Bioactive secondary metabolites from symbiotic marine dinoflagellates: symbiodinolide and durinskiols

Kita, Masakazu; Ohno, Osamu; Han, Chong; Uemura, Daisuke

doi:10.1002/tcr.200900007

Cited by 33 publications

(22 citation statements)

References 67 publications

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“…Copper-catalyzed allylation of 34 regioselectively opened the terminal epoxide to provide the secondary alcohol 35 in 95 % yield. Oxidation of 35 with Dess-Martin periodinane [35] gave the ketone 36 (97 %), chelation-controlled methylation of which with methylmagnesium chloride (Et 2 O, À78 8C) [36] afforded the tertiary alcohol 37 in quantitative yield as a single stereoisomer, as judged by 1 H NMR analysis (600 MHz). Protection of the resulting hydroxy group as its TBS ether gave the silyl ether 38 (97 %).…”

Section: Synthesis Of the De-ring Fragmentmentioning

confidence: 99%

“…[1] Marine polycyclic ether natural products, chiefly produced by dinoflagellates, are a unique class of marine metabolites, sharing a common ladder-shaped trans-fused polycyclic ether structural motif and exhibiting a broad range of biological activities with high potencies. [2] Among the family of marine polycyclic ethers, brevetoxin B (1), isolated from the Florida red-tide-forming dinoflagellate Karenia brevis as a potent ichthyotoxic constituent, was the first member to be structurally elucidated by spectroscopic and X-ray crystallographic analyses.…”

Section: Introductionmentioning

confidence: 99%

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Total Synthesis of (−)‐Brevenal: A Streamlined Strategy for Practical Synthesis of Polycyclic Ethers

Ebine

Fuwa

Sasaki

2011

Chemistry A European J

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We describe a streamlined strategy for the practical synthesis of trans-fused polycyclic ethers and its application to a concise total synthesis of (-)-brevenal, a new pentacyclic polyether natural product with intriguing biological activities. The B-, D-, and E-rings were constructed by TEMPO/PhI(OAc)(2)-mediated oxidative lactonization of the corresponding 1,6-diols, with minimal need for manipulation of oxygen functionalities. The B- and E-ring lactones were appropriately functionalized by Suzuki-Miyaura coupling of lactone-derived enol phosphates and subsequent stereoselective hydroboration. The A-ring was formed by our mixed thioacetalization methodology. The AB- and DE-ring fragments were assembled through Suzuki-Miyaura coupling, and the C-ring was forged in the same manner as that for the A-ring. More than two grams of the pentacyclic polyether core of (-)-brevenal have been synthesized by the synthetic route developed in this study.

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Section: Synthesis Of the De-ring Fragmentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Total Synthesis of (−)‐Brevenal: A Streamlined Strategy for Practical Synthesis of Polycyclic Ethers

Ebine

Fuwa

Sasaki

2011

Chemistry A European J

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“…Dinoflagellates are unicellular phytoplankton and are known to produce various bioactive secondary metabolites [1,2,3,4,5,6]. The genus, Symbiodinium , which belongs to the zooxanthellae, is a representative symbiont found in many marine invertebrates.…”

Section: Introductionmentioning

confidence: 99%

“…The genus, Symbiodinium , which belongs to the zooxanthellae, is a representative symbiont found in many marine invertebrates. They also produce unique and complex bioactive secondary metabolites [1,2,4] together with a peridinin. Peridinin is one of the carotenoids that is synthesized in dinoflagellates.…”

Section: Introductionmentioning

confidence: 99%

Peridinin from the Marine Symbiotic Dinoflagellate, Symbiodinium sp., Regulates Eosinophilia in Mice

et al. 2014

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Peridinin and fucoxanthin, which are natural carotenoids isolated from a symbiotic dinoflagellate, Symbiodinium sp., and a brown alga, Petalonia fascia, respectively, were compared for inhibitory effects on delayed-type hypersensitivity in mice. The number of eosinophils at the site of inflammation and in peripheral blood was compared for the administration of peridinin and fucoxanthin applied by painting and intraperitoneally. Peridinin, but not the structurally-related fucoxanthin, significantly suppressed the number of eosinophils in both the ear lobe and peripheral blood. Furthermore, peridinin applied topically, but not administered intraperitoneally, suppressed the level of eotaxin in the ears of sensitized mice. Fucoxanthin weakly suppressed the concentration of eotaxin in ears only by intraperitoneal administration. Although both carotenoids inhibited the migration of eosinophils toward eotaxin, the inhibitory effect of peridinin was higher than that of fucoxanthin. Peridinin may be a potential agent for suppressing allergic inflammatory responses, such as atopic dermatitis, in which eosinophils play a major role in the increase of inflammation.

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“…Furthermore, secondary metabolites obtained from marine organisms are often derived from symbiotic algae and/or symbiotic bacteria [28], [29]. Sarcophyton spp.…”

Section: Introductionmentioning

confidence: 99%

Soft Coral Sarcophyton (Cnidaria: Anthozoa: Octocorallia) Species Diversity and Chemotypes

et al. 2012

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Research on the soft coral genus Sarcophyton extends over a wide range of fields, including marine natural products and the isolation of a number of cembranoid diterpenes. However, it is still unknown how soft corals produce this diverse array of metabolites, and the relationship between soft coral diversity and cembranoid diterpene production is not clear. In order to understand this relationship, we examined Sarcophyton specimens from Okinawa, Japan, by utilizing three methods: morphological examination of sclerites, chemotype identification, and phylogenetic examination of both Sarcophyton (utilizing mitochondrial protein-coding genes MutS homolog: msh1) and their endosymbiotic Symbiodinium spp. (utilizing nuclear internal transcribed spacer of ribosomal DNA: ITS- rDNA). Chemotypes, molecular phylogenetic clades, and sclerites of Sarcophyton trocheliophorum specimens formed a clear and distinct group, but the relationships between chemotypes, molecular phylogenetic clade types and sclerites of the most common species, Sarcophyton glaucum, was not clear. S. glaucum was divided into four clades. A characteristic chemotype was observed within one phylogenetic clade of S. glaucum. Identities of symbiotic algae Symbiodinium spp. had no apparent relation to chemotypes of Sarcophyton spp. This study demonstrates that the complex results observed for S. glaucum are due to the incomplete and complex taxonomy of this species group. Our novel method of identification should help contribute to classification and taxonomic reassessment of this diverse soft coral genus.

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Bioactive secondary metabolites from symbiotic marine dinoflagellates: symbiodinolide and durinskiols

Cited by 33 publications

References 67 publications

Total Synthesis of (−)‐Brevenal: A Streamlined Strategy for Practical Synthesis of Polycyclic Ethers

Total Synthesis of (−)‐Brevenal: A Streamlined Strategy for Practical Synthesis of Polycyclic Ethers

Peridinin from the Marine Symbiotic Dinoflagellate, Symbiodinium sp., Regulates Eosinophilia in Mice

Soft Coral Sarcophyton (Cnidaria: Anthozoa: Octocorallia) Species Diversity and Chemotypes

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