Distribution patterns of flavonoids from three Momordica species by ultra-high performance liquid chromatography quadrupole time of flight mass spectrometry: a metabolomic profiling approach

Abstract

Plants from the Momordica genus. Curcubitaceae. are used for several purposes, especially for their nutritional and medicinal properties. Commonly known as bitter gourds, melon and cucumber, these plants are characterized by a bitter taste owing to the large content of cucurbitacin compounds. However, several reports have shown an undisputed correlation between the therapeutic activities and polyphenols flavonoid content. Using ultra-high performance liquid chromatography quadrupole time of flight mass spectrometry in combination with multivariate data models such as principal component analysis and hierarchical cluster analysis, three Momordica species (M. foetida Schumach., M. charantia L. and M. balsamina L) were chemo-taxonomically grouped based on their flavonoid content. Using a conventional mass spectrometric-based approach, thirteen flavonoids were tentatively identified and the three species were found to contain different isomers of the quercetin-, kaempferol- and isorhamnetin-O-glycosides. Our results indicate that Momordica species are overall very rich sources of flavonoids but do contain different forms thereof. Furthermore, to the best of our knowledge, this is a first report on the flavonoid content of M. balsamina L

References

  1. Ablajan, K., Tuoheti, A., 2013. Fragmentation characteristics and isomeric differentiation of flavonol O-rhamnosides using negative ion electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 27, 451–460.

    CAS  Article  PubMed  Google Scholar 

  2. Chen, J., Chiu, M., Nie, R., Cordell, G., Qiu, S., 2005. Cucurbitacins and cucurbitane glycosides: structures and biological activities. Nat. Prod. Rep. 22, 386–399.

    CAS  Article  PubMed  Google Scholar 

  3. Cuyckens, F., Claeys, M., 2004. Mass spectrometry in the structural analysis of flavonoids. J. Mass Spectrom. 39, 1–15.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  4. Dey, S.S., Singh, A.K., Chandel, D., Behera, T.K., 2006. Genetic diversity of bitter gourd Momordica charantia genotypes revealed by RAPD markers and agronomic traits. Sci. Hortic. 109, 21–28.

    CAS  Article  Google Scholar 

  5. El Shabrawy, M.O., Hosni, H.A., El Garf, I.A., Marzouk, M.M., Kawashty, S.A., Saleh, N.A., 2014. Flavonoids from Allium myrianthu Boiss. Biochem. Syst. Ecol. 56, 125–128.

    CAS  Article  Google Scholar 

  6. Gaikwad, A.B., Behera, T.K., Singh, A.K., Chandel, D., Karihaloo, J.L., Staub, J.E., 2008. Amplified fragment length polymorphism analysis provides strategies for improvement of bittergourd (Momordica charantia L). HortScience 43, 127–133.

    CAS  Article  Google Scholar 

  7. Geng, P., Sun, J., Zhang, R., He, J., Abliz, Z., 2009. An investigation of the fragmentation differences of isomeric flavonol-O-glycosides under different collision-induced dissociation based mass spectrometry. Rapid Commun. Mass Spectrom. 23, 1519–1524.

    CAS  Article  PubMed  Google Scholar 

  8. Gobbo-Neto, L., Gates, P.J., Lopes, N.P., 2008. Negative ion ‘chip-based’ nanospray tandem mass spectrometry for the analysis of flavonoids in glandular trichomes of Lychnophora ericoides Mart. (Asteraceae). Rapid Commun. Mass Spectrom. 22, 3802–3808.

    CAS  Article  PubMed  Google Scholar 

  9. Horax, R., Hettiarachchy, N., Islam, S., 2005. Total phenolic contents and phenolic acid constituents in 4 varieties of bitter melons (Momordica charantia) and antioxidant activities of their extracts. J. Food Sci. 70, C275–C280.

    CAS  Article  Google Scholar 

  10. Iwashina, T., 2000. The structure and distribution of the flavonoids in plants. J. Plant Res. 113, 287–299.

    CAS  Article  Google Scholar 

  11. Kenny, O., Smyth, T.J., Hewage, CM., Brunton, N.P., 2013. Antioxidant properties and quantitative UPLC-MS analysis of phenolic compounds from extracts of fenugreek (Trigonellafoenum-graecum) seeds and bitter melon (Momordica charantia) fruit. Food Chem. 141, 4295–4302.

    CAS  Article  PubMed  Google Scholar 

  12. Kubola, J., Siriamornpun, S., 2008. Phenolic contents and antioxidant activities of bitter gourd (Momordica charantia L.) leaf, stem and fruit fraction extracts in vitro. Food Chem. 110, 881–890.

    CAS  Article  PubMed  Google Scholar 

  13. Lin, J.Y., Tang, C.Y., 2007. Determination of total phenolic and flavonoid contents in selected fruits and vegetables, as well as their stimulatory effects on mouse splenocyte proliferation. Food Chem. 101, 140–147.

    CAS  Article  Google Scholar 

  14. Martucci, M.E.P., De Vos, R.C., Carollo, CA., Gobbo-Neto, L., 2014. Metabolomics as a potential chemotaxonomical tool: application in the genus Vernonia Schreb. PLoS ONE 9, e93149.

  15. Madala, N.E., Steenkamp, P.A., Piater, L.A., Dubery, I.A., 2012. Collision energy alteration during mass spectrometric acquisition is essential to ensure unbiased metabolomic analysis. Anal. Bioanal. Chem. 404, 367–372.

    CAS  Article  PubMed  Google Scholar 

  16. Madala, N.E., Tugizimana, F., Steenkamp, P.A., 2014a. Development and optimization of an UPLC-QTOF-MS/MS method based on an in-source collision induced dissociation approach for comprehensive discrimination of chloro-genic acids isomers from Momordica plant species. J. Anal. Met. Chem., https://doi.org/10.1155/2014/650879.

    Google Scholar 

  17. Madala, N.E., Piater, L.A., Steenkamp, P.A., Dubery, I.A., 2014b. Multivariate statistical models of metabolomic data reveals different metabolite distribution patterns in isonitrosoacetophenone-elicited Nicotiana tabacum and Sorghum bicolor cells. Springer Plus, https://doi.org/10.1186/2193-1801-3-254.

    Google Scholar 

  18. Nagarani, G., Abirami, A., Siddhuraju, P., 2014a. Food prospects and nutraceutical attributes of Momordica species: a potential tropical bioresources - a review. Food Sci. Hum. Wellness 3, 117–126.

    Article  Google Scholar 

  19. Nagarani, G., Abirami, A., Siddhuraju, P., 2014b. A comparative study on antioxidant potentials, inhibitory activities against key enzymes related to metabolic syndrome, and antiinflammatory activity of leaf extract from different Momordica species. Food Sci. Hum. Wellness 3, 36–46.

    Article  Google Scholar 

  20. Rios, J., Escandell, J., Recio, M., 2005. New insights into bioactivity of cucurbitacins. In: Atta-ur-Rahman (Ed.), Studies in Natural Products Chemistry. Amsterdam, pp. 429–469.

  21. Singh, A.K., Behera, T.K., Chandel, D., Sharma, P., Singh, N.K., 2007. Assessing genetic relationships among bitter gourd (Momordica charantia L.) accessions using inter-simple sequence repeat (ISSR) markers. J. Hortic. Sci. Biotechnol. 82, 217–222.

    CAS  Article  Google Scholar 

  22. Singh, J., Cumming, E., Manoharan, G., Kalasz, H., Adeghate, E., 2011. Suppl 2: Medicinal chemistry of the anti-diabetic effects of Momordica charantia: active constituents and modes of actions. Open Med. Chem. J. 5, 70.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  23. Tan, S.P., Parks, S.E., Stathopoulos, CE., Roach, P.D., 2014. Extraction of flavonoids from bitter melon. Food Nutr. Sci. 5, 458–465.

    CAS  Google Scholar 

  24. Wu, S.J., Ng, L.T., 2008. Antioxidant and free radical scavenging activities of wild bitter melon (Momordica charantia Linn. var. abbreviate Ser.) in Taiwan. LWT -Food. Sci. Technol. 41, 323–330.

    CAS  Google Scholar 

  25. Zhou, H., Tang, W., Zeng, J., Tang, C., 2014. Screening of terpene lactones and flavonoid glycosides in Gingko biloba capsule by UPLC-Orbitrap High Resolution MS, with emphasis on isomer differentiation. J. Food Nutr. Res. 2, 369–376.

    Article  Google Scholar 

  26. Zhang, Q.C, 1992. Preliminary report on the use of Momordica charantia extract by HIV patients. J. Naturpath. Med. 3, 65–69.

    Google Scholar 

  27. Zhu, Y., Dong, Y., Qian, X., Cui, F., Guo, Q., Zhou, X., Wang, Y., Zhang, Y., Xiong, Z., 2012. Effect of superfine grinding on antidiabetic activity of bitter melon powder. Int. J. Mol. Sci. 13, 14203–14218.

    CAS  Article  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

The authors would like to thank the University of Johannesburg and the NRF for financial support. Mr Muade is thanked for the donation of M. charantia plants.

Author information

Affiliations

Authors

Contributions

NEM, IAD and LAP planned the study. NEM collected the plants and extracted the metabolites. NEM, LAP, IAD and PAS conducted the UHPLC-qTOF-MS, multivariate data models and executed metabolite identification. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Ntakadzeni Edwin Madala.

Ethics declarations

The authors declare no conflicts of interest.

Rights and permissions

This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Madala, N.E., Piater, L., Dubery, I. et al. Distribution patterns of flavonoids from three Momordica species by ultra-high performance liquid chromatography quadrupole time of flight mass spectrometry: a metabolomic profiling approach. Rev. Bras. Farmacogn. 26, 507–513 (2016). https://doi.org/10.1016/j.bjp.2016.03.009

Download citation

Keywords

  • Momordica
  • UHPLC-qTOF-MS
  • Flavonoids
  • Principal component analysis
  • Chemotaxonomy
  • Hierarchical cluster analysis