6H-anthra[1,9-bc]thiophene derivatives from a bryozoan,Dakaira subovoidea

Shindo, Takamasa; Sato, Aiya; Kasanuki, Naomi; Hasegawa, Kazuo; Sato, Sadao; Iwata, Tomonori; Hata, Tadashi

doi:10.1007/bf01989426

Cited by 13 publications

(12 citation statements)

References 2 publications

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“…Watersipora larvae are free-swimming, soft-bodied, and bright orange-red, making them an appealing target for predators and likely to be chemically defended. Bioactive anthraquinones, including 1,8-dihydroxyanthraquinone, have been isolated from Japanese Watersipora species (19,30) and are one possibility for symbiont-produced chemical defense compounds. A compound similar to those isolated from Japanese Watersipora species, 1,8-dihydroxy-3-methylanthraquinone (chrysophanol), protects beetle eggs from ant predators (17).…”

Section: Discussionmentioning

confidence: 99%

α-Proteobacterial Symbionts of Marine Bryozoans in the GenusWatersipora

Anderson

Haygood

2007

Appl Environ Microbiol

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Bacterial symbionts that resembled mollicutes were discovered in the marine bryozoan Watersipora arcuata in the 1980s. In this study, we used PCR and sequencing of 16S rRNA genes, specific fluorescence in situ hybridization, and phylogenetic analysis to determine that the bacterial symbionts of "W. subtorquata" and "W. arcuata" from several locations along the California coast are actually closely related ␣-Proteobacteria, not mollicutes. We propose the names "Candidatus Endowatersipora palomitas" and "Candidatus Endowatersipora rubus" for the symbionts of "W. subtorquata" and "W. arcuata," respectively.Bacterial symbionts of bryozoans in the genus Watersipora were originally reported in 1983 (38). The bacteria were consistently observed in a surface groove with an overhanging flange unique to Watersipora larvae (38). Inside adult colonies of Watersipora, the bacterial symbionts were found in clusters surrounded by host mesodermal cells (38). The bacterial symbionts were present in Watersipora larvae immediately upon their release into the water column, indicating vertical transmission of the bacteria, although transmission has not been observed directly. With their irregular shape and apparent lack of a cell wall in transmission electron micrographs, the bacterial symbionts resembled mollicutes and were called mycoplasma-like organisms (38). In 1989, an Acholeplasma sp., a type of mollicute thought to be the symbiont, was isolated from Watersipora larvae on mycoplasma agar amended with filter-sterilized adult Watersipora extract (5). However, the molecular techniques necessary to confirm that the isolated Acholeplasma sp. was actually the symbiont were unavailable at the time.Calcareous marine bryozoans in the genus Watersipora are found worldwide in the tropics and subtropics (31). Along the coast of California, they are common on floating docks, boat bottoms, and other sturdy substrates in bays and harbors and are considered successful invaders that probably arrived in the 1960s (3). The systematics of the genus Watersipora are unresolved (15, 29, 31), making classification of host samples to the species level problematic. This is illustrated by the first report of symbionts in Watersipora, which identified the bryozoan host as Watersipora cucullata (38). Later, the identification was revised to Watersipora arcuata (37). Because of the confusion in systematics, it is critical to keep thorough records of the Watersipora samples, including host gene DNA sequences, light micrographs, and in some cases, scanning electron micrographs (SEMs), in order to study this symbiosis.Examples of associations between bryozoans and bacteria are abundant (2,24,36,38). In most cases, the roles of the bacteria in the lives of their host bryozoans are unknown. The symbiosis between the ␥-proteobacterium "Candidatus Endobugula sertula" and the bryozoan Bugula neritina is an exception for which there is extensive evidence indicating that "Candidatus Endobugula sertula" is the source of the bryostatins, a family of polyketides which...

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Section: Discussionmentioning

confidence: 99%

α-Proteobacterial Symbionts of Marine Bryozoans in the GenusWatersipora

Anderson

Haygood

2007

Appl Environ Microbiol

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“…Dakaria subovoidea, now reclassified as Watersipora subovoidea (d'Orbigny) produces three natural products which inhibit lipid peroxide formation. 139 5,7-Dihydroxy-1-hydroxymethyl-6-oxo-6H -anthra [1,9-bc]thiophene 161 and its 1-methoxycarbonyl derivative 162 are novel compounds that were isolated with the known compound 1,8dihydroxyanthraquinone 163. A third species of Watersipora, Watersipora subtorquata d'Orbigny, also produces 5,7-dihydroxy-1-methoxycarbonyl-6-oxo-6H-anthra[1,9-bc]thiophene 162 and 1,8-dihydroxyanthraquinone 163, together with the novel bryoanthrathiophene 164.…”

Section: Suborder Ascophora: Infraorder Lepraliomorphamentioning

confidence: 99%

Bryozoan metabolites: an ecological perspective

2007

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“…140 The orange anthrathiophene pigment 60 is from a bryozoan. 141 The cytotoxic sulfur-containing pale yellow alkaloid dendrodoine 61, isolated from the tunicate Dendrodoa grossularia, is unique in containing the first identified naturally occurring 1,2,4-thiadiazole ring system. 114 This compound may well equally be classified as an indole or guanidine alkaloid.…”

Section: Miscellaneous Pigmentsmentioning

confidence: 99%

The nature and role of pigments of marine invertebrates

Bandaranayake

2006

Nat. Prod. Rep.

107

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Marine animals, especially those from tropical waters, are often brilliantly coloured, and bright colouration is widespread in both sessile and non-sessile invertebrates. These spectacular natural colours are common in species inhabiting shallow waters, and appear not only in animals exposed to bright light, but also in those living in dark areas where colours are visible only with artificial illumination. Marine organisms also show variation in colour with depth and geographical location, and display great variety in colour patterning. These colour characteristics are the result of several different processes, and serve various purposes - the distribution and function of pigments seems to vary between invertebrate groups. In addition to playing an important role in how marine organisms interact, pigments may be involved in physiological processes. Although nitrogenous pigments predominate, marine organisms contain pigments belonging to all the major structural classes of natural products, as well as some that are unique to the marine environment. This review discusses the nature and significance of such pigments, the chemical and biological processes involved, the factors responsible for and affecting bright colourations, as well as their evolution and speculation as to their function.

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6H-anthra[1,9-bc]thiophene derivatives from a bryozoan,Dakaira subovoidea

Cited by 13 publications

References 2 publications

α-Proteobacterial Symbionts of Marine Bryozoans in the GenusWatersipora

α-Proteobacterial Symbionts of Marine Bryozoans in the GenusWatersipora

Bryozoan metabolites: an ecological perspective

The nature and role of pigments of marine invertebrates

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