Hydroxyl regioisomerization of anthracycline catalyzed by a four-enzyme cascade

Zhang, Zhuan; Gong, Yukang; Zhou, Qiang; Hu, Yu; Ma, Hongmin; Chen, Yongsheng; Igarashi, Yasuhiro; Pan, Lifeng; Tang, Gong‐Li

doi:10.1073/pnas.1610097114

Cited by 28 publications

(38 citation statements)

References 35 publications

(39 reference statements)

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“…Total extraction of the pigment from mycelia was obtained only with ethanol. After ethanol evaporation, the extracted pigment is not water soluble in agreement with the case of prodigiosin [30] or aglycone moiety of other anthracyclines [31,32]. Curiously, part of it could acquire water soluble ability after air dry in fume hood as indicated for the case of strain MFB21 pigment ( Figure 5) which showed 36% of soluble pigment after 24 h air dry.…”

Section: Hydrophobicity Photosensitivity and Conservation Of The Pigsupporting

confidence: 55%

Physico-chemical Characterization of a Pink Red-like Pigments Produced by Five New Bacterial Soil Strains Identified as Streptomyces coelicoflavus

Assia¹,

Hasnaa²,

Sara³

et al. 2018

AJMR

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Five new strains MFB11, MFB20, MFB21, MFB23 and MFB24 of actinomycetes showed an intracellular hydrophobic pink red-like pigment production. These pigments present similar physico-chemical characteristics with anthracycline antibiotics of prodigiosin family. Nevertheless, negative antibacterial assay, Thinlayer chromatography (TLC) and interaction with organic solvents analysis of these pigments revealed their difference from known anthracycline antibiotics. Morphological, biochemical and gene coding 16S RNA sequence analysis allowed identification of the producer strains as Streptomyces coelicoflavus; known to produce important aminoglycoside antibiotics and other bioactive compounds but not anthracyclines red-like pigments. The identification of the five strains and physico-chemical properties of the produced pink red-like pigments are presented in this report.

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Section: Hydrophobicity Photosensitivity and Conservation Of The Pigsupporting

confidence: 55%

Physico-chemical Characterization of a Pink Red-like Pigments Produced by Five New Bacterial Soil Strains Identified as Streptomyces coelicoflavus

Assia¹,

Hasnaa²,

Sara³

et al. 2018

AJMR

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“…Various reports previously summarized that anthracycline antibiotics biosynthesized by actinomycetes have numerously shown cytotoxicity against human tumors or tumor cell lines (Metsä-Ketelä et al, 2007;Zhang et al, 2017). Therefore, anthracycline antibiotics from actinomycetes have been so far, one of the most effective substances widely used in the treatment of many types of cancer (Minotti et al, 2004).…”

Section: Biosynthesis Of Anthracycline-like Compounds From Antibioticmentioning

confidence: 99%

Endophytic actinomycetes associated with Cinnamomum cassia Presl in Hoa Binh province, Vietnam: Distribution, antimicrobial activity and, genetic features

Nguyen

Dinh

et al. 2020

J. Gen. Appl. Microbiol.

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Endophytic microbes associated with medicinal plants are considered to be potential producers of various bioactive secondary metabolites. The present study investigated the distribution, antimicrobial activity and genetic features of endophytic actinomycetes isolated from the medicinal plant Cinnamomum cassia Presl collected in Hoa Binh province of northern Vietnam. Based on phenotypic characteristics, 111 actinomycetes were isolated from roots, stems and leaves of the host plants by using nine selective media. The isolated actinomycetes were mainly recovered from stems (n = 67; 60.4%), followed by roots (n = 29; 26.1%) and leaves (n = 15; 13.5%). The isolates were accordingly assigned into 5 color categories of aerial mycelium, of which gray is the most dominant (n = 42; 37.8%), followed by white (n = 33; 29.7%), yellow (n = 25; 22,5%), red (n = 8; 7.2%) and green (n = 3; 2.7%). Of the total endophytic actinomycetes tested, 38 strains (occupying 34.2%) showed antimicrobial activity against at least one of nine tested microbes and, among them, 26 actinomycetes (68.4%) revealed anthracycline-like antibiotics production. Analysis of 16S rRNA gene sequences deposited on GenBank (NCBI) of the antibioticproducing actinomycetes identified 3 distinct genera, including Streptomyces, Microbacterium, and Nocardia, among which Streptomyces genus was the most dominant and represented 25 different species. Further genetic investigation of the antibioticproducing actinomycetes found that 28 (73.7%) and 11 (28.9%) strains possessed genes encoding polyketide synthase (pks) and nonribosomal peptide synthetase (nrps), respectively. The findings in the present study highlighted endophytic actinomycetes from C. cassia Presl which possessed

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“…Gene duplication and catalytic promiscuity have been important in the evolution of the unique substructure. This chemistry originates from an unusual two‐component mono‐oxygenase system that is responsible for the installation of the C1 hydroxyl group . The system is composed of an SDR‐enzyme, SnoaW, and a protein SnoaL2 homologous to canonical polyketide cyclases such as SnoaL .…”

Section: Gene Duplication Allows Formation Of More Complex Chemical Smentioning

confidence: 99%

A pharmaceutical model for the molecular evolution of microbial natural products

Fewer

Metsä‐Ketelä

2019

The FEBS Journal

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Microbes are talented chemists with the ability to generate tremendously complex and diverse natural products which harbor potent biological activities. Natural products are produced using sets of specialized biosynthetic enzymes encoded by secondary metabolism pathways. Here, we present a two‐step evolutionary model to explain the diversification of biosynthetic pathways that account for the proliferation of these molecules. We argue that the appearance of natural product families has been a slow and infrequent process. The first step led to the original emergence of bioactive molecules and different classes of natural products. However, much of the chemical diversity observed today has resulted from the endless modification of the ancestral biosynthetic pathways. The second step rapidly modulates the pre‐existing biological activities to increase their potency and to adapt to changing environmental conditions. We highlight the importance of enzyme promiscuity in this process, as it facilitates both the incorporation of horizontally transferred genes into secondary metabolic pathways and the functional differentiation of proteins to catalyze novel chemistry. We provide examples where single point mutations or recombination events have been sufficient for new enzymatic activities to emerge. A unique feature in the evolution of microbial secondary metabolism is that gene duplication is not essential but offers opportunities to synthesize more complex metabolites. Microbial natural products are highly important for the pharmaceutical industry due to their unique bioactivities. Therefore, understanding the natural mechanisms leading to the formation of diverse metabolic pathways is vital for future attempts to utilize synthetic biology for the generation of novel molecules.

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Hydroxyl regioisomerization of anthracycline catalyzed by a four-enzyme cascade

Cited by 28 publications

References 35 publications

Physico-chemical Characterization of a Pink Red-like Pigments Produced by Five New Bacterial Soil Strains Identified as <i>Streptomyces coelicoflavus</i>

Physico-chemical Characterization of a Pink Red-like Pigments Produced by Five New Bacterial Soil Strains Identified as <i>Streptomyces coelicoflavus</i>

Endophytic actinomycetes associated with <i>Cinnamomum cassia</i> Presl in Hoa Binh province, Vietnam: Distribution, antimicrobial activity and, genetic features

A pharmaceutical model for the molecular evolution of microbial natural products

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