Isolation and structure of a mycosporine from the red alga

Tsujino, Isami; Yabe, Kazuo; Sekikawa, Isao; Hamanaka, Nobuyuki

doi:10.1016/s0040-4039(01)94556-3

Cited by 57 publications

(38 citation statements)

References 2 publications

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“…Identities of peaks were confirmed by the wavelength method (ratio of peak areas detected at 313 nm/340 nm) and by CO-chromatography with standards of mycosporine-glycine, palythine and palythinol from the zoanthid Palythoa tuberculosa (Hirata et al 1979), porphyra-334 and shinorine from the red alga Porphyra tenera ('non') , Tsujino et al 1980, asterina-330 from the ocular lens of Plectropon~us leopardus (Dunlap et al 1989), and mycosporine-2 glycine from the sea anemone Anthopleura elegantissima (W. R. Stochaj, W. C. Dunlap & J. M. Shick unpubl.). Peaks were integrated on Hewlett-Packard or SpectraPhysics integrators, and quantification of individual MAAs was corrected for extraction efficiency as described in and Dunlap et al (1989), using published molar extinction coefficients summarized by those authors and from Takano et al (1979) and Tsujino et al (1980). The molar extinction coefficient for mycosporine-2 glycine was assumed to be the same as that of the structurally simllar compound shinorine.…”

Section: Methodsmentioning

confidence: 91%

Survey of ultraviolet radiation-absorbing mycosporine-like amino acids in organs of coral reef holothuroids

Shick¹,

Dunlap²,

Chalker³

et al. 1992

Mar. Ecol. Prog. Ser.

109

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Twelve deposit-feeding species of tropical holothuroid echinoderms (families Holothuriidae and Stichopodidae) were surveyed for the presence of UV-absorbing mycosporine-like amino acids (MAAs) during Austral summer at Hicks Reef, Great Barrier Reef (GBR). An additional species belonging to the Synaptidae was collected in Austral winter from Shrimp Reef, GBR. Tissues of all species contained MAAs, including mycosporine-glycine, shinorine, porphyra-334, mycosporine-2 glycine, palythine, asterina-330 and palythinol. The MAAs in holothuroids occur predominantly in their epidermis, which suggests a photoprotective function, since the highest concentrations of these UVabsorbing compounds would be expected in tissues directly exposed to sunlight. Concentrations of total MAAs in dorsal epidermal tissues ranged from 21.9 nmol mg-' protein (Stichopus variegatus) to 2053 nmol mg-' protein (Pearsonothuria graeffei). Taxonomic, tissue-specific and ecological relationships in the occurrence of MAAs in tropical deposit-feeding holothuroids are discussed.

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Section: Methodsmentioning

confidence: 91%

Survey of ultraviolet radiation-absorbing mycosporine-like amino acids in organs of coral reef holothuroids

Shick¹,

Dunlap²,

Chalker³

et al. 1992

Mar. Ecol. Prog. Ser.

109

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“…15 Examples of such compounds are mycosporine-glycine (MGly), porphyra-334 (P334) and shinorine (SH). 13,14,[16][17][18] These molecules contain amino acid residues linked to a central ring and form resonance tautomers whose extensive conjugation facilitates the absorption of UV radiations (Figure 1a). Owing to these excellent properties, MAAs have recently been exploited as additives in products for skin protection 19,20 and as photo-stabilizers in non-biological materials for increasing the durability of plastics, paints and varnishes.…”

Section: Introductionmentioning

confidence: 99%

Exploiting Mycosporines as Natural Molecular Sunscreens for the Fabrication of UV-Absorbing Green Materials

Fernandes

Alonso‐Varona

Palomares

et al. 2015

ACS Appl. Mater. Interfaces

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Ultraviolet radiations have many detrimental effects in living organisms that challenge the stability and function of cellular structures. UV exposure also alters the properties and durability of materials and affects their lifetime. It is becoming increasingly important to develop new biocompatible and environmentally friendly materials to address these issues. Inspired by the strategy developed by fish, algae, and microorganisms exposed to UV radiations in confined ecosystems, we have constructed novel UV-protective materials that exclusively consist of natural compounds. Chitosan was chosen as the matrix for grafting mycosporines and mycosporine-like amino acids as the functional components of the active materials. Here, we show that these materials are biocompatible, photoresistant, and thermoresistant, and exhibit a highly efficient absorption of both UV-A and UV-B radiations. Thus, they have the potential to provide an efficient protection against both types of UV radiations and overcome several shortfalls of the current UV-protective products. In practice, the same concept can be applied to other biopolymers than chitosan and used to produce multifunctional materials. Therefore, it has a great potential to be exploited in a broad range of applications in living organisms and nonliving systems.

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“…2), which is characteristic for MAAs, and a [M þ H] þ ion peak at m/z 303.1614 in ESI-MS, indicating the molecular formula C 13 H 22 N 2 O 6 . The structure of 1 was determined by 1 H, 13 C, COSY, HMQC, and HMBC NMR experiments in D 2 O. All Hatoms were assigned to the corresponding C-atoms by HMQC data except exchangeable H-atoms of the OH and NH groups.…”

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confidence: 99%

Isolation and Structural Elucidation of Novel Mycosporine‐Like Amino Acids as Alarm Cues in the Defensive Ink Secretion of the Sea Hare Aplysia californica

Kamio

Kicklighter

Nguyen

et al. 2011

Helvetica Chimica Acta

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Three new mycosporine-like amino acids (MAAs), aplysiapalythines A, B, and C (1, 2, and 3, resp.) were isolated from opaline, a glandular component of the defensive ink secretion of sea hares (Aplysia californica) collected from waters off southern California. Here, we report the structure of these MAAs determined by mass spectrometry and NMR data. These new MAAs are structurally related to two known MAAs that are also present in sea hare opaline, i.e., asterina 330 (4) and palythine (5), and for which we also provide detailed data here for comparison. The fact that three of the five MAAs that we identified from sea hare opaline are novel molecules is interesting given that this represents a relatively large addition to the current list of known MAAs. This is likely because most researchers have identified MAAs through HPLC with UV detection, which is imprecise given similarities in UV spectra for different MAAs. Our findings suggest that there is much greater diversity of MAAs than is currently known. Results published elsewhere show that 1, 2, and 4 are alarm cues for conspecific sea hares at natural concentrations, but 3 and 5 are not.Introduction. -Mycosporine-like amino acids (MAAs) are widely distributed in marine organisms including bacteria, plants, invertebrates, and vertebrates [1]. Animals are generally thought to be incapable of synthesizing MAAs, but rather they are thought to sequester MAAs from their diet or from symbionts; however, this view has been questioned [2]. MAAs, of which ca. 30 are known, are traditionally considered to be screens against solar radiation, but other functions have also been proposed, including anti-oxidants, osmotic regulation, providing a source of amino acids in embryonic development, and induction of spawning [3 -10].A new function for MAAs was recently identified from our work on chemical defenses of sea hares (Aplysia californica) collected from the waters of southern California [11]. We found that MAAs are present in high concentrations in opaline, which is one of the glandular products of the sea hares ink secretion. Of the five major MAAs in opaline of these sea hares, three are novel, and two of these novel MAAs, together with nucleic acids and nucleosides in the ink component of the sea hares ink secretion, function as intraspecific alarm cues [11]. In this article, we describe the isolation and the structure elucidation of these novel MAAs.

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Isolation and structure of a mycosporine from the red alga

Cited by 57 publications

References 2 publications

Survey of ultraviolet radiation-absorbing mycosporine-like amino acids in organs of coral reef holothuroids

Survey of ultraviolet radiation-absorbing mycosporine-like amino acids in organs of coral reef holothuroids

Exploiting Mycosporines as Natural Molecular Sunscreens for the Fabrication of UV-Absorbing Green Materials

Isolation and Structural Elucidation of Novel Mycosporine‐Like Amino Acids as Alarm Cues in the Defensive Ink Secretion of the Sea Hare Aplysia californica

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