The haliclonacyclamines, cytotoxic tertiary alkaloids from the tropical marine sponge Haliclona sp

2D-NMR spectroscopic data is reported for the haliclonacyclamines A - D (1)-(4) and for two bismethiodide adducts (5) and (6). The structures of two new alkaloids, haliclonacyclamines C (3) and D (4), which are the 15,16-dihydro analogues of the haliclonacyclamines A (1) and B (2) are described. Revised assignments deduced by 2D-INADEQUATE spectroscopy are presented for (1) and (2). The alkene substituent in the C,, spacer group of (2) and (4) is positioned between C27-C28 by NMR, and confirmed by x-ray structural analysis for (2). Metabolite (3) has a C25-C26 double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.

Two new species of Neolebouria Gibson, 1976 (Digenea : Opecoelidae) from temperate marine fishes of Australia

Neolebouria moretonensis n. sp. is described from Gerres subfasciatus (Gerreidae) from Moreton Bay, south-east Queensland and N. lineatus n. sp. is described from Centroberyx lineatus (Berycidae) from off Rottnest Island, south-west Western Australia. C. lineatus represents a new host family and order (Beryciformes) for the genus. The two new species are distinguished within the genus by their entire, tandem to oblique testes and cirrus-sacs that do not extend into the hind-body, by being less than 1 mm in length, and by the position of the genital pore and the relative size of the forebody and post-testicular region. N. lineatus and N. moretonensis are very similar but are distinguished by their caeca which extend further posteriorly in N. moretonensis. There is no apparent pattern in the host-specificity of this genus.

Preptetos and Neopreptetos (Digenea: Lepocreadiidae) from Australian marine fishes

The genera Preptetos Pritchard, 1960 and Neopreptetos Machida, 1982 are redefined. The following species are described and/or recorded from marine fishes. From the Great Barrier Reef: Preptetos caballeroi Pritchard, 1960 in Naso annulatus, N. brevirostris and N. vlamingii; P. xesuri (Yamaguti, 1940) in Zebrasoma veliferum and Z.scopas; Preptetos cannoni Barker, Bray et Cribb, 1993 in Siganus doliatus and S. fuscescens; Preptetas luguncula sp. n. in Naso unicoris (type-host); P. impar sp. n. in Lutjanus erythropterus (type-host) and L. malabaricus; Neopreptetos arursettae Machida, 1982 in Pomacanthus semicirculatus; and N. kurochkini (Toman, 1989) in Chaetodontoplus meredithi. From southwestern Australia: Preptetos rotto sp. n. in Nelusetta ayraudi (type-host), Neosebastes pandus, Oplegnathus woodwardi and Pagrus auratus. The new combination Preptetos trulla (Linton, 1907) (originally Distormum then Lepocreadium) is made and the species Lepocreadium areolatum (Linton, 1900) is considered likely to belong in Preptetos.

Weketrema gen.n., a new genus for Weketrema hawaiiense (Yamaguti, 1970) comb. n. (Digenea : Lecithasteridae) recently found in Australian marine fishes

A new genus, Weketrema, is erected in the family Lecithasteridae for the species hitherto known as Lecithophyllum hawniiense. Weket, ema hawaiiense (Yamaguti, 1970) comb, n. is redescribed from Scolopsis bilineatus (Bloch) (Perciformes: Nemipteridae) from Lizard Island and Heron Island, Queensland, Plectorhinchus gibbosus (Lacepede) (Perciformes: Haemulidae) from Heron Island and Cheilodactylus nigripes Richardson (Perciformes: Cheilodactylidae) and Latridopsis forsteri (Castelnau) (Perciformes: Latridae) from Stanley, northern Tasmania. The new genus is distinguished from related members of the family Lecithasteridae by its complete lack of a sinus-sac. Although placed in the subfamily Lecithasterinae pro tem, its true subfamily position is not entirely clear. Comment is made on its unusual distribution, both in terms of zoogeography and hosts.

Antifungal alkyl amino alcohols from the tropical marine sponge Haliclona n. sp.

Three new amino alcohols presumably deriving from L-alanine were isolated from the tropical marine sponge Haliclona n. sp. and characterized by 2D NMR, while a fourth amino alcohol was characterized as an acetamide derivative. Relative stereochemistry was deduced from the NMR characteristics of oxazolidinone derivatives and absolute stereochemistry secured by preparation and analysis of an MPA ester. The amino alcohol fraction from Haliclona n. sp, acts as an antifungal agent and inhibits the development of larvae of the ascidian Herdmania curvata.

Advanced precursors in marine biosynthetic study. Part 2: The biosynthesis of isocyanides and isothiocyanates in the tropical marine sponge Axinyssa n.sp.

The biosynthetic origins of the isocyanide and isothiocyanate groups in 9-isocyanop upukeanane (2) and 9-isothiocyanato-pupukeanane (3) are investigated by incorporation of [C-14]-labelled advanced precursors into the sponge Axinyssa n.sp. (C) 2001 Elsevier Science Ltd. All rights reserved.

New chlorinated peptides from the tropical marine sponge Dysidea sp.

Five new chlorinated peptides (5)-(9) have been isolated from a Dysidea sp. and identified by two-dimensional NMR spectroscopy. The absolute stereochemistry of the metabolites was deduced by chemical correlation with S-(-)-4,4,4-trichloro-3-methylbutanoic acid (10) and with an alcohol (11). (C) 2001 Elsevier Science Ltd. All rights reserved.

Three species of Pycnadenoides Yamaguti, 1938 (Digenea: Opecoelidae), including two new species from temperate marine fishes of Australia

Pycnadenoides pagrosomi Yamaguti, 1938 and P. reversati n. sp. from Pagrus auratus (Sparidae) and P. invenustus n. sp. from Nemadactylus valenciennesi (Cheilodactylidae) are described from the temperate marine waters off south-west Western Australia and south-east Queensland. The difference in the anterior extent of the vitelline follicles observed in P. reversati n. sp. recovered from off south-east Queensland waters and the material from off Western Australia is discussed. P. reversati n. sp. is distinguished from P. pagrosomi mainly in the position of the genital pore and in the arrangement of the testes, and from P. invenustus n. sp. in the posterior extent of the cirrus-sac. P. reversati belongs to the group of species with a short cirrus-sac and P. invenustus to the group with the cirrus-sac reaching into the anterior hindbody.

Advanced precursors in marine biosynthetic study. Part 3: The biosynthesis of dichloroimines in the tropical marine sponge Stylotella aurantium

The biosynthetic origins of the dichloroimine group in the stylotellanes A and B 1,2 have been investigated by incorporation of [C-14]-labeled farnesyl isocyanide 7 and farnesyl isothiocyanate 3 into the sponge Stylotella aurantium. (C) 2002 Elsevier Science Ltd. All rights reserled.

Species of Lecithocladium Luhe, 1901 (Digenea, Hemiuridae) from Australian marine fishes, with a description of a new species from various hosts off eastern Australia

Lecithocladium moretonense sp. nov. is described from Monodactylus argenteus (type-host), Abudefduf sordidus, A. whitleyi, Herklotsichthys castelnaui, Lutjanus russelli, Platycephalus indicus, Rhabdosargus sarba, Siganus nebulosus and Scorpis lineolata from Moreton Bay, southern Queensland, and Acanthopagrus australis from off northern New South Wales. It differs from most Lecithocladium species in having a subglobular oral sucker and pharynx. Other distinguishing features are the thin-walled recurved seminal vesicle and the pars prostatica coiling over the seminal vesicle to the level of the anterior testis. Lecithocladium megalaspis Yamaguti, 1953 from Alepes apercna, Moreton Bay and L. angustiovum Yamaguti, 1953 from Scomber australasicus, Fremantle, Western Australia, are also reported, illustrated and measured.

Biosynthetic pathways to isocyanides and isothiocyanates; precursor incorporation studies on terpene metabolites in the tropical marine sponges Amphimedon terpenensis and Axinyssa n.sp.

The biosynthetic origins of the isocyanide and isothiocyanate functional groups in the marine sponge metabolites diisocyanoadociane (1), 9-isocyanopupukeanane (10) and 9- isothiocyanatopupukeanane (11) are probed by the use of [C-14]-labelled precursor experiments. Incubation of the sponge Amphimedon terpenensis with [C-14]-labelled thiocyanate resulted in radioactive diisocyanoadociane ( 1) in which the radiolabel is specifically associated with the isocyanide carbons. As expected, cyanide and thiocyanate were confirmed as precursors to the pupukeananes 10 and 11 in the sponge Axinyssa n. sp.; additionally these precursors labelled 2-thiocyanatoneopupukeanane ( 12) in this sponge. To probe whether isocyanide-isothiocyanate interconversions take place at the secondary metabolite level, the advanced precursor bisisothiocyanate 17 was supplied to A. terpenensis, but did not result in significant labelling in the natural product isocyanide 1. In contrast, in the sponge Axinyssa n. sp., feeding of [C-14]-9-isocyanopupukeanane (10) resulted in isolation of radiolabelled 9- isothiocyanatopupukeanane 11, while the feeding of [C-14]-11 resulted in labelled isocyanide 10. These results show conclusively that isocyanides and isothiocyanates are interconverted in the sponge Axinyssa n. sp., and confirm the central role that thiocyanate occupies in the terpene metabolism of this sponge.