An Enzymatic Route to Sunscreens

Schmidt, Eric W.

doi:10.1002/cbic.201000709

Cited by 9 publications

(9 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3, 6, 30 Interestingly, except for aminoDHQS, whose substrate is derived from a discrete pathway involving kanosamine 6-phosphate and 3-amino-3-deoxy-D-fructose 6-phosphate, 4, 31, 32 the substrates for DHQS, EEVS, EVS, DDGS, and DOIS are all directly derived from the pentose phosphate pathway (Scheme 2). Particularly intriguing are the EEVS, EVS, and DDGS that all utilize sedoheptulose 7-phosphate as substrate but yield three different cyclic products.…”

Section: Discussionmentioning

confidence: 99%

Evolutionary Divergence of Sedoheptulose 7-Phosphate Cyclases Leads to Several Distinct Cyclic Products

et al. 2012

View full text Add to dashboard Cite

Sedoheptulose 7-phosphate cyclases are enzymes that utilize the pentose phosphate pathway intermediate, sedoheptulose 7-phosphate, to generate cyclic precursors of many bioactive natural products, such as the antidiabetic drug acarbose, the crop protectant validamycin, and the natural sunscreens mycosporine-like amino acids. These proteins are phylogenetically related to the dehydroquinate (DHQ) synthases from the shikimate pathway, and are part of the more recently recognized superfamily of sugar phosphate cyclases, which includes DHQ synthases, aminoDHQ synthases and 2-deoxy-scyllo-inosose synthases. Through genome mining and biochemical studies, we identified yet another subset of DHQS-like proteins in the actinomycete Actinosynnema mirum and the myxobacterium Stigmatella aurantiaca DW4/3–1. These enzymes catalyze the conversion of sedoheptulose 7-phosphate to 2-epi-valiolone, which is predicted to be an alternative precursor for aminocyclitol biosynthesis. Comparative bioinformatics and biochemical analyses of these proteins with 2-epi-5-epi-valiolone synthases (EEVS) and desmethyl-4-deoxygadusol synthases (DDGS) provided further insights into their genetic diversity, conserved amino acid sequences, and plausible catalytic mechanisms. The results further highlight the uniquely diverse DHQS-like sugar phosphate cyclases, which may provide new tools for chemoenzymatic, stereospecific synthesis of various cyclic molecules.

show abstract

Section: Discussionmentioning

confidence: 99%

Evolutionary Divergence of Sedoheptulose 7-Phosphate Cyclases Leads to Several Distinct Cyclic Products

et al. 2012

View full text Add to dashboard Cite

show abstract

“…A number of research–based partnerships led to the generation of over 60 patents around the world [116]. The first application of MAAs, specifically shinorine, has been utilised in the product Helioguard ® 365 [119]. In vitro studies on the human keratinocyte cells confirmed the antiaging activity of the product when exposed to UV-A and stable activity of MAAs for a three-month period [119].…”

Section: Potential Use Of Maas In Human Skin Protectionmentioning

confidence: 99%

“…The first application of MAAs, specifically shinorine, has been utilised in the product Helioguard ® 365 [119]. In vitro studies on the human keratinocyte cells confirmed the antiaging activity of the product when exposed to UV-A and stable activity of MAAs for a three-month period [119]. There are a few other products on the market that also utilise MAAs such as Helionori ® and an increasing number of industry patents [116].…”

Section: Potential Use Of Maas In Human Skin Protectionmentioning

confidence: 99%

Mycosporine-Like Amino Acids: Making the Foundation for Organic Personalised Sunscreens

Rosic

2019

Marine Drugs

View full text Add to dashboard Cite

The surface of the Earth is exposed to harmful ultraviolet radiation (UVR: 280–400 nm). Prolonged skin exposure to UVR results in DNA damage through oxidative stress due to the production of reactive oxygen species (ROS). Mycosporine-like amino acids (MAAs) are UV-absorbing compounds, found in many marine and freshwater organisms that have been of interest in use for skin protection. MAAs are involved in photoprotection from damaging UVR thanks to their ability to absorb light in both the UV-A (315–400 nm) and UV-B (280–315 nm) range without producing free radicals. In addition, by scavenging ROS, MAAs play an antioxidant role and suppress singlet oxygen-induced damage. Currently, there are over 30 different MAAs found in nature and they are characterised by different antioxidative and UV-absorbing capacities. Depending on the environmental conditions and UV level, up- or downregulation of genes from the MAA biosynthetic pathway results in seasonal fluctuation of the MAA content in aquatic species. This review will provide a summary of the MAA antioxidative and UV-absorbing features, including the genes involved in the MAA biosynthesis. Specifically, regulatory mechanisms involved in MAAs pathways will be evaluated for controlled MAA synthesis, advancing the potential use of MAAs in human skin protection.

show abstract

“…Importantly, the reader is directed to the following excellent reviews for further details regarding MAA biosynthesis and extraction, areas that have already received considerable attention. 7,8,[18][19][20][21][22][23] MAAs present a promising form of future sunscreen filter given their strong UVR absorption, with typical extinction coefficients in the region of 30,000 M -1 cm -1 . 8 Currently, approximately 30 MAAs have been isolated which, combined, cover the ultraviolet region (UVA = 400-315 nm, UVB = 315-280 nm and UVC =280-100 nm) of the electromagnetic spectrum.…”

Section: Mycosporine and Mycosporine-like Amino Acidsmentioning

confidence: 99%

Section: Mycosporine and Mycosporine-like Amino Acidsmentioning

confidence: 99%

Unravelling photoprotection in microbial natural products

Woolley

Stavros

2019

Science Progress

View full text Add to dashboard Cite

Mycosporine-like amino acids have long been known as a natural form of photoprotection for fungi and cyanobacteria. This review will highlight the key time-resolved experimental and theoretical techniques unravelling their photochemistry and photophysics, and directly link this to their use in commercial skin-care products, namely as sunscreen filters. Three case studies have been selected, each having aided advancement in this burgeoning field of research. We discuss these studies in the context of photoprotection and conclude by evaluating the necessary future steps towards translating the photochemistry and photophysics insight of these nature derived sunscreen filters to commercial application.

show abstract

An Enzymatic Route to Sunscreens

Cited by 9 publications

References 14 publications

Evolutionary Divergence of Sedoheptulose 7-Phosphate Cyclases Leads to Several Distinct Cyclic Products

Evolutionary Divergence of Sedoheptulose 7-Phosphate Cyclases Leads to Several Distinct Cyclic Products

Mycosporine-Like Amino Acids: Making the Foundation for Organic Personalised Sunscreens

Unravelling photoprotection in microbial natural products

Contact Info

Product

Resources

About