Structure and bioactivity of a trisnorditerpenoid and a diterpenoid from an Okinawan soft coral, Cespitularia sp.

An Okinawan soft coral Cespitularia sp. has proven to be a good source of cytotoxic metabolites having a carbon skeleton of the seco-type variety of xenicin. This soft coral yielded alcyonolide, the major constituent, and other related compounds, all of which have proven to be cytotoxic. Reinvestigation of the cytotoxic ethyl acetate extracts of the coral yielded two new alcyonolide congeners, trisnorditerpenoid 1 and diterpenoid 2, possessing the same carbon skeleton. Their structures were elucidated by a detailed analysis of spectroscopic data (1D, 2D NMR, and MS). Metabolites 1 and 2 showed cytotoxicity against HCT116 cells (IC₅₀ 6.04 and 47.0 μM, respectively) and a dose dependent, anti-inflammatory effect in LPS/IFN-γ-stimulated inflammatory RAW 264.7 macrophage cells.     

Cladieunicellins A-E, new eunicellins from an Indonesian soft coral Cladiella sp

Five new eunicellin-type diterpenoids, cladieunicellins A-E (1-5), were isolated from an Indonesian soft coral identified as Cladiella sp. The structures of diterpenoids 1-5 were established using spectroscopic methods. Eunicellins 2 and 5 were found to be cytotoxic against DLD-1 and HL-60 tumor cells, respectively, and 3 displayed inhibitory effects against superoxide anion generation by human neutrophils.     

Two new glycosides from the soft coral Sinularia firma

Two new glycosides, named Firmacosides A and B, together with known fatty esters, batyl alcohol, Delta(5,20) sterol and sphingosine derivatives have been isolated from the soft coral Sinularia firma TIX-DUR. On the basis of spectroscopic analysis ((1)H-NMR, (13)C-NMR, (1)H-(1)H COSY, HMQC, HMBC and FAB-MS), Firmacoside A was established as hexadecanyl-1-O-alpha-D-arabinopyranosyloxy (1-->4)-alpha-D-arabinopyranosyloxy (1-->4)-alpha-D-arabinopyranoside (1), and firmacoside B was elucidated as docosanyl-1-O-alpha-D-arabinopyranosyloxy (1-->4)-3-O-acetyl-alpha-arabinopyranosyloxy (1-->4)-alpha-D-arabinopyranoside (2).     

15-deoxy-isoxeniolide-A,new diterpenoid from a bornean soft coral,Xenia sp.

A new xenicane diterpenoid, 15-deoxy-isoxeniolide-A (1) along with four known compounds 9-deoxy-isoxeniolide-A (2), isoxeniolide-A (3), xeniolide-A (4) and coraxeniolide-B (5) were isolated from the Bornean soft coral Xenia sp. The structures of these metabolites were elucidated on the basis of spectral analysis, NMR and HRESIMS. Compound 5 showed cytotoxic activity against ATL cell line, S1T.     

Isolation of three marine prostanoids,possible biosynthetic intermediates for clavulones,from the Okinawan soft coral Clavularia viridis

Three marine prostanoids, 1, 2, and 3, were isolated from the extract of the Okinawan soft coral Clavularia viridis. The structures of these compounds were assigned based on the results of spectroscopic analysis. Compound 1 was shown to be preclavulone-A methyl ester, and this is the first isolation of the ester of preclavulone-A as a natural product. Preclavulone-A is proposed to be the key intermediate in the biosynthesis of marine prostanoids exemplified by clavulones in C. viridis. The new prostanoid 3 was suggested to be a biosynthetic intermediate from preclavulone-A to clavulones, and a possible biogenetic pathway via 3 is proposed.     

3Alpha,7alpha,12alpha-triacetoxy-5beta-cholanic acid, a steroid from the Formosan soft coral Alcyonium sp. (Alcyoniidae)

Chemical investigation of the organic extract of a soft coral belonging to the genus Alcyonium furnished a steroid, 3alpha,7alpha,12alpha-triacetoxy-5beta-cholanic acid (1). The structure of steroid 1 was assigned on the basis of spectroscopic evidence, particularly in 1D and 2D NMR experiments. The configuration of steroid 1 was further supported by molecular mechanics calculations.     

Two new bioactive sesquiterpenes from the soft coral Sinularia sp

Two new sesquiterpenes, 1S*, 4R*, 5S*, 6R*, 7S*, 10S*-1(5), 6(7)-diepoxy-4-guaiol (1) and 1S*, 4S*, 5S*, 10R*-4,10-guaianediol (2) have been isolated from the ethyl acetate soluble portion of the soft coral Sinularia sp., and their stereostructure were determined by spectroscopic methods and by X-ray single crystal analysis. Both compounds showed antioxidant and cytotoxic activities.     

Stolonilactone, a novel terpenoid-related compound, isolated from the Okinawan soft coral Clavularia koellikeri

A novel terpenoid-related compound, stolonilactone (1), was isolated from the Okinawan soft coral Clavularia koellikeri. The structure of 1 was elucidated on the basis of spectroscopic analysis. A possible biogenesis of 1 through the [4 + 2]-cycloaddition of a trisnorsesquiterpenoid-type diene and a cembranolide-type dienophile is proposed.     

Untenolide A, a new polyketide from an Okinawan marine sponge Plakortis sp.

A new polyketide, untenolide A (1), has been isolated from an Okinawan marine sponge Plakortis species, and the structure was elucidated from spectroscopic data and X-ray analysis. Untenolide A (1) is a new polyketide possessing a fused-pentacyclic skeleton with two hexadecanyl chains.     

Paesslerins A and B: novel tricyclic sesquiterpenoids from the soft coral Alcyonium paessleri

[structure: see text] In the course of our search of new bioactive metabolites from marine invertebrates, paesslerins A and B, sesquiterpenoids with an unprecedented tricyclic skeleton, were isolated from the subAntarctic soft coral Alcyonium paessleri collected at a depth of 200 m near the South Georgia islands, and their structures were elucidated by spectroscopic techniques. These compounds show moderate cytotoxicity in preliminary assays.     

Lobozoanthamine, a new zoanthamine-type alkaloid from the Indonesian soft coral Lobophytum sp.

A new member of the family of zoanthamine-type alkaloids, lobozoanthamine (1), has been isolated from the Indonesian soft coral Lobophytum sp. This represents the first report of a zoanthamine-type alkaloid from a marine invertebrate different from zoanthids. The densely functionalized heptacyclic stereostructure of lobozoanthamine (1) has been established through the interpretation of 2D NMR data and application of the modified Mosher method.     

12-Epi-9-deacetoxyxenicin,new cytotoxic diterpenoid from a Bornean soft coral,Xenia sp.

One new compound, 12-epi-9-deacetoxyxenicin (1) along with a hydroperoxide product, 12-epi-9-deacetoxy-8-hydroperoxyxenicin (2) and two known sesquiterpenoids (3–4) were isolated from a population of Bornean soft coral Xenia sp. The structures of these secondary metabolites were elucidated based on their spectroscopic data. Compounds 1 and 2 showed cytotoxic activity against ATL cell line, S1T. In addition, compound 3 exhibited hyphal inhibition of Lagenidium thermophilum.     

Tricycloclavulone and clavubicyclone, novel prostanoid-related marine oxylipins, isolated from the Okinawan soft coral Clavularia viridis

Two novel prostanoid-related marine oxylipins, tricycloclavulone (1) and clavubicyclone (2), were isolated from the Okinawan soft coral Clavularia viridis. The structures of 1, having a tricyclo[5.3.0.0(1,4)]decane ring system, and 2, having a bicyclo[3.2.1]octane ring system, were elucidated on the basis of spectroscopic analysis. Clavubicyclone showed a moderate growth inhibition activity against tumor cells in vitro.     

Trunculins X and Y from an Okinawan sponge Sigmosceptrella sp.

Two new norsesterterpenoid cyclic peroxides, trunculins X and Y, were isolated from an Okinawan sponge Sigmosceptrella sp. Their structures were determined by spectroscopic analyses on intact molecules and derivatives and also by crystallographic study. The compounds showed cytotoxicity in a range of IC₅₀ 0.32–20 μM against three cell lines.     

Two unprecedented cembrene-type terpenes from an indonesian soft coral sarcophyton sp.

Two unusual cembranoids, sarcofuranocembrenolides A (1) and B (2), were isolated from a soft coral Sarcophyton sp. together with five known cembranoids (3-7). Compound 1 had a unique carbon skeleton of 8,19-bisnorfuranocembrenolide. Compound 2 was a furanocembrenolide, but a C₁ unit (C-20) was attached to C-10 instead of C-12 of the ordinary cembrenolides. These rearrangements are unique in the biosynthesis of cembranoid diterpenes. Lobohedleolide (5), (7Z)-lobohedleolide (6), and denticulatolide (7) inhibited the colony formation of V79 cells at ED₅₀ values of 4.6 (abt. 1.52), 3.7 (1.22), and 3.6 (1.40) μM (μg/mL), respectively, and reduced TNF-α production from LPS-stimulated RAW264.7 cells at 3.0-10.0 μM.     

Complete 1H and 13C NMR assignments of four new steroidal glycosides from a gorgonian coral Junceella juncea

Four new cholest-type steroidal glycosides, junceellosides A-D, isolated from the EtOH/CH(2)Cl(2) extracts of the South China Sea gorgonian coral Junceella juncea, were identified. Complete assignments of the (1)H and (13)C NMR chemical shifts for these compounds were achieved by means of one- and two-dimensional NMR techniques, including (1)H-(1)H COSY, HSQC, HMBC and NOESY spectra.     

Agelasine G, a new antileukemic alkaloid from the Okinawan marine sponge Agelas sp.

A new antileukemic alkaloid, agelasine G (1a), has been isolated from the Okinawan marine sponge Agelas sp. and its structure elucidated to be a bromopyrrole alkaloid containing 9-methyladenine and diterpene moieties on the basis of the spectroscopic data.