Bruce F. Bowden

Studies of Australian soft corals. XXXV

Abstract The in vivo incorporation of mevalonolactone specifically into the terpene portion of a sesquiterpene hydroquinone is reported for the soft coral Sinularia capillosa Eudesma -4 , 7(11)- diene -8β- ol ( 20 ) and the corresponding 8-keto derivative ( 21 ) have been isolated from the soft coral Nephthea species for the first time The aeolid nudibranch Phyllodesmium longicirra was collected when feeding on the soft coral Sarcophyton trocheliophorum and the known diterpene trocheliophorol (25) was found to be concentrated in the cerata of the nudibranch. The absolute stereochemistry of trocheliophorol ( 25 ) has been rigorously determined, and shown to be that previously assigned on spectroscopic grounds

A bioactive triterpene from Lantana camara

Lantana camara afforded a novel triterpene 22 beta-acetoxylantic acid and the known triterpenes, lantic acid, 22 beta-dimethylacryloyloxylantonolic acid, a mixture of 22 beta-dimethylacryloyloxy lantanolic acid and 22 beta-angeloyloxylantanolic acid and lantanolic acid. 22 beta-Acetoxylantic acid showed antimicrobial activity against Staphylococcus aureus and Salmonella typhi. This compound and 22 beta-dimethylacryloyloxy lantanolic acid also showed antimutagenic activity.

Chemical aspects of mass spawning in corals. I. Sperm-attractant molecules in the eggs of the scleractinian coral Montipora digitata

This paper provides the first evidence for sperm chemotaxis in the Scleractinia. Montipora digitata Dana, 1845 (Scleractinia: Coelenterata) is a hermaphroditic coral which reproduces bi-annually, releasing egg-sperm bundles during the mass spawning at Magnetic Island (19°10′S; 146°52′E) in late spring-early summer, and autumn each year. The buoyant egg-sperm bundles float to the surface where they break apart, releasing eggs and sperm into the ocean. Fertilisation occurs after ∼30 min. Unfertilized eggs were collected, washed free of sperm, and freeze-dried. The eggs were extracted with dichloromethane, fractionated by chromatography on silica gel, and the fractions assayed for their ability to attract M. digitata sperm. The active fraction was further fractionated by high-performance liquid chromatography, resulting in the isolation of three highly unsaturated fatty alcohols: (1) dodeca-2,4-diynol; (2) tetradec-13-ene-2,4-diynol; (3) (14Z)-heptadeca-14,16-diene-2,4-diynol. Of these three compounds, only Compound 1 attracted sperm of M. digitata. Synthetic Compound 1, produced from simple precursors by known reactions, possessed sperm-attracting activity comparable to the naturally derived attractant. Preliminary experiments suggest that the natural mixture of Compounds 1, 2 and 3 in the ratio 1:4:9 is more effective in attracting sperm from M. digitata than sperm from other Montipora species. Sperm attractants may act to reduce the incidence of hybridisation between different species of Montipora.

In situ isolation of allelochemicals released from soft corals (Coelenterata : Octocorallia): A totally submersible sampling apparatus

Abstract A submersible apparatus has been developed which permits in situ sampling of allelochemical substances released from sessile marine organisms. Concentration of the allomones from sea water is achieved by adsorption on SEP-PAK C-18, reverse-phase cartridges. The procedure is performed under water and causes minimal disturbance to the organism while in its natural habitat. Design and application of this apparatus are detailed. The isolation and identification of toxins released by two species of alcyonarian corals (order Alcyonacea) are described. This represents the first direct in situ isolation of water-borne allelochemicals released from a marine organism.

Algal overgrowth of alcyonacean soft corals

Colonies of the soft coral Lobophytum pauciflorum (Ehrenberg, 1834) (Coelenterata: Octocorallia: Alcyonacea: Alcyoniidae), some of which were heavily overgrown by the algae Ceranium flaccidum (Kuetzing) Ardissone and Enteromorpha sp., and other minor epizoites, were collected at Taylor Reef (17°50′S; 146°35′E) in the Great Barrier Reef. Overgrown colonies contained the diterpene 2-epi-sarcophytoxide as the major secondary metabolite, while conspecific colonies with clean polyparies contained two diterpenes in approximately equal amounts: 14-hydroxycembra-1,3,7,11-tetraene and 15-hydroxycembra-1,3,7,11-tetraene. By contrast, twenty conspecific pairs of overgrown and clean colonies of other alcyoniid soft corals collected from Pelorus Channel, Palm Island Group (18°34′S; 146°29′E), showed no chemical differences within in the pairs. Cultures of a common species of Ceramium [C. codii (Richards) Mazoyer] were incubated with different concentrations of nine soft-coral-derived diterpenes and significant algal growth inhibition was observed in many cases. It appears that terpenoids from soft coral may contribute to the lack of epizoic organisms on soft-coral polyparies.

Vertebrate herbivory on Eucalyptus: identification of specific feeding deterrents for common ringtail possums (Pseudocheirus peregrinus) by bioassay-guided fractionation of Eucalyptus ovata foliage

Factors determining the acceptance of Eucalyptus ovata foliage by common ringtail possums (Pseudocheirus peregrinus) were studied. Bioassay-guided fractionation was used with foliage from both browser-susceptible and browser-resistant trees to identify the chemical components underlying the resistance. In foliage from browser-resistant trees, the deterrent principles were contained in the base-soluble fraction of the chloroform extract. Further fractionation of this material yielded polar and nonpolar fractions that contained acylphloroglucinol derivatives, and from the polar fraction we isolated macrocarpal G. Addition of this compound to an artificial diet at a concentration of 2.1% of dry matter resulted in a 90% reduction of voluntary food intake compared with solvent-treated controls. This is the first time that a specific compound in Eucalyptus has been shown to inhibit feeding of any marsupial folivore.

A New Brominated Diphenyl Ether from the Marine Sponge Dysidea herbacea.

Samples of Dysidea herbacea collected at Pelorus Island, Great Barrier Reef, Australia, afforded a new polybrominated diphenyl ether (1). The structure was determined by n.m.r. two-dimensional methods and by an X-ray diffraction study. N.m.r. spectral assignments for (1) and some previously reported isomeric polybrominated diphenyl ethers are discussed.

Eusynstyelamides A, B, and C, nNOS Inhibitors, from the Ascidian Eusynstyela latericius

Eusynstyelamides A-C (1-3) were isolated from the Great Barrier Reef ascidian Eusynstyela latericius, together with the known metabolites homarine and trigonelline. The structures of 1-3, with relative configurations, were elucidated by interpretation of their spectroscopic data (NMR, MS, UV, IR, and CD). The NMR data of 1 were found to be virtually identical to that reported for eusynstyelamide (4), isolated from E. misakiensis, indicating that a revision of the structure of 4 is needed. Eusynstyelamides A-C exhibited inhibitory activity against neuronal nitric oxide synthase (nNOS), with IC(50) values of 41.7, 4.3, and 5.8 microM, respectively, whereas they were found to be nontoxic toward the three human tumor cell lines MCF-7 (breast), SF-268 (CNS), and H-460 (lung). Compounds 1 and 2 displayed mild inhibitory activity toward Staphylococcus aureus (IC(50) 5.6 and 6.5 mM, respectively) and mild inhibitory activity toward the C(4) plant regulatory enzyme pyruvate phosphate dikinase (PPDK) (IC(50) values of 19 and 20 mM, respectively).

Botryllamides A-D, new brominated tyrosine derivatives from styelid ascidians of the genus Botryllus

Abstract Four new bromotyrosine derivatives, botryllamides A-D (1–4) were isolated from the styelid ascidian Botryllus sp. from Siquijor Is., Philippines, and from Botryllus schlosseri from the Great Barrier Reef, Australia. Their structures were deduced from 1D and 2D NMR spectral data.

Transformation of soft coral (Coelenterata: Octocorallia) terpenes by Ovula ovum (Mollusca: Prosobranchia)

The faecal pellets from specimens of the prosobranch mollusc Ovula ovum found feeding on the soft coral Sarcophyton sp. at Eclipse Island, Palm Island Group (18°46′S; 146°33′E) in November 1980 were analysed. The only terpene present in the faeces, 7,8-deoxysarcophytoxide, differed from the major constituent of the soft coral, sarcophytoxide, suggesting that the latter had been transformed into the former within the cowrie. This transformation is not trivial, and could not be produced simply by acid catalysis. Subsequent analysis of tissues dissected from different regions of O. ovum indicates that the transformation is probably effected by enzymes in the digestive diverticula stomach region of the prosobranch. The transformed compound is significantly less toxic to the mosquito fish Gambusia affinis Baird and Girard than the ingested compound.