Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities

Houdai, Toshihiro; Matsuoka, Shigeru; Morsy, Nagy; Matsumori, Nobuaki; Satake, Masayuki; Murata, Michio

doi:10.1016/j.tet.2005.01.069

Cited by 63 publications

(57 citation statements)

References 43 publications

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“…Membrane pores or lesions formed by AM3 (6) have revealed features similar to those of amphotericin B, implying that the activity is due to the molecular assemblage formed in the biomembrane. [113][114][115] On the other hand, the size of pores/lesions in erythrocyte membranes were estimated to be 2.0-2.9 nm in diameter, which is significantly larger than that of amphotericin B, 0.8 nm. 116 SDS micelles are reported to adequately mimic the amphipathic nature of a bilayer membrane even for a conformationally sensitive peptide such as gramicidin A.…”

Section: Activity-relevant Conformation and Bimolecular Interactions mentioning

confidence: 94%

“…11). 115 The models appear well ordered except for the two side chains. A hydrogen-bond network, which stabilizes a hairpin conformation of AM3 in the central region, is formed around a C51-OH group.…”

Section: Activity-relevant Conformation and Bimolecular Interactions mentioning

confidence: 96%

“…10) experiments. 115 From the structures calculated for AM3 by Molecular Dynamics with NOE constrains obtained from the data in SDS micelles, five low energy conformations were retained for AM3 (Fig. 11).…”

Section: Activity-relevant Conformation and Bimolecular Interactions mentioning

confidence: 99%

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Structural Features of Dinoflagellate Toxins Underlying Biological Activity as Viewed by NMR

Murata

Matsumori

Konoki

et al. 2008

Bulletin of the Chemical Society of Japan

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Marine dinoflagellates are a rich source of structurally and biologically intriguing secondary metabolites. Among those, maitotoxin may be one of the best known examples, which is the largest natural product known to date and possesses the most potent toxicity known amongst non-proteinaceous compounds. Structural studies of maitotoxin are reviewed with a particular focus on the configuration and mode of action of this unique toxin. In addition, there are many marine natural products which bind to biomembranes to exert their biological activities. To gain a better understanding of their mode of action, conformation, and bimolecular interaction occurring in biomembranes are particularly important. Recent results from NMR studies of membrane systems in the authors' group are reviewed briefly.

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Section: Activity-relevant Conformation and Bimolecular Interactions mentioning

confidence: 94%

Section: Activity-relevant Conformation and Bimolecular Interactions mentioning

confidence: 96%

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Structural Features of Dinoflagellate Toxins Underlying Biological Activity as Viewed by NMR

Murata

Matsumori

Konoki

et al. 2008

Bulletin of the Chemical Society of Japan

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“…Amphidinols (AMs) are an important class isolated from the dinoflagellates Amphidinium klebsii that presents potent antifungal acitivity with great membranedisrupting activity (Houdai et al, 2004), and in 2008 fourteen was estimated to have been isolated (Morsy et al, 2008).The AMs antifungal activity is probably due to the interaction with membrane lipids that increase the permeability (Houdai et al, 2005).…”

Section: Marine Natural Product As Antifungal Agentmentioning

confidence: 99%

Mycoses and Antifungals: reviewing the basis of a current problem that still is a biotechnological target for marine products

et al. 2014

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Currently, the limited number of antifungals available for treating fungal infections, the increased multiresistance, and the adverse effects are the major obstacles for fungal infection therapy. Additionally, the recent emergence of opportunistic fungus infections reinforced the requirement for discovering novel antifungal agents. Herein we reviewed the main topics about fungi and its related infections, the antifungals available, their mechanism of action and resistance profile. In this work, we pointed fungi as a biotechnological target for finding new options in alternative sources such as marine products with new mechanisms of action to allow treating these dangerous infections.

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“…The only exception is maitotoxin with a molecular mass of 3422 g mol -1 , the largest non-biopolymer natural product known (Murata et al, 1994). Karlotoxins from the dinoflagellate Karlodinium veneficum (Bachvaroff et al, 2008;Van Wagoner et al, 2008) as well as amphidinols from Amphidium klebsii (Houdai et al, 2004;Houdai et al, 2005) have a similar mass range of about 1300 Da and membrane disruptive properties. These compounds form hairpin structures suggested to be important for the interaction with lipid bilayers of biomembranes.…”

Section: Unique Masses Found In Spe Fractionsmentioning

confidence: 99%

Isolation of activity and partial characterization of large non-proteinaceous lytic allelochemicals produced by the marine dinoflagellate Alexandrium tamarense

Krock

Tillmann

et al. 2011

Harmful Algae

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Certain strains of the toxigenic dinoflagellate Alexandrium tamarense produce potent allelochemicals with lytic activity against a wide variety of marine microorganisms. Our efforts to characterize these allelochemicals from a lytic strain focused on the less polar components because of their higher lytic activity.Fractionation and partial purification after solid phase extraction (SPE) were achieved via alternative chromatographic methods, namely HPLC separation on C8 and HILIC phases. Through MALDI-TOF mass spectrometry we compared the mass differences in SPE, C8 HPLC, and HILIC fractions between a lytic and non-lytic strain of A.tamarense. Several large species with masses between 7 kDa and 15 kDa were found in the HILIC lytic fraction by MALDI-TOF MS. Tryptic digestion and tryptic digestion-coupled size-exclusion chromatography (SEC) suggested that the lytic compounds are large non-proteinaceous molecules (<23.3 kDa, trypsin). Although there is no direct proof that the large molecules found in the lytic HILIC fraction are responsible for the lytic activity of this fraction, the mass range deduced from SEC strongly supports this hypothesis. Total sugar content analysis showed that the lytic HILIC fraction contained two-fold more sugar than the non-lytic one. Nevertheless, the low percentage of saccharide per dry mass equivalent (0.18 ± 0.01 %) indicates that sugar residues are likely not a major component of the lytic compounds. We concluded that at least one group of lytic allelochemicals produced by A. tamarense comprise a suite of large non-proteinaceous and probably non-polysaccharide compounds between 7 kDa and 15 kDa.

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Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities

Cited by 63 publications

References 43 publications

Structural Features of Dinoflagellate Toxins Underlying Biological Activity as Viewed by NMR

Structural Features of Dinoflagellate Toxins Underlying Biological Activity as Viewed by NMR

Mycoses and Antifungals: reviewing the basis of a current problem that still is a biotechnological target for marine products

Isolation of activity and partial characterization of large non-proteinaceous lytic allelochemicals produced by the marine dinoflagellate Alexandrium tamarense

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