Marine natural products

Faulkner, D. John

doi:10.1039/a804469d

Cited by 280 publications

(201 citation statements)

References 299 publications

(307 reference statements)

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“…In comparison, the ocean source was scarcely studied. However, since the 1970s, as a consequence of advanced technology, ocean has become an attracting area in drug development for the structural diversities and pharmacological potentials which were presented by the novel scaffold of the molecules isolated from this environment [1]. Marine natural products have been one of the main subjects of chemical and pharmacological interests for several decades, leading to an important library of diversely bioactive compounds [2].…”

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confidence: 99%

Marine Drugs – Macrolactins

Lü¹,

Xu²,

Liu³

et al. 2008

Chemistry & Biodiversity

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The increasing demands for new lead compounds in pharmaceutical and agrochemical industries have driven scientists to search for new bioactive natural products. Marine microorganisms are rich sources of novel, bioactive secondary metabolites, and have attracted much attention of chemists, pharmacologists, and molecular biologists. This mini-review mainly focuses on macrolactins, a group of 24-membered lactone marine natural products, aiming at giving an overview on their sources, structures, biological activities, as well as their potential medical applications.

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confidence: 99%

Marine Drugs – Macrolactins

Lü¹,

Xu²,

Liu³

et al. 2008

Chemistry & Biodiversity

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“…The cationic species A is the proposed branching point for the three main pathways to all sesquiterpenes (with few exceptions, see below) emitted by the streptomycete. The first branch is commenced by the attack of H 2 O to A, furnishing the sesquiterpene alcohol hedycaryol (26), or the direct loss of H , generating germacrene A (27). Bicyclogermacrene (28) arises from A by the loss of H , under formation of the cyclopropane moiety [13].…”

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confidence: 99%

Volatiles Released by aStreptomyces Species Isolated from the North Sea

Dickschat

Martens

Brinkhoff

et al. 2005

C&B

114

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The North Sea Streptomyces strain GWS-BW-H5 was investigated by analyzing headspace extracts of agar-plate cultures (HE) or liquid cultures (LCE), obtained with a closed-loop stripping apparatus (CLSA), by GC/MS (Table 1). The volatile profile of the HE is dominated by the known volatiles (-)-geosmin (4) and 2-methyisoborneol (1). Small amounts of sesquiterpenes occur, which are present in a more-diverse structural variety and in higher quantities in the LCE. The different structures can be rationalized by few cationic intermediates along their biosynthetic pathway. The most-prominent difference between the two culture methods were the presence of the Me-branched gamma- and delta-lactones 31-38, not previously reported from nature, in the LCE. Major components were 10-methyldodecan-5-olide (34), 10-methyldodec-2-en-4-olide (36), and 10-methyldodec-3-en-4-olide (38). The structures of all new lactones were verified by synthesis. Furthermore, more volatiles in higher amounts were produced by the liquid culture than by to the agar plate culture. Since 36 showed inhibitory growth effects against strain GWS-BW-H5, growth inhibition against twelve other strains isolated from the same habitat was tested. Antagonistic activity against four of the strains was observed, with a slightly higher threshold level than found for penicillin G, which was used in control experiments (Table 2).

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“…This approach can be divided into three components: the core, linker, and building blocks. As core molecule we used the triacid platform 1 developed in this research group (23)(24)(25), this triacid was inspired by a number of biologically active and peptidederived marine natural products such as dendroamide C (26)(27)(28)(29)(30). These macrocycles feature oxazole rings linked by trans amide bonds.…”

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confidence: 99%

Synthesis of galmic: A nonpeptide galanin receptor agonist

Ceide

Trembleau²,

Haberhauer³

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

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Galanin is a neuropeptide with a wide variety of biological functions. Few nonpeptide ligands, capable of activating galanin receptors, are available today. Based on known pharmacophores of galanin and the tripeptidomimetic galnon, a combinatorial library was formulated, synthesized, and screened against the galanin receptor. An active compound, galmic, was identified and tested in vitro and in vivo for its affinity and efficacy at galanin receptors. The present work describes the total synthesis of galmic, the synthesis of its oxazole precursors, the coupling of the building blocks into a linear trimer, and the macrolactamization reaction.galnon ͉ mimetic G alanin is a 29-aa-long (30 aa in humans) neuroendocrine peptide, whose physiological functions are regulated by G protein-coupled receptors. Galanin is found throughout the central and peripheral nervous systems and the gastrointestinal tract (1-4). The effects of this peptide include inhibition of insulin release (5-7), inhibition of neurotransmiters involved in regulation and memory acquisition (8), modulation of food intake (9, 10) and sexual behavior (11), as well as effects on controlling pain threshold (12, 13) and in the pathogenesis of Alzheimer's disease (14).Studies involving L-Ala-substituted analogues of galanin have identified Trp-2, Asn-5, and Tyr-9 as well as the N-terminal amino group as being critical determinants for receptor binding. These amino acids are located in the N-terminal helical part of galanin that it is made up of the same 15 aa in all species from which it was isolated (15, 16). Fragments of galanin have shown low binding affinity but these peptides are vulnerable to the action of the peptidases and unable to cross the blood-brain barrier (17,18). Two nonpeptide antagonists of the galanin receptor have been reported, spirocoumaranon (Sch202596) (19) and 2,3-dihydro-2-(4-methylphenyl)-1,4-dithiepin-1,1,4,4-tetroxide (20) (see Fig. 1), but there is only one nonpeptide galanin receptor ligand, galnon, that shows agonist activity (21).In this study, we report an example of a nonpeptide subtype selective agonist for the galanin receptor, galmic, discovered by application of a combinatorial library approach (22). MethodsExperimental. Reactions were performed under an argon atmosphere, NMR spectra were recorded on a Bruker DRX 600 spectrometer (unless otherwise mentioned), and the chemical shifts are given in ppm relative to tetramethylsilane. The spectra were referenced to deuterated solvents indicated in brackets in the analytical data. High-resolution MALDI-Fourier transform MS (FTMS) measurements were performed on an IonSPec (Lake Forest, CA) FTMS mass spectrometer by using 2,5-dihydroxybenzoic acid as the matrix. For TLC, silica plates IB2-F (J. T. Baker) were used. For column chromatography, silica gel 60, 230-400 mesh (Merck) was used. Preparative chromatographic plates and silica gel 60 F 254 (20 ϫ 20 cm, 0.5 mm) were used. Anhydrous solvents and chemicals were used as purchased from commercial suppliers. General Procedures. ...

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Marine natural products

Cited by 280 publications

References 299 publications

Marine Drugs – Macrolactins

Marine Drugs – Macrolactins

Volatiles Released by aStreptomyces Species Isolated from the North Sea

Synthesis of galmic: A nonpeptide galanin receptor agonist

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