Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

Dembitsky, Valery M.

doi:10.1007/s11745-005-1378-0

Cited by 24 publications

(13 citation statements)

References 330 publications

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“… [56] Actinobacteria Oleandomycin (C 14 -membered macrolactam glycosides) Streptomyces antibioticus [57] Actinobacteria Pikromycin, Narbomycin, 5- O -mycaminosyl-narbonolide (C 14 -membered macrolactam glycosides) Streptomyces felleus and S. narbonensis [56] Actinobacteria 10,11-Dihydropikromycin, Kayamicin (C 14 -membered macrolactam glycosides) Streptomyces narbonensis [56] Actinobacteria Spinosyns (Tetracyclic macrolide) containing forosamine (amino sugar) and tri- O -methyl rhamnose Saccharopolyspora spinosa [56] , [58] Actinobacteria Lepicidin A Saccharopolyspora spinosa [56] Actinobacteria Leucomycins, Josamycin, Platenomycins, Medicamycin, Espinomycins Streptomyces kitasatoensis [56] Actinobacteria Carbomycin B, platenomycins W1/W2, Niddamycin, Midecamycin A3/A4 Streptomyces platensis [56] Actinobacteria Acumycin (cirramycin B), Cirramycin F and derivatives Streptomyces gris eoﬂa vus, S. fradiae, S. flocculus [56] Actinobacteria Chalcomycin, Neutramycin Streptomyces bikiniensis, S. rimosus, S. hirsutus [56] Actinobacteria Aldgamycin F, E and Swalpamycin Streptomyces lavendulae, S. avidinii, S amandii (for swalpamycin) [56] Actinobacteria Spiramicins Streptomyces ambofaciens ...…”

Section: Chemical Groups and Origins Of Microbial Simple Glycolipidsmentioning

confidence: 99%

Simple glycolipids of microbes: Chemistry, biological activity and metabolic engineering

Abdel-Mawgoud

Stephanopoulos

2018

Synthetic and Systems Biotechnology

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Glycosylated lipids (GLs) are added-value lipid derivatives of great potential. Besides their interesting surface activities that qualify many of them to act as excellent ecological detergents, they have diverse biological activities with promising biomedical and cosmeceutical applications. Glycolipids, especially those of microbial origin, have interesting antimicrobial, anticancer, antiparasitic as well as immunomodulatory activities. Nonetheless, GLs are hardly accessing the market because of their high cost of production. We believe that experience of metabolic engineering (ME) of microbial lipids for biofuel production can now be harnessed towards a successful synthesis of microbial GLs for biomedical and other applications. This review presents chemical groups of bacterial and fungal GLs, their biological activities, their general biosynthetic pathways and an insight on ME strategies for their production.

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Section: Chemical Groups and Origins Of Microbial Simple Glycolipidsmentioning

confidence: 99%

Simple glycolipids of microbes: Chemistry, biological activity and metabolic engineering

Abdel-Mawgoud

Stephanopoulos

2018

Synthetic and Systems Biotechnology

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“…A putative 95 kbp biosynthetic gene cluster of elaiophylin has been proposed (Haydock et al, 2004 ). Dembitsky ( 2005a , c ) reviewed the different types of C14-membered lactam rings that are attached to an aminosugar ( 12 , Table 5 ). Fluvirucin has been isolated from various Actinomadura spp., Streptomyces spp., Microtetraspora spp., and Saccharotrix mutabilis .…”

Section: Non-trehalose Glyolipidsmentioning

confidence: 99%

Surfactants tailored by the class Actinobacteria

et al. 2015

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Globally the change towards the establishment of a bio-based economy has resulted in an increased need for bio-based applications. This, in turn, has served as a driving force for the discovery and application of novel biosurfactants. The class Actinobacteria represents a vast group of microorganisms with the ability to produce a diverse range of secondary metabolites, including surfactants. Understanding the extensive nature of the biosurfactants produced by actinobacterial strains can assist in finding novel biosurfactants with new potential applications. This review therefore presents a comprehensive overview of the knowledge available on actinobacterial surfactants, the chemical structures that have been completely or partly elucidated, as well as the identity of the biosurfactant-producing strains. Producer strains of not yet elucidated compounds are discussed, as well as the original habitats of all the producer strains, which seems to indicate that biosurfactant production is environmentally driven. Methodology applied in the isolation, purification and structural elucidation of the different types of surface active compounds, as well as surfactant activity tests, are also discussed. Overall, actinobacterial surfactants can be summarized to include the dominantly occurring trehalose-comprising surfactants, other non-trehalose containing glycolipids, lipopeptides and the more rare actinobacterial surfactants. The lack of structural information on a large proportion of actinobacterial surfactants should be considered as a driving force to further explore the abundance and diversity of these compounds. This would allow for a better understanding of actinobacterial surface active compounds and their potential for biotechnological application.

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“…A series of reviews by Dembitsky shows the astonishing structural diversity of natural glycolipids and, despite being only a minor component in biological membranes of animal cells, the presence of glycolipids in nature is pervasive [1][2][3][4][5][6][7]. This strongly suggests that their importance is no less than that of the major membrane lipid components such as phospholipids.…”

Section: Introductionmentioning

confidence: 99%

Thermotropic and lyotropic liquid crystalline phases of Guerbet branched-chain -D-glucosides

et al. 2011

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The effect of chain branching on glycolipid thermotropic and lyotropic phases was investigated for a series of synthetic β-D-glucosides derived from Guerbet alcohols, whose total hydrocarbon chain length ranged from C 8 to C 24 . The compounds, which can be viewed as isosteric mimics for glycoglycerolipids, were synthesised in high purity and their liquid crystalline phases were studied using optical polarising microscopy (OPM), and small-angle X-ray diffraction. When dry, the shortest compound (total C 8 ) exhibits a monotropic L α phase while longer ones (C 16 and C 20 ) adopt inverse hexagonal H II phases. The C 24 compound forms an ordered lamellar phase at room temperature, but exhibits a metastable H II phase upon cooling. Curiously the intermediate chain length homologue (C 12 ) adopts an isotropic inverse micellar (L 2 ) phase in the dry state over the range of temperatures studied. Upon hydration, the C 8 compound dissolves, and the C 12 compound forms a fluid lamellar L α phase. The C 16 Guerbet glucoside (i.e. β-Glc-C 10 C 6 ) exhibits an inverse bicontinuous cubic phase of space group Ia3d in excess water, never previously observed in branched-chain lipids, and very seldom observed in excess water. The C 20 compound remains in the H II phase upon hydrating, with the lattice parameter swelling substantially.

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Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

Cited by 24 publications

References 330 publications

Simple glycolipids of microbes: Chemistry, biological activity and metabolic engineering

Simple glycolipids of microbes: Chemistry, biological activity and metabolic engineering

Surfactants tailored by the class Actinobacteria

Thermotropic and lyotropic liquid crystalline phases of Guerbet branched-chain -D-glucosides

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