Marine Natural Products Volume 1: Chemical and Biological Perspectives

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Some created available northern plans, systematic as Samuel Seabury. Towards the biosynthesis of pseudopterosins. Marine derived terpenes and their terrestrial counterparts.

Contignasterol also referred contact dermatitis Haimes et al. Despite their structural rela- pany was declared bankrupt in the late s tionship to the classical glucocorticosteroids, these Faulkner, These 12 from Petrosia contignata. Biosynthesis of kelsoene and prespatane in liverworts. Due to the structural complexity and the this class of compound remains an interesting topic.

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In spite of the positive results organisms. IPL,, another member of al. Aventis group in Biosynthesis of the algal monoterpene myrcene and the sesquiterpenes a- and b-snyderol. Manoalide was licensed compound has advanced into Phase II clinical to Allergan Pharmaceuticals and reached Phase II trials as an anticancer agent against non-small cell clinical trials as a topical antipsoriatic, its develop- lung cancer and ovarian cancer.

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For the latter ment was however, discontinued due to formulation indication, in the FDA granted squalamine problems. The compound is now commercially orphan drug status. However, it did not perform available as a biochemical standard tool to block the satisfactorily as a single agent in the initial trials. Pietras and Weinberg, Squalamine could be an interesting option an oxidation product of the algal metabolite in the treatment of this ophthalmic disease, since caespitol 30 , and may be produced by the animal the current possibilities are limited.

Dactylopyranoid 24 is a unique com- intended brand name is Evizon for wet AMD pound, to date only encountered in the animal were started in and are ongoing. Due to its A. This irregular and brominated promising applications as well as the fact that the diterpene is, however, structurally also similar to compound cannot be obtained in large quantities Laurencia metabolites Wessels et al.

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  7. Acanthella klethra and Cymbastela hooperi, Some, but not all, marine terpenes are distin- two sponges that were of interest for us due to guished by characteristic structural features. Cer- their antiplasmodial activity, were found to pro- tain structural classes, e.

    View Marine Natural Products Volume 1 Chemical And Biological Perspectives 1978

    The sponge A. Isonitrile containing isocyanate, dichloroimine Figure 4 , and haloge- metabolites such as axisonitrile-3 are frequently nated Figure 3 functionalities occur predomi- accompanied by compounds with an isothiocya- nantly in marine metabolites. In most cases nate functionality, i. In was distinguished by the presence of diterpenes one of our studies several specimens of the sea hare substituted with isonitrile and isothiocyanate Aplysia dactylomela Mollusca , which is known to functionalities.

    One of the isocycloamphilectane feed on such algae and to store and enrich sec- diterpenes 47 present in C. Wessels et al. Halogenated monoterpenes, Many of these metabolites were found to have as shown in Figure 3, may originate from red alga antiplasmodial activity Wright et al. Halogenated chamigrene 1 derivatives 18, 19, 22, 23 are regular sesquiterp- According to the taxonomy of the source organism and the enone functionality, the trivial name caespitenone was assigned enes with a spiro centre and typically occur in to a pseudoguaiane sesquiterpene isolated in from the algae of the genus Laurencia, as are the further liverwort Porella caespitans Asakawa et al.

    Later on, sesqui- and diterpenoid structures depicted in this structure was revised to have an africane based terpenoid Figure 3. Most of these compounds were formerly skeleton Tori et al. Terpene 29 was regrettably also given the trivial name caespitenone Wessels et al. In some cases its enone function and the close resemblance to caespitol 30 , a however, the acetyl moiety was not present in the sequiterpene which was originally isolated from the marine red algal metabolite, i. Here we only refer to the marine itol-B-acetate 28 , acetyl-caespitol It may derived caespitenone.

    Cembranoid structures from marine soft corals. Kalihinanes, like e.

    Angerhofer et al. The most potent anti- kalihinol A 51 are diterpenoid sponge metabolites plasmodial activity of all Cymbastela metabolites with isonitrile function and were also shown to was found for diisocyanoadociane 49 with an have antimalarial properties Miyaoka et al. This activity is more pronounced than The carbon skeleton of Cymbastela diterpenes that of axisonitrile-3 32 , but unfortunately is also and kalihinanes was proposed to be biosyntheti- accompanied by some cytotoxicity.

    Indeed, a bicyclic serrulatane type within infected erythrocytes. In this way, heme accu- cyclized terpenes. Marine derived sesterterpenes. The biosynthetic relationship of the serrulatane precursors 53 , cycloamphilectanes Cymbastela metabolites, as proposed in Figure 5 is 56 derive from amphilectanes 54 through a exclusively based on the co-occurrence of these further ring closure, and the irregular isocyclo- structural types in the same sponge. There is, amphilectanes 57 are formed after migration of a however some evidence concerning the biosynthe- methyl group from cycloamphilectanes The sis of these structural types although the support- new neoamphilectane 55 skeleton in C.

    Kelsoene 64 atriene Figure 6, This enzyme shares Nabeta et al. Additionally, podu- restrial diterpene cyclases, e. Kerr, ; Ata et al. Since intriguing questions for a recent review see, Gar- the guaiane derivative 63, kelsoene 64 and pres- son and Simpson, In case of the ter- groups of the natural product Simpson and restrial liverwort Ptychanthus striatus this was Garson, , , Cyanide is also incor- proven experimentally. Studies with labeled pre- porated in the dichloroimine functionality, a rare cursors led to the deduction that kelsoene 64 is functional group to date exclusively known from formed from farnesylpyrophosphate through a marine terpenes Brust and Garson, ; Simp- germacradienyl and alloaromadendrane cation son et al.

    This biosynthetic 52 Kehraus et al. The biological origin of pathway may also occur in sponges, i. Cymbas- cyanide remains obscure, since it is only found in tela hooperi, to date, however no such biosynthetic trace amounts in sea water. The most intriguing studies on sponge terpenoids have been done. Many terpenes are easily recognized as being Marine mono- and sesquiterpenes [C10,C15]: derived from marine organisms by their charac- biosynthesis of algal metabolites teristic structural features, e.

    There are, however, also numerous cases The biosynthesis of marine algal metabolites has where marine and terrestrial terpenes have identi- hardly been investigated. One of the few studies cal or very similar structures. Flustra foliacea reported is that of Wise and Croteau who sug- colonies, distinguished by a pleasant smell of gested that the acyclic monoterpene myrcene lemon when collected freshly, produce a small Figure 9, 68 is a likely precursor of halogenated amount of essential oil, apart from their charac- compounds in the red alga Ochtodes secundiramea.

    This enzyme is 62 Peters et al. Vanadium-contain- , epoxide 75 Bernstein et al. Upon incubation plex dimers 73 Feller et al. The high with the terpenoid precursor nerolidol 69 , these functionalization often poses many stereochemical enzymes were able to produce the brominated questions. For most cembranes, however only the cyclic terpenes a- and b-snyderol 70, 71 , which relative stereochemistry was established. Hence, are known as algae-derived natural products we recently investigated the absolute stereochem- Figure 9.