Cited by 392Microbial Metabolism and ApplicationsSkin Protection and AgingMicrobial Natural Products and Biosynthesis

The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria

Proteau, P. J., Gerwick, W. H., Garcia-Pichel, F., Castenholz, R.·1993·Experientia

Abstract

Despite knowledge of the existence of the pigment called scytonemin for over 100 years, its structure has remained unsolved until now. This pigment, the first shown to be an effective, photo-stable ultraviolet shield in prokaryotes, is a novel dimeric molecule (molec. wt. 544) of indolic and phenolic subunits and is known only from the sheaths enclosing the cells of cyanobacteria. It is probable that scytonemin is formed from a condensation of tryptophan- and phenylpropanoid-derived subunits. The linkage between these units is unique among natural products and this novel ring structure is here termed the 'scytoneman skeleton'. Scytonemin absorbs strongly and broadly in the spectral region 325-425 nm (UV-A-violet-blue, with an in vivo maximum at 370 nm). However, there is also major absorption in the UV-C (lambda max = 250 nm) and UV-B (280-320 nm). The pigment has been recently shown to provide significant protection to cyanobacteria against damage by ultraviolet radiation. The pigment occurs in all phylogenetic lines of sheathed cyanobacteria and possibly represents a UV screening strategy far more ancient than that of plant flavonoids and animal melanins. How diverse organisms deal with UV radiation is considered of vital importance to global ecology.

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Crossref · 10.1007/bf01923559

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15 of 15 references verified0 citation errors · 0 not checkable

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  • Metabolites from extracts of cyanobacteria Stigonema sp., Scytonema sp. and Lyngbya sp. include scytonemin (44) and are photoprotective with λmax = 252, 278, 300, 386 nm.

    “| Metabolite from extracts of cyanobacteria Stigonema sp., Scytonema sp. and Lyngbya sp. | Scytonemin (44) | Photoprotective | λmax = 252, 278, 300, 386 nm | [121] |”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [121]

  • Scytonemin (44) has absorbance maxima at λmax = 252, 278, 300, and 386 nm.

    “scytonemin (44), a pigment and secondary metabolite produced by cyanobacteria Stigonema sp., Scytonema sp., and Lyngbya sp., was described as a potential broad-spectrum photoprotective agent due to its diverse maximum peak of absorbance (λmax = 252, 278, 300, 386 nm) [121].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [121]

  • Scytonemin (44) is a potential broad-spectrum photoprotective agent.

    “scytonemin (44), a pigment and secondary metabolite produced by cyanobacteria Stigonema sp., Scytonema sp., and Lyngbya sp., was described as a potential broad-spectrum photoprotective agent due to its diverse maximum peak of absorbance (λmax = 252, 278, 300, 386 nm) [121].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [121]

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Authors
Proteau, P. J., Gerwick, W. H., Garcia-Pichel, F., & Castenholz, R.
Affiliations
Oregon State University (US)
Venue
Experientia
Published
1993-09
Volume
49
Issue
9
Pages
825-829
ISSN
  • 1420-682X (ISSN-L)
  • 0014-4754
  • 1420-9071
OpenAlex
W1979948787
Cited by
392
References
17
Citations by year
2026: 9 · 2025: 13 · 2024: 10 · 2023: 13 · 2022: 17 · 2021: 18 · 2020: 16 · 2019: 11 · 2018: 17 · 2017: 14 · 2016: 15 · 2015: 15 · 2014: 23 · 2013: 19 · 2012: 23
FWCI
2.62
Type
journal article
Language
en
Open access
closed
Locations
  • Cellular and Molecular Life Sciences (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • National Cancer Institute (CA52955)
  • National Center for Research Resources (NIH RR04039, DRR 1S10RR01409)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Microbial Metabolism and Applications
  • Health Sciences › Medicine › Dermatology › Skin Protection and Aging
  • Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
Keywords
scytonemin, UV protection, UV-absorbing pigments, tryptophan, phenylpropanoids, UV screening, photostability, UVB absorption, UVA absorption, natural product structure
MeSH terms
Cyanobacteria, Indoles, Magnetic Resonance Spectroscopy, Phenols, Pigments, Biological, Spectrophotometry, Ultraviolet, Sunscreening Agents, Ultraviolet Rays, Molecular Structure, Spectrometry, Mass, Fast Atom Bombardment

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