Gallic Acid and Gallic Acid Derivatives: Effects on Drug Metabolizing Enzymes

Abstract

Gallic acid and its structurally related compounds are found widely distributed in fruits and plants. Gallic acid, and its catechin derivatives are also present as one of the main phenolic components of both black and green tea. Esters of gallic acid have a diverse range of industrial uses, as antioxidants in food, in cosmetics and in the pharmaceutical industry. In addition, gallic acid is employed as a source material for inks, paints and colour developers. Studies utilising these compounds have found them to possess many potential therapeutic properties including anti-cancer and antimicrobial properties. In this review, studies of the effects of gallic acid, its esters, and gallic acid catechin derivatives on Phase I and Phase II enzymes are examined. Many published reports of the effects of the in vitro effects of gallic acid and its derivatives on drug metabolising enzymes concern effects directly on substrate (generally drug or mutagen) metabolism or indirectly through observed effects in Ames tests. In the case of the Ames test an antimutagenic effect may be observed through inhibition of CYP activation of indirectly acting mutagens and/or by scavenging of metabolically generated mutagenic electrophiles. There has been considerable interest in the in vivo effects of the gallate esters because of their incorporation into foodstuffs as antioxidants and in the catechin gallates with their potential role as chemoprotective agents. Principally an induction of Phase II enzymes has been observed however more recent studies using HepG2 cells and primary cultures of human hepatocytes provide evidence for the overall complexity of actions of individual components versus complex mixtures, such as those in food. Further systematic studies of mechanisms of induction and inhibition of drug metabolising enzymes by this group of compounds are warranted in the light of their distribution and consequent ingestion, current uses and suggested therapeutic potential. However, it must be noted that numerous constituents of foodstuffs have been found to be potent modulators of xenobiotic metabolism and the net human health effects may depend on concentrations of individual components and individual genetic makeup.

Uncovering the Lactobacillus plantarum WCFS1 Gallate Decarboxylase Involved in Tannin Degradation

“…In addition to esters, gallic acid can be found in plants in the free state or in the form of ethers (e.g., syringic acid and other lignins constituents), being a major pollutant present in the wastewater generated in processes involving the boiling of cork and in food manufacturing industries. Gallic acid and its derivatives are used in industry as antioxidants (3).…”

SKRINING SENYAWA METABOLIT SEKUNDER EKSTRAK RUMPUT MUTIARA (Hedyotis Corymbosa (L.) Lamk.) DENGAN METODE GC-MS

“…Camphene Monoterpena Antioksidan (Tiwari, et al, 2009), Hipokolesterolmia (Vallianou, et al, 2011 Limonene Sikloterpena Antiasetilkolinesterase (Aazza, et al, 2011) Antiasma (Tanaka dan Takahashi, 2013, Antibakteri (Bevilacqua, 2010), Anti kanker (Gould, 1997), Antiinflamasi (d'Alessio, et al, 2013), Imunomodulator (Astani, et al, 2014) 4 Myrcene Monoterpena Antibakteri (Gonzaga, et al, 2003), Antinosiseptif (Rao, et al, 1990), Kemopreventif (Esmaelli, et al, 2011), Analgesik (Lorenzett, et al, 1991, Antikonvulsan (Viana, et al, 2000), Antioksidan (Ciftci, et al, 2011) 5 Pinene Monoterpena Ekspektoran (Schmitt, et al, 2009), Antibakteri (Silva, et al, 2012) 6 Camphor Monoterpena Analgesik (Xu, et al, 2005), Antidiare (Hamidpour, et al, 2014), Dekongestan (Xu, et al, 2005), Ekspektoran (Zuccarini, et al, 2009) 7 Cineole Monoterpena Anastesi (Zalachoras, et al, 2010), Antitusif (Laude, et al, 1994), Anti helmintikum (Taur, et al, 2010), Dekongestan (Takaishi, et al, 2012) 8 Geraniol Monoterpena Antitumor (Tiwari, et al, 2009), Antibakteri (Pattnaik, et al, 1997), Anti TBC (Soto, et al, 2014) 9 Citronellol Monoterpena Antibakteri (Pattnaik, et al, 1996) 10 Gallic acid Fenolat Antialergi (Liu, et al, 2013), Antibakteri (Borges, et al, 2013), Antikanker (Faried, et al, 2007), Antiinflamasi (Kou, et al, 2008), Insulin-sparing (Doan, et al, 2015), Analgesik (Krogh, et al, 2000), Antiasma (Dorsch, et al, 1992), Antibronkitis (Ow, et al, 2003) , Antihepatotoksik (Hoffman, et al, 1992), Antioksidan (Kim, 2007) 11…”

“…Berdasarkan hasil GC-MS senyawa Gallic Acid terdapat pada no titik puncak 10, dengan bobot molekul 170,12 dan memiliki rumus molekul C7H6O5 serta terklasifikasi pada golongan Fenolat. Menurut kajian referensi, golongan ini memiliki beberapa fungsi yaitu antialergi (Liu, et al, 2013), antibakteri (Borges, et al, 2013), antikanker (Faried, et al, 2007), antiinflamasi (Kou, et al, 2008), insulinsparing (Doan, et al, 2015), analgesik (Krogh, et al, 2000), antiasma (Dorsch, et al, 1992), antibronkitis (Ow and Stupans, 2003), antihepatotoksik (Hoffmann-bohm, et al, 1992), dan antioksidan (Kim, 2007). Senyawa dengan komposisi tertinggi kedua adalah Catechin yang terdapat pada no titik puncak 19.…”

Characteristics and Applications of Bioactive Peptides in Skin Care

“…GA는 코코아 (cocoa), 오배자 (gallnut), 녹차 (green tea), 참나 무껍데기 (oak bark) 등에 함유된 식물 유래의 polyphenol 성 분으로 건선 (psoriasis)과 같은 피부질환 환자에 효과적이고 항산화, 항염 기능이 우수하여 피부트러블 및 피부기능 개선 소재로 보고되고 있다 [44,45]. GA의 항산화 효과는 비타민 C와 그 효능이 유사하며 색소질환의 피부에 미백 효과를 나타 낸다 [46].…”