Characterization and Quantification of Compounds in the Hydroalcoholic Extract of the Leaves from Terminalia catappa Linn. (Combretaceae) and Their Mutagenic Activity

Abstract

Terminalia is a genus of Combretaceous plants widely distributed in tropical and subtropical regions. Thus, the aim of this study was to quantify the majority compounds of the hydroalcoholic extract (7 : 3, v/v) of the leaves from T. catappa by HPLC-PDA, chemically characterize by hyphenated techniques (HPLC-ESI-IT-MSn) and NMR, and evaluate its mutagenic activity by the Salmonella/microsome assay on S. typhimurium strains TA98, TA97a, TA100, and TA102. The quantification of analytes was performed using an external calibration standard. Punicalagin is the most abundant polyphenol found in the leaves. The presence of this compound as a mixture of anomers was confirmed using HPLC-PDA and 1H and 13C NMR. Mutagenic activity was observed in strains TA100 and TA97a. As the extract is a complex mixture of punicalagin, its derivatives, and several other compounds, the observed mutagenicity may be explained in part by possible synergistic interaction between the compounds present in the extract. These studies show that mutagenic activity of T. catappa in the Ames test can only be observed when measured at high concentrations. However, considering the mutagenic effects observed for T. catappa, this plant should be used cautiously for medicinal purposes.

Evaluation of mutagenicity and metabolism-mediated cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin from Paepalanthus latipes

“…Some of these compounds have been incorporated into drugs such as antineoplastics-vinblastine and vincristine isolated from Catharanthus roseus, camptothecin derivatives obtained from Camptotheca acuminata, derivatives of podophyllotoxin from the rhizomes of Podophyllum peltatum and P. hexandrum, and taxol extracted from Taxus brevifolia (Cragg and Newman, 2005;Srivastava et al, 2005;Basmadjian et al, 2014). However, the literature also describes many plants containing mutagenic compounds, such as furocoumarins, tannins, anthraquinones, alkaloids, and flavonoids (Rietjens et al, 2005;Nesslany et al, 2009;Guterres et al, 2013;Mininel et al, 2014). This evidence draws attention to the importance of studying the genetic risks of plant compounds, since the presence of mutagens in medicines can be dangerous to human health.…”

An updated review of Terminalia catappa

“…Classified in the oleic-linoleic acid group, the oils contain huge levels of unsaturated fatty acids, exclusively oleic (up to 31.48%) and linoleic (up to 28.93%). More recently, Mininel et al [2] isolated punicalagin (polyphenol), its derivatives, and other several compounds in the leaves of T. catappa .…”

Terminalia catappa L.: A medicinal plant from the Caribbean pharmacopeia with anti-Helicobacter pylori and antiulcer action in experimental rodent models

“…The identification of the different compounds in the chromatographic profile of the aqueous fraction was done by comparing their retention times (t r ) and the UV spectra with those isolates previously described in the literature (Mininel et al, 2014). The dried aqueous fraction was diluted to 10 mg/mL in HPLC solvent.…”

“…In Asian countries, the leaves of this species are commonly used for the treatment of dermatitis, hepatitis, diarrhea and pyresis (Chen et al, 2000). The literature also shows that the polar extract from different parts (leaves, fruits and bark) of Terminalia catappa have shown the following biological activities: antimicrobial, antifungal (Fyhrquist et al, 2002), antioxidant (Masuda et al, 1999;Chen and Li, 2005;Pandya et al, 2013), antimetastatic (Yeh et al, 2012(Yeh et al, , 2014, anti-inflammatory (Fan et al, 2004;Lin et al, 1999), hepatoprotective (Lin et al, 1997;Chen et al, 2000;Tang et al, 2006;Chen and Li, 2005), mutagenic (Mininel et al, 2014), aphrodisiac (Ratnasooriya and Dharmasiri, 2000) and antidiabetic (Nagappa et al, 2003). The literature also shows that the polar extract from different parts (leaves, fruits and bark) of Terminalia catappa have shown the following biological activities: antimicrobial, antifungal (Fyhrquist et al, 2002), antioxidant (Masuda et al, 1999;Chen and Li, 2005;Pandya et al, 2013), antimetastatic (Yeh et al, 2012(Yeh et al, , 2014, anti-inflammatory (Fan et al, 2004;Lin et al, 1999), hepatoprotective (Lin et al, 1997;Chen et al, 2000;Tang et al, 2006;Chen and Li, 2005), mutagenic (Mininel et al, 2014), aphrodisiac (Ratnasooriya and Dharmasiri, 2000) and antidiabetic (Nagappa et al, 2003).…”