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Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4- O -benzoyl- α - l -rhamnopyranoside Derivatives

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ABSTRACT

45775648484848: Benzyl α-l-rhamnopyranoside , obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside in reasonable yield. Di-O-acetyl derivative of benzoate was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR) of the designed compounds was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides and exhibited slight distortion from regular 1C4 conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides – were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives – were 0.49 < Pa < 0.60 (where Pa is probability ‘to be active’) as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives – were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures – have not been reported with antimicrobial activity, making it a possible valuable lead compound.

No MeSH data available.


Naturally occurring important rhamnopyranosides (1), (2) and (3).
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ijms-17-01412-f001: Naturally occurring important rhamnopyranosides (1), (2) and (3).

Mentions: l-Rhamnose is widely distributed in nature and is found as a constituent of plant glycosides, gums and also in bacterial polysaccharides [1]. The presence l-rhamnose, as the aglycone moiety, in various oligosaccharides was found to be essential for identification of immunodominant groups in polysaccharides which have antigenic activity [2]. For example, 5-O-α-l-rhamnopyranosyl-β-l-arabinofuranose 1 in Figure 1 was found as the sugar component of sitosterol glycoside, which exhibited rhamnosidase specificity in Aspergillus niger [3]. Kaempferol-3-O-(3′,4′-di-O-acetyl-α-L-rhamnopyranoside) 2 was isolated from nature. Its diacetyl derivative, also called SL0101 3, is a highly specific protein kinase (RSK) inhibitor [4] and was isolated from Forsteronia refracta. Diacetyl compound 3 was found to have 12 times more in vitro RSK inhibitor than that of its non-acetyl analogue 2. It was concluded that acylation of the rhamnose moiety in these natural products is essential for high affinity binding and selectivity as well as for the development of anticancer agents (RSK inhibitors) [4].


Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4- O -benzoyl- α - l -rhamnopyranoside Derivatives
Naturally occurring important rhamnopyranosides (1), (2) and (3).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5037692&req=5

ijms-17-01412-f001: Naturally occurring important rhamnopyranosides (1), (2) and (3).
Mentions: l-Rhamnose is widely distributed in nature and is found as a constituent of plant glycosides, gums and also in bacterial polysaccharides [1]. The presence l-rhamnose, as the aglycone moiety, in various oligosaccharides was found to be essential for identification of immunodominant groups in polysaccharides which have antigenic activity [2]. For example, 5-O-α-l-rhamnopyranosyl-β-l-arabinofuranose 1 in Figure 1 was found as the sugar component of sitosterol glycoside, which exhibited rhamnosidase specificity in Aspergillus niger [3]. Kaempferol-3-O-(3′,4′-di-O-acetyl-α-L-rhamnopyranoside) 2 was isolated from nature. Its diacetyl derivative, also called SL0101 3, is a highly specific protein kinase (RSK) inhibitor [4] and was isolated from Forsteronia refracta. Diacetyl compound 3 was found to have 12 times more in vitro RSK inhibitor than that of its non-acetyl analogue 2. It was concluded that acylation of the rhamnose moiety in these natural products is essential for high affinity binding and selectivity as well as for the development of anticancer agents (RSK inhibitors) [4].

View Article: PubMed Central - PubMed

ABSTRACT

45775648484848: Benzyl α-l-rhamnopyranoside , obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside in reasonable yield. Di-O-acetyl derivative of benzoate was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR) of the designed compounds was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides and exhibited slight distortion from regular 1C4 conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides – were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives – were 0.49 < Pa < 0.60 (where Pa is probability ‘to be active’) as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives – were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures – have not been reported with antimicrobial activity, making it a possible valuable lead compound.

No MeSH data available.