Skip to main navigation menu Skip to main content Skip to site footer
Plant Science Today (PST)

Research Articles

Vol. 10 No. 2 (2023)

Four bioactive compounds isolated from the stem of Anethum sowa L. and their bioactivities

DOI
https://doi.org/10.14719/pst.2201
Submitted
22 October 2022
Published
24-04-2023 — Updated on 19-05-2023
Versions

Abstract

Anethum sowa L., (a well-known herb in folk medicine, has a greater medicinal significance due to its diversified activities such as antioxidant, antimicrobial and antispasmodic activity. Very few bioactive compounds have been reported from this species. Our study focused on the isolation, structure elucidation and bioactivity assay of the compounds. In the present work, 6-hydroxy-1, 3-dimethoxy-7-methyl-xanthen-9-one (AS-1) from dichloromethane extract and scopoletin (AS-2), 1, 3, 4-trimethoxy-xanthen-9-one (AS-3), graveolone (AS-4) from ethyl acetate extract of stem of A. sowa were isolated from the stem as well as the plant for the first time. All the characterizations and chemical structures of the compounds were determined by extensive modern spectroscopic techniques such as ultraviolet (UV), infrared (IR), mass, Nuclear Magnetic Resonance (NMR) spectrophotometer. Moreover, the cytotoxic, antimicrobial and antioxidant activity of AS-2, AS-3 and AS-4 were assessed. AS-2 exhibited significant activity against Salmonella typhi while mild antifungal activity against Aspergillus niger. Furthermore AS-3 revealed significant antifungal activity against Sacharomyces cerevacae as well as antibacterial activity against Salmonella typhi. Besides AS-4 exhibited moderate antibacterial activity against Bacillus megaterium. In addition AS-2, AS-3 and AS-4 presented mild cytotoxic with respect to positive control (Vincristine sulphate) while AS-3 exhibited moderate antioxidant activity as compared to positive control (Ascorbic acid).

References

  1. Javaid A, Khan IH, Ferdosi MFH. Bioactive constituents of wild Cannabis sativa roots from Pakistan. Pakistan Journal of Weed Science Research. 2021; 27(3):359-368. https://doi.org/10.28941/pjwsr.v27i3.984
  2. Ferdosi MFH, Khan IH, Javaid A, Nadeem M, Munir A. Biochemical profile of Calotropis procera flowers. Pakistan Journal of Weed Science Research. 2021;27(3):341-349. https://doi.org/10.28941/pjwsr.v27i3.982
  3. Khan IH, Javaid A. Hexane soluble bioactive components of leaf extract of quinoa. Journal of Animal and Plant Sciences. 2022; 32(2):309-314.
  4. Javaid A, Naqvi SF, Khan IH. Ethyl acetate extract of Chenopodium murale root, a source of bioactive compounds. Pakistan Journal of Weed Science Research. 2021 ;27(1):93. https://doi.org/10.28941/pjwsr.v27i1.926
  5. Saranya R, Thirumalai T, Hemalatha M, Balaji R, David E. Pharmacognosy of Enicostemma littorale: A review. Asian Pacific Journal of Tropical Biomedicine. 2013; 3(1):79-84. https://doi.org/10.1016/S2221-1691(13)60028-3
  6. Tiwari S. Plants: A rich source of herbal medicine. Journal of natural products.2008; 1:27-35.
  7. Ferdosi MFH, Javaid A, Khan IH, Khan S, Shad N. Analysis of n-butanol flower extract of Cassia fistula through GC-MS and identification of antimicrobial compounds. Pakistan Journal of Phytopathology. 2021; 33(1):103-107. https://doi.org/10.33866/phytopathol.033.01.0661
  8. Javaid A, Chaudhury FA, Khan IH, Ferdosi MFH. Potential health-related phytoconstituents in leaves of Chenopodium quinoa. Advancements in Life Sciences.2022; 9(4): 574-578.
  9. Khan IH, Javaid A. Antifungal, antibacterial and antioxidant components of ethyl acetate extract of quinoa stem. Plant Protection.2019; 3(3): 125-130. https://doi.org/10.33804/pp.003.03.3109
  10. Khan IH, Javaid A. Anticancer, antimicrobial and antioxidant compounds of quinoa inflorescence. Advancements in Life Sciences.2020; 8(1): 68-72.
  11. National Plant Data Center, NRCS, USDA. http://plants.usda.gov.
  12. Al Mansur MA, Siddiqi MMA, Saha K. Analgesic, Antidiarrheal and Antidepressant Activities of Anethum sowa Linn. in Swiss-Albino Mice Model. Bangladesh Pharmaceutical Journal. 2018; 21(1):1-6. https://doi.org/10.3329/bpj.v21i1.37899
  13. Tomar SS, Maheshwari ML, Mukerjee SK. Synthesis and synergistic activity of dillapiole based pyrethrum synergists. Journal of Agricultural and Food chemistry. 1979; 27(3):547-50. https://doi.org/10.1021/jf60223a012
  14. Tripathi A, Prajapati V, Aggarwal K, Kumar S. Insecticidal and Ovicidal Activity of the Essential Oil of Anethum sowa Kurz against Callosobruchus maculatus F. (Coleoptera: Bruchidae). International Journal of Tropical Insect Science.2001; 21(1):61-66. https://doi.org/10.1017/S1742758400020051
  15. Belzile AS, Majerus SL, Podeszfinski C, Guillet G, Durst T, Arnason JT. Dillapiol derivatives as synergists: structure–activity relationship analysis. Pesticide Biochemistry and Physiology. 2000; 66(1):33-40. https://doi.org/10.1006/pest.1999.2453
  16. Tripathi AK, Prajapati V, Aggarwal KK, Khanuja SPS, Kumar S. Toxicity of fractionated essential oil from Anethum sowa seed towards Tribolium castaneum Herbst. Journal of Medicinal and Aromatic Plant Sciences.2001; 22(4a):146-150.
  17. Chaurasia SC, Jain PC. Antibacterial activity of essential oils of four medicinal plants. Indian Journal of Hospital Pharmacy. 1978; 15(6):166-8.
  18. Saleh-E-In MM, Choi YE. Anethum sowa Roxb. ex Fleming: A review on traditional uses, phytochemistry, pharmacological and toxicological activities. Journal of Ethnopharmacology. 2021;280:113967. https://doi.org/10.1016/j.jep.2021.113967
  19. Jana S, Shekhawat GS. Anethum graveolens: An Indian traditional medicinal herb and spice. Pharmacognosy reviews. 2010; 4(8):179. https://doi.org/10.4103/0973-7847.70915
  20. Pruthi JS. Spices and condiments. National Bank Trust, New Delhi, India. 1976; 226.
  21. Tomar SS, Dureja P. New minor constituents from Anethum sowa. Fitoterapia. 2001; 72(1):76-7. https://doi.org/10.1016/S0367-326X(00)00235-5
  22. Jain AK, Sharma ND, Gupta SR. Occurrence of an Alkaloid in the seeds of Anethum sowa. Indian Journal of Chemistry Section B-Organic Chemistry including medicinal chemistry. 1986; 25(9):979.
  23. Tomar SS, Mukerjee SK. Dillapional, A New Constituent of Anethum sowa Roxb. Indian Indian Journal of Chemistry Section B-Organic Chemistry including medicinal chemistry. 1981; 20(8):723-4.
  24. Aggarwal KK, Khanuja SP, Ahmad A, Santha Kumar TR, Gupta VK, Kumar S. Antimicrobial activity profiles of the two enantiomers of limonene and carvone isolated from the oils of Mentha spicata and Anethum sowa. Flavour and Fragrance Journal. 2002; 17(1):59-63. https://doi.org/10.1002/ffj.1040
  25. Meyer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, McLaughlin JL. Brine shrimp: a convenient general bioassay for active plant constituents. Planta medica. 1982; 45(05):31-4. https://doi.org/10.1055/s-2007-971236
  26. Ntungwe N E, Domínguez-Martín EM, Roberto A, Tavares J, Isca VMS, Pereira P, Cebola MJ, Rijo P. Artemia species: An Important Tool to Screen General Toxicity Samples. Curr Pharm Des. 2020; 26 (24):2892-2908. https://doi.org/10.2174/1381612826666200406083035
  27. Elumalai EK, Ramachandran M, Thirumalai T, Vinothkumar P. Antibacterial activity of various leaf extracts of Merremia emarginata. Asian Pacific Journal of Tropical Biomedicine. 2011; 1(5):406-8. https://doi.org/10.1016/S2221-1691(11)60089-0
  28. Mostafa AA, Al-Askar AA, Almaary KS, Dawoud TM, Sholkamy EN, Bakri MM. Antimicrobial activity of some plant extracts against bacterial strains causing food poisoning diseases. Saudi Journal of Biological Sciences. 2018; 25(2):361-6. https://doi.org/10.1016/j.sjbs.2017.02.004
  29. Braca A, De Tommasi N, Di Bari L, Pizza C, Politi M, Morelli I. Antioxidant Principles from Bauhinia tarapotensis. Journal of Natural Products. 2001; 64 (7): 892-5. https://doi.org/10.1021/np0100845
  30. Angeli L, Imperiale S, Ding Y, Scampicchio M, Morozova K. A Novel stoichio-kinetic model for the DPPH• assay: The importance of the side reaction and application to complex mixtures. Antioxidants. 2021; 10(7):1019. https://doi.org/10.3390/antiox10071019
  31. Vieira IJ, Cecchi CM, Mathias L, Braz-Filho R, Rodrigues-Filho E. A New Depside Isolated from the Bark of Rauwolfia mattfeldiana. Journal of the Brazilian Chemical Society.1998; 9: 91-95. https://doi.org/10.1590/S0103-50531998000100016
  32. Darmawan A, Kosela S, Kardono LB, Syah YM. Scopoletin, a coumarin derivative compound isolated from Macaranga gigantifolia Merr. Journal of Applied Pharmaceutical Science. 2012 ; 2(12):175-7. https://doi.org/10.7324/JAPS.2012. 21231
  33. Huang Z, Yang R, Yin X, She Z, Lin Y. Structure elucidation and NMR assignments for two xanthone derivatives from a mangrove endophytic fungus (No. ZH19). Magnetic Resonance in Chemistry. 2010; 48(1):80-2. https://doi.org/10.1002/mrc.2539
  34. Abdel-Kader MS. New ester and furocoumarins from the roots of Pituranthos tortuosus. Journal of the Brazilian Chemical Society. 2003;14:48-51. https://doi.org/10.1590/S0103-50532003000100008

Downloads

Download data is not yet available.