Mycosporine-like amino acids and scytonemin: Regulations, roles for adaptation of cyanobacteria to the environment, and potential applications

Kageyama, Hakuto; Waditee‐Sirisattha, Rungaroon

doi:10.1016/b978-0-323-96106-6.00016-2

Cited by 1 publication

(6 citation statements)

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“…Saclipin A and B have absorption maxima at 316 and 319 nm, respectively, and can efficiently absorb UVB and short-wavelength UVA regions (Figure C,D). MAAs and scytonemin are well-known UV-absorbing substances that cyanobacteria accumulate, and various research findings about these substances have been reported . As saclipins have chemical structures different from those of MAAs and scytonemin, they can be considered to be a novel class of UV-absorbing substances in cyanobacteria.…”

Section: Discussionmentioning

confidence: 99%

“…MAAs and scytonemin are well-known UV-absorbing substances that cyanobacteria accumulate, and various research findings about these substances have been reported. 6 As saclipins have chemical structures different from those of MAAs and scytonemin, they can be considered to be a novel class of UV-absorbing substances in cyanobacteria. MAAs are already in the market as ingredients in the cosmetic materials Helioguard365 and Helinori.…”

Section: Identification Of Uva-/uvb-absorbing Compounds Inmentioning

confidence: 99%

“…MAAs are already in the market as ingredients in the cosmetic materials Helioguard365 and Helinori. 6 The absorption wavelength region of saclipins overlaps with many MAAs; 25 therefore, saclipins may also have potential applications in the cosmetics field. The large molar extinction coefficients of saclipins are also noteworthy.…”

Section: Identification Of Uva-/uvb-absorbing Compounds Inmentioning

confidence: 99%

“…The UV-absorbing substances, on the other hand, include mycosporine-like amino acids (MAAs) and scytonemin. 6 MAAs are water-soluble, low-molecular-weight compounds that absorb UVA and UVB, and more than 40 types of chemical structures have been discovered so far. 7 Scytonemin exhibits hydrophobic properties, has maximum absorption at 370 nm in the UVA region, and also absorbs radiation in the UVB and UVC regions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…These compounds function to regulate the osmotic pressure inside cells, helping cells adapt to the osmotic pressure of the external environment. The UV-absorbing substances, on the other hand, include mycosporine-like amino acids (MAAs) and scytonemin . MAAs are water-soluble, low-molecular-weight compounds that absorb UVA and UVB, and more than 40 types of chemical structures have been discovered so far .…”

Section: Introductionmentioning

confidence: 99%

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Identification of Desiccation Stress-Inducible Antioxidative and Antiglycative Ultraviolet-Absorbing Oxylipins, Saclipin A and Saclipin B, in an Edible Cyanobacterium Aphanothece sacrum

Uchida,

Maoka,

Palaga

et al. 2023

J. Agric. Food Chem.

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Aphanothece sacrum, a freshwater cyanobacterium, is an edible cyanobacterial strain. We identified two compounds belonging to the oxylipin family that possess UV-absorbing abilities and accumulate in the dried sample of A. sacrum. The compounds, named saclipin A and saclipin B, exhibited strong UV-absorption properties with the absorption maxima at 316 and 319 nm, respectively, and the molar extinction coefficients of 26,454 and 30,555 M–1 cm–1, respectively. The chemical structures of saclipins A and B have been elucidated, revealing that they have an all-E and a 12Z isomeric relationship within the triene structure. The saclipins could be isomerized by photoirradiation, with the cis-form saclipin B proving to be more stable in methanol, ethanol, or acetonitrile. Under drought stress conditions, the accumulation of saclipins A and B in A. sacrum was found to be increased 20- and 10-fold, respectively. Purified saclipins from A. sacrum showed biocompatibility and valuable bioactivities. Specifically, saclipins exhibited radical scavenging activity, maintaining their activity even 40 min after the reaction began. Additionally, they demonstrated inhibitory activity against glycation of elastin and collagen, which are constituents of dermal tissue. Notably, saclipins showed higher activity than the well-known glycation inhibitor aminoguanidine against collagen glycation.

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Section: Discussionmentioning

confidence: 99%

Section: Identification Of Uva-/uvb-absorbing Compounds Inmentioning

confidence: 99%