Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp

Sakemi, Shinichi; Ichiba, Toshio; Kohmoto, Shigeo; Saucy, G.; Higa, Tatsuo

doi:10.1021/ja00222a068

Cited by 174 publications

(78 citation statements)

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“…[35] In 1988, onnamide A (15) was isolated from an Okinawan species of Theonella. [36] Onnamide A (15), whose structure strikingly resembled that of the insect toxin pederin, [37] was shown to possess antiviral properties and was subsequently synthesized by Hong and Kishi. [38] An additional nine compounds in the onnamide series were subsequently reported together with their cytotoxicities against the P388 cell line.…”

Section: Macrolides and Acetogeninsmentioning

confidence: 99%

Lithistid Sponges: Star Performers or Hosts to the Stars

Bewley

Faulkner

1998

Angewandte Chemie International Edition

190

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Extremely careful separation of the symbiotic bacteria from the cells of lithistid sponges has provided evidence that in the case of Theonella swinhoei the chemically diverse and biologically active metabolites, swinholide A and theopalauamide (1), are produced by symbionts. Marine sponges of the order Lithistida contain a diverse range of exotic natural products with valuable biological and pharmacological activities.

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Section: Macrolides and Acetogeninsmentioning

confidence: 99%

Lithistid Sponges: Star Performers or Hosts to the Stars

Bewley

Faulkner

1998

Angewandte Chemie International Edition

190

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“…The sponge produces the macrolactone swinholide (Carmely and Kashman, 1985), a powerful cytotoxic and antifungal compound whose structure was revised to dimer 18 (Kitagawa et al 1990). The genus Theonella was then intensively studied and several other bioactive substances have been obtained, such as onnamide A, an antiviral guanidine derivative from mixed biosynthetic origin (Sakemi et al 1988), macrocyclic tridecadepsipeptides, e.g. theonellamine B that inhibits the Na/K-transporting ATPase (Kitagawa et al 1986, Nakamura et al 1986, and the cyclic glycopeptide theopalauamide (19).…”

Section: Resultsmentioning

confidence: 99%

Secondary metabolites from marine microorganisms

Kelecom

2002

An. Acad. Bras. Ciênc.

164

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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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“…factor' possesses gene clusters for almost all biologically active polyketide and peptide natural products previously isolated from T. swinhoei. These include onamides [157], cyclotheonamides [158], keramamides [159], and konbamides [160] to name a few [15,88]. Lackner et al [161] carried out investigations into this fascinating bacterial group through genomic and chemical methods and have suggested a metabolic model of 'Ca.…”

Section: Production Of Natural Products By Sponge Symbiontsmentioning

confidence: 99%

An Overview on Marine Sponge-Symbiotic Bacteria as Unexhausted Sources for Natural Product Discovery

2017

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Microbial symbiotic communities of marine macro-organisms carry functional metabolic profiles different to the ones found terrestrially and within surrounding marine environments. These symbiotic bacteria have increasingly been a focus of microbiologists working in marine environments due to a wide array of reported bioactive compounds of therapeutic importance resulting in various patent registrations. Revelations of symbiont-directed host specific functions and the true nature of host-symbiont interactions, combined with metagenomic advances detecting functional gene clusters, will inevitably open new avenues for identification and discovery of novel bioactive compounds of biotechnological value from marine resources. This review article provides an overview on bioactive marine symbiotic organisms with specific emphasis placed on the sponge-associated ones and invites the international scientific community to contribute towards establishment of in-depth information of the environmental parameters defining selection and acquisition of true symbionts by the host organisms.

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Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp

Cited by 174 publications

References 1 publication

Lithistid Sponges: Star Performers or Hosts to the Stars

Lithistid Sponges: Star Performers or Hosts to the Stars

Secondary metabolites from marine microorganisms

An Overview on Marine Sponge-Symbiotic Bacteria as Unexhausted Sources for Natural Product Discovery

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