Assembly Line and Post-PKS Modifications in the Biosynthesis of Marine Polyketide Natural Products

Ma, Liang; Zhang, Qingbo; Yang, Chunfang; Zhu, Yiguang; Zhang, Liping; Wang, Lijuan; Liu, Zhiwen; Zhang, Guangtao

doi:10.1016/b978-0-12-409547-2.14711-0

Cited by 10 publications

(7 citation statements)

References 318 publications

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“…Ansamycin's synthetic and semisynthetic analogues are originally identified as potent inhibitors of certain kinases and are later shown to act by stimulating kinase degradation, specifically by targeting ‘molecular chaperones’, i.e. heat shock proteins (Ma et al ., 2020). Other studies have shown that the benzoquinonoid ansamycin antibiotics had strong anti-tumour activity in vivo and in vitro by specifically binding geldanamycin (GA) and Hsp90 (Whitesell et al ., 1992).…”

Section: Discussionmentioning

confidence: 99%

Compositional and functional features of the gut microbiota of the intertidal snailNerita yoldiialong China's coast

et al. 2021

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The gut microbiota plays an important role in animals’ survival in their local environments. The intertidal rocky shore is a key interface of oceanic, atmospheric and terrestrial environments, and the transmission modes of microbes between an intertidal host and the environment are complex and largely ignored. In the present study, we characterized the gut microbiota of the intertidal snail Nerita yoldii, which is experiencing a northward range shift under the combined impacts of climate change and anthropogenic seascape transformation, and also determined the nearby environmental microbiota on the rock and in the seawater at five locations along the snail's distribution range in China. The gut microbial communities were significantly different from the environmental microbial communities, and the dominant phyla were Tenericutes, Cyanobacteria and Bacteroidetes, and Proteobacteria in the gut, rock and seawater microbial communities, respectively. At the genus level, Mycoplasma, with a relative abundance of 48.0 ± 10.2%, was the dominant genus in the gut microbial community, however, the relative abundances of this genus on the rock and in the water were low. These results imply that the gut microbial community of the intertidal snail N. yoldii is relatively independent from the environmental microbial community, and the dominant genus Mycoplasma in the gut, that is rare in the environment, can potentially assist the snail living in the harsh intertidal environment, especially at its northernmost distribution range edge.

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Section: Discussionmentioning

confidence: 99%

Compositional and functional features of the gut microbiota of the intertidal snailNerita yoldiialong China's coast

et al. 2021

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“…Polyketide synthases (PKS) enzymes produce them and have wide structural diversity due to various building blocks. They are also known to have significant bioactivity and the potential for novel natural product drug discovery (Ridley and Khosla, 2009;Ma et al, 2020;Yuzawa and Kuzuyama, 2020). Polyketides like anaephenes A-C and Cylindrofridins effectively against pathogens like Methicillin Resistant Staphylococcus aureus, Bacillus cereus, Mycobacterium tuberculosis, Streptococcus pneumonia (Preisitsch et al, 2015b;Brumley et al, 2018).…”

Section: Polyketidesmentioning

confidence: 99%

Revisiting the role of cyanobacteria-derived metabolites as antimicrobial agent: A 21st century perspective

et al. 2022

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Cyanobacterial species are ancient photodiazotrophs prevalent in freshwater bodies and a natural reservoir of many metabolites (low to high molecular weight) such as non-ribosomal peptides, polyketides, ribosomal peptides, alkaloids, cyanotoxins, and isoprenoids with a well-established bioactivity potential. These metabolites enable cyanobacterial survival in extreme environments such as high salinity, heavy metals, cold, UV-B, etc. Recently, these metabolites are gaining the attention of researchers across the globe because of their tremendous applications as antimicrobial agents. Many reports claim the antimicrobial nature of these metabolites; unfortunately, the mode of action of such metabolites is not well understood and/or known limited. Henceforth, this review focuses on the properties and potential application, also critically highlighting the possible mechanism of action of these metabolites to offer further translational research. The review also aims to provide a comprehensive insight into current gaps in research on cyanobacterial biology as antimicrobials and hopes to shed light on the importance of continuing research on cyanobacteria metabolites in the search for novel antimicrobials.

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“…Containing two rings, it is highly susceptible to diverse substitution patterns, resulting in new compounds with many interesting features. Its derivatives can be synthesized or acquired from natural sources [ 26 , 27 , 28 ], and they are important in numerous applications. Members of this group of compounds exhibit antifungal and antibacterial properties [ 29 , 30 ], can be used as very potent pesticides [ 31 ] and have many potential medical applications, spanning from anti-inflammatory pharmacotherapy [ 32 ] to oncology [ 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

How Substitution Combines with Non-Covalent Interactions to Modulate 1,4-Naphthoquinone and Its Derivatives Molecular Features—Multifactor Studies

Pocheć

Kułacz

Panek

et al. 2021

IJMS

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Substitution is well-known to modulate the physico-chemical properties of molecules. In this study, a combined, multifactor approach was employed to determine a plethora of substitution patterns using –Br and –O-H in 1,4-naphthoquinone and its derivatives. On the basis of classical Density Functional Theory (DFT), 25 models divided into three groups were developed. The first group contains 1,4-naphthoquinone and its derivatives substituted only by –Br. The second group consists of compounds substituted by –Br and one –O-H group. As a result of the substitution, an intramolecular hydrogen bond was formed. The third group also contains –Br as a substituent, but two –O-H groups were introduced and two intramolecular hydrogen bonds were established. The simulations were performed at the ωB97XD/6-311++G(2d,2p) level of theory. The presence of substituents influenced the electronic structure of the parent compound and its derivatives by inductive effects, but it also affected the geometry of the 2 and 3 groups, due to the intramolecular hydrogen bonding and the formation of a quasi-ring/rings. The static DFT models were applied to investigate the aromaticity changes in the fused rings based on the Harmonic Oscillator Model of Aromaticity (HOMA). The OH stretching was detected for the compounds from groups 2 and 3 and further used to find correlations with energetic parameters. The evolution of the electronic structure was analyzed using Hirshfeld atomic charges and the Substituent Active Region (cSAR) parameter. The proton reaction path was investigated to provide information on the modulation of hydrogen bridge properties by diverse substitution positions on the donor and acceptor sides. Subsequently, Car–Parrinello Molecular Dynamics (CPMD) was carried out in the double-bridged systems (group 3) to assess the cooperative effects in double –O-H-substituted systems. It was determined that the –O-H influence on the core of the molecule is more significant than that of –Br, but the latter has a major impact on the bridge dynamics. The competitive or synergic effect of two –Br substituents was found to depend on the coupling between the intramolecular hydrogen bridges. Thus, the novel mechanism of a secondary (cooperative) substituent effect was established in the double-bridged systems via DFT and CPMD results comparison, consisting of a mediation of the bromine substitutions’ influence by the cooperative proton transfer events in the hydrogen bridges.

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Assembly Line and Post-PKS Modifications in the Biosynthesis of Marine Polyketide Natural Products

Cited by 10 publications

References 318 publications

Compositional and functional features of the gut microbiota of the intertidal snailNerita yoldiialong China's coast

Compositional and functional features of the gut microbiota of the intertidal snailNerita yoldiialong China's coast

Revisiting the role of cyanobacteria-derived metabolites as antimicrobial agent: A 21st century perspective

How Substitution Combines with Non-Covalent Interactions to Modulate 1,4-Naphthoquinone and Its Derivatives Molecular Features—Multifactor Studies

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