Antimicrobial gastrodin derivatives isolated from Bacopa procumbens

Manasés González-Cortazar, Valentín López-Gayou, Jaime Tortoriello, Blanca E. Domínguez-Mendoza, Ada M. Ríos-Cortes, Raúl Delgado-Macuil, Elías E. Hernández-Beteta, Ever A. Blé-González, Alejandro Zamilpa

Research output: Contribution to journalArticleResearchpeer-review

Abstract

© 2019 Phytochemical Society of Europe The bioassay-guided fractionation of the hydroalcoholic extract from aerial parts of Bacopa procumbens (Mill.) Greenm., allowed to isolate the known phenolic compound arbutin (1) as well as three new gastrodin derivatives which were denominated procumgastrodin A, procumgastrodin B and procumgastrodin C. These bioactive compounds were characterized using spectroscopic ( 1 H-NMR, 13 C-NMR, 1 H- 1 H COSY, HSQC, HMBC) and spectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-coumaroyl)-shikimate (3) and gastrodin 5-(trans-p-coumaroyl)-shikimate (4). The extracts and fractions showed antimicrobial activity with minimum inhibitory concentration (MIC) between 75 and 400 μg/mL and isolated compounds (1-4) showed activities of 12.5 to 100 μg/mL. All analyzed compounds displayed activity against any of the bacteria and yeast evaluated. A mixture of 3 and 4 exhibited particularly potent activity against the yeast Candida albicans.
Original languageAmerican English
Pages (from-to)33-38
Number of pages29
JournalPhytochemistry Letters
DOIs
StatePublished - 1 Jun 2019

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Bacopa
anti-infective agents
chemical derivatives
yeasts
Derivatives
extracts
minimum inhibitory concentration
Candida albicans
Yeast
aerial parts
phenolic compounds
fractionation
bioassays
Arbutin
Yeasts
Nuclear magnetic resonance
Bioassay
Candida
bacteria
Microbial Sensitivity Tests

Cite this

González-Cortazar, M., López-Gayou, V., Tortoriello, J., Domínguez-Mendoza, B. E., Ríos-Cortes, A. M., Delgado-Macuil, R., ... Zamilpa, A. (2019). Antimicrobial gastrodin derivatives isolated from Bacopa procumbens. Phytochemistry Letters, 33-38. https://doi.org/10.1016/j.phytol.2019.03.005
González-Cortazar, Manasés ; López-Gayou, Valentín ; Tortoriello, Jaime ; Domínguez-Mendoza, Blanca E. ; Ríos-Cortes, Ada M. ; Delgado-Macuil, Raúl ; Hernández-Beteta, Elías E. ; Blé-González, Ever A. ; Zamilpa, Alejandro. / Antimicrobial gastrodin derivatives isolated from Bacopa procumbens. In: Phytochemistry Letters. 2019 ; pp. 33-38.
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abstract = "{\circledC} 2019 Phytochemical Society of Europe The bioassay-guided fractionation of the hydroalcoholic extract from aerial parts of Bacopa procumbens (Mill.) Greenm., allowed to isolate the known phenolic compound arbutin (1) as well as three new gastrodin derivatives which were denominated procumgastrodin A, procumgastrodin B and procumgastrodin C. These bioactive compounds were characterized using spectroscopic ( 1 H-NMR, 13 C-NMR, 1 H- 1 H COSY, HSQC, HMBC) and spectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-coumaroyl)-shikimate (3) and gastrodin 5-(trans-p-coumaroyl)-shikimate (4). The extracts and fractions showed antimicrobial activity with minimum inhibitory concentration (MIC) between 75 and 400 μg/mL and isolated compounds (1-4) showed activities of 12.5 to 100 μg/mL. All analyzed compounds displayed activity against any of the bacteria and yeast evaluated. A mixture of 3 and 4 exhibited particularly potent activity against the yeast Candida albicans.",
author = "Manas{\'e}s Gonz{\'a}lez-Cortazar and Valent{\'i}n L{\'o}pez-Gayou and Jaime Tortoriello and Dom{\'i}nguez-Mendoza, {Blanca E.} and R{\'i}os-Cortes, {Ada M.} and Ra{\'u}l Delgado-Macuil and Hern{\'a}ndez-Beteta, {El{\'i}as E.} and Bl{\'e}-Gonz{\'a}lez, {Ever A.} and Alejandro Zamilpa",
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González-Cortazar, M, López-Gayou, V, Tortoriello, J, Domínguez-Mendoza, BE, Ríos-Cortes, AM, Delgado-Macuil, R, Hernández-Beteta, EE, Blé-González, EA & Zamilpa, A 2019, 'Antimicrobial gastrodin derivatives isolated from Bacopa procumbens', Phytochemistry Letters, pp. 33-38. https://doi.org/10.1016/j.phytol.2019.03.005

Antimicrobial gastrodin derivatives isolated from Bacopa procumbens. / González-Cortazar, Manasés; López-Gayou, Valentín; Tortoriello, Jaime; Domínguez-Mendoza, Blanca E.; Ríos-Cortes, Ada M.; Delgado-Macuil, Raúl; Hernández-Beteta, Elías E.; Blé-González, Ever A.; Zamilpa, Alejandro.

In: Phytochemistry Letters, 01.06.2019, p. 33-38.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Antimicrobial gastrodin derivatives isolated from Bacopa procumbens

AU - González-Cortazar, Manasés

AU - López-Gayou, Valentín

AU - Tortoriello, Jaime

AU - Domínguez-Mendoza, Blanca E.

AU - Ríos-Cortes, Ada M.

AU - Delgado-Macuil, Raúl

AU - Hernández-Beteta, Elías E.

AU - Blé-González, Ever A.

AU - Zamilpa, Alejandro

PY - 2019/6/1

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N2 - © 2019 Phytochemical Society of Europe The bioassay-guided fractionation of the hydroalcoholic extract from aerial parts of Bacopa procumbens (Mill.) Greenm., allowed to isolate the known phenolic compound arbutin (1) as well as three new gastrodin derivatives which were denominated procumgastrodin A, procumgastrodin B and procumgastrodin C. These bioactive compounds were characterized using spectroscopic ( 1 H-NMR, 13 C-NMR, 1 H- 1 H COSY, HSQC, HMBC) and spectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-coumaroyl)-shikimate (3) and gastrodin 5-(trans-p-coumaroyl)-shikimate (4). The extracts and fractions showed antimicrobial activity with minimum inhibitory concentration (MIC) between 75 and 400 μg/mL and isolated compounds (1-4) showed activities of 12.5 to 100 μg/mL. All analyzed compounds displayed activity against any of the bacteria and yeast evaluated. A mixture of 3 and 4 exhibited particularly potent activity against the yeast Candida albicans.

AB - © 2019 Phytochemical Society of Europe The bioassay-guided fractionation of the hydroalcoholic extract from aerial parts of Bacopa procumbens (Mill.) Greenm., allowed to isolate the known phenolic compound arbutin (1) as well as three new gastrodin derivatives which were denominated procumgastrodin A, procumgastrodin B and procumgastrodin C. These bioactive compounds were characterized using spectroscopic ( 1 H-NMR, 13 C-NMR, 1 H- 1 H COSY, HSQC, HMBC) and spectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-coumaroyl)-shikimate (3) and gastrodin 5-(trans-p-coumaroyl)-shikimate (4). The extracts and fractions showed antimicrobial activity with minimum inhibitory concentration (MIC) between 75 and 400 μg/mL and isolated compounds (1-4) showed activities of 12.5 to 100 μg/mL. All analyzed compounds displayed activity against any of the bacteria and yeast evaluated. A mixture of 3 and 4 exhibited particularly potent activity against the yeast Candida albicans.

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