In silico analysis of enzymes involved in mycosporine-like amino acids biosynthesis in Euhalothece sp.: Structural and functional characterization

Mogany, Trisha; Kumari, Sheena; Swalaha, Feroz Mahomed; Bux, Faizal

doi:10.1016/j.algal.2022.102806

Cited by 8 publications

(8 citation statements)

References 67 publications

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“…UHCC 0926 was based on structural intermediates detected as well as established biochemical reactions and bioinformatic predictions (Figure , Tables S1,S6). MysA is a phosphate cyclase that acts on either sedoheptulose-7-phosphate from the pentose phosphate pathway or the 3-deoxy- d -arabino-heptulosonate-7-phosphate (DAHP) from the shikimate pathway to produce either dimethyl-4-deoxygadusol or 3-dehydroquinate, respectively. ,− MysB is an O-methyltransferase, which methylates a 3-dehydroquinate intermediate to form the 4-deoxygadusol chromophore . The MysC is an ATP-grasp ligase that catalyzes the addition of glycine (Gly) onto the C1 forming mycosporine-glycine .…”

Section: Resultsmentioning

confidence: 99%

“…This finding is consistent with previous literature as MAA core forming MysA, MysB, and MysC enzymes are thought to be conserved in all MAA producing organisms. , The formation of two distant clades in the MysA phylogenetic tree could be linked to difference between 2-epi-5-epi-valiolone synthase and 3-dehydroquinate synthase-type MysA enzymes (Figure S19). Additionally, the topology of the phylogenetic tree constructed using methyltransferase enzymes further indicated that the MysF enzymes found in the MAA biosynthetic gene clusters are indeed distinct from MysB enzymes as they formed a distant clade of their own (Figure S20).…”

Section: Resultsmentioning

confidence: 99%

“…34,35 The formation of two distant clades in the MysA phylogenetic tree could be linked to difference between 2-epi-5-epi-valiolone synthase and 3-dehydroquinate synthase-type MysA enzymes (Figure S19). 28 Additionally, the topology of the phylogenetic tree constructed using methyltransferase enzymes further indicated that the MysF enzymes found in the MAA biosynthetic gene clusters are indeed distinct from MysB enzymes as they formed a distant clade of their own (Figure S20). We constructed a phylogenetic tree based on the MysC protein (Figure S21).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

Arsın,

Delbaje,

Jokela

et al. 2023

ACS Chem. Biol.

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Mycosporine-like amino acids (MAAs) are small, colorless, and water-soluble secondary metabolites. They have high molar extinction coefficients and a unique UV radiation absorption mechanism that make them effective sunscreens. Here we report the discovery of two structurally distinct MAAs from the lichen symbiont strain Nostoc sp. UHCC 0926. We identified these MAAs as aplysiapalythine E (C 23 H 38 N 2 O 15 ) and tricore B (C 34 H 53 N 4 O 15 ) using a combination of high-resolution liquid chromatography− mass spectrometry (HR-LCMS) analysis and nuclear magnetic resonance (NMR) spectroscopy. We obtained a 8.3 Mb complete genome sequence of Nostoc sp. UHCC 0926 to gain insights into the genetic basis for the biosynthesis of these two structural distinct MAAs. We identified MAA biosynthetic genes encoded in three separate locations of the genome. The organization of biosynthetic enzymes in Nostoc sp. UHCC 0926 necessitates a branched biosynthetic pathway to produce two structurally distinct MAAs. We detected the presence of such discontiguous MAA biosynthetic gene clusters in 12% of the publicly available complete cyanobacterial genomes. Bioinformatic analysis of public MAA biosynthetic gene clusters suggests that they are subject to rapid evolutionary processes resulting in highly plastic biosynthetic pathways that are responsible for the chemical diversity in this family of microbial sunscreens.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

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A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

Arsın,

Delbaje,

Jokela

et al. 2023

ACS Chem. Biol.

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“…Using genome mining approaches [45,[155][156][157], the discovery of MAA biosynthetic pathways occurred through the identification of the gene counterparts in different Gram-positive bacteria [154], cyanobacteria [150,152,156,158,159], and microalgae Symbiodiniaceae [160,161]. All species capable of MAA synthesis were found to have highly similar sequences corresponding to genes from the MAA shikimate or pentose phosphate pathways [160].…”

Section: Genetics Of Marine Organisms Producing Maasmentioning

confidence: 99%

Exploring Mycosporine-like Amino Acid UV-Absorbing Natural Products for a New Generation of Environmentally Friendly Sunscreens

et al. 2023

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Human skin needs additional protection from damaging ultraviolet radiation (UVR: 280–400 nm). Harmful UVR exposure leads to DNA damage and the development of skin cancer. Available sunscreens offer chemical protection from detrimental sun radiation to a certain extent. However, many synthetic sunscreens do not provide sufficient UVR protection due to the lack of photostability of their UV-absorbing active ingredients and/or the lack of ability to prevent the formation of free radicals, inevitably leading to skin damage. In addition, synthetic sunscreens may negatively affect human skin, causing irritation, accelerating skin aging and even resulting in allergic reactions. Beyond the potential negative effect on human health, some synthetic sunscreens have been shown to have a harmful impact on the environment. Consequently, identifying photostable, biodegradable, non-toxic, and renewable natural UV filters is imperative to address human health needs and provide a sustainable environmental solution. In nature, marine, freshwater, and terrestrial organisms are protected from harmful UVR through several important photoprotective mechanisms, including the synthesis of UV-absorbing compounds such as mycosporine-like amino acids (MAAs). Beyond MAAs, several other promising, natural UV-absorbing products could be considered for the future development of natural sunscreens. This review investigates the damaging impact of UVR on human health and the necessity of using sunscreens for UV protection, specifically UV-absorbing natural products that are more environmentally friendly than synthetic UV filters. Critical challenges and limitations related to using MAAs in sunscreen formulations are also evaluated. Furthermore, we explain how the genetic diversity of MAA biosynthetic pathways may be linked to their bioactivities and assess MAAs’ potential for applications in human health.

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“…MAAs are water soluble, colourless secondary metabolites found in variety of marine and aquatic organisms including algae, bacteria, fungi, lichens, corals, sponges, sea urchins, scallop and fish [11][12][13] in order to mitigate the harmful effects of UV irradiation [14], as well as desiccation or osmotic stress [15]. They also serve as nitrogen reservoirs during nitrogen limitation [16].…”

Section: Introductionmentioning

confidence: 99%

Isolation and Structure Elucidation of Novel Mycosporine-like Amino Acids from the Two Intertidal Red Macroalgae Bostrychia scorpioides and Catenella caespitosa

Orfanoudaki,

Alilou,

Hartmann

et al. 2023

Marine Drugs

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This study presents a phytochemical survey of two common intertidal red algal species, Bostrychia scorpioides and Catenella caespitosa, regarding their MAA (mycosporine-like amino acid) composition, which are known as biogenic sunscreen compounds. Six novel MAAs from Bostrychia scorpioides named bostrychines and two novel MAAs from Catenella caespitosa named catenellines were isolated using a protocol which included silica gel column chromatography, flash chromatography on reversed phase material and semipreparative HPLC (High-Performance Liquid Chromatography). The structure of the novel MAAs was elucidated using NMR (Nuclear Magnetic Resonance) and HR-MS (High-Resolution Mass Spectrometry), and their absolute configuration was confirmed by ECD (Electronic Circular Dichroism). All isolated MAAs possess a cyclohexenimine scaffold, and the metabolites from B. scorpioides are related to the known MAAs bostrychines A-F, which contain glutamine, glutamic acid and/or threonine in their side chains. The new MAAs from C. caespitosa contain taurine, an amino sulfonic acid that is also present in another MAA isolated from this species, namely, catenelline. Previous and new data confirm that intertidal red algae are chemically rich in MAAs, which explains their high tolerance against biologically harmful ultraviolet radiation.

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In silico analysis of enzymes involved in mycosporine-like amino acids biosynthesis in Euhalothece sp.: Structural and functional characterization

Cited by 8 publications

References 67 publications

A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

Exploring Mycosporine-like Amino Acid UV-Absorbing Natural Products for a New Generation of Environmentally Friendly Sunscreens

Isolation and Structure Elucidation of Novel Mycosporine-like Amino Acids from the Two Intertidal Red Macroalgae Bostrychia scorpioides and Catenella caespitosa

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