New Quinone Sulfates from the Crinoids Tropiometra afra macrodiscus and Oxycomanthus japonicus

Takahashi, Daizo; Maoka, Takashi; Tsushima, Miyuki; Fujitani, Kazuyoshi; Kozuka, Mutsuo; Matsuno, Takao; Shingu, Tetsuro

doi:10.1002/chin.200318216

Cited by 7 publications

(16 citation statements)

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“…Both 1 and 2 were also found in extracts from the crinoids Heterometra savi, Lamprometra kluzingeri (Erdman and Thomson 1972), and Oxycomanthus japonicus (Takahashi et al 2002).…”

Section: Discussionmentioning

confidence: 93%

Hydroxylated anthraquinones produced by Geosmithia species

et al. 2009

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Geosmithia fungi are little known symbionts of bark beetles. Secondary metabolites of lilac colored species G. lavendula and other nine Geosmithia species were investigated in order to elucidate their possible role in the interactions of the fungi with environment. Hydroxylated anthraquinones (yellow, orange, and red pigments), were found to be the most abundant compounds produced into the medium during the submerged cultivation. Three main compounds were identified as 1,3,6,8-tetrahydroxyanthraquinone (1), rhodolamprometrin (1-acetyl-2,4,5,7-tetrahydroxyanthraquinone; 2), and 1-acetyl-2,4,5,7,8-pentahydroxyanthraquinone (3). Compounds 2 and 3 (representing the majority of produced metabolites) inhibited the growth of G+-bacteria Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration of 64-512 microg/mL. Anti-inflammatory activity detected as inhibition of cyclooxygenase-2 was found only for compound 3 at 1 and 10 microg/mL. Compound 2 interfered with the morphology, compound 3 with cell-cycle dynamics of adherent mammalian cell lines.

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“…Both 1 and 2 were also found in extracts from the crinoids Heterometra savi, Lamprometra kluzingeri (Erdman and Thomson 1972), and Oxycomanthus japonicus (Takahashi et al 2002).…”

Section: Discussionmentioning

confidence: 93%

Hydroxylated anthraquinones produced by Geosmithia species

et al. 2009

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“…However, secondary metabolites such as quinones may also play a role in chemical defense. Hypericin and gymnochromes are well known for their biological activity (8,24), and antifeedant activities against fish have been reported for structurally related anthraquinone pigments from comatulids (27,28). Previous observations on two extant isocrinids, Endoxocrinus parrae and Neocrinus decorus, suggested that stalked crinoids lack chemical defense against fish predation, supporting the hypothesis that restriction of stalked crinoids to deep-water habitats may have resulted from the Mesozoic radiation of durophagous fishes in shallow seas (29).…”

Section: Resultsmentioning

confidence: 77%

Persistent and widespread occurrence of bioactive quinone pigments during post-Paleozoic crinoid diversification

Wolkenstein

2015

Proc. Natl. Acad. Sci. U.S.A.

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Secondary metabolites often play an important role in the adaptation of organisms to their environment. However, little is known about the secondary metabolites of ancient organisms and their evolutionary history. Chemical analysis of exceptionally well-preserved colored fossil crinoids and modern crinoids from the deep sea suggests that bioactive polycyclic quinones related to hypericin were, and still are, globally widespread in post-Paleozoic crinoids. The discovery of hypericinoid pigments both in fossil and in presentday representatives of the order Isocrinida indicates that the pigments remained almost unchanged since the Mesozoic, also suggesting that the original color of hypericinoid-containing ancient crinoids may have been analogous to that of their modern relatives. The persistent and widespread occurrence, spatially as well as taxonomically, of hypericinoid pigments in various orders during the adaptive radiation of post-Paleozoic crinoids suggests a general functional importance of the pigments, contributing to the evolutionary success of the Crinoidea.crinoids | molecular preservation | marine natural products | polyketides | liquid chromatography-mass spectrometry

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“…Hypericin‐like compounds (Fig. 1) occur in diverse taxa and include stentorin, the blepharismins and maristentorin in heterotrich ciliates (6–10), fringelites in fossil crinoids (11), brominated gymnochromes in modern crinoids (11–14) and fagopyrin in Fagopyrum (buckwheat) (5). Among the more striking aspects of hypericin and the hypericin‐like pigments are their absorption and emission spectra.…”

Section: Introductionmentioning

confidence: 99%

Photophysics and Multifunctionality of Hypericin‐Like Pigments in Heterotrich Ciliates: A Phylogenetic Perspective

Lobban

Hallam

Mukherjee

et al. 2007

Photochem & Photobiology

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In this paper, we review the literature and present some new data to examine the occurrence and photophysics of the diverse hypericin-like chromophores in heterotrichs, the photoresponses of the cells, the various roles of the pigments and the taxa that might be studied to advance our understanding of these pigments. Hypericin-like chromophores are known chemically and spectrally so far only from the stentorids and Fabrea, the latter now seen to be sister to stentorids in the phylogenetic tree. For three hypericin-like pigments, the structures are known but these probably do not account for all the colors seen in stentorids. At least eight physiological groups of Stentor exist depending on pigment color and presence ⁄ absence of zoochlorellae, and some species can be bleached, leading to many opportunities for comparison of pigment chemistry and cell behavior. Several different responses to light are exhibited among heterotrichs, sometimes by the same cell; in particular, cells with algal symbionts are photophilic in contrast to the well-studied sciaphilous (shadeloving) species. Hypericin-like pigments are involved in some well-known photophobic reactions but other pigments (rhodopsin and flavins) are also involved in photoresponses in heterotrichs and other protists. The best characterized role of hypericin-like pigments in heterotrichs is in photoresponses and they have at least twice evolved a role as photoreceptors. However, hypericin and hypericin-like pigments in diverse organisms more commonly serve as predator defense and the pigments are multifunctional in heterotrichs. A direct role for the pigments in UV protection is possible but evidence is equivocal. New observations are presented on a folliculinid from deep water, including physical characterization of its hypericin-like pigment and its phylogenetic position based on SSU rRNA sequences. The photophysics of hypericin and hypericin-like pigments is reviewed. Particular attention is given to how their excited-state properties are modified by the environment. Dramatic changes in excited-state behavior are observed as hypericin is moved from the homogeneous environment of organic solvents to the much more structured surroundings provided by the complexes it forms with proteins. Among these complexes, it is useful to consider the differences between environments where hypericin is not found naturally and those where it is, notably, for example, in heterotrichs. It is clear that interaction with a protein modifies the photophysics of hypericin and understanding the molecular basis of this interaction is one of the outstanding problems in elucidating the function of hypericin and hypericin-like chromophores.

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New Quinone Sulfates from the Crinoids Tropiometra afra macrodiscus and Oxycomanthus japonicus

Abstract: New Quinone Sulfates from the Crinoids Tropiometra afra macrodiscus and Oxycomanthus japonicus -[isolation, structure elucidation and antifeedant activity]. -(TAKAHASHI, D.; MAOKA*, T.; TSUSHIMA, M.; FUJITANI, K.; KOZUKA, M.; MATSUNO, T.; SHINGU, T.; Chem.

Cited by 7 publications

References 1 publication

Hydroxylated anthraquinones produced by Geosmithia species

Hydroxylated anthraquinones produced by Geosmithia species

Persistent and widespread occurrence of bioactive quinone pigments during post-Paleozoic crinoid diversification

Photophysics and Multifunctionality of Hypericin‐Like Pigments in Heterotrich Ciliates: A Phylogenetic Perspective

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