A guaianolide pigment from a deep sea gorgonian

Yellow pigment 3 is one of the minor constituents of a deep sea gorgonian, Placogorgia sp.     

Halogenated blue pigments of a deep sea gorgonian

Three halogenated azulenes (2-4), one of the chiral, have been isolated from a deep sea gorgonian which was collected by minisubmersible at ?350 m.     

Junceols D-H, new polyoxygenated briaranes from sea whip gorgonian coral Junceella juncea (Ellisellidae)

Chemical investigations on the sea whip gorgonian coral Junceella juncea have led to the isolation of five new 8-hydroxybriarane diterpenoids, junceols D-H (1-5). The structures of briaranes 1-5 were determined on the basis of spectroscopic methods and the methylenecyclohexane rings were found to exist in boat form in these new diterpenoids. Junceols D (1) and F-H (3-5) exhibited cytotoxicity toward CCRF-CEM and DLD-1 tumor cells and junceols E-H (2-5) displayed weak inhibitory effects on superoxide anion generation by human neutrophils.     

The synthesis of dendrodoine, 5-[3-(N,N-dimethylamino- 1,2,4-thiadiazolyl]-3-indolylmethanone,a metabolite of the marine tunicate dendroda grossular

The cytotoxic natural product dendrodoine has been synthesised by a 1,3-dipolar addition reaction between indolyl-3-carbonyl nitrile and N,N-dimethylaminonitrile sulphide generated $\text{in}$$\text{situ}$ through the thermolysis of 5-(N,N-dimethylamino)-1,3,4-oxathiazol-2-one.     

Emerixanthone E,a new xanthone derivative from deep sea fungus Emericella sp SCSIO 05240

The marine fungus Emericella sp was isolated from the deep sea sediments. The fungus was identified by its morphology and ITS region. A new emerixanthone E (1) together with four (2–5) known emodin derivatives were isolated from the metabolites of the fungus Emericella SCSIO05240. The structures were elucidated on the basis of NMR spectroscopic analysis and mass spectrometry. The biological properties of those compounds (1–5) were explored for antimicrobial, antifungal and antitumor activity.     

Westerdijkin A,a new hydroxyphenylacetic acid derivative from deep sea fungus Aspergillus westerdijkiae SCSIO 05233

A new methyl 2-(4-((2-hydroxy-3-methylbut-3-en-1-yl)oxy)phenyl) acetate 1, together with five known compounds 2–6, was isolated from the culture of the deep sea-derived fungus Aspergillus westerdijkiae SCSIO 05233. The new structure was determined by NMR (¹H and ¹³C NMR, HSQC, HMBC and MS) and optical rotation analysis. Compound 5 displayed weak inhibitory activities towards K562 and promyelocytic HL-60 with IC₅₀ values of 25.8 and 44.9 μM, and compound 6 showed strong antifouling activity with EC₅₀ value 8.81 μg/mL.     

Trisorbicillinone A, a novel sorbicillin trimer, from a deep sea fungus, Phialocephala sp. FL30r

A novel sorbicillin trimer, trisorbicillinone A (1), was isolated from a deep sea fungus, Phialocephala sp. FL30r. The structure and relative stereochemistry of 1 were determined based on spectroscopic methods. Trisorbicillinone A (1) showed cytotoxicity against P388 and HL60 cells with the IC₅₀ value of 9.10 and 3.14 μM, respectively.     

New marine diterpenoids,including a unique hydroperoxide,from a caribbean gorgonian coral of the genus pseudopterogorgia

Three new diterpenoids related to the aglycone components of the recently described pseudopterosins and seco-pseudopterosins have been isolated from an undescribed Pseudopterogorgia species from the Caribbean Sea. The new compounds, described on the basis of their NMR properties and chemical interconversions, appear to be related illustrating some interesting rearrangements of a tertiary hydroperoxide in this series.     

Chemical composition of magnetic spherules collected from deep sea sediment

Chemical composition of 15 magnetic spherules collected from deep sea sediment was determined by instrumental neutron activation analysis (INAA) under two different irradiation conditions using the Kyoto University Reactor (KUR). Based on their chemical composition, nine spherules were judged to be of extraterrestrial origin. The differences in the chemical composition of the nine spherules are discussed in terms of condensation temperatures for the elements. Comparing the detection limits derived from INAA under two different irradiation conditions, the sensitivity for INAA using KUR is discussed.     

Rumphellclovane A, a novel clovane-related sesquiterpenoid from the gorgonian coral Rumphella antipathies

A novel clovane-related derivative, rumphellclovane A (1), which was found to possess a new carbon skeleton, and a new natural clovane, 2β-hydroxyclovan-9-one (2), were isolated from the gorgonian coral Rumphella antipathies. The structures of metabolites 1 and 2 were elucidated by spectroscopic analysis and by comparison of the spectral data with those of related clovane analogues. A plausible biosynthetic pathway of 1 was proposed.     

Rumphellaone A, a novel caryophyllane-related derivative from the gorgonian coral Rumphella antipathies

A novel 4,5-seco-caryophyllane sesquiterpenoid derivative, rumphellaone A (1), which was found to possess an unprecedented γ-lactone moiety, was isolated from the gorgonian coral Rumphella antipathies. The structure of 1 was elucidated by spectroscopic method. A plausible biosynthetic pathway of compound 1 was proposed.     

Recyclization of 5-allenyl-2,5-dichloro-3-N,N-dimethylamino-4,4-dimethoxycyclopent-2-enone under the action of SmI2−(Me2N)3P. Functionalizedcis-, trans-cycloocta-2,6-dienones

Reaction of 5-allenyl-2,5-dichloro-3-N,N-dimethylamino-4,4-dimethoxycyclopent-2-enone with Sml₂−(Me₂N)₃P affords new functionalizedcis-,trans-cycloocta-2,6-dienones. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2552–2553, December, 1998.     

Briarenol A, a new diterpenoid from a gorgonian '\Briareum sp. (Briareidae)

A new polyoxygenated briarane-type diterpenoid, briarenol A (1), has been isolated from a gorgonian coral belonging to the genus Briareum. The structure, including the relative stereochemistry of briarane 1, was elucidated by the interpretation of spectral data. The configuration of 1 was further supported by molecular mechanics calculations.     

Bipinnapterolide B, a bioactive oxapolycyclic diterpene from the Colombian gorgonian coral Pseudopterogorgia bipinnata

A unique oxapolycyclic diterpenoid, named bipinnapterolide B, has been isolated from the Colombian gorgonian octocoral Pseudopterogorgia bipinnata, and its structure was deduced from spectral and X-ray diffraction studies. Bipinnapterolide B (3) inhibits the growth of Mycobacterium tuberculosis.     

(-)-Hydroxylindestrenolide, a new sesquiterpenoid from a gorgonian coral Menella sp. (Plexauridae)

(-)-Hydroxylindestrenolide (1), an enantiomer of the known sesquiterpenoid, (+)-hydroxylindestrenolide (2), was isolated from a gorgonian coral identified as Menella sp. The structure, including the relative stereochemistry of 1 was established by spectroscopic methods and by comparison the spectral and physical data with those of 2. Sesquiterpenoid 1 exhibited marginal cytotoxicity toward HL-60 and K562 leukemia tumor cells, and displayed a weak inhibitory effect on superoxide anion generation at a concentration of 10 μg/ml by human neutrophils.     

Discovery of novel sesquiterpenoids from a gorgonian Menella sp.

A novel sesquiterpenoid, menelloide A (1), which was found to possess a new carbon skeleton, and a new guaiane-type sesquiterpenoid, menelloide B (2), along with (+)-chloranthalactone B (3), an enantiomer of the known sesquiterpenoid, chloranthalactone B (4), were isolated from a gorgonian coral identified as Menella sp. The structures of sesquiterpenoids 1-3 were established by spectroscopic methods and by comparison of the data with those of related metabolites. Sesquiterpenoids 1 and 3 displayed inhibitory effects on the generation of superoxide anion by human neutrophils.     

Briarane derivatives from the gorgonian coral Junceella fragilis

A new trihydroxyl briarane-type diterpenoid, junceellolide H (1), along with two known compounds, praelolide (2) and junceellin (3), have been isolated from the gorgonian coral Junceella fragilis. The structure, including the relative configuration of the new diterpenoid 1, was elucidated by extensive spectroscopic methods.