Bacillibactin and Bacillomycin Analogues with Cytotoxicities against Human Cancer Cell Lines from Marine Bacillus sp. PKU-MA00093 and PKU-MA00092

Zhou, Mengjie; Liu, Fawang; Yang, Xiaoyan; Jin, Jing; Dong, Xin; Zeng, Ke-Wu; Liu, Dong; Zhang, Yingtao; Ma, Ming; Yang, Donghui

doi:10.3390/md16010022

Cited by 34 publications

(19 citation statements)

References 49 publications

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“…Among these methods, PCR-based genome mining using degenerate primers is valued for its ability to rapidly identify strains potentially producing the desired structural class of compounds before the whole genomes of the microbes are sequenced. In recent years, PCR-based genome mining has been successfully utilized to discover novel natural products (Liu et al, 2018;Zhou et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Potashchelins, a Suite of Lipid Siderophores Bearing Both L-threo and L-erythro Beta-Hydroxyaspartic Acids, Acquired From the Potash-Salt-Ore-Derived Extremophile Halomonas sp. MG34

Liu

Zhang

et al. 2020

Front. Chem.

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Four new lipid siderophores bearing both L-threo-and L-erythro-β-hydroxyaspartic acids, potashchelins A-D (1-4), were isolated from the potash-salt-ore-derived extremophile Halomonas sp. MG34. The planar structures of 1-4 were elucidated on the basis of extensive 1D and 2D NMR studies and MS/MS data. Potashchelins 1-4 contain a hydrophilic nonapeptide headgroup sequentially consisting of β-hydroxyaspartic acid, serine, glycine, serine, serine, β-hydroxyaspartic acid, threonine, serine, and cyclic N(δ)-hydroxy-ornithine, which is appended by one of a series of fatty acids ranging from dodecanoic acid to tetradecanoic acid. The absolute configurations of the amino acids of potashchelins 1-4 were determined by C 3 and advanced Marfey's reaction, partial hydrolysis, and bioinformatics analysis, which revealed that potashchelins 1-4 bear both L-threo-and L-erythro-β-hydroxyaspartic acid. Phylogenetic analysis showed that the stand-alone β-hydroxylase, PtcA, and the fused domain with β-hydroxylase activity in PtcB are expected to be responsible for the formation of L-erythro and L-threo diastereomers, respectively. Additionally, utilizing a comparative genomics approach, we revealed an evolutionary mechanism for lipid siderophores in Halomonas involving horizontal transfer. Bioassays showed that potashchelin A and D had weak antibacterial activity against B. subtilis CPCC 100029 with an MIC value of 64 µg/mL.

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Section: Introductionmentioning

confidence: 99%

Potashchelins, a Suite of Lipid Siderophores Bearing Both L-threo and L-erythro Beta-Hydroxyaspartic Acids, Acquired From the Potash-Salt-Ore-Derived Extremophile Halomonas sp. MG34

Liu

Zhang

et al. 2020

Front. Chem.

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“…We have constructed a marine bacteria library containing strains isolated from sponges, corals and deposits collected from South China Sea [ 19 ]. To discover more aromatic polyketides from this library, we carried out a PCR screening targeting type II PKSs with genomic DNAs of strains in the library as the templates, using the degenerate primers designed from the conserved sequences of KS α s and KS β s in tetracenomycin, daunorubicin, actinorhodin and fredericamycin biosynthesis [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…We have previously reported the isolation of 180 marine bacteria from 15 sponge samples that were collected from South China Sea [ 19 ]. We have extracted all strains’ genomic DNAs and discovered nonribosomal peptides (bacillibactin and bacillomycin D analogues) by using a PCR screening method [ 19 ]. In this study, the forward primer (5′-GGCAGCGGITTCGGCGGITTCCAG-3′) and the reverse primer (5′-CGITGTTIACIGCGTAGAACCAGGCG-3′), designed from the conserved sequences of KS α and KS β in the biosynthesis of tetracenomycin, daunorubicin, actinorhodin and fredericamycin [ 20 ], were used in the PCR screening for aromatic polyketide producers.…”

Section: Methodsmentioning

confidence: 99%

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Fluostatins M–Q Featuring a 6-5-6-6 Ring Skeleton and High Oxidized A-Rings from Marine Streptomyces sp. PKU-MA00045

et al. 2018

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Aromatic polyketides from marine actinomycetes have received increasing attention due to their unusual structures and potent bioactivities. Compared to their terrestrial counterparts, marine aromatic polyketides have been less discovered and their structural and biological diversities are far from being fully investigated. In this study, we employed a PCR-based genome mining method to discover aromatic polyketides in our marine bacteria collection. Five new atypical angucyclinones, fluostatins M–Q (1–5) featuring a unique 6-5-6-6 ring skeleton, were discovered from one “positive” Streptomyces sp. PKU-MA00045. The structures of fluostatins M–Q (1–5) were elucidated based on comprehensive spectroscopic analyses and the crystallographic structure of fluostatin P (4), which contains the most oxidized A-ring, was solved by X-ray diffraction analysis with Cu Kα radiation. Compared to the published 16 fluostatin analogues, fluostatins M–Q (1–5) contained a different methoxy group attached at C-7 and hydroxy group attached at C-4, enriching the structural diversity of aromatic polyketides from marine actinomycetes. Genome sequencing of Streptomyces sp. PKU-MA00045 revealed the biosynthetic gene cluster of fluostatins M–Q (1–5), which contained different genes and gene organizations compared to known fluostatin gene clusters, facilitating the investigation of the biosynthesis of the unique 6-5-6-6 ring skeleton in all fluostatins.

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“…The structures of these natural products feature a tetracyclic benz(a)anthracene skeleton, which can be modified by enzymatic or nonenzymatic reactions to achieve impressive structural diversity. As a part of our ongoing project for natural product discovery and biosynthesis from marine bacteria [2][3][4][5][6], we previously discovered an unusual phenylamine-incorporated angucyclinone (1) featuring 1phenylbenzo(cd)indol-3(1H)-one moiety from a marine Streptomyces sp. PKU-MA00218 [2].…”

Section: Introductionmentioning

confidence: 99%

Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone

Xiao

Wang

et al. 2021

Molecules

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Angucyclinones are aromatic polyketides that possess impressive structural diversity and significant biological activities. The structural diversity of these natural products is attributed to various enzymatic or nonenzymatic modifications on their tetracyclic benz(a)anthracene skeleton. Previously, we discovered an unusual phenylamine-incorporated angucyclinone (1) from a marine Streptomyces sp. PKU-MA00218, and identified that it was produced from the nonenzymatic conversion of a C-ring-cleaved angucyclinone (2) with phenylamine. In this study, we tested the nonenzymatic conversion of 2 with more phenylamine analogues, to expand the utility of this feasible conversion in unusual angucyclinones generation. The (3-ethynyl)phenylamine and disubstituted analogues including (3,4-dimethyl)phenylamine, (3,4-methylenedioxy)phenylamine, and (4-bromo-3-methyl)phenylamine were used in the conversion of 2, which was isolated from the fermentation of Streptomyces sp. PKU-MA00218. All four phenylamine analogues were incorporated into 2 efficiently under mild conditions, generating new compounds 3–6. The activation of 3–6 on nuclear factor erythroid 2-related factor 2 (Nrf2) transcription were tested, which showed that 4 possessing a dimethyl-substitution gave most potent activity. These results evidenced that disubstitutions on phenylamine can be roughly tolerated in the nonenzymatic reactions with 2, suggesting extended applications of more disubstituted phenylamines incorporation to generate new bioactive angucyclinones in the future.

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Bacillibactin and Bacillomycin Analogues with Cytotoxicities against Human Cancer Cell Lines from Marine Bacillus sp. PKU-MA00093 and PKU-MA00092

Cited by 34 publications

References 49 publications

Potashchelins, a Suite of Lipid Siderophores Bearing Both L-threo and L-erythro Beta-Hydroxyaspartic Acids, Acquired From the Potash-Salt-Ore-Derived Extremophile Halomonas sp. MG34

Potashchelins, a Suite of Lipid Siderophores Bearing Both L-threo and L-erythro Beta-Hydroxyaspartic Acids, Acquired From the Potash-Salt-Ore-Derived Extremophile Halomonas sp. MG34

Fluostatins M–Q Featuring a 6-5-6-6 Ring Skeleton and High Oxidized A-Rings from Marine Streptomyces sp. PKU-MA00045

Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone

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