Sulfated O-polysaccharide with anticancer activity from the marine bacterium Poseidonocella sedimentorum KMM 9023T

Kokoulin, Maxim S.; Kuzmich, Alexandra S.; Romanenko, Lyudmila A.; Menchinskaya, Ekaterina S.; Mikhailov, Valery V.; Chernikov, Oleg V.

doi:10.1016/j.carbpol.2018.08.107

Cited by 10 publications

(5 citation statements)

References 28 publications

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“…For example, O -methylation of glycans have only been reported in bacteria, fungi, algae, plants, worms, and mollusks but not in mammals . In sialic acids derivatives, O -methylation has been observed at the O8 and O9 positions, such as in the case of the recently reported Kdn8Me and Neu5Gc8Me residues found in the glycome of the cephalochordate B. belcheri , and the Kdn9Me residue found in the O-antigen PS from P. sedimentorum KMM 9023 T . The proton and carbon resonances of this substituent are observed at characteristic δ H ∼ 3.4 and δ C ∼ 59 .…”

Section: Identification Of Structural Partsmentioning

confidence: 99%

“…sedimentorum KMM 9023 T . 238 The proton and carbon resonances of this substituent are observed at characteristic δ H ∼ 3.4 and δ C ∼ 59. 239 Besides amide and ester linkages, lactic acid residues can be attached to glycans through ether bonds, and the N-acetyl muramic acid residue found in the peptidoglycan is an example of the latter (Figure 5a); in that case, the proton resonances of the lactyl group are observed at δ H ∼ 1.4 (CH 3 ) and 4.4 (CH), and the ether linkage can be recognized by the characteristic downfield chemical shift of the C2 resonance of the lactic acid moiety (δ C2 ∼ 78 ppm).…”

Section: Substituents Appended To Sugarsmentioning

confidence: 99%

“…When unaccounted 1 H and 13 C chemical shift displacements are observed at specific positions of monosaccharide residues and key resonances and correlations from other substituents are absent in the 1 H, 13 C, 15 N, and 31 P based experiments, the presence of O -sulfation can be suspected . This modification can typically be found at O8 and O9 positions of some Neu5Ac derivatives and is heterogeneously distributed over different Fuc and GalNAc residues in the fucosylated chondroitin sulfate isolated form the sea cucumber P. pygmaea and Gal residues in the sulfated galactan obtained from the red alga B. occidentalis . , Residues displaying this type of modification have also been found in several O-antigen polysaccharides isolated from marine bacteria, including α- d -Glc p A2S3Ac in the PS from P. sedimentorum KMM 9023 T , β- d -Qui p 2S3N(4Hb) in the PS of I. abyssalis KMM 227 T , α- d -Glc p 2Ac3S and β- d -Gal p 3S residues in the PS of C. pacifica KMM 3879 T , and β- d -Gal p 2S3S residue in the PS of C. pacifica KMM 3878. ,− …”

Section: Identification Of Structural Partsmentioning

confidence: 99%

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Primary Structure of Glycans by NMR Spectroscopy

Fontana

Widmalm

2023

Chem. Rev.

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Glycans, carbohydrate molecules in the realm of biology, are present as biomedically important glycoconjugates and a characteristic aspect is that their structures in many instances are branched. In determining the primary structure of a glycan, the sugar components including the absolute configuration and ring form, anomeric configuration, linkage(s), sequence, and substituents should be elucidated. Solution state NMR spectroscopy offers a unique opportunity to resolve all these aspects at atomic resolution. During the last two decades, advancement of both NMR experiments and spectrometer hardware have made it possible to unravel carbohydrate structure more efficiently. These developments applicable to glycans include, inter alia, NMR experiments that reduce spectral overlap, use selective excitations, record tilted projections of multidimensional spectra, acquire spectra by multiple receivers, utilize polarization by fast-pulsing techniques, concatenate pulse-sequence modules to acquire several spectra in a single measurement, acquire pure shift correlated spectra devoid of scalar couplings, employ stable isotope labeling to efficiently obtain homo-and/or heteronuclear correlations, as well as those that rely on dipolar cross-correlated interactions for sequential information. Refined computer programs for NMR spin simulation and chemical shift prediction aid the structural elucidation of glycans, which are notorious for their limited spectral dispersion. Hardware developments include cryogenically cold probes and dynamic nuclear polarization techniques, both resulting in enhanced sensitivity as well as ultrahigh field NMR spectrometers with a 1 H NMR resonance frequency higher than 1 GHz, thus improving resolution of resonances. Taken together, the developments have made and will in the future make it possible to elucidate carbohydrate structure in great detail, thereby forming the basis for understanding of how glycans interact with other molecules.

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Section: Identification Of Structural Partsmentioning

confidence: 99%

Section: Substituents Appended To Sugarsmentioning

confidence: 99%

Section: Identification Of Structural Partsmentioning

confidence: 99%

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Primary Structure of Glycans by NMR Spectroscopy

Fontana

Widmalm

2023

Chem. Rev.

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“…[ 4 ] Numerous research conducted over the past 10 years has demonstrated the role of marine‐derived compounds as anticancer agents. [ 5–7 ] More than 20,000 natural products from algae, sponges, fungi, corals, molluscs, and ascidians of marine origin have been characterized. [ 8 ] Among them, about 150 compounds are cytotoxic to tumor cells, and at least 12 of these compounds are now in various stages of clinical trials.…”

Section: Introductionmentioning

confidence: 99%

Using nanotechnology to progress the utilization of marine natural products in combating multidrug resistance in cancer: A prospective strategy

Bhusare,

Gade,

Kumar

2024

J Biochem & Molecular Tox

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Achieving targeted, customized, and combination therapies with clarity of the involved molecular pathways is crucial in the treatment as well as overcoming multidrug resistance (MDR) in cancer. Nanotechnology has emerged as an innovative and promising approach to address the problem of drug resistance. Developing nano‐formulation‐based therapies using therapeutic agents poses a synergistic effect to overcome MDR in cancer. In this review, we aimed to highlight the important pathways involved in the progression of MDR in cancer mediated through nanotechnology‐based approaches that have been employed to circumvent them in recent years. Here, we also discussed the potential use of marine metabolites to treat MDR in cancer, utilizing active drug‐targeting nanomedicine‐based techniques to enhance selective drug accumulation in cancer cells. The discussion also provides future insights for developing complex targeted, multistage responsive nanomedical drug delivery systems for effective cancer treatments. We propose more combinational studies and their validation for the possible marine‐based nanoformulations for future development.

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“…Polysaccharides are widely found in plants, animals, bacteria and microorganisms [ 1 ]. Due to their good antioxidant [ 2 ], antitumor [ 3 ], immune regulation [ 4 ], antiviral [ 5 ], anticoagulant [ 6 ] and other biological activities, they have been the focus of scholars in the medical field. Since 1943, polysaccharides have been used as medicines to treat diseases [ 7 ] and, up until now, have gradually been developed into functional foods with the development of technology, which are well liked by people.…”

Section: Introductionmentioning

confidence: 99%

Chemical Modification of Polysaccharides: A Review of Synthetic Approaches, Biological Activity and the Structure–Activity Relationship

et al. 2023

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Natural polysaccharides are macromolecular substances with great potential owing to their wide biological activity and low toxicity. However, not all polysaccharides have significant pharmacodynamic activity; hence, appropriate chemical modification methods can be selected according to the unique structural characteristics of polysaccharides to assist in enhancing and promoting the presentation of their biological activities. This review summarizes research progress on modified polysaccharides, including common chemical modification methods, the change in biological activity following modification, and the factors affecting the biological activity of chemically modified polysaccharides. At the same time, the difficulties and challenges associated with the structural modification of natural polysaccharides are also outlined in this review. Thus, research on polysaccharide structure modification is critical for improving the development and utilization of sugar products.

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Sulfated O-polysaccharide with anticancer activity from the marine bacterium Poseidonocella sedimentorum KMM 9023T

Cited by 10 publications

References 28 publications

Primary Structure of Glycans by NMR Spectroscopy

Primary Structure of Glycans by NMR Spectroscopy

Using nanotechnology to progress the utilization of marine natural products in combating multidrug resistance in cancer: A prospective strategy

Chemical Modification of Polysaccharides: A Review of Synthetic Approaches, Biological Activity and the Structure–Activity Relationship

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