produced by fermentation of soil microorganisms. Additionally, structural modifications using both chemical and microbiological means have yielded biologically active semisynthetic derivatives. The term macrolide was introduced to denote the class of substances produced by Streptomyces species containing a macrocyclic lactone ring. Traditional macrolide antibiotics are divided into three families according to the size of the aglycone, which can be 12‐, 14‐, or 16‐membered. Naturally occurring 14‐membered macrolides include erythromycin A (C 37 H 67 NO 13 ), erythromycin B (C 37 H 67 NO 12 ), erythromycin C (C 36 H 65 NO 13 ), erythromycin D (C 36 H 65 NO 12 ), erythromycin F (C 37 H 67 NO 14 ), and erythromycin E (C 37 H 65 NO 14 ), as well as others. Erythromycin has been the principal subject of modification of 14‐membered macrolides; some of the derivatives of erythromycin and oleandomycin include 2′‐ O ‐acetylerythromycin (C 39 H 69 NO 14 ), 2′‐ O ‐propionylerythromycin (C 40 H 71 NO 14 ), erythromycin ethyl carbonate (C 40 H 71 NO 15 ), and others. 16‐Membered macrolides are divided into leucomycin‐ and tylosin‐related groups, which differ in the substitution pattern of their aglycones. Natural products include leucomycin A 1 (C 40 H 67 NO 14 ), leucomycin A 5 (C 39 H 65 NO 14 ), leucomycin A 7 (C 38 H 63 NO 14 ), midecamycin A 2 (C 42 H 69 NO 15 ), and others. A second large group of 16‐membered macrolides differs from the leucomycins in the substitution pattern of the aglycone. One difference is a methyl or hydroxymethyl group at C‐14. The most prominent member of this group is tylosin, an important veterinary antibiotic produced by S. fradiae. Tylosin and related products include tylosin (C 46 H 77 NO 17 ), relomycin (20‐dihydrotylosin) (C 46 H 79 NO 17 ), macrocin (C 45 H 75 NO 17 ), O ‐demethylmacrocin (C 44 H 73 NO 17 ), and others. Other macrolides have been made by chemical, bioconversion, or genetic manipulations which represent hybrids of structures within the 14‐membered family, within the 16‐membered family, or between the two families. The advent of molecular biology has opened new possibilities for producing hybrid macrolides. Genetic manipulations of biosynthetic pathways in macrolide‐producing microorganisms complement traditional chemical and microbiological approaches. Macrolides inhibit growth of gram‐positive bacteria, Mycoplasma species, and certain gram‐negative and anaerobic bacteria. Susceptible gram‐positive bacteria include many species of Staphylococcus and Streptococcus; susceptible gram‐negative bacteria include Bordetella pertussis, Legionella pneumophila, Moraxella catarrhalis (formerly Branhamella ), and Haemophilus ducreyi. Macrolides inhibit growth of bacteria by inhibiting protein synthesis on ribosomes. Bacterial resistance to macrolides is often accompanied by cross‐resistance to lincosamide and streptogramin B antibiotics (MLS‐resistance). Bacterial resistance to antibiotics usually results from modification of a target site, enzymatic inactivation, or reduced uptake into or increased efflux from bacterial cells. The principal side effects of macrolides are gastrointestinal problems, such as pain, indigestion, diarrhea, nausea, and vomiting. Macrolides are obtained by controlled submerged aerobic fermentations of soil microorganisms. Although species of Streptomyces have dominated, species of Saccharopolyspora, Micromonospora, and Streptoverticillium are also well represented. Macrolide antibiotics are used clinically to treat infections resulting from susceptible organisms in the upper and lower respiratory tract, skin and soft tissues, and genital tract. They are generally used orally, although they can be given intravenously. Macrolides are regarded as among the safest of antibiotics. Relatively few macrolides are used in veterinary medicine. The most important is tylosin (Tylan, Elanco Products), which is used to control chronic respiratory disease caused by Mycoplasma gallisepticum in poultry.

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Isolation and Identification of Picronolide, Methynolide and Neomethynolide Produced by Streptomyces Venezuelae

Cited by 22 publications

References 4 publications

Isolation and Structure Determination of Novamethymycin, a New Bioactive Metabolite of the Methymycin Biosynthetic Pathway in Streptomyces venezuelae

Isolation and Structure Determination of Novamethymycin, a New Bioactive Metabolite of the Methymycin Biosynthetic Pathway in Streptomyces venezuelae

Translation and Protein Synthesis: Macrolides

Macrolides

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