Total synthesis of caminoside B, a novel antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia

Zhang, Zaihong; Zong, Chengli; Song, Gaopeng; Lv, Guokai; Chun, Yuexing; Wang, Peng; Ding, Ning; Li, Yingxia

doi:10.1016/j.carres.2010.01.015

Cited by 21 publications

(14 citation statements)

References 32 publications

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“…Interestingly, although caminoside A has no cytotoxic effect against EPEC, it does have cytotoxic activity against Gram-positive methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (MIC = 12 µg/mL for each). Since the discovery of the caminosides, full syntheses of caminoside A and B have been published [42,43], detailing a synthetic process of 33 and 25 steps, respectively. Despite the promising activity of the caminosides against EPEC, very little has been done since their discovery to further develop these natural products for use as T3SS inhibitors due to difficulties in production or synthesis of the compounds.…”

Section: Aurodoxmentioning

confidence: 99%

Natural Product Type III Secretion System Inhibitors

Pendergrass

May

2019

Antibiotics

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Many known inhibitors of the bacterial type III secretion system (T3SS), a virulence factor used by pathogenic bacteria to infect host cells, are natural products. These compounds, produced by bacteria, fungi, and plants, may have developed as prophylactic treatments for potential attack by bacterial pathogens or as an attempt by symbiotic organisms to protect their hosts. Regardless, better understanding of the structures and mechanisms of action of these compounds may open opportunities for drug development against diseases caused by pathogens utilizing the T3SS. This review will cover selected known natural products of the T3SS and detail what is known of their origin and mechanism of action. These inhibitors highlight nature’s ability to modulate interactions between organisms at a cellular level.

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Section: Aurodoxmentioning

confidence: 99%

Natural Product Type III Secretion System Inhibitors

Pendergrass

May

2019

Antibiotics

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“…Interestingly, 6-deoxytalose and l -quinovose are rare in nature. Furthermore, the monosaccharide units are partly acylated ( Figure 5 ) [ 54 , 56 ]. Caminosides A ( 16 ), B ( 17 ) and D ( 19 ) are effective against Gram-positive methicillin-resistant S. aureus (MIC = 12.5, 6.3, and 6.3 μg/disk, respectively) and vancomycin-resistant Enteroccocus (MIC = 6.3, 3.1, and 6.3 μg/disk, respectively), but show no activity against the Gram-negative bacterium E. coli [ 54 ].…”

Section: Biological Activities Of Marine Carbohydrate and Glycosidmentioning

confidence: 99%

The Effects of Marine Carbohydrates and Glycosylated Compounds on Human Health

Kang

Seo

Park

2015

IJMS

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Marine organisms have been recognized as a valuable source of bioactive compounds with industrial and nutraceutical potential. Recently, marine-derived carbohydrates, including polysaccharides and low molecular weight glycosylated oligosaccharides, have attracted much attention because of their numerous health benefits. Moreover, several studies have reported that marine carbohydrates exhibit various biological activities, including antioxidant, anti-infection, anticoagulant, anti-inflammatory, and anti-diabetic effects. The present review discusses the potential industrial applications of bioactive marine carbohydrates for health maintenance and disease prevention. Furthermore, the use of marine carbohydrates in food, cosmetics, agriculture, and environmental protection is discussed.

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“…The product caminoside (Table 1; depicts key compounds described in this review) was found to have these properties with an IC 50 of 5.1 μg/ml. Despite the promise of this caminoside, its cellular targets were not identified due to the difficulty of synthesizing this natural compound (Zhang et al, 2010). …”

Section: The Search For T3ss Inhibitorsmentioning

confidence: 99%

From screen to target: insights and approaches for the development of anti-virulence compounds

Beckham

Roe

2014

Front. Cell. Infect. Microbiol.

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A detailed understanding of host-pathogen interactions provides exciting opportunities to interfere with the infection process. Anti-virulence compounds aim to modulate or pacify pathogenesis by reducing expression of critical virulence determinants. In particular, prevention of attachment by inhibiting adhesion mechanisms has been the subject of intense research. Whilst it has proven relatively straightforward to develop robust screens for potential anti-virulence compounds, understanding their precise mode of action has proven much more challenging. In this review we illustrate this challenge from our own experiences working with the salicylidene acylhydrazide group of compounds. We aim to provide a useful perspective to guide researchers interested in this field and to avoid some of the obvious pitfalls.

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Total synthesis of caminoside B, a novel antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia

Cited by 21 publications

References 32 publications

Natural Product Type III Secretion System Inhibitors

Natural Product Type III Secretion System Inhibitors

The Effects of Marine Carbohydrates and Glycosylated Compounds on Human Health

From screen to target: insights and approaches for the development of anti-virulence compounds

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