Identification of new phytoconstituents and antimicrobial activity in stem bark of Mangifera indica (L.)

https://doi.org/10.1016/j.jpba.2014.12.010Get rights and content

Highlights

  • Soxhlet extraction of mango wood in hexane and methanol.

  • Three new compounds separated by TLC and column chromatography.

  • Compounds characterized by infrared spectroscopy and GC–MS.

  • Hexane and methanol extracts exhibited antimicrobial activity.

  • INAA data showed higher contents of Ca, K, Fe, Mg, Mn and Zn.

Abstract

Mangifera indica, commonly called mango or amra belonging to a family of Anacardiaceae, is an important medicinal plant widely used in a variety of Ayurvedic preparations. Extract of its bark, leaves, flowers and kernels are being extensively used for curing various chronic diseases. Mango wood is used in yagya as base fire through which medicated smoke is generated. Three new compounds have been isolated from methanolic and hexane extracts of stem bark: 1,2-benzenedicarboxylic acid, mono(2-ethylhexyl)ester and 9,12-tetradecadiene-1-ol-acetate from the hexane extract and 3-chloro-N-(2-phenylethyl) propanamide from the methanolic extract. These were first separated by thin layer chromatography and later in a silica gel column and identified by characteristic infrared bands corresponding to respective functional groups. The compounds were further confirmed on the basis of GC–MS fragmentation pattern after comparing the data with NIST mass spectral database. All three compounds exhibited antimicrobial activity due to triterpenoids and flavonoids. Elemental analyses by INAA show it to be enriched in essential nutrient elements such as Ca, Fe, K, Mn and Zn which all play an important role in enzymatic processes.

Introduction

The mango is native to South and Southeast Asia from where it has been distributed worldwide to become one of the most cultivated fruits in the tropics. Mango belongs to the family Anacardiaceae, order Rutales and genus Mangifera. It is one of the most popular tropical fruit bearing trees in the world with global production exceeding 30 million tonnes [1]. It contains mangiferin, a pharmacologically active flavonoid-natural xanthone C-glycoside with antioxidant activity [2]. If fully ripe, mango is high in vitamin A (β carotene – a cancer fighting agent), vitamin C, and vitamin B1, B2, potassium, iron and fibre. On the contrary unripe mangoes have oxalic, citric, malic, and tartaric and succinic acids resulting in its sour taste [3]. Extract of Mangifera indica have been reported to possess antiviral, antibacterial, analgesic, anti-inflammatory and immuno-modulatory activities [4], in vitro ant amoebic activity [5], interesting α-amylase and α-glycosidase inhibitory activities [6] and cardio toxic and diuretic properties [7].

Scartezzini and Speroni [7] and Ross [8] have reviewed medicinal importance including antioxidant activity of different constituents of M. indica. Bark is reported to contain protocatechic acid, catechin, mangiferin, alanine, glycine, γ-amino-butyric acid, kinic acid, shikimic acid and the tetra cyclic triterpenoids cycloart-24-en-3β, 26-diol, 3 keto dammar-24 (E)-en-20 S, 26-diol, C-24 epimers of cycloart-25-en-3β, 24, 27-triol and cycloartan-3β, 24,27-triol [9].

Present work was undertaken to isolate and identify new organic compounds from the hexane and alcoholic extracts of M. indica L. The compounds were identified by infrared spectral and gas chromatography–mass spectrometry (GC–MS) techniques. The antibacterial activities of both the extracts have also been studied. Also its elemental contents were determined by instrumental neutron activation analysis (INAA).

Section snippets

General

All the solvents such as methanol (MOH), dichloromethane (CH2Cl2, DCM), chloroform (CHCl3, CFM), carbon tetrachloride (CCl4, CTC), n-hexane (C6H14, HEX), benzene (C6H6, BZ) and ethyl acetate (CH3COOC2H5, EAC) were distilled before use. Silica gel containing 13% CaSO4 as binder (SRL, Mumbai) was used as adsorbent for thin layer chromatography (TLC). Silica Gel-G (Merck, Mumbai) 60–120 mesh was used for column chromatography. Antibacterial standards tetracycline (Sigma–Aldrich, Taufkirchen,

Chemical analysis

Three new compounds two from HEX extract and one from MOH extract were separated and identified by characteristic IR frequencies and GC–MS fragmentation lines after comparing the data with NIST mass spectral database [12]. The compounds identified are 1,2-benzenedicarboxylic acid, mono(2-ethylhexyl)ester (A); 9,12-tetradecadiene,1-ol,acetate (B) and 3-chloro-N-(2-phenylethyl) propanamide (C), last one being used as antimalarial [13]. It may be noted that A is an allelopathic compound that

Conclusion

Three new compounds have been separated from methanol and hexane extracts of mango wood by thin layer and column chromatography and identified by IR and GC–MS studies. One of these is reported to be antimalarial and another one is used for weed management. Both the extracts exhibit antimicrobial activity which may be exploited for developing new antibiotics. Elemental analyses by INAA suggest the wood to be enriched in Ca, K, Mn, Fe, and Zn all essential nutrients. It is suggested that these

Acknowledgements

The authors gratefully acknowledge Professors M.R. Maurya and R.K. Dutta, Department of Chemistry, Indian Institute of Technology, Roorkee for providing laboratory facilities. We also thank Dr R. Acharya, Radiochemistry Division, BARC, Mumbai for irradiation and counting facilities.

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