Stereoselective synthesis of the lichen metabolite, (+) montagnetol and its congeners as antimicrobial agents

Abstract

In view of structural diversity, (+) montagnetol, the major metabolite of the fruticose lichen, Roccella montagnei was synthesized along with three of its congeners by employing highly efficient protocols. (+) Montagnetol (2 R, 3S; 11) and (-) montagnetol (2S, 3R; 5) were synthesized in 7 and 9 steps, respectively, from L-ascorbic acid. The two new congeners 3 (2 R, 3R) and 6 (2S, 3S), which differ in configuration at C-2 and C-3 positions of the (+) montagnetol, were synthesized from (−) diethyl D-tartrate and (+) diethyl L-tartrate, respectively. The synthesized compounds were evaluated in vitro for antimicrobial activity against two Gram-positive (S. aureus and E. coli) and two Gram-negative (S. typhi and P. aeruginosa) bacteria and one fungal strain Candida albicans. Interestingly, the congener 3 showed promising anti-bacterial activity (MIC: 0.062 µg/ml) against P. aeruginosa, whereas the congener 6 displayed potent anti-fungal activity (MIC: 0.062 µg/ml) against C. Albicans.

Graphical Abstract

Keywords:

• Antimicrobial activity
• diethyl tartrate
• L-ascorbic acid
• montagnetol
• Roccella montagnei

Acknowledgements

We are thankful to Director, CSIR-IICT for support and encouragement.

Additional information

Funding

We are thankful to CSIR, Government of India, New Delhi for the award of Senior Research Fellowship to BRK.