Norhalichondrin A: an antitumor polyether macrolide from a marine sponge

Uemura, Daisuke; Takahashi, Kanji; Yamamoto, Toshihiro; Katayama, Chuji; Tanaka, Jirō; Okumura, Yasuaki; Hiratå, Yoshimasa

doi:10.1021/ja00302a042

Cited by 277 publications

(124 citation statements)

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“…Moreover, specimens of Halichondria sp. (Kernan et al, 1988), H. okadai (Tachibana et aL, 1981) and H. melanodocia (Uemura et al, 1985) have been found to possess cytotoxic polyethers (e.g. okadaic acid) which are known to be of dinoflagellate origin (Murakami et al, 1982).…”

Section: H2n/~ N CI 39 Girollinementioning

confidence: 99%

Chemotaxonomy of Agelas (Porifera: Demospongiae)

Braekman¹,

Daloze²,

Stoller³

et al. 1992

Biochemical Systematics and Ecology

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Chemotaxonomy of the genus AgelasBraekman, J.C.; Stoller, C.; van Soest, R.W.M. Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. Download date: 09 May 2018Biochemical Systernatics and Ecology, Vol. 20. No. 5. pp, 417-431, 1992 Abstract--The secondary metabolite content of four different species of Agelas (Porifera) from the West Indies has been studied. All the compounds isolated are already known metabolites whose identification was confirmed by comparison of their spectral properties with those reported in the literature. They pertain to two different classes of compounds: terpenoids and pyrrole-2-carboxylic acid derivatives. The chemotaxonomic value of these secondary metabolites has been evaluated. Their distribution amongst the Porifera, as well as that of isocyanide derivatives, suggests a close relationship between the Agelasidae, the Axinellidae and the Halichondriidae.

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Section: H2n/~ N CI 39 Girollinementioning

confidence: 99%

Chemotaxonomy of Agelas (Porifera: Demospongiae)

Braekman¹,

Daloze²,

Stoller³

et al. 1992

Biochemical Systematics and Ecology

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“…Thus, the sponge Halichondria okadai furnishes okadaic acid (6) (Tachibana et al 1981) and the antitumor principle norhalichondrine A (20) (Uemura et al 1985). Okadaic acid was thought to be produced by a microbial or microalgal symbiont of the sponge, since 6 was also obtained from the dinoflagellate, Prorocentrum lima (Murakami et al 1982).…”

Section: Resultsmentioning

confidence: 99%

Secondary metabolites from marine microorganisms

Kelecom

2002

An. Acad. Bras. Ciênc.

163

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After 40 years of intensive research, chemistry of marine natural products has become a mature field. Since 1995, there are signals of decreased interest in the search of new metabolites from traditional sources such as macroalgae and octocorals, and the number of annual reports on marine sponges stabilized. On the contrary, metabolites from microorganisms is a rapidly growing field, due, at least in part, to the suspicion that a number of metabolites obtained from algae and invertebrates may be produced by associated microorganisms. Studies are concerned with bacteria and fungi, isolated from seawater, sediments, algae, fish and mainly from marine invertebrates such as sponges, mollusks, tunicates, coelenterates and crustaceans. Although it is still to early to define tendencies, it may be stated that the metabolites from microorganisms are in most cases quite different from those produced by the invertebrate hosts. Nitrogenated metabolites predominate over acetate derivatives, and terpenes are uncommon. Among the latter, sesquiterpenes, diterpenes and carotenes have been isolated; among nitrogenated metabolites, amides, cyclic peptides and indole alkaloids predominate.

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“…Eribulin is a macrocyclic ketonic polyether macrolide [76]. Both eribulin and its parent compound halichondrin B are antimicrotubule agents whose mechanism of action is binding to a unique binding site on the plus end of the tubulin polymer (not monomer), inhibiting further microtubule growth via continued polymerization.…”

Section: Examples Of Pharmaceutical Agentsmentioning

confidence: 99%

“…Ara-C (cytarabine) is an aranucleoside, first discovered in 1945 by Warner Bergmann [76] in the Florida Keys, and isolated from the marine sponge Cryptotethia crypta sp. Originally termed a "spongonucleoside" this molecule acts as an effective and toxic anti-cancer drug, targeting cancer cells due to their rapid production of DNA as the cancer cells proliferate.…”

Section: Ara-c (Cytarabine)mentioning

confidence: 99%

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Novel Natural Product Discovery from Marine Sponges and their Obligate Symbiotic Organisms

Monaco

Quinlan

2014

Preprint

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Discovery of novel natural products is an accepted method for the elucidation of pharmacologically active molecules and drug leads. Best known sources for such discovery have been terrestrial plants and microbes, accounting for about 85% of the approved natural products in pharmaceutical use (1), and about 60% of approved pharmaceuticals and new drug applications annually (2). Discovery in the marine environment has lagged due to the difficulty of exploration in this ecological niche. Exploration began in earnest in the 1950's, after technological advances such as scuba diving allowed collection of marine organisms, primarily at a depth to about 15m. Natural products from filter feeding marine invertebrates and in particular, sponges, have proven to be a rich source of structurally unique pharmacologically active compounds, with over 16,000 molecules isolated thus far (3, 1) and a continuing pace of discovery at hundreds of novel bioactive molecules per year. All classes of pharmaceuticals have been represented in this discovery process, including antiprotazoals, pesticides, TGF-beta inhibitors, cationic channel blockers, anticancer, cytotoxic, antiviral, anti-inflammatory and antibacterial compounds. Important biosynthetic pathways found in sponges which give rise to these compounds include the terpenoid (4), fatty acid, polyketoid, quinone reductase, alkaloid, isoprenoid (5), and non-ribosomal protein synthase pathways.

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Norhalichondrin A: an antitumor polyether macrolide from a marine sponge

Cited by 277 publications

References 1 publication

Chemotaxonomy of Agelas (Porifera: Demospongiae)

Chemotaxonomy of Agelas (Porifera: Demospongiae)

Secondary metabolites from marine microorganisms

Novel Natural Product Discovery from Marine Sponges and their Obligate Symbiotic Organisms

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