Antimicrobial gastrodin derivatives isolated from Bacopa procumbens

Ada María Rios Cortés

doi:https://doi.org/10.1016/j.phytol.2019.03.005

Antimicrobial gastrodin derivatives isolated from Bacopa procumbens

Ada María Rios Cortés

Centro de Investigación en Biotecnología Aplicada (CIBA), Unidad Tlaxcala

Research output: Contribution to journal › Article › peer-review

Abstract

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 (1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC) and
spectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-cou-
maroyl)-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

Translated title of the contribution	Aislados antimicrobianos derivados de gastrodina a partir de Bacopa procumbens
Original language	English
Article number	31
Pages (from-to)	33
Number of pages	38
Journal	Phytochemistry Letters
Volume	31
DOIs	https://doi.org/10.1016/j.phytol.2019.03.005
State	Published - 7 Mar 2019

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Cite this

@article{eff9fef6447b4f28ba56e6b937a30842,

title = "Antimicrobial gastrodin derivatives isolated from Bacopa procumbens",

abstract = "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 derivativeswhich were denominated procumgastrodin A, procumgastrodin B and procumgastrodin C. These bioactivecompounds were characterized using spectroscopic (1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC) andspectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-cou-maroyl)-shikimate (3) and gastrodin 5-(trans-p-coumaroyl)-shikimate (4). The extracts and fractions showedantimicrobial activity with minimum inhibitory concentration (MIC) between 75 and 400 μg/mL and isolatedcompounds (1-4) showed activities of 12.5 to 100 μg/mL. All analyzed compounds displayed activity against anyof the bacteria and yeast evaluated. A mixture of 3 and 4 exhibited particularly potent activity against the yeastCandida albicans",

keywords = "Antimicrobial, Bacopa procumbens, polyphenols, procumgastrodines, shikimate, derivatives",

author = "{Rios Cort{\'e}s}, {Ada Mar{\'i}a}",

year = "2019",

month = mar,

day = "7",

doi = "https://doi.org/10.1016/j.phytol.2019.03.005",

language = "Ingl{\'e}s",

volume = "31",

pages = "33",

journal = "Phytochemistry Letters",

issn = "1874-3900",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - Antimicrobial gastrodin derivatives isolated from Bacopa procumbens

AU - Rios Cortés, Ada María

PY - 2019/3/7

Y1 - 2019/3/7

N2 - 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 derivativeswhich were denominated procumgastrodin A, procumgastrodin B and procumgastrodin C. These bioactivecompounds were characterized using spectroscopic (1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC) andspectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-cou-maroyl)-shikimate (3) and gastrodin 5-(trans-p-coumaroyl)-shikimate (4). The extracts and fractions showedantimicrobial activity with minimum inhibitory concentration (MIC) between 75 and 400 μg/mL and isolatedcompounds (1-4) showed activities of 12.5 to 100 μg/mL. All analyzed compounds displayed activity against anyof the bacteria and yeast evaluated. A mixture of 3 and 4 exhibited particularly potent activity against the yeastCandida albicans

AB - 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 derivativeswhich were denominated procumgastrodin A, procumgastrodin B and procumgastrodin C. These bioactivecompounds were characterized using spectroscopic (1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC) andspectrometric analysis (HRFAB-MS) as gastrodin 5-(4′”-hydroxybenzoyl)-shikimate (2), gastrodin 5-(cis-p-cou-maroyl)-shikimate (3) and gastrodin 5-(trans-p-coumaroyl)-shikimate (4). The extracts and fractions showedantimicrobial activity with minimum inhibitory concentration (MIC) between 75 and 400 μg/mL and isolatedcompounds (1-4) showed activities of 12.5 to 100 μg/mL. All analyzed compounds displayed activity against anyof the bacteria and yeast evaluated. A mixture of 3 and 4 exhibited particularly potent activity against the yeastCandida albicans

KW - Antimicrobial

KW - Bacopa procumbens

KW - polyphenols

KW - procumgastrodines

KW - shikimate

KW - derivatives

U2 - https://doi.org/10.1016/j.phytol.2019.03.005

DO - https://doi.org/10.1016/j.phytol.2019.03.005

M3 - Artículo

SN - 1874-3900

VL - 31

SP - 33

JO - Phytochemistry Letters

JF - Phytochemistry Letters

M1 - 31

ER -