Dataset Information

Bostrychines A-F, Six Novel Mycosporine-Like Amino-Acids and a Novel Betaine from the Red Alga Bostrychia scorpioides.

ABSTRACT: Various red algae have repeatedly been reported to produce a variety of UV-absorbing mycosporine-like amino acids (MAAs), compounds that are well-known as natural sun-screens, as well as a plethora of betaines, metabolites which contribute to the osmotic balance under salt stress. Among other Rhodophyta, Bostrychia scorpioides, which is thriving as epiphyte on salt marsh plants in Europe and hence experiences extreme environmental conditions such as desiccation, UV-stress and osmotic stress, has barely been investigated for its secondary metabolites. In the present study, seven mycosporine like-amino acids and two betaines were isolated from Bostrychia scorpioides using various chromatographic techniques. Their structures were confirmed by Nuclear Magnetic Resonance (NMR) spectroscopy and High Resolution Mass Spectrometry (HRMS). Six MAAs and one betaine were chemically characterized as new natural products.

SUBMITTER: Orfanoudaki M

PROVIDER: S-EPMC6627687 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Publications

Bostrychines A-F, Six Novel Mycosporine-Like Amino-Acids and a Novel Betaine from the Red Alga <i>Bostrychia scorpioides</i>.

Orfanoudaki Maria M Hartmann Anja A Miladinovic Helena H Nguyen Ngoc Hieu H Karsten Ulf U Ganzera Markus M

Marine drugs 20190614 6

Various red algae have repeatedly been reported to produce a variety of UV-absorbing mycosporine-like amino acids (MAAs), compounds that are well-known as natural sun-screens, as well as a plethora of betaines, metabolites which contribute to the osmotic balance under salt stress. Among other Rhodophyta, <i>Bostrychia scorpioides</i>, which is thriving as epiphyte on salt marsh plants in Europe and hence experiences extreme environmental conditions such as desiccation, UV-stress and osmotic stre ...[more]

PMID: 31207903

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Project description:Marine macroalgae is known to be a good source of mycosporine-like amino acids (MAAs), especially red macroalgae. As a new type of active substance with commercial development prospects, the current progress in the extraction, isolation and characterization of MAAs is far from sufficient in terms of effectiveness in application. To determine the extraction processes of MAAs from four species of red macroalgae (Bangia fusco-purpurea, Gelidium amansii, Gracilaria confervoides, and Gracilaria sp.), a series of single-factor and orthogonal experiments were carried out in which the effects of solvents, the solid-liquid ratio, the time of extraction, the extraction degree and the temperature, on the yields of MAA extracts, were analyzed. Further, the isolation and identification of MAAs from Bangia fusco-purpurea and Gracilaria sp. were investigated. The results showed that the solid-liquid ratio, the time of extraction, the extraction degree and the temperature were 1:20 g/mL, 2 h, three times and 40 °C, respectively, when 25% methanol or 25% ethanol were used as the extraction solvent; these values were found to be suitable for the extraction of MAAs from four species of red macroalgae. Silica gel thin-layer chromatography was successfully used, for the first time, for the detection MAAs in this work, and it could be clearly seen that Bangia fusco-purpurea had the highest contents of MAAs among the four species of red macroalgae. MAA extracts from Bangia fusco-purpurea (or Gracilaria sp.) were isolated by silica gel column chromatography to obtain one fraction (or two fractions). The compositions and proportions of the MAAs in these fractions were determined via HPLC-ESI-MS spectra and by comparison with existing studies. Shinorine, palythine and porphyra-334 were found in 95.4% of the T1 fraction, and palythenic acid was found in 4.6% of this fraction, while shinorine, palythine and porphyra-334 were found in 96.3% of the J1 fraction, palythenic acid was found in 3.7% of the J2 fraction, and palythine was found in 100% of the J2 fraction, taken from the MAA extracts found in Bangia fusco-purpurea and Gracilaria sp., respectively. In addition, the relevant compositions and proportions of the MAA extracts taken from Gelidium amansii and Gracilaria confervoides were identified. This was the first study to report on the extraction process, isolation and identification of MAAs from Bangia fusco-purpurea, Gelidium amansii, Gracilaria confervoides, and Gracilaria sp.

Project description:BackgroundMycosporine-like amino acids (MAAs), including shinorine and porphyra-334, are gaining attention as safe natural sunscreens. The production of MAAs has been achieved in diverse microbial hosts, including Saccharomyces cerevisiae. While S. cerevisiae is the most extensively studied model yeast, the oleaginous yeast Yarrowia lipolytica has emerged as a promising candidate for the synthesis of valuable products. In this study, we explored the potential of Y. lipolytica as a host for producing MAAs, utilizing its advantages such as a robust pentose phosphate pathway flux and versatile carbon source utilization.ResultsWe produced MAAs in Y. lipolytica by introducing the MAA biosynthetic genes from cyanobacteria Nostoc punctiforme and Anabaena variabilis. These genes include mysA, mysB, and mysC responsible for producing mycosporine-glycine (MG) from sedoheptulose 7-phosphate (S7P). The two strains utilize different enzymes, D-Ala-D-Ala ligase homologue (MysD) in N. punctiforme and NRPS-like enzyme (MysE) in A. variabilis, for amino acid conjugation to MG. MysE specifically generated shinorine, a serine conjugate of MG, while MysD exhibited substrate promiscuity, yielding both shinorine and a small amount of porphyra-334, a threonine conjugate of MG. We enhanced MAAs production by selecting mysA, mysB, and mysC from A. variabilis and mysD from N. punctiforme based on their activities. We further improved production by strengthening promoters, increasing gene copies, and introducing the xylose utilization pathway. Co-utilization of xylose with glucose or glycerol increased MAAs production by boosting the S7P pool through the pentose phosphate pathway. Overexpressing GND1 and ZWF1, key genes in the pentose phosphate pathway, further enhanced MAAs production. The highest achieved MAAs level was 249.0 mg/L (207.4 mg/L shinorine and 41.6 mg/L of porphyra-334) in YP medium containing 10 g/L glucose and 10 g/L xylose.ConclusionsY. lipolytica was successfully engineered to produce MAAs, primarily shinorine. This achievement involved the introduction of MAA biosynthetic genes from cyanobacteria, establishing xylose utilizing pathway, and overexpressing the pentose phosphate pathway genes. These results highlight the potential of Y. lipolytica as a promising yeast chassis strain for MAAs production, notably attributed to its proficient expression of MysE enzyme, which remains non-functional in S. cerevisiae, and versatile utilization of carbon sources like glycerol.

Dataset Information

Bostrychines A-F, Six Novel Mycosporine-Like Amino-Acids and a Novel Betaine from the Red Alga Bostrychia scorpioides.

Publications

Bostrychines A-F, Six Novel Mycosporine-Like Amino-Acids and a Novel Betaine from the Red Alga <i>Bostrychia scorpioides</i>.

Similar Datasets

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