Isolation and Biological Activity of 9-Tetrodotoxin and Isolation of Tb-242B, Possible Biosynthetic Shunt Products of Tetrodotoxin from Pufferfish.

Tetrodotoxin (TTX, ) is a potent voltage-gated sodium channel blocker detected in certain marine and terrestrial organisms. We report here a new TTX analogue, 9-TTX (), and a TTX-related compound, Tb-242B (), isolated from the pufferfish and , respectively. NMR analysis suggested that exists as a mixture of hemilactal and 10,8-lactone forms, whereas other reported TTX analogues are commonly present as an equilibrium mixture of hemilactal and 10,7-lactone forms.

Attenuation of zinc-enhanced inflammatory M1 phenotype of microglia by peridinin protects against short-term spatial-memory impairment following cerebral ischemia in mice.

Activated microglia exhibit two opposite activation states, the inflammatory M1 and the anti-inflammatory M2 activation states. In the mammalian brain, ischemia elicits a massive release of zinc from hippocampal neurons, and the extracellular zinc primes M1 microglia-by inducing reactive oxygen species (ROS) generation-to enhance their production of proinflammatory cytokines, which ultimately results in short-term spatial memory impairment. Here, we examined how peridinin, a carotenoid in dinoflagellates, affects the zinc-enhanced inflammatory M1 phenotype of microglia.

Spiro Bicyclic Guanidino Compounds from Pufferfish: Possible Biosynthetic Intermediates of Tetrodotoxin in Marine Environments.

Tetrodotoxin (TTX, 1) is a potent neurotoxin that is widely found in both terrestrial and marine animals; however, the biosynthetic pathway and genes for TTX have not yet been elucidated. Previously, we proposed that TTX originated from a monoterpene; this hypothesis was based on the structures of cyclic guanidino compounds that are commonly found in toxic newts. However, these compounds have not been detected in marine organisms.

Aurantiacicella marina gen. nov., sp. nov., a myxol-producing bacterium from surface seawater.

A Gram-stain-negative, non-motile, mesophilic, aerobic, rod-shaped bacterium, strain 2A-8T, was isolated from surface seawater at Muroto city, Kochi prefecture, Japan. The strain produced myxol as a major carotenoid. Phylogenetic analyses based on 16S rRNA gene sequences showed that the strain fell within the family Flavobacteriaceae and was related most closely to the genus Aquimarina (91.

Peridinin from the marine symbiotic dinoflagellate, Symbiodinium sp., regulates eosinophilia in mice.

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.

Okicamelliaside, an extraordinarily potent anti-degranulation glucoside isolated from leaves of Camellia japonica.

Guided by anti-degranulation assays, we isolated from leaves of Camellia japonica an ellagic acid glucoside named okicamelliaside. The structure was elucidated as 3,4-dioxoloellagic acid 4'-O-β-D-glucopyranoside by spectroscopic and chemical methods. Okicamelliaside was 12,000 times more potent than the antihistaminic drug, ketotifen fumarate, in inhibiting the degranulation of RBL-2H3 cells.

Zooxanthellamide D, a polyhydroxy polyene amide from a marine dinoflagellate, and chemotaxonomic perspective of the Symbiodinium polyols.

A long-chain polyhydroxy polyene amide, zooxanthellamide D (ZAD-D, 1, C54H83NO19), was isolated from a cultured marine dinoflagellate of the genus Symbiodinium. ZAD-D (1) is a polyhydroxy amide consisting of a C22-acid part and a C32-amine part and furnishes three tetrahydropyran rings and six isolated butadiene chromophores. The relative stereochemistry of the tetrahydropyran ring systems was elucidated by NMR techniques.

Camellianoside, a novel antioxidant glycoside from the leaves of Camellia japonica.

A novel flavonol glycoside named camellianoside and three known flavonol glycosides were isolated from the leaves of Camellia japonica. The structure of camellianoside was established as quercetin-3-O-beta-D-xylopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->6)-O-beta-D-glucopyranoside by spectroscopic and chemical methods. The antioxidant activities of these glycosides evaluated by the diphenylpicrylhydrazyl (DPPH) radical scavenging reaction was higher than those of L-cysteine and L-ascorbic acid used as the reference antioxidants.

Zooxanthellamide Cs: vasoconstrictive polyhydroxylated macrolides with the largest lactone ring size from a marine dinoflagellate of Symbiodinium sp.

Zooxanthellamide Cs (ZAD-Cs), C(128)H(220)N(2)O(53)S(2) (ca. 2.7 kDa), was obtained from a cultured marine dinoflagellate of the genus Symbiodinium as an inseparable isomeric mixture of polyhydroxylated 61- to 66-membered macrolides.

Zooxanthellamide B, a novel large polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium sp.

Zooxanthellamide B, C(128)H(220)N(2)O(53)S(2), a polyhydroxy secondary metabolite, was isolated from a cultured marine dinoflagellate of the genus Symbiodinium. A detailed 2D NMR analysis revealed the chemical structure as a delta-lactone analogue of zooxanthellamide A, which had previously been isolated from the same dinoflagellate by us. The relative configuration of the delta-lactone moiety was determined by NOE experiments and a coupling constant analysis, and that of other ring systems was found to be the same as zooxanthellamide A by the chemical correlation between zooxanthellamides A and B.

Zooxanthellactone, a novel gamma-lactone-type oxylipine from dinoflagellates of Symbiodinium sp.: structure, distribution, and biological activity.

A novel fatty acid derivative named zooxanthellactone (ZL) was isolated from several strains of symbiotic microalgae, dinoflagellates of the genus Symbiodinium. The metabolite is structurally related to docosahexaenoic acid (DHA) and seems to be biosynthesized by oxidation and subsequent lactonization. The absolute stereochemistry was determined from the specific rotation of the perhydro derivative.