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GC MS/MS analysis of Bioactive Compounds in Alcoholic Seed Extract of Gauzuma ulmifolia

Ponnusamy, Banu, Vedigounder, and Narayanswamy: GC MS/MS analysis of Bioactive Compounds in Alcoholic Seed Extract of Gauzuma ulmifolia Lam

Authors

INTRODUCTION

Gauzuma ulmifolia Lam. (GU) is wildly distributed in tropical America from Mexico to the northern part of Argentina and the middle part of Brazil. It has been naturalized to the local climatic conditions. This species has high economic importance. GU grows to 30 m in height and 30-40 cm in diameter with a rounded crown and drooping foliage. Bark is grey or grey brown becoming furrowed and rough with age. Young branches are covered with stellate hairs. Leaves are simple, alternate, with serrate margins, 5-7 cm long. Flowers are yellow-brown, about 1 cm long in 3-5 cm long axillary inflorescences. The fruit is a round or elliptic 5 celled capsule that opens at the apex. When the fruit is ripe, it is black and contains 40-80 seeds, each 3-5 mm in diameter. There is approximately 100 g of clean seed in 1Kg of fruits and 1,50,000 clean seeds per Kg.1

The use of the plant is well documented in the traditional literature as a remedy for various ailments, such as bronchitis, burns, diarrhoea, asthma, inflammation, alopecia, diuretic, astringent and veneral diseases.2 Previous investigations of the chemical composition of GU have indicated the occurrence of flavon-3-ol procyanidins,2 nitrile and a glucoside, menisdaurin.8 This plant was reported to have anti-oxidant,3 antidiabetic,4,5 hypotensive,6 vasorelaxant, antiulcer,7 antibacterial9,10 and antiviral11 activity.

Considering all these facts, the present study was designed to investigate the presence of chemical composition of the seed extract.

MATERIALS AND METHODS

The fruits of Gauzuma ulmifolia Lam. was collected and dried at 60 °C for 24 hrs. The dried fruits were pulverized manually to remove the seeds. The seeds were purified and stored in air tight container.

The GU seed was extracted with ethanol and analyzed through Gas Chromatography- Mass Spectrometry/Mass Spectrometry for identification of different components.12

The analyses of the alcoholic extract were run on 436-GC Bruker operating in the EI mode at 70 eV, equipped with a split/splitless injector (280°C). Column BR-5MS (5% Dimethyl polysiloxane), 30 m × 0.2 mm ID × 0.25 μm df). Oven temperature was programmed as follows, 110°C hold for 3.50 min, then increased upto 200°C at the rate of 10°C per min with no hold, then increased upto 280 °C at the rate of 5°C per min for 12 min hold. Carrier gas (1 ml/min), Split 10:1, Sample injected was 2 μl and Injector temperature was 280°C. Total GC running time was 40.50 min. TQ Quadrupole Mass Spectrometer detector and Software MS Work station 8 was used for the analysis.11

Table 1

List of compounds identified in Gauzuma ulmifolia Lam.

S.No.RTName of the CompoundMolecular FormulaeMolecular WeightPeak Area %
112.974-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenolC10 H12 O31800.01
215.06Hexadecanoic acid, methyl esterC17H34O22700.01
315.84α- GuaieneC15H242040.19
417.379, 12- Octadecadienoic acid, methyl esterC19H34O22940.18
518.861,3-Benzodioxole, 5,5’-(tetrahydro-1H, 3H-furo[3,4-c] furan-1,4-diyl) bis-, [1S-(1α,3aα, 4β, 6aα]- D-AsarininC20H18O635465.02
622.879,12,15-Octadecatrienoic acid, methyl ester, (Z, Z,Z)-C19H32O22920.80
724.52o-Anisic acid, tridec-2-ynyl esterC21H30O33303.33
826.07Butyl 9, 12-octadecadienoateC22H40O23360.66
927.55Ethyl iso-allocholateC26H44O54360.15
1028.812,6-Bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo (3.3.0)octaneC20H18O635420.12
1130.111-Dodecanone, 2-(imidazol-1-yl)-1-(4-methoxyphenyl)-C22H32N2O23567.54
1231.22γ - TocopherolC28H48O24160.47
1332.75Vitamin EC29H50O24300.11
1434.81Ergost-5-en-3-ol, (3β)-C28H48O4000.12
1535.49StigmasterolC29H48O4120.07
1637.18β - SitosterolC29H50O4141.22
Figure 1

Structure of compounds identified in Ethanolic extract of Gauzuma ulmifolia Lam.

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Figure 2

GC-MS/MS Chromatogram of Ethanolic extract of GU.

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Library used NIST Version- 11; Inlet line temperature 290°C, Source temperature 250°C, Electron energy 70 eV, Mass scan (m/z) 50- 500 amu, Solvent Delay was 0 - 3.5 min and Total MS running time was 40.50 min.

RESULTS AND DISCUSSION

The different compounds identified in the alcoholic extract of GU, along with their molecular formulae, molecular weight and the % peak area are listed in Table 1. A total of 16 compounds were identified and the structures of these compounds are predicted in Figure 1. Their GC-MS/MS chromatogram has been shown in Figure 2.

Among the various compounds identified, 2,6-Bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo (3.3.0) octane, commonly known as D-Asarinin, Vitamin E, γ – Tocopherol have been reported to possess antihypertensive, oxidative stress management13 and hyperlipidemic activities.14

Further, some phytosterols like Ergost-5-en-3-ol, (3β)-, commonly known as Campesterol is known to inhibit intestinal absorption of cholesterol.15 Stigmasterol, a precursor in manufacturing of semisynthetic progesterone and vitamin D3, also an intermediate in biosynthesis of androgens, estrogens and corticoids.16,17 β– Sitosterol, a potential dietary phytosterol for prevention and therapy for human cancer.18

CONCLUSION

The present study was focused on characterization of bioactive compounds of alcoholic extract of seeds of GU by GC MS/ MS analysis and the 16 compounds identified are responsible for the various pharmacological actions shown by GU. Therefore, the above results confirmed Gauzuma ulmifolia Lam. as a new valuable component for food and nutraceutical applications in the promotion of health.

GRAPHICAL ABSTRACT

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SUMMARY

  • The present study has highlighted on the chemical profile of the seeds of GU for the first time by GC MS/MS method. A total of 16 compounds with their proportions have been identified. Further exploration on isolation of these phytoconstituents may develop many novel compounds with potent medicinal properties.

ACKNOWLEDGEMENT

The authors wish to acknowledge Rajiv Gandhi University of Health Sciences, for providing the financial assistance to pursue the study, and extend our thanks to The Director, Indian Institute of Crop Processing Technology, Thanjavur, Tamil Nadu for GC MS/MS analysis.

ABOUT AUTHORS

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Dr.P. Sivakami Sundari, Department of pharmacognosy, Dayananda Sagar College of Pharmacy, Bangalore, India, sivakamiponnudamy@yahoo.co.in

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Dr. Shanaz Banu, Department of Pharmacognosy, Dayananda Sagar College of Pharmacy, Bangalore, India, shana2906@gmail.com

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Dr. V. Murugan, Prinicipal, Dayananda Sagar College of Pharmacy, Bangalore, India, murugan_9362@yahoo.com

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N. Dhanashree, Dayananda Sagar University, College of Pharmaceutical Sciences, Bangalore, India, gandhamdhanashree12@gmail.com

Notes

[1] Conflicts of interest CONFLICT OF INTEREST The authors declare that we do not have any conflict of interest.

ABBREVIATION USED

GU

Gauzuma ulmifolia

GC MS/MS

Gas Chromatography -Mass Spectrometry/Mass Spectrometry

m/z

Mass to charge ratio

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